Ibuprofen

Identification

Summary

Ibuprofen is an NSAID and non-selective COX inhibitor used to treat mild-moderate pain, fever, and inflammation.

Brand Names
Addaprin, Advil, Advil Cold and Sinus, Advil Congestion Relief, Advil PM, Advil Sinus Congestion and Pain, Alivio, Caldolor, Cedaprin, Children's Ibuprofen, Combogesic, Diphen, Duexis, Ibu, Ibutab, Junior Strength Motrin, Motrin, Motrin PM, Neoprofen, Nuprin, Pedea, Proprinal, Reprexain, Sudafed PE Head Congestion Plus Pain, Vicoprofen, Wal-profen Congestion Relief and Pain
Generic Name
Ibuprofen
DrugBank Accession Number
DB01050
Background

Ibuprofen is a non-steroidal anti-inflammatory drug (NSAID) derived from propionic acid and it is considered the first of the propionics.7 The formula of ibuprofen is 2-(4-isobutylphenyl) propionic acid and its initial development was in 1960 while researching for a safer alternative for aspirin.8 Ibuprofen was finally patented in 1961 and this drug was first launched against rheumatoid arthritis in the UK in 1969 and USA in 1974. It was the first available over-the-counter NSAID.9

On the available products, ibuprofen is administered as a racemic mixture. Once administered, the R-enantiomer undergoes extensive interconversion to the S-enantiomer in vivo by the activity of the alpha-methylacyl-CoA racemase. In particular, it is generally proposed that the S-enantiomer is capable of eliciting stronger pharmacological activity than the R-enantiomer.24

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 206.2808
Monoisotopic: 206.13067982
Chemical Formula
C13H18O2
Synonyms
  • (±)-2-(p-isobutylphenyl)propionic acid
  • (±)-ibuprofen
  • (±)-p-isobutylhydratropic acid
  • (±)-α-methyl-4-(2-methylpropyl)benzeneacetic acid
  • (4-isobutylphenyl)-α-methylacetic acid
  • (RS)-ibuprofen
  • 2-(4-isobutylphenyl)propanoic acid
  • 4-isobutylhydratropic acid
  • Ibuprofen
  • Ibuprofene
  • Ibuprofeno
  • Ibuprofenum
  • Ibuprophen
  • α-(4-isobutylphenyl)propionic acid
  • α-(p-isobutylphenyl)propionic acid

Pharmacology

Indication

Ibuprofen is the most commonly used and prescribed NSAID. It is a very common over-the-counter medication widely used as an analgesic, anti-inflammatory and antipyretic.11

The use of ibuprofen and its enantiomer Dexibuprofen in a racemic mix is common for the management of mild to moderate pain related to dysmenorrhea, headache, migraine, postoperative dental pain, spondylitis, osteoarthritis, rheumatoid arthritis, and soft tissue disorder.12

Due to its activity against prostaglandin and thromboxane synthesis, ibuprofen has been attributed to alteration of platelet function and prolongation of gestation and labour.10

As ibuprofen is a widely used medication, the main therapeutic indications are:

  • Patent Ductus Arteriosus - it is a neonatal condition wherein the ductus arteriosus (blood vessel that connects the main pulmonary artery to the proximal descending aorta) fails to close after birth causing severe risk of heart failure. The prostaglandin inhibition of ibuprofen has been studied for the treatment of this condition as it is known that prostaglandin E2 is responsible for keeping the ductus arteriosus open.13

  • Rheumatoid- and osteo-arthritis - ibuprofen is very commonly used in the symptomatic treatment of inflammatory, musculoskeletal and rheumatic disorders.14

  • Cystic fibrosis - the use of high dosages of ibuprofen has been proven to decrease inflammation and decreasing polymorphonuclear cell influx in the lungs.15

  • Orthostatic hypotension - ibuprofen can induce sodium retention and antagonize the effect of diuretics which has been reported to be beneficial for patients with severe orthostatic hypotension.1

  • Dental pain - ibuprofen is used to manage acute and chronic orofacial pain.16

  • Pain - ibuprofen is widely used to reduce minor aches and pains as well as to reduce fever and manage dysmenorrhea. It is very commonly used for the relief of acute indications such as fever and tension headaches.10 It is also used to manage mild to moderate pain and moderate to severe pain as an adjunct to opioid analgesics.28

  • Investigational uses - efforts have been put into developing ibuprofen for the prophylaxis of Alzheimer's disease, Parkinson disease, and breast cancer.10

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to manageAcute painCombination Product in combination with: Hydrocodone (DB00956)••••••••••••
Used in combination to manageAcute painCombination Product in combination with: Oxycodone (DB00497)••••••••••••
Management ofAnkylosing spondylitis••• •••••
Used in combination for symptomatic treatment ofCommon coldCombination Product in combination with: Phenylephrine (DB00388), Desloratadine (DB00967)••• ••••••••••• ••••••
Used in combination for symptomatic treatment ofCommon coldCombination Product in combination with: Cetirizine (DB00341), Phenylephrine (DB00388)••• ••••••••••• ••••••• •••••••• •••••• ••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Ibuprofen has multiple actions in different inflammatory pathways involved in acute and chronic inflammation. The main effects reported in ibuprofen are related to the control of pain, fever and acute inflammation by the inhibition of the synthesis of prostanoids by COX-1 and COX-2. Pain relief is attributed to peripheral affected regions and central nervous system effects in the pain transmission mediated by the dorsal horn and higher spinothalamic tract. Some reports have tried to link the pain regulation with a possible enhancement on the synthesis of endogenous cannabinoids and action on the NMDA receptors. The effect on pain has been shown to be related to the cortically evoked potentials.23

The antipyretic effect is reported to be linked to the effect on the prostanoid synthesis due to the fact that the prostanoids are the main signaling mediator of pyresis in the hypothalamic-preoptic region.23

The use of ibuprofen in dental procedures is attributed to the local inhibition of prostanoid production as well as to anti-oedemic activity and an increase of plasma beta-endorphins. Some reports have suggested a rapid local reduction of the expression of COX-2 in dental pulp derived by the administration of ibuprofen.23

The administration of ibuprofen in patients with rheumatic diseases has shown to control joint symptoms.10

Ibuprofen is largely used in OTC products such as an agent for the management of dysmenorrhea which has been proven to reduce the amount of menstrual prostanoids and to produce a reduction in the uterine hypercontractility.17 As well, it has been reported to reduce significantly the fever and the pain caused by migraines.18,19 This effect is thought to be related to the effect on platelet activation and thromboxane A2 production which produces local vascular effects in the affected regions. This effect is viable as ibuprofen can enter in the central nervous system.23

In the investigational uses of ibuprofen, it has been reported to reduce neurodegeneration when given in low doses over a long time.20 On the other hand, its use in Parkinson disease is related to the importance of inflammation and oxidative stress in the pathology of this condition.21 The use of ibuprofen for breast cancer is related to a study that shows a decrease of 50% in the rate of breast cancer.22

Mechanism of action

The exact mechanism of action of ibuprofen is unknown. However, ibuprofen is considered an NSAID and thus it is a non-selective inhibitor of cyclooxygenase, which is an enzyme involved in prostaglandin (mediators of pain and fever) and thromboxane (stimulators of blood clotting) synthesis via the arachidonic acid pathway.27

Ibuprofen is a non-selective COX inhibitor and hence, it inhibits the activity of both COX-1 and COX-2. The inhibition of COX-2 activity decreases the synthesis of prostaglandins involved in mediating inflammation, pain, fever, and swelling while the inhibition of COX-1 is thought to cause some of the side effects of ibuprofen including GI ulceration.25

TargetActionsOrganism
AProstaglandin G/H synthase 2
inhibitor
Humans
AC-X-C chemokine receptor type 2
inhibitor
Humans
AInterleukin-8
inhibitor
Humans
AC-X-C chemokine receptor type 1
inhibitor
Humans
AProstaglandin G/H synthase 1
inhibitor
Humans
UApoptosis regulator Bcl-2
modulator
Humans
UThrombomodulin
inducer
Humans
UFatty acid-binding protein, intestinal
binder
Humans
UPeroxisome proliferator-activated receptor gamma
activator
Humans
UCystic fibrosis transmembrane conductance regulator
inhibitor
Humans
UPeroxisome proliferator-activated receptor alpha
activator
Humans
UPlatelet glycoprotein Ib alpha chain
inducer
Humans
UProtein S100-A7
inducer
Humans
Absorption

It is very well absorbed orally and the peak serum concentration can be attained in 1 to 2 hours after extravascular administration. When ibuprofen is administered immediately after a meal there is a slight reduction in the absorption rate but there is no change in the extent of the absorption.10

When orally administered, the absorption of ibuprofen in adults is very rapidly done in the upper GI tract.23 The average Cmax, Tmax and AUC ranges around 20 mcg/ml, 2 h and 70 mcg.h/ml. These parameters can vary depending on the enantiomer form, route, and dose of administration.23

Volume of distribution

The apparent volume of distribution of ibuprofen is of 0.1 L/kg.25

Protein binding

Ibuprofen dosage is more than 99% bound to plasma proteins and site II of purified albumin, binding appears to be saturable and becomes non-linear at concentrations exceeding 20 mcg/ml.10

Metabolism

Ibuprofen is rapidly metabolized and biotransformed in the liver to the formation of major metabolites which are the hydroxylated and carboxylated derivatives.10 As soon as it is absorbed, the R-enantiomer undergoes extensive enantiomeric conversion (53-65%) to the more active S-enantiomer in vivo by the activity of alpha-methylacyl-CoA racemase.24

Ibuprofen metabolism can be divided in phase I which is represented by the hydroxylation of the isobutyl chains for the formation of 2 or 3-hydroxy derivatives followed by oxidation to 2-carboxy-ibuprofen and p-carboxy-2-propionate. These oxidative reactions are performed by the activity of the cytochrome P450 isoforms CYP 2C9, CYP 2C19 and CYP 2C8. Therefore, these enzymes participate in the oxidation of the alkyl side chain to hydroxyl and carboxyl derivatives. From this enzymes, the major catalyst in the formation of oxidative metabolites is the isoform CYP 2C9.23

The metabolic phase I is followed by a phase II in which the oxidative metabolites may be conjugated to glucuronide prior to excretion. This activity forms phenolic and acyl glucuronides.23

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Route of elimination

Ibuprofen is rapidly metabolized and eliminated in the urine thus, this via accounts for more than 90% of the administered dose. It is completely eliminated in 24 hours after the last dose and almost all the administered dose goes through metabolism, representing about 99% of the eliminated dose.10 The biliary excretion of unchanged drug and active phase II metabolites represents 1% of the administered dose.23

In summary, ibuprofen is excreted as metabolites or their conjugates. The elimination of ibuprofen is not impaired by old age or the presence of renal impairment.10

Half-life

The serum half-life of ibuprofen is 1.2-2 hours.10 In patients with a compromised liver function, the half-life can be prolonged to 3.1-3.4 hours.23

Clearance

The clearance rate ranges between 3-13 L/h depending on the route of administration, enantiomer type and dosage.23

Adverse Effects
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Toxicity

The symptoms of overdose are presented in individuals that consumed more than 99 mg/kg. Most common symptoms of overdose are abdominal pain, nausea, vomiting, lethargy, vertigo, drowsiness (somnolence), dizziness and insomnia. Other symptoms of overdose include headache, loss of consciousness, tinnitus, CNS depression, convulsions and seizures. May rarely cause metabolic acidosis, abnormal hepatic function, hyperkalemia, renal failure, dyspnea, respiratory depression, coma, acute renal failure, and apnea (primarily in very young pediatric patients).26

The reported LD50 of ibuprofen is of 636 mg/kg in rat, 740 mg/kg in mouse and 495 mg/kg in guinea pig.MSDS

Pathways
PathwayCategory
Ibuprofen Action PathwayDrug action
Ibuprofen Metabolism PathwayDrug metabolism
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirIbuprofen may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbametapirThe serum concentration of Ibuprofen can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Ibuprofen can be increased when combined with Abatacept.
AbciximabThe risk or severity of bleeding can be increased when Ibuprofen is combined with Abciximab.
AbirateroneThe metabolism of Ibuprofen can be decreased when combined with Abiraterone.
Food Interactions
  • Avoid alcohol.
  • Take with food. Food reduces irritation.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Ibuprofen aluminumD0YGZ1VO1B61054-06-6QAZIXAUMDFPQRW-UHFFFAOYSA-K
Ibuprofen arginineXV17W49C9U57469-82-6GCCOJNYCFNSJII-VWMHFEHESA-N
Ibuprofen lysineN01ORX9D6S57469-77-9IHHXIUAEPKVVII-ZSCHJXSPSA-N
Ibuprofen potassium48304089JJ79261-49-7XJELUCTZEAQYGF-UHFFFAOYSA-M
Ibuprofen sodiumRM1CE97Z4N527688-20-6VTGPMVCGAVZLQI-UHFFFAOYSA-M
Product Images
International/Other Brands
Act-3 (Healthcare Logistics) / Actiprofen (Sterling Health) / Adex (Dexxon) / Aktren (Bayer) / Alges-X (Axapharm) / Algoflex (Chinoin) / Algofren (Intermed) / Alivium (Bristol-Myers Squibb) / Artofen (Teva) / Betagesic (Adcock Ingram Pharmaceuticals) / Betaprofen (Be-Tabs Pharmaceuticals) / Bonifen (Krka) / Brufen (Abbott) / Brupro (Sandoz) / Buburone (Towa Yakuhin) / Buprovil (Multilab Industry and Trade of Pharmaceuticals) / Burana (Orion) / Butylenin (Sanken) / Calprofen (McNeil) / Cap-Profen (PERRIGO) / Capsibu (Sandoz) / Children's Elixsure (Pfizer) / Children's Ibuprofen (Pfizer) / Dalsy (Abbott) / Dismenol (Merz) / Diverin (ACI Ltd) / Dolgirid (LGC) / Dolgit (Dolorgiet) / Doloraz (Jordanian Pharmaceutical Manufacturing Co.) / Dolormin (Johnson & Johnson GmbH) / Ebufac (DDSA Pharmaceuticals) / EmuProfen (Progressive Emu, Inc) / Epobron (Ono) / Fenbid (Smith Kline and Beecham) / Fenpaed (Rite Aid Corporation) / Fenpain (Sandoz) / Ibalgin (Zentiva) / IBU-Ratiopharm (Ratiopharm GmbH) / Ibuflam (Natco Pharma Ltd) / Ibugel (Dermal Laboratories Ltd) / Ibugesic (Cipra Ltd) / IbuHEXAL (Hexal AG) / Ibuleve (Diomed Development Ltd) / Ibum (PPF Hasco-Lek SA) / Ibumax (standford Biotech Pvt Ltd) / Ibumetin (Nycomed Denmark Aps) / Ibupain (Sandoz) / Ibuprocin (Nisshin) / Ibuprom (USP Zdrowie) / Ibuprox (Norway) / Ibustar (Berlin-Chemie Menarini Croatia) / Ibutren (Sandoz) / Ibux (Weifa AS) / Ibuxin (Pliva Hrvatska) / Junior Strength Motrin (J&J Consumer Inc) / Kratalgin (Austria) / Lamidon (Kowa) / Lebrufen / Liptan (Kowa) / Lotem (Adcock Ingram) / Medicol (United Lab) / Medipren (Johnson & Johnson) / Mynosedin (Toho Yakuhin) / Mypaid (Ai Pharm) / Myprodol (Adcock Ingram) / Narfen (Alter) / Naron Ace (Primary Care Tokyo) / Neobrufen (Crookes) / Nobfen (Toho) / Nobgen (Toho) / Norvectan / Nuprin (Upjohn Company) / Nureflex (Boots Healthcare, Courbevoie) / Nurofen (Crookes) / Orbifen (Boehringer Ingelheim International GmbH) / Panafen (GlaxoSmithKline Consumer Healthcare Australia Pty Ltd) / Pediaprofen (Whitehall Laboratories) / Rapidol (Actavis) / Rimafen / Roidenin (Showa) / Rufen (Boots) / Salvarina (Salvat, Barcelona) / Seclodin (Whitehall Labs, Maidenhead) / Speedpain NANO (Goodsense) / Spidifen (Zambon) / Suspren / Tabalon (Sanofi India Ltd) / Trendar (Whitehall-Robins) / Urem (Kade, MErlin)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CaldolorInjection800 mg/8mLIntravenousCumberland Pharmaceuticals Inc.2009-06-11Not applicableUS flag
CaldolorSolution100 mg / mLIntravenousCumberland Pharmaceuticals Inc2012-06-15Not applicableCanada flag
CaldolorInjection100 mg/1mLIntravenousCumberland Pharmaceuticals Inc.2009-08-272009-06-24US flag
CaldolorInjection800 mg/200mLIntravenousCumberland Pharmaceuticals Inc.2020-01-01Not applicableUS flag
IbupakKit600 mg/1OralPureTek Corporation2020-05-22Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AlivioTablet600 mg/600mgOralAlivio Medical Products, Llc2015-07-01Not applicableUS flag
AlivioTablet800 mg/800mgOralAlivio Medical Products, Llc2015-07-01Not applicableUS flag
AlivioTablet400 mg/400mgOralAlivio Medical Products, Llc2015-07-01Not applicableUS flag
Alti-ibuprofen Tab 600mgTablet600 mgOralAltimed Pharma Inc.1984-12-311999-09-17Canada flag
Apo-ibuprofen Tab 600mgTablet600 mgOralApotex Corporation1984-12-31Not applicableCanada flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
24/7 Life IBUPROFENTablet, film coated200 mg/1OralLil' Drug Store Products, Inc.2020-12-16Not applicableUS flag
365 Everday Value IbuprofenTablet, film coated200 mg/1OralWhole Foods Market, Inc.2020-08-24Not applicableUS flag
365 Everyday Value IbuprofenTablet, film coated200 mg/1OralWhole Foods Market, Inc.2018-08-29Not applicableUS flag
7 Select Childrens IbuprofenSuspension100 mg/5mLOral7-Eleven2014-08-052021-04-30US flag
7 Select IbuprofenCapsule, liquid filled200 mg/1Oral7-Eleven2018-02-022021-03-31US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
10 Person ANSIIbuprofen (200 mg/1) + Acetaminophen (325 mg/1) + Acetylsalicylic acid (325 mg/1) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (0.40 mL/100mL) + Benzocaine (6 mL/100mL) + Ethanol (60 mL/100mL) + Lidocaine (0.5 1/100g) + Neomycin sulfate (5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)KitOphthalmic; Oral; TopicalGenuine First Aid2010-04-24Not applicableUS flag
25 Person ANSIIbuprofen (200 mg/1) + Acetaminophen (325 mg/1) + Acetylsalicylic acid (325 mg/1) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (0.40 mL/100mL) + Benzocaine (6 mL/100mL) + Ethanol (60 mL/100mL) + Ethanol (62 g/100g) + Isopropyl alcohol (70 mL/100mL) + Lidocaine (0.5 g/100g) + Neomycin sulfate (5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)KitOphthalmic; Oral; TopicalGenuine First Aid2010-04-25Not applicableUS flag
4389 First Aid KitIbuprofen (200 mg/1) + Acetaminophen (500 mg/1) + Acetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Lidocaine hydrochloride (2 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)KitOphthalmic; Oral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4390 First Aid KitIbuprofen (200 mg/1) + Acetaminophen (325 mg/1) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (0.13 g/100mL) + Calcium carbonate (420 mg/1) + Ethanol (62 mL/100mL) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (24.64 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Phenylephrine hydrochloride (5 mg/1) + Water (98.6 mL/100mL)KitOphthalmic; Oral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4392 First Aid KitIbuprofen (200 mg/1) + Acetaminophen (325 mg/1) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (0.13 g/100mL) + Calcium carbonate (420 mg/1) + Ethanol (62 mL/100mL) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (24.64 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Phenylephrine hydrochloride (5 mg/1) + Water (98.6 mL/100mL)KitOphthalmic; Oral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
4389 First Aid KitIbuprofen (200 mg/1) + Acetaminophen (500 mg/1) + Acetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Lidocaine hydrochloride (2 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)KitOphthalmic; Oral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4390 First Aid KitIbuprofen (200 mg/1) + Acetaminophen (325 mg/1) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (0.13 g/100mL) + Calcium carbonate (420 mg/1) + Ethanol (62 mL/100mL) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (24.64 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Phenylephrine hydrochloride (5 mg/1) + Water (98.6 mL/100mL)KitOphthalmic; Oral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4392 First Aid KitIbuprofen (200 mg/1) + Acetaminophen (325 mg/1) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (0.13 g/100mL) + Calcium carbonate (420 mg/1) + Ethanol (62 mL/100mL) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (24.64 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Phenylephrine hydrochloride (5 mg/1) + Water (98.6 mL/100mL)KitOphthalmic; Oral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4395 First Aid KitIbuprofen (200 mg/1) + Acetaminophen (500 mg/1) + Acetylsalicylic acid (325 mg/1) + Benzalkonium chloride (1.3 mg/1mL) + Benzalkonium chloride (0.13 g/100g) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g)Cream; Kit; Liquid; Ointment; Swab; TabletOral; TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
Cimetidine 5% / Ibuprofen 2% / Salicylic Acid 17%Ibuprofen (2 g/100g) + Cimetidine (5 g/100g) + Salicylic acid (17 g/100g)GelTopicalSincerus Florida, LLC2019-05-17Not applicableUS flag

Categories

ATC Codes
C01EB16 — IbuprofenR02AX02 — IbuprofenN02AJ19 — Oxycodone and ibuprofenM01AE51 — Ibuprofen, combinationsG02CC01 — IbuprofenM01AE01 — IbuprofenM02AA13 — IbuprofenN02AJ08 — Codeine and ibuprofenN02AJ23 — Hydrocodone and ibuprofen
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Phenylpropanoic acids
Sub Class
Not Available
Direct Parent
Phenylpropanoic acids
Alternative Parents
Monocyclic monoterpenoids / Aromatic monoterpenoids / Phenylpropanes / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
2-phenylpropanoic-acid / Aromatic homomonocyclic compound / Aromatic monoterpenoid / Benzenoid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Monocyclic benzene moiety
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
monocarboxylic acid (CHEBI:5855)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
WK2XYI10QM
CAS number
15687-27-1
InChI Key
HEFNNWSXXWATRW-UHFFFAOYSA-N
InChI
InChI=1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)
IUPAC Name
2-[4-(2-methylpropyl)phenyl]propanoic acid
SMILES
CC(C)CC1=CC=C(C=C1)C(C)C(O)=O

References

General References
  1. Zawada ET Jr: Renal consequences of nonsteroidal antiinflammatory drugs. Postgrad Med. 1982 May;71(5):223-30. [Article]
  2. Townsend KP, Pratico D: Novel therapeutic opportunities for Alzheimer's disease: focus on nonsteroidal anti-inflammatory drugs. FASEB J. 2005 Oct;19(12):1592-601. [Article]
  3. Chen H, Jacobs E, Schwarzschild MA, McCullough ML, Calle EE, Thun MJ, Ascherio A: Nonsteroidal antiinflammatory drug use and the risk for Parkinson's disease. Ann Neurol. 2005 Dec;58(6):963-7. [Article]
  4. Geisslinger G, Dietzel K, Bezler H, Nuernberg B, Brune K: Therapeutically relevant differences in the pharmacokinetical and pharmaceutical behavior of ibuprofen lysinate as compared to ibuprofen acid. Int J Clin Pharmacol Ther Toxicol. 1989 Jul;27(7):324-8. [Article]
  5. Bergner T, Przybilla B: Photosensitization caused by ibuprofen. J Am Acad Dermatol. 1992 Jan;26(1):114-6. [Article]
  6. Dill J, Patel AR, Yang XL, Bachoo R, Powell CM, Li S: A molecular mechanism for ibuprofen-mediated RhoA inhibition in neurons. J Neurosci. 2010 Jan 20;30(3):963-72. doi: 10.1523/JNEUROSCI.5045-09.2010. [Article]
  7. Adams SS: The propionic acids: a personal perspective. J Clin Pharmacol. 1992 Apr;32(4):317-23. [Article]
  8. Rainsford KD: Discovery, mechanisms of action and safety of ibuprofen. Int J Clin Pract Suppl. 2003 Apr;(135):3-8. [Article]
  9. Halford GM, Lordkipanidze M, Watson SP: 50th anniversary of the discovery of ibuprofen: an interview with Dr Stewart Adams. Platelets. 2012;23(6):415-22. doi: 10.3109/09537104.2011.632032. Epub 2011 Nov 18. [Article]
  10. Bushra R, Aslam N: An overview of clinical pharmacology of Ibuprofen. Oman Med J. 2010 Jul;25(3):155-1661. doi: 10.5001/omj.2010.49. [Article]
  11. Adams SS, McCullough KF, Nicholson JS: The pharmacological properties of ibuprofen, an anti-inflammatory, analgesic and antipyretic agent. Arch Int Pharmacodyn Ther. 1969 Mar;178(1):115-29. [Article]
  12. Potthast H, Dressman JB, Junginger HE, Midha KK, Oeser H, Shah VP, Vogelpoel H, Barends DM: Biowaiver monographs for immediate release solid oral dosage forms: ibuprofen. J Pharm Sci. 2005 Oct;94(10):2121-31. doi: 10.1002/jps.20444. [Article]
  13. Sharma PK, Garg SK, Narang A: Pharmacokinetics of oral ibuprofen in premature infants. J Clin Pharmacol. 2003 Sep;43(9):968-73. [Article]
  14. Tan SC, Patel BK, Jackson SH, Swift CG, Hutt AJ: Ibuprofen stereochemistry: double-the-trouble? Enantiomer. 1999;4(3-4):195-203. [Article]
  15. Konstan MW, Krenicky JE, Finney MR, Kirchner HL, Hilliard KA, Hilliard JB, Davis PB, Hoppel CL: Effect of ibuprofen on neutrophil migration in vivo in cystic fibrosis and healthy subjects. J Pharmacol Exp Ther. 2003 Sep;306(3):1086-91. doi: 10.1124/jpet.103.052449. Epub 2003 Jun 13. [Article]
  16. Moore PA, Hersh EV: Celecoxib and rofecoxib. The role of COX-2 inhibitors in dental practice. J Am Dent Assoc. 2001 Apr;132(4):451-6. [Article]
  17. Dawood MY: Primary dysmenorrhea: advances in pathogenesis and management. Obstet Gynecol. 2006 Aug;108(2):428-41. doi: 10.1097/01.AOG.0000230214.26638.0c. [Article]
  18. Krishna S, Pukrittayakamee S, Supanaranond W, ter Kuile F, Ruprah M, Sura T, White NJ: Fever in uncomplicated Plasmodium falciparum malaria: randomized double-'blind' comparison of ibuprofen and paracetamol treatment. Trans R Soc Trop Med Hyg. 1995 Sep-Oct;89(5):507-9. [Article]
  19. Evers S, Rahmann A, Kraemer C, Kurlemann G, Debus O, Husstedt IW, Frese A: Treatment of childhood migraine attacks with oral zolmitriptan and ibuprofen. Neurology. 2006 Aug 8;67(3):497-9. doi: 10.1212/01.wnl.0000231138.18629.d5. Epub 2006 Jun 14. [Article]
  20. Casper D, Yaparpalvi U, Rempel N, Werner P: Ibuprofen protects dopaminergic neurons against glutamate toxicity in vitro. Neurosci Lett. 2000 Aug 11;289(3):201-4. [Article]
  21. Ton TG, Heckbert SR, Longstreth WT Jr, Rossing MA, Kukull WA, Franklin GM, Swanson PD, Smith-Weller T, Checkoway H: Nonsteroidal anti-inflammatory drugs and risk of Parkinson's disease. Mov Disord. 2006 Jul;21(7):964-9. doi: 10.1002/mds.20856. [Article]
  22. Harris RE, Kasbari S, Farrar WB: Prospective study of nonsteroidal anti-inflammatory drugs and breast cancer. Oncol Rep. 1999 Jan-Feb;6(1):71-3. [Article]
  23. Rainsford KD: Ibuprofen: pharmacology, efficacy and safety. Inflammopharmacology. 2009 Dec;17(6):275-342. doi: 10.1007/s10787-009-0016-x. Epub 2009 Nov 21. [Article]
  24. Tracy TS, Hall SD: Metabolic inversion of (R)-ibuprofen. Epimerization and hydrolysis of ibuprofenyl-coenzyme A. Drug Metab Dispos. 1992 Mar-Apr;20(2):322-7. [Article]
  25. Rao P, Knaus EE: Evolution of nonsteroidal anti-inflammatory drugs (NSAIDs): cyclooxygenase (COX) inhibition and beyond. J Pharm Pharm Sci. 2008 Sep 20;11(2):81s-110s. [Article]
  26. Hall AH, Smolinske SC, Conrad FL, Wruk KM, Kulig KW, Dwelle TL, Rumack BH: Ibuprofen overdose: 126 cases. Ann Emerg Med. 1986 Nov;15(11):1308-13. [Article]
  27. Current issues in pharmacy and medical sciences [Link]
  28. FDA Approved Drug Products: Caldolor (ibuprofen) solution for intravenous injection [Link]
Human Metabolome Database
HMDB0001925
KEGG Drug
D00126
KEGG Compound
C01588
PubChem Compound
3672
PubChem Substance
46507255
ChemSpider
3544
BindingDB
50009859
RxNav
5640
ChEBI
5855
ChEMBL
CHEMBL521
Therapeutic Targets Database
DAP000780
PharmGKB
PA449957
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Ibuprofen
FDA label
Download (1.77 MB)
MSDS
Download (73.5 KB)

Clinical Trials

Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package
PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
Not AvailableActive Not RecruitingNot AvailableMyocardial Dysfunction / Newborn Morbidity / Obesity, Maternal1somestatusstop reasonjust information to hide
Not AvailableActive Not RecruitingPreventionOpioid Misuse / Opioids Use / Pain / Postoperative pain1somestatusstop reasonjust information to hide
Not AvailableActive Not RecruitingTreatmentPatent Ductus Arteriosus in Preterm Infants1somestatusstop reasonjust information to hide
Not AvailableCompletedNot AvailableAdverse Events / Overdose1somestatusstop reasonjust information to hide
Not AvailableCompletedNot AvailableAging / Physical Fitness1somestatusstop reasonjust information to hide

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Abbott Laboratories Ltd.
  • Actavis Group
  • Advanced Pharmaceutical Services Inc.
  • Aidarex Pharmacuticals LLC
  • Altura Pharmaceuticals Inc.
  • Amerisource Health Services Corp.
  • Amneal Pharmaceuticals
  • Apotheca Inc.
  • Apothecary Shop Wholesale
  • A-S Medication Solutions LLC
  • Ascend Laboratories LLC
  • Atlantic Biologicals Corporation
  • BASF Corp.
  • Bayer Healthcare
  • Ben Venue Laboratories Inc.
  • Blenheim Pharmacal
  • Breckenridge Pharmaceuticals
  • Bryant Ranch Prepack
  • Bv Pharbita
  • Cardinal Health
  • Caremark LLC
  • Central Texas Community Health Centers
  • Centrix Pharmaceuticals
  • Chain Drug
  • Corepharma LLC
  • Coupler Enterprises Inc.
  • Cumberland Pharmaceuticals
  • CVS Pharmacy
  • Darby Dental Supply Co. Inc.
  • Dept Health Central Pharmacy
  • DHHS Program Support Center Supply Service Center
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Doctor Reddys Laboratories Ltd.
  • Dorx LLC
  • Eckerd
  • Equaline Vitamins
  • Gm Pharmaceuticals Inc.
  • Golden State Medical Supply Inc.
  • Greenstone LLC
  • Group Health Cooperative
  • H and H Laboratories
  • H.J. Harkins Co. Inc.
  • Hawthorn Pharmaceuticals
  • Heartland Repack Services LLC
  • Hl Moore Drug Exchange
  • Imiren Pharmaceuticals Inc.
  • Innoviant Pharmacy Inc.
  • Ivax Pharmaceuticals
  • Kaiser Foundation Hospital
  • Keltman Pharmaceuticals Inc.
  • Kowa Pharmaceuticals America Inc.
  • Lake Erie Medical and Surgical Supply
  • LeaderPharma
  • Legacy Pharmaceuticals Packaging LLC
  • Liberty Pharmaceuticals
  • Lundbeck Inc.
  • Major Pharmaceuticals
  • Mckesson Corp.
  • McNeil Laboratories
  • Medicine Shop
  • Medique Products
  • Medisca Inc.
  • Medvantx Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • Par Pharmaceuticals
  • Particle Dynamics Co.
  • Patient First Corp.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Perrigo Co.
  • Pharmaceutical Association
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmacia Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Poly Pharmaceuticals Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Prescript Pharmaceuticals
  • Prescription Dispensing Service Inc.
  • Publix Super Markets
  • Qualitest
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Rite Aid Corp.
  • Sandhills Packaging Inc.
  • Shanghai Ziyuan Pharmaceutical Co. Ltd.
  • Shasun Chemicals & Drugs Ltd.
  • Southwood Pharmaceuticals
  • St Mary's Medical Park Pharmacy
  • Stat Rx Usa
  • Sunmark
  • Talbert Medical Management Corp.
  • Teva Pharmaceutical Industries Ltd.
  • UDL Laboratories
  • Ultras Pharmaceuticals Inc.
  • Va Cmop Dallas
  • Vangard Labs Inc.
  • Veratex Corp.
  • Vintage Pharmaceuticals Inc.
  • Vistapharm Inc.
  • Walgreen Co.
  • Watson Pharmaceuticals
  • Wyeth Pharmaceuticals
  • Xactdose Inc.
Dosage Forms
FormRouteStrength
KitOphthalmic; Oral; Respiratory (inhalation); Topical
Cream; kit; liquid; ointment; swab; tabletOral; Topical
KitOphthalmic; Oral; Topical
TabletNot applicable
Injection, powder, for solutionIntramuscular
CapsuleOral400.000 mg
GelCutaneous5.00 g
Capsule, liquid filledOral600 mg
Tablet, sugar coatedOral
SuspensionOral400 mg
KitOral; Topical
KitTopical
Tablet, coatedTopical200 mg/1
TabletOral600.000 mg
Tablet, extended releaseOral600 mg
Capsule; kitOral
Tablet, coatedOral200 mg
Tablet, coatedOral256 mg/1
Tablet, coatedOral200 mg/1000mg
SuspensionOral2.000 g
CapsuleOral
CapsuleOral200 mg
CapsuleOral200.000 mg
CapsuleOral600.000 mg
CapsuleOral200.000 mg
SuspensionOral20 MG/ML
TabletOral400 mg/400mg
TabletOral600 mg/600mg
TabletOral800 mg/800mg
SuspensionOral100 mg
TabletOral200 mg
TabletOral300 mg
TabletOral600 mg
CapsuleOral600.0000 mg
TabletOral1212.100 mg
CapsuleOral250 MG
Injection, powder, for solutionIntramuscular400 MG/3ML
Injection, solutionIntramuscular400 MG/3ML
SolutionIntramuscular400 mg/3ml
SolutionVaginal10 MG/ML
SuppositoryRectal250 MG
TabletOral500 MG
TabletOral20.000 mg
GelTopical5 g
SolutionIntravenous10 mg
TabletOral800.00 mg
CreamTopical10 G/100G
CreamTopical30 G
Pill300 MG
Pill400 MG
Tablet, coated600 MG
Tablet, coated800 MG
Tablet, film coatedOral
Tablet, coatedOral400 mg
Tablet, delayed releaseOral800 mg
OintmentTopical
Powder, for solutionOral
SuspensionOral200 mg/5mL
SuspensionOral200000 g
PowderOral200 MG
PowderOral400 MG
InjectionIntravenous
InjectionIntravenous100 mg/1mL
InjectionIntravenous800 mg/200mL
InjectionIntravenous800 mg/8mL
SolutionIntravenous100 mg / mL
GranuleOral2.2 g
SuspensionOral100 mg / 5 mL
Tablet, chewableOral50 mg
TabletOral50 mg
SolutionOral100 mg/5mL
SuspensionOral200 mg/10mL
Suspension / dropsOral100 mg/5mL
SuspensionOral100 mg/10mL
SuspensionOral
Tablet, delayed releaseOral
GelTopical
Kit; tabletOral
Tablet, film coated
InjectionIntravenous
SolutionIntravenous
Kit; tabletOral800 mg/1
PowderNot applicable66 mg/100mg
Powder85 mg/100mg
SyrupOral
Capsule, liquid filledOral200 mg/1
PatchTopical
Cream; kit; liquid; ointment; tablet; tablet, chewable; tablet, film coatedOral; Topical
GelTopical50 mg/g
GelTopical
LiquidOral100 mg/100mL
CreamTopical
CreamTopical5 %
Tablet, sugar coatedOral400 mg/1
Tablet, sugar coatedOral600 mg/1
GelTopical400 mg/1
CapsuleOral50 mg/g
SuspensionOral200000000 mg
Solution / dropsOral
Capsule, liquid filledOral200 mg
SuspensionOral40 MG/ML
Capsule, coatedOral200 mg
GelTopical10 %
Injection, solutionIntravenous400 mg/100ml
Injection, solution, concentrateIntravenous20 mg/2ml
Capsule, liquid filledOral200 mg/1201
Powder, for solutionVaginal
SolutionVaginal
PowderOral0.2 g
GranuleOral200 mg
GranuleOral13.33 g
SuspensionOral40.000 mg
SolutionTopical
Pill
Tablet, orally disintegratingOral200 MG
SuspensionOral4 g
Granule, effervescentOral200 MG
Granule, effervescentOral400 MG
CapsuleOral400.000000 mg
CapsuleOral
CapsuleOral600 mg
SuspensionOral50 mg/1.25mL
Tablet, film coatedOral
SuppositoryRectal
Tablet, film coatedOral293 MG
Tablet, film coatedOral500 MG
SyrupOral20 MG/ML
SyrupOral40 MG/ML
Tablet, film coatedOral800 MG
Powder; powder, for solution; powder, for suspensionOral200 MG
Powder; powder, for solution; powder, for suspensionOral400 MG
Tablet, film coatedOral684 MG
SyrupOral100 mg
Tablet, extended releaseOral800 MG
SuppositoryRectal60 mg
PatchTopical136 MG
SolutionOral40 mg
Tablet, film coatedOral100 mg
Injection, solution5 mg/ml
Capsule, coatedOral200 mg/1
Capsule, liquid filledOral200 mg/2001
Kit; tablet, film coatedOral
SuspensionOral100 mg/5mL
TabletNot applicable200 mg/1
TabletOral
TabletOral0.2 g/1g
TabletOral200 mg/1
TabletOral400 mg/1
TabletOral600 mg/1
TabletOral800 mg/1
Tablet, coatedOral200 mg/1
Tablet, coatedOral400 mg/1
Tablet, coatedOral600 mg/1
Tablet, coatedOral800 mg/1
Tablet, film coatedOral200 1/1
Tablet, film coatedOral200 mg/1
Tablet, film coatedOral200 mg/1 1
Tablet, film coatedOral256 mg/1
Tablet, film coatedOral400 mg/301
Tablet, film coatedOral400 mg/400mg
Tablet, film coatedOral400 mg/1
Tablet, film coatedOral600 mg/600mg
Tablet, film coatedOral600 mg/1
Tablet, film coatedOral800 mg/1
Tablet, film coatedOral800 mg/800mg
Tablet, sugar coatedOral200 mg/1
Capsule, extended releaseOral400 MG
SuppositoryRectal500 MG
CapsuleOral200 mg/1
SuppositoryRectal600 mg
Tablet, sugar coatedOral
SolutionParenteral
Solution4 mg/ml
Solution6 mg/ml
Tablet, chewableOral
Tablet, chewableOral100 mg/1
SolutionParenteral400 mg
SuspensionOral
Capsule, liquid filledOral
GelTopical50 mg
GranuleOral400 MG
GranuleOral600 MG
SyrupOral
GranuleOral
Injection, solution
Granule, effervescentOral600 MG
Injection, solution400 MG
Injection, solution600 MG
Injection, solutionIntravenous5 mg/mL
SuspensionOral200 MG
Tablet, coatedOral4000 mg
SuspensionOral2 g
Tablet, coatedOral470.5882 mg
Tablet, delayed releaseOral400 mg
SolutionIntravenous4 mg/mL
Solution, concentrateIntravenous600 mg
Tablet, coatedOral800 mg
Tablet, delayed releaseOral600 mg
SuspensionOral200 g
SuspensionOral2.0832 g
Tablet, delayed releaseOral200 mg
Capsule, gelatin coated
CreamTopical50 mg
SolutionIntravenous400 mg
Tablet, film coatedOral1000 MG
Tablet, coatedOral
Solution / dropsOral40 mg / mL
TabletOral800 mg
InjectionIntravenous100 MG/ML
Injection, solutionIntravenous400 mg/4ml
Injection, solutionIntravenous800 mg/8ml
EnemaRectal125 MG
SolutionIntravenous400.000 mg
GelTopical100 MG/G
Tablet, chewableOral100 mg
Tablet, coatedOral100 mg/1
TabletOral100 mg
Tablet, coatedOral400 mg (titer)
SuspensionOral100 ml
GelTopical0.5 g
Tablet400 MG
Capsule, coatedOral400 mg
Capsule, coatedOral
Solution / drops; suspension / drops40 MG/ML
Granule, for solutionOral200 MG
Solution / dropsOral20 G/100ML
Tablet, chewableOral200 MG
Tablet, effervescentOral200 MG
PowderOral
Granule, for solutionOral
TabletOral200 mg / tab
Tablet, film coatedOral100 mg/1
TabletOral800.000 mg
Kit; tablet; tablet, orally disintegratingOral
Capsule, liquid filledOral800 mg
TabletOral350 mg
Granule, effervescentOral
Injection, solutionIntravenous10 mg/1mL
SolutionIntravenous10 mg/1mL
Capsule, liquid filledOral400 mg
Suspension; syrupOral100 MG/5ML
Kit; liquid; tabletOral; Topical
Tablet, coated200 MG
Tablet, coated400 MG
Tablet, orally disintegratingOral
PlasterTopical
Tablet, film coatedOral200 mg
Capsule, liquid filledOral
CapsuleOral342 mg
TabletOral342 mg
SyrupOral200 mg/5mL
Tablet, coatedOral30 MG
SuspensionOral40 MG
SuspensionOral20 MG
SuspensionOral2 %
Tablet, sugar coatedOral400 mg
TabletOral200.00 mg
SuspensionOral100 mg/1mL
Injection, solutionIntravenous
LiquidOral50 mg/1.25mL
Injection, solutionIntravenous10 mg/2ml
Tablet, sugar coatedOral200 mg
Kit; tabletOral600 mg/1
SuspensionOral4000 mg
TabletOral400 mg
TabletOral400.000 mg
TabletOral400 mg/537mg
GelTopical5 %
CreamTopical50 mg/g
SuppositoryRectal125 mg
Tablet, coatedOral80000000 mg
Tablet, film coatedOral292.6 mg
Tablet, film coatedOral200 1/2001
Tablet, coatedOral400 mg
Tablet; tablet, film coatedOral400 MG
TabletOral
Granule, for solutionOral400 mg
Solution / dropsOral200 MG/ML
Granule, for solutionOral600 MG
Granule, for suspensionOral400 MG
Granule, for suspensionOral600 MG
Patch136 MG
SuspensionOral2000 mg
SuspensionOral4.000 g
Tablet, coatedOral200 mg
KitOral
CreamTopical
KitOral600 mg/1
SuspensionOral5 mg/ml
Tablet, effervescentOral
Tablet, coatedOral
TabletOral200.000 mg
SyrupOral2 g
LiquidOral100 mg/5mL
Suspension / dropsOral50 mg/1.25mL
SuspensionOral2 %w/v
SuspensionOral20.0 mg
TabletOral400.00 mg
SyrupOral100 mg/5ml
Tablet, film coatedOral600 mg
Tablet, film coatedOral400 mg
GelTopical5 %w/w
Tablet, film coatedOral342 mg
Tablet, coatedOral684 mg
Tablet, coatedOral600 mg
Tablet, film coatedOral200 mg
CapsuleOral400 mg
Prices
Unit descriptionCostUnit
Neoprofen 20 mg/2 ml vial304.5USD ml
Caldolor 400 mg/4 ml vial2.21USD ml
Caldolor 800 mg/8 ml vial1.58USD ml
Nuprin arthritis patch1.11USD patch
Ibuprofen powder1.04USD g
Nuprin muscle & joint patch1.03USD patch
Profen II 45-800 mg 12 Hour tablet0.69USD tablet
Motrin 800 mg tablet0.59USD tablet
Advil allergy sinus caplet0.5USD caplet
Ibu-drops 40 mg/ml suspension drops0.42USD ml
Motrin 600 mg tablet0.4USD tablet
Ibuprofen 800 mg tablet0.36USD tablet
Ibuprofen 400 mg tablet0.35USD tablet
Infant's motrin 50 mg/1.25 ml0.34USD ml
Childs ibuprofen susp drp0.33USD ml
Ibuprofen 600 mg tablet0.33USD tablet
Wal-profen cold & sinus cplt0.3USD caplet
Infant ibuprofen susp drop0.29USD ml
Motrin 400 mg tablet0.29USD tablet
CVS Pharmacy infant ibuprofen susp drop0.25USD ml
Infants medi-profen susp0.23USD ml
Advil cold & sinus caplet0.22USD caplet
Advil pm caplet0.22USD caplet
Soba profen cold-sinus tablet0.22USD tablet
Midol caplet0.21USD caplet
Advil migraine 200 mg capsule0.2USD capsule
Ibuprofen cold-sinus caplet0.2USD caplet
Motrin 100 mg caplet0.2USD caplet
Motrin pm caplet0.2USD caplet
Advil 200 mg liqui-gel capsule0.19USD capsule
Soba profen ib caplet0.19USD caplet
Motrin 100 mg tablet chew0.18USD tablet
Pub infants profenib drops0.18USD ml
Sm ibuprofen ib 100 mg tablet0.18USD tablet
Eck ibuprofen jr caplet0.17USD caplet
Ibuprofen pm caplet0.17USD caplet
Advil 200 mg caplet0.15USD capsule
Advil 200 mg gel caplet0.15USD caplet
Advil 200 mg tablet0.15USD tablet
Ibuprofen 100 mg tablet chew0.15USD tablet
Motrin ib 200 mg caplet0.15USD caplet
Apo-Ibuprofen 600 mg Tablet0.14USD tablet
CVS Pharmacy ibuprofen jr str 100 mg tablet0.14USD tablet
Nu-Ibuprofen 600 mg Tablet0.14USD tablet
Motrin ib 200 mg tablet0.13USD tablet
Motrin ib 200 mg gelcap0.12USD capsule
Nuprin 200 mg caplet0.12USD caplet
Wal-profen 200 mg caplet0.12USD caplet
Wal-profen 200 mg tablet0.12USD tablet
Eql ibuprofen 200 mg tablet0.1USD tablet
Nuprin 200 mg tablet0.1USD tablet
Apo-Ibuprofen 400 mg Tablet0.08USD tablet
Ibuprofen ib 200 mg tablet0.08USD tablet
Novo-Profen 400 mg Tablet0.08USD tablet
Apo-Ibuprofen 300 mg Tablet0.07USD tablet
Medi-profen 200 mg tablet0.07USD tablet
Ibuprofen 100 mg/5ml Suspension0.06USD ml
Ibuprofen 200 mg caplet0.06USD caplet
Child ibuprofen susp0.05USD ml
Children's medi-profen susp0.05USD ml
Children's motrin cold suspension0.05USD ml
CVS Pharmacy ibuprofen 200 mg tablet0.05USD tablet
Ibuprofen cold suspension0.05USD ml
I-prin 200 mg tablet0.05USD tablet
Novo-Profen 600 mg Tablet0.05USD tablet
Children's motrin cold0.04USD ml
Pv ibuprofen 200 mg caplet0.04USD caplet
Soba children's profenib susp0.04USD ml
Ibuprofen 200 mg tablet0.03USD tablet
CVS Pharmacy ibuprofen 200 mg caplet0.02USD caplet
Pv ibuprofen 200 mg tablet0.02USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5215755No1993-06-012010-06-01US flag
US6599531No2003-07-292017-06-10US flag
US6348216No2002-02-192017-06-10US flag
US6342530No2002-01-292020-11-14US flag
US6344479No2002-02-052021-03-20US flag
US8415337No2013-04-092032-03-02US flag
US6211246No2001-04-032019-06-10US flag
US8883849No2014-11-112022-01-17US flag
US9155718No2015-10-132022-01-17US flag
US8263647No2012-09-112022-05-30US flag
US7863287No2011-01-042027-02-28US flag
US6251426No2001-06-262018-06-25US flag
US6727286No2004-04-272021-11-27US flag
US8735452No2014-05-272029-09-30US flag
US9138404No2015-09-222029-09-30US flag
US9114068No2015-08-252029-09-30US flag
US8871810No2014-10-282029-09-30US flag
US9012508No2015-04-212030-09-14US flag
US9295639No2016-03-292029-09-30US flag
US8067451No2011-11-292026-07-18US flag
US8501228No2013-08-062026-07-18US flag
US8318202No2012-11-272026-07-18US flag
US8449910No2013-05-282026-07-18US flag
US8309127No2012-11-132026-07-18US flag
US8067033No2011-11-292026-07-18US flag
US9649284No2017-05-162029-09-30US flag
US9072710No2015-07-072032-03-16US flag
US9072661No2015-07-072032-03-16US flag
US10238640No2019-03-262024-05-25US flag
US10532036No2020-01-142025-09-22US flag
US11197830No2021-12-142039-02-27US flag
US11534407No2019-02-272039-02-27US flag
US11446266No2011-10-262031-10-26US flag
US11806400No2012-03-162032-03-16US flag
US11213498No2016-01-142036-01-14US flag
US11389416No2015-07-172035-07-17US flag
US11896567No2011-10-262031-10-26US flag
US11918693No2021-07-092041-07-09US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)75-77.5 ºCU.S. Patent 3,228,831 U.S. Patent 3,385,886
boiling point (°C)157 ºC'AlfaAesar MSDS'
water solubility21 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP3.97AVDEEF,A (1997)
logS-3.99ADME Research, USCD
Caco2 permeability-4.28ADME Research, USCD
pKa5.3Bushra and Aslam. Oman Med. 25, 3. (2010)
Predicted Properties
PropertyValueSource
Water Solubility0.0684 mg/mLALOGPS
logP3.5ALOGPS
logP3.84Chemaxon
logS-3.5ALOGPS
pKa (Strongest Acidic)4.85Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area37.3 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity60.73 m3·mol-1Chemaxon
Polarizability23.76 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9927
Blood Brain Barrier+0.9619
Caco-2 permeable+0.8866
P-glycoprotein substrateNon-substrate0.759
P-glycoprotein inhibitor INon-inhibitor0.9705
P-glycoprotein inhibitor IINon-inhibitor0.9323
Renal organic cation transporterNon-inhibitor0.9323
CYP450 2C9 substrateNon-substrate0.7594
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.6877
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9305
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9881
CYP450 3A4 inhibitorNon-inhibitor0.9655
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9691
Ames testNon AMES toxic0.9894
CarcinogenicityCarcinogens 0.5553
BiodegradationReady biodegradable0.5142
Rat acute toxicity2.3092 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9719
hERG inhibition (predictor II)Non-inhibitor0.9734
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (11.4 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)GC-MSsplash10-02t9-1910000000-23f448d7be7d5cc35682
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)GC-MSsplash10-02t9-1910000000-cbe52d63986b68a2cec0
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)GC-MSsplash10-00di-9300000000-cc259b7768023e4cdba8
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0296-3900000000-497aad6d6a3e7af1ac0a
GC-MS Spectrum - EI-BGC-MSsplash10-03di-3910000000-618880f8fd7b8ec3d473
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-02t9-1910000000-23f448d7be7d5cc35682
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-02t9-1910000000-cbe52d63986b68a2cec0
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-9300000000-cc259b7768023e4cdba8
Mass Spectrum (Electron Ionization)MSsplash10-03xr-3900000000-e20ef3c30496e17720ba
MS/MS Spectrum - Quattro_QQQ 10V, N/ALC-MS/MSsplash10-03di-0910000000-90bf6813134491c9fbfd
MS/MS Spectrum - Quattro_QQQ 25V, N/ALC-MS/MSsplash10-001i-9800000000-56f599abc462380b648c
MS/MS Spectrum - EI-B (HITACHI RMU-6E) , PositiveLC-MS/MSsplash10-03di-3910000000-618880f8fd7b8ec3d473
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0006-0497000000-fa397d6ffd29da116900
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0a4i-0690000000-f598b8bee69a6b62e817
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-1900000000-f1b7a986fee133d97eb1
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-0920000000-aa36b3244e32560bb9d5
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-1930000000-728a67daaea8ecb1b60a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0190000000-e8049d9759b81f0d56b0
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-05mo-5900000000-3c32234af86d6b3a2656
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-02ai-0900000000-e1c07c4d6d5219e98219
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ldl-4900000000-7635978e2602fb36e1ce
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0900000000-b1bbd0cff6f4f6df9ebc
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-161.798312
predicted
DarkChem Lite v0.1.0
[M-H]-145.04115
predicted
DeepCCS 1.0 (2019)
[M+H]+148.78854
predicted
DeepCCS 1.0 (2019)
[M+Na]+157.5005
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Dual cyclooxygenase and peroxidase in the biosynthesis pathway of prostanoids, a class of C20 oxylipins mainly derived from arachidonate ((5Z,8Z,11Z,14Z)-eicosatetraenoate, AA, C20:4(n-6)), with a particular role in the inflammatory response (PubMed:11939906, PubMed:16373578, PubMed:19540099, PubMed:22942274, PubMed:26859324, PubMed:27226593, PubMed:7592599, PubMed:7947975, PubMed:9261177). The cyclooxygenase activity oxygenates AA to the hydroperoxy endoperoxide prostaglandin G2 (PGG2), and the peroxidase activity reduces PGG2 to the hydroxy endoperoxide prostaglandin H2 (PGH2), the precursor of all 2-series prostaglandins and thromboxanes (PubMed:16373578, PubMed:22942274, PubMed:26859324, PubMed:27226593, PubMed:7592599, PubMed:7947975, PubMed:9261177). This complex transformation is initiated by abstraction of hydrogen at carbon 13 (with S-stereochemistry), followed by insertion of molecular O2 to form the endoperoxide bridge between carbon 9 and 11 that defines prostaglandins. The insertion of a second molecule of O2 (bis-oxygenase activity) yields a hydroperoxy group in PGG2 that is then reduced to PGH2 by two electrons (PubMed:16373578, PubMed:22942274, PubMed:26859324, PubMed:27226593, PubMed:7592599, PubMed:7947975, PubMed:9261177). Similarly catalyzes successive cyclooxygenation and peroxidation of dihomo-gamma-linoleate (DGLA, C20:3(n-6)) and eicosapentaenoate (EPA, C20:5(n-3)) to corresponding PGH1 and PGH3, the precursors of 1- and 3-series prostaglandins (PubMed:11939906, PubMed:19540099). In an alternative pathway of prostanoid biosynthesis, converts 2-arachidonoyl lysophopholipids to prostanoid lysophopholipids, which are then hydrolyzed by intracellular phospholipases to release free prostanoids (PubMed:27642067). Metabolizes 2-arachidonoyl glycerol yielding the glyceryl ester of PGH2, a process that can contribute to pain response (PubMed:22942274). Generates lipid mediators from n-3 and n-6 polyunsaturated fatty acids (PUFAs) via a lipoxygenase-type mechanism. Oxygenates PUFAs to hydroperoxy compounds and then reduces them to corresponding alcohols (PubMed:11034610, PubMed:11192938, PubMed:9048568, PubMed:9261177). Plays a role in the generation of resolution phase interaction products (resolvins) during both sterile and infectious inflammation (PubMed:12391014). Metabolizes docosahexaenoate (DHA, C22:6(n-3)) to 17R-HDHA, a precursor of the D-series resolvins (RvDs) (PubMed:12391014). As a component of the biosynthetic pathway of E-series resolvins (RvEs), converts eicosapentaenoate (EPA, C20:5(n-3)) primarily to 18S-HEPE that is further metabolized by ALOX5 and LTA4H to generate 18S-RvE1 and 18S-RvE2 (PubMed:21206090). In vascular endothelial cells, converts docosapentaenoate (DPA, C22:5(n-3)) to 13R-HDPA, a precursor for 13-series resolvins (RvTs) shown to activate macrophage phagocytosis during bacterial infection (PubMed:26236990). In activated leukocytes, contributes to oxygenation of hydroxyeicosatetraenoates (HETE) to diHETES (5,15-diHETE and 5,11-diHETE) (PubMed:22068350, PubMed:26282205). Can also use linoleate (LA, (9Z,12Z)-octadecadienoate, C18:2(n-6)) as substrate and produce hydroxyoctadecadienoates (HODEs) in a regio- and stereospecific manner, being (9R)-HODE ((9R)-hydroxy-(10E,12Z)-octadecadienoate) and (13S)-HODE ((13S)-hydroxy-(9Z,11E)-octadecadienoate) its major products (By similarity). During neuroinflammation, plays a role in neuronal secretion of specialized preresolving mediators (SPMs) 15R-lipoxin A4 that regulates phagocytic microglia (By similarity)
Specific Function
enzyme binding
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
References
  1. Chavez ML, DeKorte CJ: Valdecoxib: a review. Clin Ther. 2003 Mar;25(3):817-51. [Article]
  2. Ouellet M, Falgueyret JP, Percival MD: Detergents profoundly affect inhibitor potencies against both cyclo-oxygenase isoforms. Biochem J. 2004 Feb 1;377(Pt 3):675-84. [Article]
  3. Gallego-Sandin S, Novalbos J, Rosado A, Gisbert JP, Galvez-Mugica MA, Garcia AG, Pajares JM, Abad-Santos F: Effect of ibuprofen on cyclooxygenase and nitric oxide synthase of gastric mucosa: correlation with endoscopic lesions and adverse reactions. Dig Dis Sci. 2004 Sep;49(9):1538-44. [Article]
  4. Murphey LJ, Williams MK, Sanchez SC, Byrne LM, Csiki I, Oates JA, Johnson DH, Morrow JD: Quantification of the major urinary metabolite of PGE2 by a liquid chromatographic/mass spectrometric assay: determination of cyclooxygenase-specific PGE2 synthesis in healthy humans and those with lung cancer. Anal Biochem. 2004 Nov 15;334(2):266-75. [Article]
  5. Sanchez-Fidalgo S, Martin-Lacave I, Illanes M, Motilva V: Angiogenesis, cell proliferation and apoptosis in gastric ulcer healing. Effect of a selective cox-2 inhibitor. Eur J Pharmacol. 2004 Nov 28;505(1-3):187-94. [Article]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  7. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Receptor for interleukin-8 which is a powerful neutrophil chemotactic factor (PubMed:1891716). Binding of IL-8 to the receptor causes activation of neutrophils. This response is mediated via a G-protein that activates a phosphatidylinositol-calcium second messenger system (PubMed:8662698). Binds to IL-8 with high affinity. Also binds with high affinity to CXCL3, GRO/MGSA and NAP-2
Specific Function
C-C chemokine binding
Gene Name
CXCR2
Uniprot ID
P25025
Uniprot Name
C-X-C chemokine receptor type 2
Molecular Weight
40758.735 Da
References
  1. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Chemotactic factor that mediates inflammatory response by attracting neutrophils, basophils, and T-cells to clear pathogens and protect the host from infection (PubMed:18692776, PubMed:7636208). Also plays an important role in neutrophil activation (PubMed:2145175, PubMed:9623510). Released in response to an inflammatory stimulus, exerts its effect by binding to the G-protein-coupled receptors CXCR1 and CXCR2, primarily found in neutrophils, monocytes and endothelial cells (PubMed:1840701, PubMed:1891716). G-protein heterotrimer (alpha, beta, gamma subunits) constitutively binds to CXCR1/CXCR2 receptor and activation by IL8 leads to beta and gamma subunits release from Galpha (GNAI2 in neutrophils) and activation of several downstream signaling pathways including PI3K and MAPK pathways (PubMed:11971003, PubMed:8662698)
Specific Function
chemokine activity
Gene Name
CXCL8
Uniprot ID
P10145
Uniprot Name
Interleukin-8
Molecular Weight
11097.98 Da
References
  1. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Receptor to interleukin-8, which is a powerful neutrophils chemotactic factor (PubMed:1840701). Binding of IL-8 to the receptor causes activation of neutrophils. This response is mediated via a G-protein that activates a phosphatidylinositol-calcium second messenger system (PubMed:8662698)
Specific Function
C-C chemokine binding
Gene Name
CXCR1
Uniprot ID
P25024
Uniprot Name
C-X-C chemokine receptor type 1
Molecular Weight
39790.735 Da
References
  1. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Dual cyclooxygenase and peroxidase that plays an important role in the biosynthesis pathway of prostanoids, a class of C20 oxylipins mainly derived from arachidonate ((5Z,8Z,11Z,14Z)-eicosatetraenoate, AA, C20:4(n-6)), with a particular role in the inflammatory response. The cyclooxygenase activity oxygenates AA to the hydroperoxy endoperoxide prostaglandin G2 (PGG2), and the peroxidase activity reduces PGG2 to the hydroxy endoperoxide prostaglandin H2 (PGH2), the precursor of all 2-series prostaglandins and thromboxanes. This complex transformation is initiated by abstraction of hydrogen at carbon 13 (with S-stereochemistry), followed by insertion of molecular O2 to form the endoperoxide bridge between carbon 9 and 11 that defines prostaglandins. The insertion of a second molecule of O2 (bis-oxygenase activity) yields a hydroperoxy group in PGG2 that is then reduced to PGH2 by two electrons (PubMed:7947975). Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the generation of thromboxane A2 (TXA2), which promotes platelet activation and aggregation, vasoconstriction and proliferation of vascular smooth muscle cells (Probable). Can also use linoleate (LA, (9Z,12Z)-octadecadienoate, C18:2(n-6)) as substrate and produce hydroxyoctadecadienoates (HODEs) in a regio- and stereospecific manner, being (9R)-HODE ((9R)-hydroxy-(10E,12Z)-octadecadienoate) and (13S)-HODE ((13S)-hydroxy-(9Z,11E)-octadecadienoate) its major products (By similarity)
Specific Function
heme binding
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. Chavez ML, DeKorte CJ: Valdecoxib: a review. Clin Ther. 2003 Mar;25(3):817-51. [Article]
  2. Patrignani P: Aspirin insensitive eicosanoid biosynthesis in cardiovascular disease. Thromb Res. 2003 Jun 15;110(5-6):281-6. [Article]
  3. Gupta K, Kaub CJ, Carey KN, Casillas EG, Selinsky BS, Loll PJ: Manipulation of kinetic profiles in 2-aryl propionic acid cyclooxygenase inhibitors. Bioorg Med Chem Lett. 2004 Feb 9;14(3):667-71. [Article]
  4. Martic M, Tatic I, Markovic S, Kujundzic N, Kostrun S: Synthesis, biological activity and molecular modeling studies of novel COX-1 inhibitors. Eur J Med Chem. 2004 Feb;39(2):141-51. [Article]
  5. Hillarp A: [Acetylsalicylic acid resistance--clinical diagnosis with unclear mechanism]. Lakartidningen. 2004 Nov 4;101(45):3504-6, 3508-9. [Article]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  7. Yu L, Shi D, Ma L, Zhou Q, Zeng S: Influence of CYP2C8 polymorphisms on the hydroxylation metabolism of paclitaxel, repaglinide and ibuprofen enantiomers in vitro. Biopharm Drug Dispos. 2013 Jul;34(5):278-87. doi: 10.1002/bdd.1842. Epub 2013 Jun 3. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Modulator
General Function
Suppresses apoptosis in a variety of cell systems including factor-dependent lymphohematopoietic and neural cells (PubMed:1508712, PubMed:8183370). Regulates cell death by controlling the mitochondrial membrane permeability (PubMed:11368354). Appears to function in a feedback loop system with caspases (PubMed:11368354). Inhibits caspase activity either by preventing the release of cytochrome c from the mitochondria and/or by binding to the apoptosis-activating factor (APAF-1) (PubMed:11368354). Also acts as an inhibitor of autophagy: interacts with BECN1 and AMBRA1 during non-starvation conditions and inhibits their autophagy function (PubMed:18570871, PubMed:20889974, PubMed:21358617). May attenuate inflammation by impairing NLRP1-inflammasome activation, hence CASP1 activation and IL1B release (PubMed:17418785)
Specific Function
BH domain binding
Gene Name
BCL2
Uniprot ID
P10415
Uniprot Name
Apoptosis regulator Bcl-2
Molecular Weight
26265.66 Da
References
  1. Palayoor ST, J-Aryankalayil M, Makinde AY, Cerna D, Falduto MT, Magnuson SR, Coleman CN: Gene expression profile of coronary artery cells treated with nonsteroidal anti-inflammatory drugs reveals off-target effects. J Cardiovasc Pharmacol. 2012 Jun;59(6):487-99. doi: 10.1097/FJC.0b013e31824ba6b5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Thrombomodulin is a specific endothelial cell receptor that forms a 1:1 stoichiometric complex with thrombin. This complex is responsible for the conversion of protein C to the activated protein C (protein Ca). Once evolved, protein Ca scissions the activated cofactors of the coagulation mechanism, factor Va and factor VIIIa, and thereby reduces the amount of thrombin generated
Specific Function
calcium ion binding
Gene Name
THBD
Uniprot ID
P07204
Uniprot Name
Thrombomodulin
Molecular Weight
60328.72 Da
References
  1. Palayoor ST, J-Aryankalayil M, Makinde AY, Cerna D, Falduto MT, Magnuson SR, Coleman CN: Gene expression profile of coronary artery cells treated with nonsteroidal anti-inflammatory drugs reveals off-target effects. J Cardiovasc Pharmacol. 2012 Jun;59(6):487-99. doi: 10.1097/FJC.0b013e31824ba6b5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
FABPs are thought to play a role in the intracellular transport of long-chain fatty acids and their acyl-CoA esters. FABP2 is probably involved in triglyceride-rich lipoprotein synthesis. Binds saturated long-chain fatty acids with a high affinity, but binds with a lower affinity to unsaturated long-chain fatty acids. FABP2 may also help maintain energy homeostasis by functioning as a lipid sensor
Specific Function
fatty acid binding
Gene Name
FABP2
Uniprot ID
P12104
Uniprot Name
Fatty acid-binding protein, intestinal
Molecular Weight
15237.195 Da
References
  1. Velkov T, Chuang S, Wielens J, Sakellaris H, Charman WN, Porter CJ, Scanlon MJ: The interaction of lipophilic drugs with intestinal fatty acid-binding protein. J Biol Chem. 2005 May 6;280(18):17769-76. Epub 2005 Feb 18. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
General Function
Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis. ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer. Acts as a critical regulator of gut homeostasis by suppressing NF-kappa-B-mediated pro-inflammatory responses. Plays a role in the regulation of cardiovascular circadian rhythms by regulating the transcription of BMAL1 in the blood vessels (By similarity)
Specific Function
alpha-actinin binding
Gene Name
PPARG
Uniprot ID
P37231
Uniprot Name
Peroxisome proliferator-activated receptor gamma
Molecular Weight
57619.58 Da
References
  1. Dill J, Patel AR, Yang XL, Bachoo R, Powell CM, Li S: A molecular mechanism for ibuprofen-mediated RhoA inhibition in neurons. J Neurosci. 2010 Jan 20;30(3):963-72. doi: 10.1523/JNEUROSCI.5045-09.2010. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Epithelial ion channel that plays an important role in the regulation of epithelial ion and water transport and fluid homeostasis (PubMed:26823428). Mediates the transport of chloride ions across the cell membrane (PubMed:10792060, PubMed:11524016, PubMed:11707463, PubMed:12519745, PubMed:12529365, PubMed:12588899, PubMed:12727866, PubMed:15010471, PubMed:17036051, PubMed:1712898, PubMed:17182731, PubMed:19398555, PubMed:19621064, PubMed:22178883, PubMed:25330774, PubMed:26846474, PubMed:28087700, PubMed:8910473, PubMed:9804160). Possesses an intrinsic ATPase activity and utilizes ATP to gate its channel; the passive flow of anions through the channel is gated by cycles of ATP binding and hydrolysis by the ATP-binding domains (PubMed:11524016, PubMed:15284228, PubMed:26627831, PubMed:8910473). The ion channel is also permeable to HCO(3)(-); selectivity depends on the extracellular chloride concentration (PubMed:15010471, PubMed:19019741). In vitro, mediates ATP-dependent glutathione flux (PubMed:12727866). Exerts its function also by modulating the activity of other ion channels and transporters (PubMed:12403779, PubMed:22121115, PubMed:22178883, PubMed:27941075). Plays an important role in airway fluid homeostasis (PubMed:16645176, PubMed:19621064, PubMed:26823428). Contributes to the regulation of the pH and the ion content of the airway surface fluid layer and thereby plays an important role in defense against pathogens (PubMed:14668433, PubMed:16645176, PubMed:26823428). Modulates the activity of the epithelial sodium channel (ENaC) complex, in part by regulating the cell surface expression of the ENaC complex (PubMed:17182731, PubMed:17434346, PubMed:27941075). Inhibits the activity of the ENaC channel containing subunits SCNN1A, SCNN1B and SCNN1G (PubMed:17182731). Inhibits the activity of the ENaC channel containing subunits SCNN1D, SCNN1B and SCNN1G, but not of the ENaC channel containing subunits SCNN1A, SCNN1B and SCNN1G (PubMed:17182731, PubMed:27941075). May regulate bicarbonate secretion and salvage in epithelial cells by regulating the transporter SLC4A7 (PubMed:12403779). Can inhibit the chloride channel activity of ANO1 (PubMed:22178883). Plays a role in the chloride and bicarbonate homeostasis during sperm epididymal maturation and capacitation (PubMed:19923167, PubMed:27714810)
Specific Function
ABC-type transporter activity
Gene Name
CFTR
Uniprot ID
P13569
Uniprot Name
Cystic fibrosis transmembrane conductance regulator
Molecular Weight
168139.895 Da
References
  1. Devor DC, Schultz BD: Ibuprofen inhibits cystic fibrosis transmembrane conductance regulator-mediated Cl- secretion. J Clin Invest. 1998 Aug 15;102(4):679-87. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
General Function
Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleylethanolamide, a naturally occurring lipid that regulates satiety. Receptor for peroxisome proliferators such as hypolipidemic drugs and fatty acids. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as a transcription activator for the ACOX1 and P450 genes. Transactivation activity requires heterodimerization with RXRA and is antagonized by NR2C2. May be required for the propagation of clock information to metabolic pathways regulated by PER2
Specific Function
DNA binding
Gene Name
PPARA
Uniprot ID
Q07869
Uniprot Name
Peroxisome proliferator-activated receptor alpha
Molecular Weight
52224.595 Da
References
  1. Lehmann JM, Lenhard JM, Oliver BB, Ringold GM, Kliewer SA: Peroxisome proliferator-activated receptors alpha and gamma are activated by indomethacin and other non-steroidal anti-inflammatory drugs. J Biol Chem. 1997 Feb 7;272(6):3406-10. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
GP-Ib, a surface membrane protein of platelets, participates in the formation of platelet plugs by binding to the A1 domain of vWF, which is already bound to the subendothelium
Specific Function
thrombin-activated receptor activity
Gene Name
GP1BA
Uniprot ID
P07359
Uniprot Name
Platelet glycoprotein Ib alpha chain
Molecular Weight
71539.265 Da
References
  1. Palayoor ST, J-Aryankalayil M, Makinde AY, Cerna D, Falduto MT, Magnuson SR, Coleman CN: Gene expression profile of coronary artery cells treated with nonsteroidal anti-inflammatory drugs reveals off-target effects. J Cardiovasc Pharmacol. 2012 Jun;59(6):487-99. doi: 10.1097/FJC.0b013e31824ba6b5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Not Available
Specific Function
calcium ion binding
Gene Name
S100A7
Uniprot ID
P31151
Uniprot Name
Protein S100-A7
Molecular Weight
11470.87 Da
References
  1. Fujiwara R, Takenaka S, Hashimoto M, Narawa T, Itoh T: Expression of human solute carrier family transporters in skin: possible contributor to drug-induced skin disorders. Sci Rep. 2014 Jun 11;4:5251. doi: 10.1038/srep05251. [Article]

Enzymes

Details
1. Cytochrome P450 2C9
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)
Specific Function
(R)-limonene 6-monooxygenase activity
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Carlile DJ, Hakooz N, Bayliss MK, Houston JB: Microsomal prediction of in vivo clearance of CYP2C9 substrates in humans. Br J Clin Pharmacol. 1999 Jun;47(6):625-35. [Article]
  2. Flockhart Table of Drug Interactions [Link]
  3. FDA label, Ibuprofen [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Primarily catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) with a preference for the last double bond (PubMed:15766564, PubMed:19965576, PubMed:7574697). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes all trans-retinoic acid toward its 4-hydroxylated form (PubMed:11093772). Displays 16-alpha hydroxylase activity toward estrogen steroid hormones, 17beta-estradiol (E2) and estrone (E1) (PubMed:14559847). Plays a role in the oxidative metabolism of xenobiotics. It is the principal enzyme responsible for the metabolism of the anti-cancer drug paclitaxel (taxol) (PubMed:26427316)
Specific Function
arachidonic acid epoxygenase activity
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Yu L, Shi D, Ma L, Zhou Q, Zeng S: Influence of CYP2C8 polymorphisms on the hydroxylation metabolism of paclitaxel, repaglinide and ibuprofen enantiomers in vitro. Biopharm Drug Dispos. 2013 Jul;34(5):278-87. doi: 10.1002/bdd.1842. Epub 2013 Jun 3. [Article]
  2. Chang SY, Li W, Traeger SC, Wang B, Cui D, Zhang H, Wen B, Rodrigues AD: Confirmation that cytochrome P450 2C8 (CYP2C8) plays a minor role in (S)-(+)- and (R)-(-)-ibuprofen hydroxylation in vitro. Drug Metab Dispos. 2008 Dec;36(12):2513-22. doi: 10.1124/dmd.108.022970. Epub 2008 Sep 11. [Article]
  3. Hamman MA, Thompson GA, Hall SD: Regioselective and stereoselective metabolism of ibuprofen by human cytochrome P450 2C. Biochem Pharmacol. 1997 Jul 1;54(1):33-41. doi: 10.1016/s0006-2952(97)00143-3. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
A cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position (PubMed:18577768). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:20972997). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine. Hydroxylates fenbendazole at the 4' position (PubMed:23959307)
Specific Function
(R)-limonene 6-monooxygenase activity
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55944.565 Da
References
  1. Rainsford KD: Ibuprofen: pharmacology, efficacy and safety. Inflammopharmacology. 2009 Dec;17(6):275-342. doi: 10.1007/s10787-009-0016-x. Epub 2009 Nov 21. [Article]
  2. Goldstein JA: Clinical relevance of genetic polymorphisms in the human CYP2C subfamily. Br J Clin Pharmacol. 2001 Oct;52(4):349-55. [Article]
  3. Mazaleuskaya LL, Theken KN, Gong L, Thorn CF, FitzGerald GA, Altman RB, Klein TE: PharmGKB summary: ibuprofen pathways. Pharmacogenet Genomics. 2015 Feb;25(2):96-106. doi: 10.1097/FPC.0000000000000113. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:15472229, PubMed:18674515, PubMed:18719240, PubMed:23288867, PubMed:23756265, PubMed:24641623). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:23756265). Catalyzes the glucuronidation of endogenous estrogen hormones such as estradiol and estrone (PubMed:15472229, PubMed:18719240, PubMed:23288867). Contributes to bile acid (BA) detoxification by catalyzing the glucuronidation of BA substrates, which are natural detergents for dietary lipids absorption (PubMed:23756265). Involved in the glucuronidation of calcidiol, which is the major circulating form of vitamin D3, essential for the regulation of calcium and phosphate homeostasis (PubMed:24641623). Involved in the glucuronidation of the AGTR1 angiotensin receptor antagonists losartan, candesartan and zolarsartan, which can inhibit the effect of angiotensin II (PubMed:18674515)
Specific Function
enzyme binding
Gene Name
UGT1A3
Uniprot ID
P35503
Uniprot Name
UDP-glucuronosyltransferase 1A3
Molecular Weight
60337.835 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:12181437, PubMed:15470161, PubMed:15472229, PubMed:18004212, PubMed:18052087, PubMed:18674515, PubMed:19545173). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:12181437, PubMed:18004212). Catalyzes the glucuronidation of endogenous estrogen hormones such as estradiol and estrone (PubMed:15472229). Also catalyzes the glucuronidation of the isoflavones genistein, daidzein, glycitein, formononetin, biochanin A and prunetin, which are phytoestrogens with anticancer and cardiovascular properties (PubMed:18052087, PubMed:19545173). Involved in the glucuronidation of the AGTR1 angiotensin receptor antagonist caderastan, a drug which can inhibit the effect of angiotensin II (PubMed:18674515). Involved in the biotransformation of 7-ethyl-10-hydroxycamptothecin (SN-38), the pharmacologically active metabolite of the anticancer drug irinotecan (PubMed:12181437, PubMed:20610558). Also metabolizes mycophenolate, an immunosuppressive agent (PubMed:15470161, PubMed:18004212)
Specific Function
enzyme binding
Gene Name
UGT1A9
Uniprot ID
O60656
Uniprot Name
UDP-glucuronosyltransferase 1A9
Molecular Weight
59940.495 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:18719240, PubMed:23288867). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:18719240, PubMed:23288867). Catalyzes the glucuronidation of the endogenous estrogen hormones such as estradiol and estriol (PubMed:18719240, PubMed:23288867)
Specific Function
glucuronosyltransferase activity
Gene Name
UGT2B4
Uniprot ID
P06133
Uniprot Name
UDP-glucuronosyltransferase 2B4
Molecular Weight
60512.035 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
UDP-glucuronosyltransferase (UGT) that catalyzes phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase the metabolite's water solubility, thereby facilitating excretion into either the urine or bile (PubMed:10702251, PubMed:15470161, PubMed:15472229, PubMed:17442341, PubMed:18674515, PubMed:18719240, PubMed:19022937, PubMed:23288867, PubMed:23756265, PubMed:26220143). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:15470161, PubMed:18674515, PubMed:23756265). Catalyzes the glucuronidation of endogenous steroid hormones such as androgens (epitestosterone, androsterone) and estrogens (estradiol, epiestradiol, estriol, catechol estrogens) (PubMed:15472229, PubMed:17442341, PubMed:18719240, PubMed:19022937, PubMed:2159463, PubMed:23288867, PubMed:26220143). Also regulates the levels of retinoic acid, a major metabolite of vitamin A involved in apoptosis, cellular growth and differentiation, and embryonic development (PubMed:10702251). Contributes to bile acid (BA) detoxification by catalyzing the glucuronidation of BA substrates, which are natural detergents for dietary lipids absorption (PubMed:23756265). Involved in the glucuronidation of the AGTR1 angiotensin receptor antagonist losartan, caderastan and zolarsatan, drugs which can inhibit the effect of angiotensin II (PubMed:18674515). Also metabolizes mycophenolate, an immunosuppressive agent (PubMed:15470161)
Specific Function
glucuronosyltransferase activity
Gene Name
UGT2B7
Uniprot ID
P16662
Uniprot Name
UDP-glucuronosyltransferase 2B7
Molecular Weight
60720.15 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Not Available
Specific Function
catalytic activity
Gene Name
AMACR
Uniprot ID
D6RB81
Uniprot Name
Alpha-methylacyl-CoA racemase
Molecular Weight
40674.37 Da
References
  1. Rainsford KD: Ibuprofen: pharmacology, efficacy and safety. Inflammopharmacology. 2009 Dec;17(6):275-342. doi: 10.1007/s10787-009-0016-x. Epub 2009 Nov 21. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
Specific Function
1,8-cineole 2-exo-monooxygenase activity
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Mazaleuskaya LL, Theken KN, Gong L, Thorn CF, FitzGerald GA, Altman RB, Klein TE: PharmGKB summary: ibuprofen pathways. Pharmacogenet Genomics. 2015 Feb;25(2):96-106. doi: 10.1097/FPC.0000000000000113. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Binder
General Function
Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
Specific Function
antioxidant activity
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Albumin
Molecular Weight
69365.94 Da
References
  1. Yamasaki K, Rahman MH, Tsutsumi Y, Maruyama T, Ahmed S, Kragh-Hansen U, Otagiri M: Circular dichroism simulation shows a site-II-to-site-I displacement of human serum albumin-bound diclofenac by ibuprofen. AAPS PharmSciTech. 2000 May 14;1(2):E12. [Article]
  2. Galantini L, Leggio C, Konarev PV, Pavel NV: Human serum albumin binding ibuprofen: a 3D description of the unfolding pathway in urea. Biophys Chem. 2010 Apr;147(3):111-22. doi: 10.1016/j.bpc.2010.01.002. Epub 2010 Jan 18. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Mediates the Na(+)-independent transport of steroid sulfate conjugates and other specific organic anions (PubMed:10873595, PubMed:11159893, PubMed:11932330, PubMed:12724351, PubMed:14610227, PubMed:16908597, PubMed:18501590, PubMed:20507927, PubMed:22201122, PubMed:23531488, PubMed:25132355, PubMed:26383540, PubMed:27576593, PubMed:28408210, PubMed:29871943, PubMed:34628357). Responsible for the transport of estrone 3-sulfate (E1S) through the basal membrane of syncytiotrophoblast, highlighting a potential role in the placental absorption of fetal-derived sulfated steroids including the steroid hormone precursor dehydroepiandrosterone sulfate (DHEA-S) (PubMed:11932330, PubMed:12409283). Also facilitates the uptake of sulfated steroids at the basal/sinusoidal membrane of hepatocytes, therefore accounting for the major part of organic anions clearance of liver (PubMed:11159893). Mediates the intestinal uptake of sulfated steroids (PubMed:12724351, PubMed:28408210). Mediates the uptake of the neurosteroids DHEA-S and pregnenolone sulfate (PregS) into the endothelial cells of the blood-brain barrier as the first step to enter the brain (PubMed:16908597, PubMed:25132355). Also plays a role in the reuptake of neuropeptides such as substance P/TAC1 and vasoactive intestinal peptide/VIP released from retinal neurons (PubMed:25132355). May act as a heme transporter that promotes cellular iron availability via heme oxygenase/HMOX2 and independently of TFRC (PubMed:35714613). Also transports heme by-product coproporphyrin III (CPIII), and may be involved in their hepatic disposition (PubMed:26383540). Mediates the uptake of other substrates such as prostaglandins D2 (PGD2), E1 (PGE1) and E2 (PGE2), taurocholate, L-thyroxine, leukotriene C4 and thromboxane B2 (PubMed:10873595, PubMed:14610227, PubMed:19129463, PubMed:29871943, Ref.25). May contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable). Shows a pH-sensitive substrate specificity which may be ascribed to the protonation state of the binding site and leads to a stimulation of substrate transport in an acidic microenvironment (PubMed:14610227, PubMed:19129463, PubMed:22201122). The exact transport mechanism has not been yet deciphered but most likely involves an anion exchange, coupling the cellular uptake of organic substrate with the efflux of an anionic compound (PubMed:19129463, PubMed:20507927, PubMed:26277985). Hydrogencarbonate/HCO3(-) acts as a probable counteranion that exchanges for organic anions (PubMed:19129463). Cytoplasmic glutamate may also act as counteranion in the placenta (PubMed:26277985). An inwardly directed proton gradient has also been proposed as the driving force of E1S uptake with a (H(+):E1S) stoichiometry of (1:1) (PubMed:20507927)
Specific Function
bile acid transmembrane transporter activity
Gene Name
SLCO2B1
Uniprot ID
O94956
Uniprot Name
Solute carrier organic anion transporter family member 2B1
Molecular Weight
76697.93 Da
References
  1. Satoh H, Yamashita F, Tsujimoto M, Murakami H, Koyabu N, Ohtani H, Sawada Y: Citrus juices inhibit the function of human organic anion-transporting polypeptide OATP-B. Drug Metab Dispos. 2005 Apr;33(4):518-23. Epub 2005 Jan 7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
Specific Function
ABC-type xenobiotic transporter activity
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
ATP-dependent translocase ABCB1
Molecular Weight
141477.255 Da
References
  1. Faassen F, Vogel G, Spanings H, Vromans H: Caco-2 permeability, P-glycoprotein transport ratios and brain penetration of heterocyclic drugs. Int J Pharm. 2003 Sep 16;263(1-2):113-22. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
ATP-dependent transporter of the ATP-binding cassette (ABC) family that actively extrudes physiological compounds and xenobiotics from cells. Transports a range of endogenous molecules that have a key role in cellular communication and signaling, including cyclic nucleotides such as cyclic AMP (cAMP) and cyclic GMP (cGMP), bile acids, steroid conjugates, urate, and prostaglandins (PubMed:11856762, PubMed:12523936, PubMed:12835412, PubMed:12883481, PubMed:15364914, PubMed:15454390, PubMed:16282361, PubMed:17959747, PubMed:18300232, PubMed:26721430). Mediates the ATP-dependent efflux of glutathione conjugates such as leukotriene C4 (LTC4) and leukotriene B4 (LTB4) too. The presence of GSH is necessary for the ATP-dependent transport of LTB4, whereas GSH is not required for the transport of LTC4 (PubMed:17959747). Mediates the cotransport of bile acids with reduced glutathione (GSH) (PubMed:12523936, PubMed:12883481, PubMed:16282361). Transports a wide range of drugs and their metabolites, including anticancer, antiviral and antibiotics molecules (PubMed:11856762, PubMed:12105214, PubMed:15454390, PubMed:17344354, PubMed:18300232). Confers resistance to anticancer agents such as methotrexate (PubMed:11106685)
Specific Function
15-hydroxyprostaglandin dehydrogenase (NAD+) activity
Gene Name
ABCC4
Uniprot ID
O15439
Uniprot Name
ATP-binding cassette sub-family C member 4
Molecular Weight
149525.33 Da
References
  1. Reid G, Wielinga P, Zelcer N, van der Heijden I, Kuil A, de Haas M, Wijnholds J, Borst P: The human multidrug resistance protein MRP4 functions as a prostaglandin efflux transporter and is inhibited by nonsteroidal antiinflammatory drugs. Proc Natl Acad Sci U S A. 2003 Aug 5;100(16):9244-9. Epub 2003 Jun 30. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Mediates export of organic anions and drugs from the cytoplasm (PubMed:10064732, PubMed:11114332, PubMed:16230346, PubMed:7961706, PubMed:9281595). Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotrexate, antiviral drugs and other xenobiotics (PubMed:10064732, PubMed:11114332, PubMed:16230346, PubMed:7961706, PubMed:9281595). Confers resistance to anticancer drugs by decreasing accumulation of drug in cells, and by mediating ATP- and GSH-dependent drug export (PubMed:9281595). Hydrolyzes ATP with low efficiency (PubMed:16230346). Catalyzes the export of sphingosine 1-phosphate from mast cells independently of their degranulation (PubMed:17050692). Participates in inflammatory response by allowing export of leukotriene C4 from leukotriene C4-synthezing cells (By similarity). Mediates ATP-dependent, GSH-independent cyclic GMP-AMP (cGAMP) export (PubMed:36070769). Thus, by limiting intracellular cGAMP concentrations negatively regulates the cGAS-STING pathway (PubMed:36070769)
Specific Function
ABC-type glutathione S-conjugate transporter activity
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Reid G, Wielinga P, Zelcer N, van der Heijden I, Kuil A, de Haas M, Wijnholds J, Borst P: The human multidrug resistance protein MRP4 functions as a prostaglandin efflux transporter and is inhibited by nonsteroidal antiinflammatory drugs. Proc Natl Acad Sci U S A. 2003 Aug 5;100(16):9244-9. Epub 2003 Jun 30. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Na(+)-independent transporter that mediates the cellular uptake of a broad range of organic anions such as the endogenous bile salts cholate and deoxycholate, either in their unconjugated or conjugated forms (taurocholate and glycocholate), at the plasmam membrane (PubMed:19129463, PubMed:7557095). Responsible for intestinal absorption of bile acids (By similarity). Transports dehydroepiandrosterone 3-sulfate (DHEAS), a major circulating steroid secreted by the adrenal cortex, as well as estrone 3-sulfate and 17beta-estradiol 17-O-(beta-D-glucuronate) (PubMed:11159893, PubMed:12568656, PubMed:19129463, PubMed:23918469, PubMed:25560245, PubMed:9539145). Mediates apical uptake of all-trans-retinol (atROL) across human retinal pigment epithelium, which is essential to maintaining the integrity of the visual cycle and thus vision (PubMed:25560245). Involved in the uptake of clinically used drugs (PubMed:17301733, PubMed:20686826, PubMed:27777271). Capable of thyroid hormone transport (both T3 or 3,3',5'-triiodo-L-thyronine, and T4 or L-tyroxine) (PubMed:19129463, PubMed:20358049). Also transports prostaglandin E2 (PubMed:19129463). Plays roles in blood-brain and -cerebrospinal fluid barrier transport of organic anions and signal mediators, and in hormone uptake by neural cells (By similarity). May also play a role in the reuptake of neuropeptides such as substance P/TAC1 and vasoactive intestinal peptide/VIP released from retinal neurons (PubMed:25132355). May play an important role in plasma and tissue distribution of the structurally diverse chemotherapeutic drugs methotrexate and paclitaxel (PubMed:23243220). Shows a pH-sensitive substrate specificity which may be ascribed to the protonation state of the binding site and leads to a stimulation of substrate transport in an acidic microenvironment (PubMed:19129463). Hydrogencarbonate/HCO3(-) acts as the probable counteranion that exchanges for organic anions (PubMed:19129463). May contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable)
Specific Function
bile acid transmembrane transporter activity
Gene Name
SLCO1A2
Uniprot ID
P46721
Uniprot Name
Solute carrier organic anion transporter family member 1A2
Molecular Weight
74144.105 Da
References
  1. Shitara Y, Sugiyama D, Kusuhara H, Kato Y, Abe T, Meier PJ, Itoh T, Sugiyama Y: Comparative inhibitory effects of different compounds on rat oatpl (slc21a1)- and Oatp2 (Slc21a5)-mediated transport. Pharm Res. 2002 Feb;19(2):147-53. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Secondary active transporter that functions as a Na(+)-independent organic anion (OA)/dicarboxylate antiporter where the uptake of one molecule of OA into the cell is coupled with an efflux of one molecule of intracellular dicarboxylate such as 2-oxoglutarate or glutarate (PubMed:11669456, PubMed:11907186, PubMed:14675047, PubMed:22108572, PubMed:23832370, PubMed:28534121, PubMed:9950961). Mediates the uptake of OA across the basolateral side of proximal tubule epithelial cells, thereby contributing to the renal elimination of endogenous OA from the systemic circulation into the urine (PubMed:9887087). Functions as a biopterin transporters involved in the uptake and the secretion of coenzymes tetrahydrobiopterin (BH4), dihydrobiopterin (BH2) and sepiapterin to urine, thereby determining baseline levels of blood biopterins (PubMed:28534121). Transports prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) and may contribute to their renal excretion (PubMed:11907186). Also mediates the uptake of cyclic nucleotides such as cAMP and cGMP (PubMed:26377792). Involved in the transport of neuroactive tryptophan metabolites kynurenate (KYNA) and xanthurenate (XA) and may contribute to their secretion from the brain (PubMed:22108572, PubMed:23832370). May transport glutamate (PubMed:26377792). Also involved in the disposition of uremic toxins and potentially toxic xenobiotics by the renal organic anion secretory pathway, helping reduce their undesired toxicological effects on the body (PubMed:11669456, PubMed:14675047). Uremic toxins include the indoxyl sulfate (IS), hippurate/N-benzoylglycine (HA), indole acetate (IA), 3-carboxy-4- methyl-5-propyl-2-furanpropionate (CMPF) and urate (PubMed:14675047, PubMed:26377792). Xenobiotics include the mycotoxin ochratoxin (OTA) (PubMed:11669456). May also contribute to the transport of organic compounds in testes across the blood-testis-barrier (PubMed:35307651)
Specific Function
alpha-ketoglutarate transmembrane transporter activity
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Mulato AS, Ho ES, Cihlar T: Nonsteroidal anti-inflammatory drugs efficiently reduce the transport and cytotoxicity of adefovir mediated by the human renal organic anion transporter 1. J Pharmacol Exp Ther. 2000 Oct;295(1):10-5. [Article]
  2. Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [Article]
  3. Uwai Y, Saito H, Inui K: Interaction between methotrexate and nonsteroidal anti-inflammatory drugs in organic anion transporter. Eur J Pharmacol. 2000 Dec 1;409(1):31-6. [Article]
  4. Apiwattanakul N, Sekine T, Chairoungdua A, Kanai Y, Nakajima N, Sophasan S, Endou H: Transport properties of nonsteroidal anti-inflammatory drugs by organic anion transporter 1 expressed in Xenopus laevis oocytes. Mol Pharmacol. 1999 May;55(5):847-54. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Functions as an organic anion/dicarboxylate exchanger that couples organic anion uptake indirectly to the sodium gradient (PubMed:14586168, PubMed:15644426, PubMed:15846473, PubMed:16455804, PubMed:31553721). Transports organic anions such as estrone 3-sulfate (E1S) and urate in exchange for dicarboxylates such as glutarate or ketoglutarate (2-oxoglutarate) (PubMed:14586168, PubMed:15846473, PubMed:15864504, PubMed:22108572, PubMed:23832370). Plays an important role in the excretion of endogenous and exogenous organic anions, especially from the kidney and the brain (PubMed:11306713, PubMed:14586168, PubMed:15846473). E1S transport is pH- and chloride-dependent and may also involve E1S/cGMP exchange (PubMed:26377792). Responsible for the transport of prostaglandin E2 (PGE2) and prostaglandin F2(alpha) (PGF2(alpha)) in the basolateral side of the renal tubule (PubMed:11907186). Involved in the transport of neuroactive tryptophan metabolites kynurenate and xanthurenate (PubMed:22108572, PubMed:23832370). Functions as a biopterin transporters involved in the uptake and the secretion of coenzymes tetrahydrobiopterin (BH4), dihydrobiopterin (BH2) and sepiapterin to urine, thereby determining baseline levels of blood biopterins (PubMed:28534121). May be involved in the basolateral transport of steviol, a metabolite of the popular sugar substitute stevioside (PubMed:15644426). May participate in the detoxification/ renal excretion of drugs and xenobiotics, such as the histamine H(2)-receptor antagonists fexofenadine and cimetidine, the antibiotic benzylpenicillin (PCG), the anionic herbicide 2,4-dichloro-phenoxyacetate (2,4-D), the diagnostic agent p-aminohippurate (PAH), the antiviral acyclovir (ACV), and the mycotoxin ochratoxin (OTA), by transporting these exogenous organic anions across the cell membrane in exchange for dicarboxylates such as 2-oxoglutarate (PubMed:11669456, PubMed:15846473, PubMed:16455804). Contributes to the renal uptake of potent uremic toxins (indoxyl sulfate (IS), indole acetate (IA), hippurate/N-benzoylglycine (HA) and 3-carboxy-4-methyl-5-propyl-2-furanpropionate (CMPF)), pravastatin, PCG, E1S and dehydroepiandrosterone sulfate (DHEAS), and is partly involved in the renal uptake of temocaprilat (an angiotensin-converting enzyme (ACE) inhibitor) (PubMed:14675047). May contribute to the release of cortisol in the adrenals (PubMed:15864504). Involved in one of the detoxification systems on the choroid plexus (CP), removes substrates such as E1S or taurocholate (TC), PCG, 2,4-D and PAH, from the cerebrospinal fluid (CSF) to the blood for eventual excretion in urine and bile (By similarity). Also contributes to the uptake of several other organic compounds such as the prostanoids prostaglandin E(2) and prostaglandin F(2-alpha), L-carnitine, and the therapeutic drugs allopurinol, 6-mercaptopurine (6-MP) and 5-fluorouracil (5-FU) (By similarity). Mediates the transport of PAH, PCG, and the statins pravastatin and pitavastatin, from the cerebrum into the blood circulation across the blood-brain barrier (BBB). In summary, plays a role in the efflux of drugs and xenobiotics, helping reduce their undesired toxicological effects on the body (By similarity)
Specific Function
organic anion transmembrane transporter activity
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Organic anion transporter 3
Molecular Weight
59855.585 Da
References
  1. Cha SH, Sekine T, Fukushima JI, Kanai Y, Kobayashi Y, Goya T, Endou H: Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. Mol Pharmacol. 2001 May;59(5):1277-86. [Article]
  2. Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [Article]
  3. Kobayashi Y, Ohshiro N, Tsuchiya A, Kohyama N, Ohbayashi M, Yamamoto T: Renal transport of organic compounds mediated by mouse organic anion transporter 3 (mOat3): further substrate specificity of mOat3. Drug Metab Dispos. 2004 May;32(5):479-83. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Antiporter that mediates the transport of conjugated steroids and other specific organic anions at the basal membrane of syncytiotrophoblast and at the apical membrane of proximal tubule epithelial cells, in exchange for anionic compounds (PubMed:10660625, PubMed:11907186, PubMed:15037815, PubMed:15102942, PubMed:15291761, PubMed:15576633, PubMed:17229912, PubMed:18501590, PubMed:26277985, PubMed:28027879). May be responsible for placental absorption of fetal-derived steroid sulfates such as estrone sulfate (E1S) and the steroid hormone precursor dehydroepiandrosterone sulfate (DHEA-S), as well as clearing waste products and xenobiotics from the fetus (PubMed:12409283). Maybe also be involved in placental urate homeostasis (PubMed:17229912). Facilitates the renal reabsorption of organic anions such as urate and derived steroid sulfates (PubMed:15037815, PubMed:17229912). Organic anion glutarate acts as conteranion for E1S renal uptake (PubMed:15037815, PubMed:17229912). Possible transport mode may also include DHEA-S/E1S exchange (PubMed:28027879). Also interacts with inorganic anions such as chloride and hydroxyl ions, therefore possible transport modes may include E1S/Cl(-), E1S/OH(-), urate/Cl(-) and urate/OH(-) (PubMed:17229912). Also mediates the transport of prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) and may be involved in their renal excretion (PubMed:11907186). Also able to uptake anionic drugs, diuretics, bile salts and ochratoxin A (PubMed:10660625, PubMed:26277985). Mediates the unidirectional efflux of glutamate and aspartate (PubMed:28027879). Glutamate efflux down its transmembrane gradient may drive SLC22A11/OAT4-mediated placental uptake of E1S (PubMed:26277985)
Specific Function
organic anion transmembrane transporter activity
Gene Name
SLC22A11
Uniprot ID
Q9NSA0
Uniprot Name
Solute carrier family 22 member 11
Molecular Weight
59970.945 Da
References
  1. Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [Article]
  2. Cha SH, Sekine T, Kusuhara H, Yu E, Kim JY, Kim DK, Sugiyama Y, Kanai Y, Endou H: Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta. J Biol Chem. 2000 Feb 11;275(6):4507-12. [Article]

Drug created at June 13, 2005 13:24 / Updated at October 07, 2024 13:58