Flurbiprofen
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Identification
- Summary
Flurbiprofen is an NSAID used to treat the signs and symptoms of osteoarthritis and rheumatoid arthritis.
- Generic Name
- Flurbiprofen
- DrugBank Accession Number
- DB00712
- Background
Flurbiprofen, a propionic acid derivative, is a nonsteroidal anti-inflammatory agent (NSAIA) with antipyretic and analgesic activity. Oral formulations of flurbiprofen may be used for the symptomatic treatment of rheumatoid arthritis, osteoarthritis and anklylosing spondylitis. Flurbiprofen may also be used topically prior to ocular surgery to prevent or reduce intraoperative miosis. Flurbiprofen is structurally and pharmacologically related to fenoprofen, ibuprofen, and ketoprofen.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
- Weight
- Average: 244.2609
Monoisotopic: 244.089957865 - Chemical Formula
- C15H13FO2
- Synonyms
- (±)-2-fluoro-α-methyl-4-biphenylacetic acid
- 2-(2-fluorobiphenyl-4-yl)propanoic acid
- 2-fluoro-α-methyl-(1,1'-biphenyl)-4-acetic acid
- 3-fluoro-4-phenylhydratropic acid
- Flurbiprofen
- Flurbiprofene
- Flurbiprofeno
- Flurbiprofenum
- External IDs
- BTS 18 322
- BTS 18,322
- FP 70
- FP 83
- U 27182
- U-27,182
Pharmacology
- Indication
Flurbiprofen tablets are indicated for the acute or long-term symptomatic treatment of rheumatoid arthritis, osteorarthritis and anklosing spondylitis. It may also be used to treat pain associated with dysmenorrhea and mild to moderate pain accompanied by inflammation (e.g. bursitis, tendonitis, soft tissue trauma). Topical ophthalmic formulations may be used pre-operatively to prevent intraoperative miosis.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Symptomatic treatment of Ankylosing spondylitis •••••••••••• Used in combination for symptomatic treatment of Back pain, acute Combination Product in combination with: Thiocolchicoside (DB11582) •••••••••••• ••• Used in combination for symptomatic treatment of Back pain, acute Combination Product in combination with: Thiocolchicoside (DB11582) •••••••••••• ••••• Used in combination for symptomatic treatment of Chronic back pain Combination Product in combination with: Thiocolchicoside (DB11582) •••••••••••• ••• Used in combination for symptomatic treatment of Chronic back pain Combination Product in combination with: Thiocolchicoside (DB11582) •••••••••••• ••••• - Contraindications & Blackbox Warnings
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- Pharmacodynamics
Flurbiprofen, a nonsteroidal anti-inflammatory agent (NSAIA) of the propionic acid class, is structually and pharmacologically related to fenoprofen, ibuprofen, and ketoprofen, and has similar pharmacological actions to other prototypica NSAIAs. Flurbiprofen exhibits antiinflammatory, analgesic, and antipyretic activities. The commercially available flurbiprofen is a racemic mixture of (+)S- and (-) R-enantiomers. The S-enantiomer appears to possess most of the anti-inflammatory, while both enantiomers may possess analgesic activity.
- Mechanism of action
Similar to other NSAIAs, the anti-inflammatory effect of flurbiprofen occurs via reversible inhibition of cyclooxygenase (COX), the enzyme responsible for the conversion of arachidonic acid to prostaglandin G2 (PGG2) and PGG2 to prostaglandin H2 (PGH2) in the prostaglandin synthesis pathway. This effectively decreases the concentration of prostaglandins involved in inflammation, pain, swelling and fever. Flurbiprofen is a non-selective COX inhibitor and inhibits the activity of both COX-1 and -2. It is also one of the most potent NSAIAs in terms of prostaglandin inhibitory activity.
Target Actions Organism AProstaglandin G/H synthase 2 inhibitorHumans UProstaglandin G/H synthase 1 inhibitorHumans - Absorption
Fluribiprofen is rapidly and almost completely absorbed following oral administration. Peak plasma concentrations are reached 0.5 - 4 hours after oral administration.
- Volume of distribution
- 14 L [Normal Healthy Adults]
- 12 L [Geriatric Arthritis Patients]
- 10 L [End Stage Renal Disease Patients]
- 14 L [Alcoholic Cirrhosis Patients]
- 0.12 L/kg
- Protein binding
> 99% bound, primarily to albumin. Binds to a different primary binding site on albumin than anticoagulants, sulfonamides and phenytoin.
- Metabolism
Hepatic. Cytochrome P450 2C9 plays an important role in the metabolism of flurbiprofen to its major metabolite, 4’-hydroxy-flurbiprofen. The 4’-hydroxy-flurbiprofen metabolite showed little anti-inflammatory activity in animal models of inflammation.
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- Route of elimination
Flurbiprofen is poorly excreted into human milk. Following dosing with flurbiprofen, less than 3% of flurbiprofen is excreted unchanged in the urine, with about 70% of the dose eliminated in the urine as parent drug and metabolites. Renal elimination is a significant pathway of elimination of flurbiprofen metabolites.
- Half-life
R-flurbiprofen, 4.7 hours; S-flurbiprofen, 5.7 hours
- Clearance
Not Available
- Adverse Effects
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- Toxicity
LD50=10 mg/kg (orally in dogs).
Selective COX-2 inhibitors have been associated with increased risk of serious cardiovascular events (e.g. myocardial infarction, stroke) in some patients. Current data is insufficient to assess the cardiovascular risk of flurbiprofen. Flurbiprofen may increase blood pressure and/or cause fluid retention and edema. Use caution in patients with fluid retention or heart failure. Risk of GI toxicity including bleeding, ulceration and perforation. Risk of direct renal injury, including renal papillary necrosis. Anaphylactoid and serious skin reactions (e.g. exfoliative dermatitis, Stevens-Johnson syndrome, toxic epidermal necrolysis) may occur. Common adverse events include abdominal pain, constipation, diarrhea, dyspepsia, flatulence, GI bleeding, GI perforation, nausea, peptic ulcer, vomiting, renal function abnormalities, anemia, dizziness, edema, liver function test abnormalities, headache, prolonged bleeding time, pruritus, rash, tinnitus. Although rarely documented in the case of flurbiprofen, oral propionic acid derivatives have been associated with a relatively high frequency of allergic reactions.
- Pathways
Pathway Category Flurbiprofen Action Pathway Drug action - Pharmacogenomic Effects/ADRs
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Cytochrome P450 2C9 CYP2C9*2 Not Available 430C>T Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*3 Not Available 1075A>C Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*4 Not Available 1076T>C Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*5 Not Available 1080C>G Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*8 Not Available 449G>A Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*11 Not Available 1003C>T Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*12 Not Available 1465C>T Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*13 Not Available 269T>C Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*14 Not Available 374G>A Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*16 Not Available 895A>G Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*18 Not Available 1075A>C / 1190A>C … show all Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*26 Not Available 389C>G Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*28 Not Available 641A>T Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*30 Not Available 1429G>A Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*33 Not Available 395G>A Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*6 Not Available 818delA Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*15 Not Available 485C>A Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*25 Not Available 353_362delAGAAATGGAA Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C9 CYP2C9*35 Not Available 374G>T / 430C>T Effect Inferred Poor drug metabolizer. Details
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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir The metabolism of Abacavir can be decreased when combined with Flurbiprofen. Abatacept The metabolism of Flurbiprofen can be increased when combined with Abatacept. Abciximab The risk or severity of bleeding and hemorrhage can be increased when Flurbiprofen is combined with Abciximab. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Flurbiprofen. Acamprosate The excretion of Acamprosate can be decreased when combined with Flurbiprofen. - Food Interactions
- Avoid alcohol.
- Take with food. Food reduces irritation.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Flurbiprofen sodium M3QE6AS001 Not Available AUAGTGKMTMVIKN-UHFFFAOYSA-M - Product Images
- International/Other Brands
- Acustop Cataplasma (Sang-A) / Adofeed (Lead Chemical) / Antadys (Theramex) / Cebutid (Almirall) / Flurofen (Abbott Laboratories Ltd.) / Ocuflur (Allergan) / Stayban (Tokuhon) / Strefen (Reckitt Benckiser) / Strepfen (Reckitt Benckiser) / Strepsils (Reckitt Benckiser) / Strepsils Intensive (Reckitt Benckiser) / TransAct (Reckitt Benckiser) / Urbifen (General Pharma) / Zepolas (Mikasa Seiyaku)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ansaid Tablet, film coated 50 mg/1 Oral Pharmacia & Upjohn Inc 1988-10-31 2009-01-12 US Ansaid Tablet, film coated 100 mg/1 Oral Physicians Total Care, Inc. 1988-10-31 2008-08-31 US Ansaid Tablet, film coated 100 mg/1 Oral Pharmacia & Upjohn Inc 1988-10-31 2009-01-12 US Ansaid Tablets 100 mg Tablet 100 mg Oral Pfizer Italia S.R.L. 1985-12-31 2013-07-25 Canada Ansaid Tablets 50 mg Tablet 50 mg Oral Pfizer Italia S.R.L. 1985-12-31 2013-07-25 Canada - Generic Prescription Products
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image ACUSTOP CATAPLASMA PLASTER 40 mg/sheet Patch 40 mg Transdermal EMERGING PHARMA (S) PTE LTD 2002-09-30 Not applicable Singapore Antiphlamine Pain Relieving Patch 33 mg/51 Topical Hanul Trading Co., Ltd. 2015-09-01 Not applicable US STREPSILS MAX PRO DIRECT SPRAY 8.75MG PER DOSE Spray 8.7480 mg Oropharyngeal Reckitt Benckiser 2017-11-29 Not applicable Singapore Strepsils MaxPro Honey and Lemon lozenges 8.75mg Lozenge 8.75 mg Oral Reckitt Benckiser 2013-11-06 Not applicable Singapore - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image FULDUO 100 MG/8 MG FİLM KAPLI TABLET, 14 ADET Flurbiprofen (100 mg) + Thiocolchicoside (8 mg) Tablet, coated Oral GENVEON İLAÇ SAN. VE TİC. A.Ş. 2020-02-05 Not applicable Turkey KLORHEX PLUS 2.5 MG/ML + 1.2 MG/ML GARGARA,200 ML Flurbiprofen (2.5 mg/ml) + Chlorhexidine gluconate (1.2 mg/ml) Rinse Oral DROGSAN İLAÇLARI SAN. VE TİC. A.Ş. 2015-03-06 2024-03-13 Turkey KLORHEX PLUS 2.5 MG/ML + 1.2 MG/ML ORAL SPREY, ÇÖZELTİ, 30 ML Flurbiprofen (2.5 mg/ml) + Chlorhexidine gluconate (1.2 mg/ml) Spray Oral DROGSAN İLAÇLARI SAN. VE TİC. A.Ş. 2015-09-02 Not applicable Turkey MAJEZIK DUO %5 + %0.25 TOPIKAL JEL, 30 G Flurbiprofen (1.5 g) + Thiocolchicoside (75 mg) Gel Topical SANOVEL İLAÇ SAN. VE TİC. A.Ş. 2012-01-23 2021-10-04 Turkey MAJEZIK DUO %5 + %0.25 TOPIKAL JEL, 50 G Flurbiprofen (2.5 g) + Thiocolchicoside (125 mg) Gel Topical SANOVEL İLAÇ SAN. VE TİC. A.Ş. 2012-01-23 2021-10-04 Turkey - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Antiphlamine Pain Relieving Flurbiprofen (33 mg/51) Patch Topical Hanul Trading Co., Ltd. 2015-09-01 Not applicable US
Categories
- ATC Codes
- M02AA19 — Flurbiprofen
- M02AA — Antiinflammatory preparations, non-steroids for topical use
- M02A — TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
- M02 — TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
- M — MUSCULO-SKELETAL SYSTEM
- M01AE — Propionic acid derivatives
- M01A — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
- M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
- M — MUSCULO-SKELETAL SYSTEM
- R02AX — Other throat preparations
- R02A — THROAT PREPARATIONS
- R02 — THROAT PREPARATIONS
- R — RESPIRATORY SYSTEM
- Drug Categories
- Acids, Acyclic
- Agents causing hyperkalemia
- Agents that produce hypertension
- Analgesics
- Analgesics, Non-Narcotic
- Anti-Inflammatory Agents
- Anti-Inflammatory Agents, Non-Steroidal
- Anti-Inflammatory Agents, Non-Steroidal (Non-Selective)
- Antiinflammatory and Antirheumatic Products
- Antiinflammatory and Antirheumatic Products, Non-Steroids
- Antiinflammatory Preparations, Non-Steroids for Topical Use
- Antirheumatic Agents
- Arylpropionic acid NSAIDS
- Benzene Derivatives
- Biphenyl Compounds
- Central Nervous System Agents
- Cyclooxygenase Inhibitors
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 Substrates
- Drugs causing inadvertant photosensitivity
- Drugs that are Mainly Renally Excreted
- Enzyme Inhibitors
- Musculo-Skeletal System
- Nephrotoxic agents
- Non COX-2 selective NSAIDS
- OAT1/SLC22A6 inhibitors
- Ophthalmologicals
- Other Nonsteroidal Anti-inflammatory Agents
- Peripheral Nervous System Agents
- Photosensitizing Agents
- Propionates
- Sensory Organs
- Sensory System Agents
- Throat Preparations
- Topical Products for Joint and Muscular Pain
- UGT1A1 Inhibitors
- UGT1A1 Substrates
- UGT1A3 substrates
- UGT1A9 Substrates
- UGT2B7 substrates
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Biphenyls and derivatives
- Direct Parent
- Biphenyls and derivatives
- Alternative Parents
- Phenylpropanoic acids / Monocyclic monoterpenoids / Aromatic monoterpenoids / Fluorobenzenes / Aryl fluorides / Monocarboxylic acids and derivatives / Carboxylic acids / Organofluorides / Organic oxides / Hydrocarbon derivatives show 1 more
- Substituents
- 2-phenylpropanoic-acid / Aromatic homomonocyclic compound / Aromatic monoterpenoid / Aryl fluoride / Aryl halide / Biphenyl / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Fluorobenzene show 11 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- fluorobiphenyl (CHEBI:5130)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 5GRO578KLP
- CAS number
- 5104-49-4
- InChI Key
- SYTBZMRGLBWNTM-UHFFFAOYSA-N
- InChI
- InChI=1S/C15H13FO2/c1-10(15(17)18)12-7-8-13(14(16)9-12)11-5-3-2-4-6-11/h2-10H,1H3,(H,17,18)
- IUPAC Name
- 2-{2-fluoro-[1,1'-biphenyl]-4-yl}propanoic acid
- SMILES
- CC(C(O)=O)C1=CC(F)=C(C=C1)C1=CC=CC=C1
References
- Synthesis Reference
Yutaka Mizushima, Hiroyuki Okamoto, Shigetoshi Sugio, Kazumasa Yokoyama, Tadakazu Suyama, Masao Tohno, Makoto Okumura, Yoshiaki Konishi, Kiyonoshin Ichikawa, Katsuhiro Uchida, "Flurbiprofen derivative ophthalmic preparation." U.S. Patent US5171566, issued January, 1984.
US5171566- General References
- Geerts H: Drug evaluation: (R)-flurbiprofen--an enantiomer of flurbiprofen for the treatment of Alzheimer's disease. IDrugs. 2007 Feb;10(2):121-33. [Article]
- 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]
- Calapai G, Imbesi S, Cafeo V, Ventura Spagnolo E, Minciullo PL, Caputi AP, Gangemi S, Milone L: Fatal hypersensitivity reaction to an oral spray of flurbiprofen: a case report. J Clin Pharm Ther. 2013 Aug;38(4):337-8. doi: 10.1111/jcpt.12073. Epub 2013 May 13. [Article]
- Mironov GG, Logie J, Okhonin V, Renaud JB, Mayer PM, Berezovski MV: Comparative study of three methods for affinity measurements: capillary electrophoresis coupled with UV detection and mass spectrometry, and direct infusion mass spectrometry. J Am Soc Mass Spectrom. 2012 Jul;23(7):1232-40. doi: 10.1007/s13361-012-0386-y. Epub 2012 Apr 28. [Article]
- External Links
- Human Metabolome Database
- HMDB0014850
- KEGG Drug
- D00330
- PubChem Compound
- 3394
- PubChem Substance
- 46505550
- ChemSpider
- 3277
- BindingDB
- 50074922
- 4502
- ChEBI
- 5130
- ChEMBL
- CHEMBL563
- Therapeutic Targets Database
- DAP000621
- PharmGKB
- PA449683
- Guide to Pharmacology
- GtP Drug Page
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Flurbiprofen
- FDA label
- Download (234 KB)
- MSDS
- Download (75 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 Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Analgesia / Hemorrhage / Postoperative pain / Promotion of wound healing 1 somestatus stop reason just information to hide Not Available Completed Not Available Arthritis / Gout Flares / Headache / Migraine / Muscle Spasms / Radicular syndrome / Synovitis / Tendonitis 1 somestatus stop reason just information to hide Not Available Completed Not Available Healthy Volunteers (HV) 1 somestatus stop reason just information to hide Not Available Completed Prevention Postoperative Sorethroat / Sore Throat 1 somestatus stop reason just information to hide Not Available Completed Treatment Patient Controlled Analgesia 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Pharmacia and upjohn co
- Caraco pharmaceutical laboratories ltd
- Ivax pharmaceuticals inc sub teva pharmaceuticals usa
- Mylan pharmaceuticals inc
- Pliva inc
- Sandoz inc
- Teva pharmaceuticals usa inc
- Theragen inc
- Bausch and lomb inc
- Allergan pharmaceutical
- Packagers
- Advanced Pharmaceutical Services Inc.
- Allergan Inc.
- Amerisource Health Services Corp.
- A-S Medication Solutions LLC
- Atlantic Biologicals Corporation
- Bausch & Lomb Inc.
- Caraco Pharmaceutical Labs
- Direct Dispensing Inc.
- Dispensing Solutions
- Greenstone LLC
- H.J. Harkins Co. Inc.
- Ivax Pharmaceuticals
- Lake Erie Medical and Surgical Supply
- Major Pharmaceuticals
- Medisca Inc.
- Murfreesboro Pharmaceutical Nursing Supply
- Mylan
- Novopharm Ltd.
- Nucare Pharmaceuticals Inc.
- Pacific Pharma Lp
- PD-Rx Pharmaceuticals Inc.
- Pharmaceutical Utilization Management Program VA Inc.
- Pharmacia Inc.
- Physicians Total Care Inc.
- Sandhills Packaging Inc.
- Southwood Pharmaceuticals
- St Mary's Medical Park Pharmacy
- Stat Rx Usa
- Teva Pharmaceutical Industries Ltd.
- UDL Laboratories
- Dosage Forms
Form Route Strength Patch Transdermal 40 mg Tablet, film coated Oral Capsule, coated pellets Oral 200 mg Tablet Oral 100.000 mg Tablet, film coated Oral 50 mg/1 Tablet, coated Oral Patch Topical 33 mg/51 Mouthwash Oral 250 mg/100ml Tablet Transmucosal Mouthwash Oropharyngeal Spray Oropharyngeal Granule Spray Buccal 2.5 MG/ML Capsule Oral 200 mg Tablet, film coated Oral 100 mg Tablet, coated Oral 100 mg Lozenge Oral Tablet Oral 100 mg/1 Tablet Oral 100 mg Tablet Oral 50 mg/1 Tablet Oral 50 mg Tablet, film coated Oral 100 mg/1 Solution / drops Ophthalmic 0.242 mg/1mL Solution / drops Ophthalmic 0.3 mg/1mL Capsule, extended release Oral Tablet Transmucosal 8.75 MG Rinse Oral 0.25 % Gel Topical Granule, effervescent 100 MG Injection, powder, lyophilized, for solution Intramuscular 150 mg Mouthwash Oral 0.25 % Pill 100 MG Pill 50 MG Spray Oral 0.25 % Suppository 100 MG Syrup Oral 0.5 g/100ml Syrup Oral 5 MG/ML Capsule, extended release Oral 200 mg Tablet Oral 100 mg / tab Tablet Oral 50 mg / tab Capsule, extended release Oral 200 mg / cap Capsule, coated pellets Oral Tablet, coated Oral Tablet Oral; Transmucosal 8.75 MG Solution Buccal 16.200 mg Tablet Oral 8.750 mg Spray Oral Gel Topical 5 % Capsule, delayed release pellets Oral 200 mg Capsule, delayed release pellets Oral Tablet, film coated Oral 50 mg Gel Topical Tablet, film coated Oral Tablet, orally disintegrating Oral 100 mg Rinse Oral Rinse Oral Capsule Oral Spray Topical Solution Conjunctival; Ophthalmic 0.03 g Capsule Oral Mouthwash Oral Tablet Oral Tablet, orally disintegrating Transmucosal Mouthwash Oral 2.5 MG/ML Capsule, extended release Oral 200 mg / src Solution / drops Ophthalmic 0.03 % Solution / drops Ophthalmic 0.3 MG/ML Liquid Ophthalmic 0.03 % Spray Topical 5 % Spray 8.75 mg Spray Oral 8.75 mg Tablet Oral 8.75 mg Spray Oral Tablet Buccal; Oral 8.75 mg Solution Oral; Oropharyngeal 8.748 mg Spray Oral; Transmucosal 8.75 mg Spray Oropharyngeal 8.7480 mg Solution Conjunctival; Ophthalmic 1 mg Patch Topical Patch Topical 40 MG Lozenge Oral 8.75 mg - Prices
Unit description Cost Unit Ocufen 0.03% Solution 2.5ml Bottle 22.7USD bottle Flurbiprofen powder 20.9USD g Flurbiprofen Sodium 0.03% Solution 2.5ml Bottle 15.99USD bottle Ocufen 0.03% eye drops 10.63USD ml Flurbiprofen 0.03% eye drop 4.37USD ml Ansaid 100 mg tablet 2.1USD tablet Flurbiprofen 100 mg tablet 1.08USD tablet Flurbiprofen 50 mg tablet 0.8USD tablet Ansaid 50 mg Tablet 0.58USD tablet Apo-Flurbiprofen 100 mg Tablet 0.37USD tablet Novo-Flurprofen 100 mg Tablet 0.37USD tablet Nu-Flurbiprofen 100 mg Tablet 0.37USD tablet Apo-Flurbiprofen 50 mg Tablet 0.27USD tablet Novo-Flurprofen 50 mg Tablet 0.27USD tablet Nu-Flurbiprofen 50 mg Tablet 0.27USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 110-111 °C Adams, S.S., Bernard, J., Nicholson, J.S. and Blancafort, A.R.; U.S. Patent 3,755,427; Aug. 28, 1973; assigned to The Boots Company Ltd. water solubility 8 mg/L (at 22 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 4.16 HANSCH,C ET AL. (1995) logS -4.49 ADME Research, USCD - Predicted Properties
Property Value Source Water Solubility 0.0249 mg/mL ALOGPS logP 3.57 ALOGPS logP 3.94 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 4.42 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 37.3 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 67.29 m3·mol-1 Chemaxon Polarizability 25.23 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9824 Caco-2 permeable + 0.8866 P-glycoprotein substrate Non-substrate 0.76 P-glycoprotein inhibitor I Non-inhibitor 0.9061 P-glycoprotein inhibitor II Non-inhibitor 0.9739 Renal organic cation transporter Non-inhibitor 0.912 CYP450 2C9 substrate Non-substrate 0.7247 CYP450 2D6 substrate Non-substrate 0.9249 CYP450 3A4 substrate Non-substrate 0.7205 CYP450 1A2 substrate Inhibitor 0.8663 CYP450 2C9 inhibitor Inhibitor 0.8949 CYP450 2D6 inhibitor Non-inhibitor 0.9546 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.9674 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8752 Ames test Non AMES toxic 0.9659 Carcinogenicity Non-carcinogens 0.5554 Biodegradation Not ready biodegradable 0.9861 Rat acute toxicity 3.1121 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9849 hERG inhibition (predictor II) Non-inhibitor 0.9116
Spectra
- Mass Spec (NIST)
- Download (126 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 165.6553027 predictedDarkChem Lite v0.1.0 [M-H]- 155.37337 predictedDeepCCS 1.0 (2019) [M+H]+ 157.76894 predictedDeepCCS 1.0 (2019) [M+Na]+ 163.78603 predictedDeepCCS 1.0 (2019)
Targets
- 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
- Bayly CI, Black WC, Leger S, Ouimet N, Ouellet M, Percival MD: Structure-based design of COX-2 selectivity into flurbiprofen. Bioorg Med Chem Lett. 1999 Feb 8;9(3):307-12. [Article]
- van Haeringen NJ, van Sorge AA, Carballosa Core-Bodelier VM: Constitutive cyclooxygenase-1 and induced cyclooxygenase-2 in isolated human iris inhibited by S(+) flurbiprofen. J Ocul Pharmacol Ther. 2000 Aug;16(4):353-61. [Article]
- Smith T, McCracken J, Shin YK, DeWitt D: Arachidonic acid and nonsteroidal anti-inflammatory drugs induce conformational changes in the human prostaglandin endoperoxide H2 synthase-2 (cyclooxygenase-2). J Biol Chem. 2000 Dec 22;275(51):40407-15. [Article]
- Hinz B, Brune K, Rau T, Pahl A: Flurbiprofen enantiomers inhibit inducible nitric oxide synthase expression in RAW 264.7 macrophages. Pharm Res. 2001 Feb;18(2):151-6. [Article]
- Hewett SJ, Uliasz TF, Vidwans AS, Hewett JA: Cyclooxygenase-2 contributes to N-methyl-D-aspartate-mediated neuronal cell death in primary cortical cell culture. J Pharmacol Exp Ther. 2000 May;293(2):417-25. [Article]
- Basselin M, Villacreses NE, Lee HJ, Bell JM, Rapoport SI: Flurbiprofen, a cyclooxygenase inhibitor, reduces the brain arachidonic acid signal in response to the cholinergic muscarinic agonist, arecoline, in awake rats. Neurochem Res. 2007 Nov;32(11):1857-67. Epub 2007 Jun 12. [Article]
- Nivsarkar M, Banerjee A, Padh H: Cyclooxygenase inhibitors: a novel direction for Alzheimer's management. Pharmacol Rep. 2008 Sep-Oct;60(5):692-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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
- Rieke CJ, Mulichak AM, Garavito RM, Smith WL: The role of arginine 120 of human prostaglandin endoperoxide H synthase-2 in the interaction with fatty acid substrates and inhibitors. J Biol Chem. 1999 Jun 11;274(24):17109-14. [Article]
- Hewett SJ, Uliasz TF, Vidwans AS, Hewett JA: Cyclooxygenase-2 contributes to N-methyl-D-aspartate-mediated neuronal cell death in primary cortical cell culture. J Pharmacol Exp Ther. 2000 May;293(2):417-25. [Article]
- Kurahashi K, Shirahase H, Nakamura S, Tarumi T, Koshino Y, Wang AM, Nishihashi T, Shimizu Y: Nicotine-induced contraction in the rat coronary artery: possible involvement of the endothelium, reactive oxygen species and COX-1 metabolites. J Cardiovasc Pharmacol. 2001 Oct;38 Suppl 1:S21-5. [Article]
- Klegeris A, McGeer PL: Cyclooxygenase and 5-lipoxygenase inhibitors protect against mononuclear phagocyte neurotoxicity. Neurobiol Aging. 2002 Sep-Oct;23(5):787-94. [Article]
- Droge MJ, van Sorge AA, van Haeringen NJ, Quax WJ, Zaagsma J: Alternative splicing of cyclooxygenase-1 mRNA in the human iris. Ophthalmic Res. 2003 May-Jun;35(3):160-3. [Article]
- Basselin M, Villacreses NE, Lee HJ, Bell JM, Rapoport SI: Flurbiprofen, a cyclooxygenase inhibitor, reduces the brain arachidonic acid signal in response to the cholinergic muscarinic agonist, arecoline, in awake rats. Neurochem Res. 2007 Nov;32(11):1857-67. Epub 2007 Jun 12. [Article]
- Nivsarkar M, Banerjee A, Padh H: Cyclooxygenase inhibitors: a novel direction for Alzheimer's management. Pharmacol Rep. 2008 Sep-Oct;60(5):692-8. [Article]
Enzymes
- 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
- 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
- SubstrateInhibitor
- 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:15472229, PubMed:18004206, PubMed:18004212, PubMed:18719240, PubMed:19830808, PubMed:23288867). Essential for the elimination and detoxification of drugs, xenobiotics and endogenous compounds (PubMed:12181437, PubMed:18004206, PubMed:18004212). Catalyzes the glucuronidation of endogenous estrogen hormones such as estradiol, estrone and estriol (PubMed:15472229, PubMed:18719240, PubMed:23288867). Involved in the glucuronidation of bilirubin, a degradation product occurring in the normal catabolic pathway that breaks down heme in vertebrates (PubMed:17187418, PubMed:18004206, PubMed:19830808, PubMed:24525562). Also catalyzes the glucuronidation 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 losartan, 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:18004212, PubMed:20610558)
- Specific Function
- enzyme binding
- Gene Name
- UGT1A1
- Uniprot ID
- P22309
- Uniprot Name
- UDP-glucuronosyltransferase 1A1
- Molecular Weight
- 59590.91 Da
References
- 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: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
- 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
- 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
- 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
- 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
- Wang L, Bao SH, Pan PP, Xia MM, Chen MC, Liang BQ, Dai DP, Cai JP, Hu GX: Effect of CYP2C9 genetic polymorphism on the metabolism of flurbiprofen in vitro. Drug Dev Ind Pharm. 2015;41(8):1363-7. doi: 10.3109/03639045.2014.950274. Epub 2014 Aug 21. [Article]
- Zgheib NK, Frye RF, Tracy TS, Romkes M, Branch RA: Evaluation of flurbiprofen urinary ratios as in vivo indices for CYP2C9 activity. Br J Clin Pharmacol. 2007 Apr;63(4):477-87. doi: 10.1111/j.1365-2125.2006.02781.x. Epub 2006 Oct 19. [Article]
- Flurbiprofen FDA label [File]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Other/unknown
- 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
- Aarons L, Khan AZ, Grennan DM, Alam-Siddiqi M: The binding of flurbiprofen to plasma proteins. J Pharm Pharmacol. 1985 Sep;37(9):644-6. [Article]
- Takla PG, Schulman SG, Perrin JH: Measurement of flurbiprofen-human serum albumin interaction by fluorimetry. J Pharm Biomed Anal. 1985;3(1):41-50. [Article]
Transporters
- 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
- 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
- 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
- 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]
- 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]
Drug created at June 13, 2005 13:24 / Updated at October 29, 2024 18:18