Dexamethasone
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Identification
- Summary
Dexamethasone is a glucocorticoid available in various modes of administration that is used for the treatment of various inflammatory conditions, including bronchial asthma, as well as endocrine and rheumatic disorders.
- Brand Names
- Baycadron, Ciprodex, Decadron, Dexamethasone Intensol, Dextenza, Dioptrol, Hexadrol, Hidex 6-day Taper, Maxidex, Maxitrol, Neofordex, Ozurdex, Taperdex 12 Day Taper, Taperdex 6 Day Taper, Taperdex 7-day Taper, Tobradex, Zcort 7 Day Taper
- Generic Name
- Dexamethasone
- DrugBank Accession Number
- DB01234
- Background
Dexamethasone, or MK-125, is a corticosteroid fluorinated at position 9 used to treat endocrine, rheumatic, collagen, dermatologic, allergic, ophthalmic, gastrointestinal, respiratory, hematologic, neoplastic, edematous, and other conditions.13 Developed in 1957, it is structurally similar to other corticosteroids like hydrocortisone and prednisolone.9
Dexamethasone was granted FDA approval on 30 October 1958.11 In a press release for the Randomized Evaluation of COVID-19 Therapy (RECOVERY) trial on 16 June 2020, dexamethasone was recommended for use in COVID-19 patients with severe respiratory symptoms. Dexamethasone reduced deaths by approximately one third in patients requiring ventilation and by one fifth in those requiring oxygen.22
- Type
- Small Molecule
- Groups
- Approved, Investigational, Vet approved
- Structure
- Weight
- Average: 392.4611
Monoisotopic: 392.199902243 - Chemical Formula
- C22H29FO5
- Synonyms
- 1-Dehydro-16alpha-methyl-9alpha-fluorohydrocortisone
- 1-Dehydro-16α-methyl-9α-fluorohydrocortisone
- 16alpha-Methyl-9alpha-fluoro-1-dehydrocortisol
- 16α-Methyl-9α-fluoro-1-dehydrocortisol
- 9alpha-Fluoro-16alpha-methylprednisolone
- 9α-Fluoro-16α-methylprednisolone
- Dexametasona
- Dexamethasone
- Dexaméthasone
- Dexamethasonum
- External IDs
- ISV-305
- NSC-34521
- OTO-104
Pharmacology
- Indication
Dexamethasone and ciprofloxacin otic suspension is indicated for bacterial infections with inflammation in acute otitis media and acute otitis externa.12 Intramuscular and intravenous injections are indicated for a number of endocrine, rheumatic, collagen, dermatologic, allergic, ophthalmic, gastrointestinal, respiratory, hematologic, neoplastic, edematous, and other conditions.13 Oral tablets are indicated for the treatment of multiple myeloma.16 An intravitreal implant is indicated for some forms of macular edema and non-infectious posterior uveitis affecting the posterior of the eye.19 Various ophthalmic formulations are indicated for inflammatory conditions of the eye.14,15,17,18,20,21
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Acne rosacea •••••••••••• Management of Acquired hemolytic anemia •••••••••••• Management of Acute gouty arthritis •••••••••••• Management of Acute leukemia •••••••••••• Used in combination to treat Acute otitis externa Combination Product in combination with: Ciprofloxacin (DB00537) •••••••••••• •••••• •••••••••• ••••••• •••••••••• - Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
Corticosteroids bind to the glucocorticoid receptor, inhibiting pro-inflammatory signals, and promoting anti-inflammatory signals.3 Dexamethasone's duration of action varies depending on the route.12,13,14,15,16,17,18,19,20,21 Corticosteroids have a wide therapeutic window as patients may require doses that are multiples of what the body naturally produces.3 Patients taking corticosteroids should be counselled regarding the risk of hypothalamic-pituitary-adrenal axis suppression and increased susceptibility to infections.3
- Mechanism of action
The short term effects of corticosteroids are decreased vasodilation and permeability of capillaries, as well as decreased leukocyte migration to sites of inflammation.3 Corticosteroids binding to the glucocorticoid receptor mediates changes in gene expression that lead to multiple downstream effects over hours to days.3
Glucocorticoids inhibit neutrophil apoptosis and demargination; they inhibit phospholipase A2, which decreases the formation of arachidonic acid derivatives; they inhibit NF-Kappa B and other inflammatory transcription factors; they promote anti-inflammatory genes like interleukin-10.3
Lower doses of corticosteroids provide an anti-inflammatory effect, while higher doses are immunosuppressive.3 High doses of glucocorticoids for an extended period bind to the mineralocorticoid receptor, raising sodium levels and decreasing potassium levels.3
Target Actions Organism AGlucocorticoid receptor agonistHumans UNuclear receptor subfamily 0 group B member 1 stimulatorHumans UAnnexin A1 agonistHumans UNitric oxide synthase, inducible negative modulatorHumans UNuclear receptor subfamily 1 group I member 2 agonistHumans - Absorption
Absorption via the intramuscular route is slower than via the intravenous route.13 A 3mg intramuscular dose reaches a Cmax of 34.6±6.0ng/mL with a Tmax of 2.0±1.2h and an AUC of 113±38ng*h/mL.5 A 1.5mg oral dose reaches a Cmax of 13.9±6.8ng/mL with a Tmax of 2.0±0.5h and an AUC of 331±50ng*h/mL.5 Oral dexamethasone is approximately 70-78% bioavailable in healthy subjects.6
- Volume of distribution
A 1.5mg oral dose of dexamethasone has a volume of distribution of 51.0L, while a 3mg intramuscular dose has a volume of distribution of 96.0L.5
- Protein binding
Dexamethasone is approximately 77% protein bound in plasma.16 The majority of protein binding is with serum albumin.10 Dexamethasone does not significantly bind to corticosteroid binding protein.10
- Metabolism
Dexamethasone is 6-hydroxylated by CYP3A4 to 6α- and 6β-hydroxydexamethasone.1 Dexamethasone is reversibly metabolized to 11-dehydrodexamethasone by corticosteroid 11-beta-dehydrogenase isozyme 2 and can also be converted back to dexamethasone by Corticosteroid 11-beta-dehydrogenase isozyme 1.7,8
Hover over products below to view reaction partners
- Route of elimination
Corticosteroids are generally eliminated predominantly in the urine.4 However, dexamethasone is <10% elminated in urine.16
- Half-life
The mean terminal half life of a 20mg oral tablet is 4 hours.16 A 1.5mg oral dose of dexamethasone has a half life of 6.6±4.3h, while a 3mg intramuscular dose has a half life of 4.2±1.2h.5
- Clearance
A 20mg oral tablet has a clearance of 15.7L/h.16 A 1.5mg oral dose of dexamethasone has a clearance of 15.6±4.9L/h while a 3.0mg intramuscular dose has a clearance of 9.9±1.4L/h.5
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
The oral LD50 in female mice was 6.5g/kg and 794mg/kg via the intravenous route.13
Overdoses are not expected with otic formulations.12 Chronic high doses of glucocorticoids can lead to the development of cataract, glaucoma, hypertension, water retention, hyperlipidemia, peptic ulcer, pancreatitis, myopathy, osteoporosis, mood changes, psychosis, dermal atrophy, allergy, acne, hypertrichosis, immune suppression, decreased resistance to infection, moon face, hyperglycemia, hypocalcemia, hypophosphatemia, metabolic acidosis, growth suppression, and secondary adrenal insufficiency.2 Overdose may be treated by adjusting the dose or stopping the corticosteroid as well as initiating symptomatic and supportive treatment.2
- Pathways
- Not Available
- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The metabolism of 1,2-Benzodiazepine can be increased when combined with Dexamethasone. Abametapir The serum concentration of Dexamethasone can be increased when it is combined with Abametapir. Abatacept The metabolism of Dexamethasone can be increased when combined with Abatacept. Abemaciclib The metabolism of Abemaciclib can be increased when combined with Dexamethasone. Abiraterone The metabolism of Abiraterone can be increased when combined with Dexamethasone. - 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 Dexamethasone phosphate 2BP70L44PR 312-93-6 VQODGRNSFPNSQE-CXSFZGCWSA-N Dexamethasone sodium phosphate AI9376Y64P 2392-39-4 PLCQGRYPOISRTQ-FCJDYXGNSA-L - Product Images
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Accufix II Dec Model 033-212 Implant 0.7 mg / imp Intravitreal Telectronics Pacing Systems Inc. 1994-12-31 1999-08-27 Canada Decadron Tablet 0.75 mg/1 Oral Merck Sharp & Dohme B.V. 1958-10-30 2007-11-30 US Decadron Tablet 0.5 mg/1 Oral Merck Sharp & Dohme B.V. 1958-10-30 2007-11-30 US Decadron Phosphate Eye Ear Sol 0.1% Liquid 1 mg / mL Auricular (otic); Ophthalmic Merck Frosst Canada & Cie, Merck Frosst Canada & Co. 1960-12-31 1998-04-21 Canada Decadron Phosphate Inj 4mg/ml Liquid 4 mg / mL Intramuscular; Intravenous Merck Frosst Canada & Cie, Merck Frosst Canada & Co. 1959-12-31 2001-08-01 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-dexamethasone Tablet 0.5 mg Oral Apotex Corporation 2004-11-17 Not applicable Canada Apo-dexamethasone Tablet 4 mg Oral Apotex Corporation 2004-03-08 Not applicable Canada Baycadron Elixir 0.5 mg/5mL Oral Wockhardt 1983-07-27 Not applicable US Decadron Tablet 0.5 mg/1 Oral Pragma Pharmaceuticals, LLC 2018-02-28 2022-03-31 US Decadron Tablet 6 mg/1 Oral Pragma Pharmaceuticals, LLC 2018-02-28 2022-03-31 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 999 Itch Relief Dexamethasone (15 mg/20000mg) + Menthol (200 mg/20000mg) + Synthetic camphor (200 mg/20000mg) Ointment Topical China Resources Sanjiu Medical & Pharmaceutical Co., Ltd. 2003-07-03 Not applicable US ACEFOS DUO® SUSPENSIÓN INYECTABLE Dexamethasone (8 mg) + Dexamethasone (2 mg) Suspension Intra-articular; Intralesional; Intramuscular ARBOFARMA S.A.S. 2018-06-20 Not applicable Colombia ACEFOS DUO® SUSPENSIÓN INYECTABLE Dexamethasone (8 mg) + Dexamethasone (2 mg) Suspension Intra-articular; Intralesional; Intramuscular ARBOFARMA S.A.S. 2018-06-20 Not applicable Colombia AK-Trol Dexamethasone (1 mg/1g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (10000 [USP'U]/1g) Ointment Ophthalmic Physicians Total Care, Inc. 1996-01-05 2000-06-30 US ALEGI Dexamethasone (0.5 mg) + Dexchlorpheniramine maleate (2 mg) Tablet L API Laboratories 2019-01-24 2029-01-24 Indonesia - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Dex-Moxi Dexamethasone sodium phosphate (1 mg/1mL) + Moxifloxacin hydrochloride monohydrate (5 mg/1mL) Injection, solution Ophthalmic Imprimis Njof, Llc 2018-01-05 Not applicable US Dex-Moxi PF Dexamethasone sodium phosphate (1 mg/1mL) + Moxifloxacin hydrochloride monohydrate (5 mg/1mL) Injection, solution Intraocular ImprimisRx NJ 2018-01-01 Not applicable US Dex-Moxi-Ketor Dexamethasone sodium phosphate (1 mg/1mL) + Ketorolac tromethamine (0.4 mg/1mL) + Moxifloxacin hydrochloride monohydrate (0.5 mg/1mL) Injection, solution Ophthalmic Imprimis Njof, Llc 2018-01-05 Not applicable US Dexamethasone Sodium Phosphate 0.1% / Finasteride 0.1% / Minoxidil 5% Dexamethasone sodium phosphate (0.1 g/100g) + Finasteride (0.1 g/100g) + Minoxidil (5 g/100g) Solution Topical Sincerus Florida, LLC 2019-05-09 Not applicable US Dexamethasone Sodium Phosphate 0.1% / Finasteride 0.1% / Minoxidil 5% / Tretinoin 0.025% Dexamethasone sodium phosphate (0.1 g/100g) + Finasteride (0.1 g/100g) + Minoxidil (5 g/100g) + Tretinoin (0.025 g/100g) Solution Topical Sincerus Florida, LLC 2019-05-09 Not applicable US
Categories
- ATC Codes
- R01AD53 — Dexamethasone, combinations
- R01AD — Corticosteroids
- R01A — DECONGESTANTS AND OTHER NASAL PREPARATIONS FOR TOPICAL USE
- R01 — NASAL PREPARATIONS
- R — RESPIRATORY SYSTEM
- D07XB — Corticosteroids, moderately potent, other combinations
- D07X — CORTICOSTEROIDS, OTHER COMBINATIONS
- D07 — CORTICOSTEROIDS, DERMATOLOGICAL PREPARATIONS
- D — DERMATOLOGICALS
- R01AD — Corticosteroids
- R01A — DECONGESTANTS AND OTHER NASAL PREPARATIONS FOR TOPICAL USE
- R01 — NASAL PREPARATIONS
- R — RESPIRATORY SYSTEM
- D10AA — Corticosteroids, combinations for treatment of acne
- D10A — ANTI-ACNE PREPARATIONS FOR TOPICAL USE
- D10 — ANTI-ACNE PREPARATIONS
- D — DERMATOLOGICALS
- S01CB — Corticosteroids/antiinfectives/mydriatics in combination
- S01C — ANTIINFLAMMATORY AGENTS AND ANTIINFECTIVES IN COMBINATION
- S01 — OPHTHALMOLOGICALS
- S — SENSORY ORGANS
- S02CA — Corticosteroids and antiinfectives in combination
- S02C — CORTICOSTEROIDS AND ANTIINFECTIVES IN COMBINATION
- S02 — OTOLOGICALS
- S — SENSORY ORGANS
- S03CA — Corticosteroids and antiinfectives in combination
- S03C — CORTICOSTEROIDS AND ANTIINFECTIVES IN COMBINATION
- S03 — OPHTHALMOLOGICAL AND OTOLOGICAL PREPARATIONS
- S — SENSORY ORGANS
- C05AA — Corticosteroids
- C05A — AGENTS FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE
- C05 — VASOPROTECTIVES
- C — CARDIOVASCULAR SYSTEM
- S01CA — Corticosteroids and antiinfectives in combination
- S01C — ANTIINFLAMMATORY AGENTS AND ANTIINFECTIVES IN COMBINATION
- S01 — OPHTHALMOLOGICALS
- S — SENSORY ORGANS
- D07CB — Corticosteroids, moderately potent, combinations with antibiotics
- D07C — CORTICOSTEROIDS, COMBINATIONS WITH ANTIBIOTICS
- D07 — CORTICOSTEROIDS, DERMATOLOGICAL PREPARATIONS
- D — DERMATOLOGICALS
- H02AB — Glucocorticoids
- H02A — CORTICOSTEROIDS FOR SYSTEMIC USE, PLAIN
- H02 — CORTICOSTEROIDS FOR SYSTEMIC USE
- H — SYSTEMIC HORMONAL PREPARATIONS, EXCL. SEX HORMONES AND INSULINS
- S01BA — Corticosteroids, plain
- S01B — ANTIINFLAMMATORY AGENTS
- S01 — OPHTHALMOLOGICALS
- S — SENSORY ORGANS
- A01AC — Corticosteroids for local oral treatment
- A01A — STOMATOLOGICAL PREPARATIONS
- A01 — STOMATOLOGICAL PREPARATIONS
- A — ALIMENTARY TRACT AND METABOLISM
- S03BA — Corticosteroids
- S03B — CORTICOSTEROIDS
- S03 — OPHTHALMOLOGICAL AND OTOLOGICAL PREPARATIONS
- S — SENSORY ORGANS
- D07AB — Corticosteroids, moderately potent (group II)
- D07A — CORTICOSTEROIDS, PLAIN
- D07 — CORTICOSTEROIDS, DERMATOLOGICAL PREPARATIONS
- D — DERMATOLOGICALS
- Drug Categories
- Adrenal Cortex Hormones
- Adrenals
- Agents Causing Muscle Toxicity
- Agents for Treatment of Hemorrhoids and Anal Fissures for Topical Use
- Alimentary Tract and Metabolism
- Anti-Acne Preparations
- Anti-Acne Preparations for Topical Use
- Anti-Inflammatory Agents
- Antiemetics
- Antineoplastic Agents
- Antineoplastic Agents, Hormonal
- Autonomic Agents
- BCRP/ABCG2 Inhibitors
- BSEP/ABCB11 inducers
- Central Nervous System Agents
- Corticosteroid Hormone Receptor Agonists
- Corticosteroids
- Corticosteroids for Local Oral Treatment
- Corticosteroids for Systemic Use
- Corticosteroids for Systemic Use, Plain
- Corticosteroids, Dermatological Preparations
- Corticosteroids, Moderately Potent (Group II)
- Cytochrome P-450 CYP2A6 Inducers
- Cytochrome P-450 CYP2B6 Inducers
- Cytochrome P-450 CYP2B6 Inducers (strength unknown)
- Cytochrome P-450 CYP2C19 Inducers
- Cytochrome P-450 CYP2C19 Inducers (strength unknown)
- Cytochrome P-450 CYP2C8 Inducers
- Cytochrome P-450 CYP2C8 Inducers (strength unknown)
- Cytochrome P-450 CYP2E1 Inducers
- Cytochrome P-450 CYP2E1 Inducers (strength unknown)
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A Inducers (strong)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (moderate)
- Cytochrome P-450 CYP3A4 Inducers (strong)
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (weak)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Inducers
- Cytochrome P-450 CYP3A5 Inducers (moderate)
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 CYP3A7 Inducers
- Cytochrome P-450 CYP3A7 Inducers (strength unknown)
- Cytochrome P-450 CYP3A7 Substrates
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Dermatologicals
- Experimental Unapproved Treatments for COVID-19
- Fused-Ring Compounds
- Gastrointestinal Agents
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Hyperglycemia-Associated Agents
- Immunosuppressive Agents
- Inducers of Drug Clearance
- Nasal Preparations
- OAT3/SLC22A8 Substrates
- Ophthalmological and Otological Preparations
- Ophthalmologicals
- Otologicals
- P-glycoprotein inducers
- P-glycoprotein inhibitors
- P-glycoprotein substrates
- Peripheral Nervous System Agents
- Pregnadienes
- Pregnadienetriols
- Pregnanes
- Sensory Organs
- Steroids
- Steroids, Fluorinated
- Stomatological Preparations
- Systemic Hormonal Preparations, Excl. Sex Hormones and Insulins
- Vasoprotectives
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Hydroxysteroids
- Direct Parent
- 21-hydroxysteroids
- Alternative Parents
- Gluco/mineralocorticoids, progestogins and derivatives / 20-oxosteroids / 11-beta-hydroxysteroids / 17-hydroxysteroids / 3-oxo delta-1,4-steroids / Halogenated steroids / Delta-1,4-steroids / Tertiary alcohols / Alpha-hydroxy ketones / Secondary alcohols show 8 more
- Substituents
- 11-beta-hydroxysteroid / 11-hydroxysteroid / 17-hydroxysteroid / 20-oxosteroid / 21-hydroxysteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / 9-halo-steroid / Alcohol / Aliphatic homopolycyclic compound show 23 more
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- 11beta-hydroxy steroid, 17alpha-hydroxy steroid, glucocorticoid, 20-oxo steroid, fluorinated steroid, 3-oxo-Delta(1),Delta(4)-steroid, 21-hydroxy steroid (CHEBI:41879) / Pregnane and derivatives [Fig] (C15643)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 7S5I7G3JQL
- CAS number
- 50-02-2
- InChI Key
- UREBDLICKHMUKA-CXSFZGCWSA-N
- InChI
- InChI=1S/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,17+,19+,20+,21+,22+/m1/s1
- IUPAC Name
- (1R,2R,3aS,3bS,9aS,9bR,10S,11aS)-9b-fluoro-1,10-dihydroxy-1-(2-hydroxyacetyl)-2,9a,11a-trimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
- SMILES
- [H][C@@]12C[C@@H](C)[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
References
- Synthesis Reference
Fried, J.; US. Patent 2,852.51 1; September 16, 1958; assigned to Olin Mathieson Chemical Corporation. Muller, G., Bardoneschi, R. and Jolly, J.; U.S. Patent 3,007,923; November 7, 1961; assigned to Les Laboratories Francais de Chimiotherapie, France.
- General References
- Tomlinson ES, Maggs JL, Park BK, Back DJ: Dexamethasone metabolism in vitro: species differences. J Steroid Biochem Mol Biol. 1997 Jul;62(4):345-52. doi: 10.1016/s0960-0760(97)00038-1. [Article]
- Ciriaco M, Ventrice P, Russo G, Scicchitano M, Mazzitello G, Scicchitano F, Russo E: Corticosteroid-related central nervous system side effects. J Pharmacol Pharmacother. 2013 Dec;4(Suppl 1):S94-8. doi: 10.4103/0976-500X.120975. [Article]
- Yasir M, Sonthalia S: Corticosteroid Adverse Effects . [Article]
- Czock D, Keller F, Rasche FM, Haussler U: Pharmacokinetics and pharmacodynamics of systemically administered glucocorticoids. Clin Pharmacokinet. 2005;44(1):61-98. doi: 10.2165/00003088-200544010-00003. [Article]
- Loew D, Schuster O, Graul EH: Dose-dependent pharmacokinetics of dexamethasone. Eur J Clin Pharmacol. 1986;30(2):225-30. doi: 10.1007/bf00614309. [Article]
- Spoorenberg SM, Deneer VH, Grutters JC, Pulles AE, Voorn GP, Rijkers GT, Bos WJ, van de Garde EM: Pharmacokinetics of oral vs. intravenous dexamethasone in patients hospitalized with community-acquired pneumonia. Br J Clin Pharmacol. 2014 Jul;78(1):78-83. doi: 10.1111/bcp.12295. [Article]
- Diederich S, Hanke B, Oelkers W, Bahr V: Metabolism of dexamethasone in the human kidney: nicotinamide adenine dinucleotide-dependent 11beta-reduction. J Clin Endocrinol Metab. 1997 May;82(5):1598-602. [Article]
- Diederich S, Hanke B, Burkhardt P, Muller M, Schoneshofer M, Bahr V, Oelkers W: Metabolism of synthetic corticosteroids by 11 beta-hydroxysteroid-dehydrogenases in man. Steroids. 1998 May-Jun;63(5-6):271-7. doi: 10.1016/s0039-128x(98)00039-7. [Article]
- BUNIM JJ, BLACK RL, LUTWAK L, PETERSON RE, WHEDON GD: Studies on dexamethasone, a new synthetic steroid, in rheurheumatoid arthritis: a preliminary report; adrenal cortical, metabolic and early clinical effects. Arthritis Rheum. 1958 Aug;1(4):313-31. doi: 10.1002/art.1780010404. [Article]
- Cummings DM, Larijani GE, Conner DP, Ferguson RK, Rocci ML Jr: Characterization of dexamethasone binding in normal and uremic human serum. DICP. 1990 Mar;24(3):229-31. doi: 10.1177/106002809002400301. [Article]
- FDA Approved Drug Products: Decadron Dexamethasone Oral Tablet (Discontinued) [Link]
- FDA Approved Drug Products: Ciprodex Dexamethasone and Ciprofloxacin Otic Suspension [Link]
- FDA Approved Drug Products: Dexamethasone Injection [Link]
- FDA Approved Drug Products: Dextenza Dexamethasone Ophthalmic Insert [Link]
- FDA Approved Drug Products: Dexycu Dexamethasone Intraocular Suspension [Link]
- FDA Approved Drug Products: Hemady Dexamethasone Oral Tablets [Link]
- FDA Approved Drug Products: Maxidex Dexamethasone Ophthalmic Suspension [Link]
- FDA Approved Drug Products: Maxitrol Neomycin, Polymyxin B, and Dexamethasone Ophthalmic Suspension [Link]
- FDA Approved Drug Products: Ozurdex Dexamethasone Intravitreal Implant [Link]
- FDA Approved Drug Products: Maxitrol Neomycin, Polymyxin B, and Dexamethasone Ophthalmic Ointment [Link]
- FDA Approved Drug Products: Tobradex Tobramycin and Dexamethasone Ophthlamic Suspension [Link]
- RECOVERY trial news release: dexamethasone [Link]
- External Links
- Human Metabolome Database
- HMDB0015364
- KEGG Drug
- D00292
- KEGG Compound
- C15643
- PubChem Compound
- 5743
- PubChem Substance
- 46508930
- ChemSpider
- 5541
- BindingDB
- 18207
- 3264
- ChEBI
- 41879
- ChEMBL
- CHEMBL384467
- ZINC
- ZINC000003875332
- Therapeutic Targets Database
- DAP000007
- PharmGKB
- PA449247
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- DEX
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Dexamethasone
- PDB Entries
- 1m2z / 1p93 / 3mne / 3mno / 3mnp / 4uda / 4udc / 6nwk / 6xk0 / 7krj … show 8 more
- FDA label
- Download (96 KB)
- MSDS
- Download (74.8 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 Active Not Recruiting Not Available Multiple Myeloma (MM) 2 somestatus stop reason just information to hide Not Available Active Not Recruiting Basic Science Hyperandrogenemia / Obesity / Polycystic Ovarian Syndrome (PCOS) 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Basic Science Hyperandrogenism / Obesity / Polycystic Ovarian Syndrome (PCOS) 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Diagnostic Lung Cancer, Nonsmall Cell, Stage IIIA / Recurrent Non-Small Cell Lung Carcinoma / Stage IIIB Non-Small Cell Lung Cancer / Stage IV Non-small Cell Lung Cancer (NSCLC) 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Supportive Care Breast Cancer / Post Operative Nausea and Vomiting (PONV) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Advanced Pharmaceutical Services Inc.
- Akorn Inc.
- Alcon Laboratories
- Allergan Inc.
- Amend
- American Regent
- Amerisource Health Services Corp.
- Apotheca Inc.
- APP Pharmaceuticals
- A-S Medication Solutions LLC
- Atlantic Biologicals Corporation
- Bausch & Lomb Inc.
- Baxter International Inc.
- Bimeda Inc.
- Blansett Pharmacal Co. Inc.
- Bryant Ranch Prepack
- C.O. Truxton Inc.
- Cardinal Health
- Carlisle Laboratories Inc.
- Clint Pharmaceutical Inc.
- Consolidated Midland Corp.
- Darby Dental Supply Co. Inc.
- Direct Dispensing Inc.
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- ECR Pharmaceuticals
- Falcon Pharmaceuticals Ltd.
- General Injectables and Vaccines Inc.
- Generics Puerto Rico Inc.
- Keene Pharmaceuticals Inc.
- Lake Erie Medical and Surgical Supply
- Luitpold Pharmaceuticals Inc.
- Major Pharmaceuticals
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- Merck & Co.
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- Murfreesboro Pharmaceutical Nursing Supply
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- National Pharmaceuticals
- Neuman Distributors Inc.
- Nord Ost Corp.
- Nucare Pharmaceuticals Inc.
- Ocusoft
- Paddock Labs
- Par Pharmaceuticals
- PCA LLC
- PD-Rx Pharmaceuticals Inc.
- Pharmedix
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- Preferred Pharmaceuticals Inc.
- Prescript Pharmaceuticals
- Primedics Laboratories
- Qualitest
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- Rebel Distributors Corp.
- Redpharm Drug
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- St Mary's Medical Park Pharmacy
- Stat Rx Usa
- Strides Arcolab Limited
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- Dosage Forms
Form Route Strength Implant Intravitreal 0.7 mg / imp Tablet Oral 0.500 mg Tablet Tablet Oral 0.75 mg Elixir Oral 0.5 mg/5mL Cream 10 mg/g Tablet Oral 0.5 MG/2MG Solution Parenteral 8.745 mg Solution / drops Ophthalmic 3 mg Injection, solution Parenteral 4 MG/1ML Solution / drops Ophthalmic 1 mg/ml Ointment Ophthalmic 1 mg/g Solution Intra-articular; Intralesional; Intramuscular; Intravenous 8 mg Solution Auricular (otic) 0.3 % Suspension Auricular (otic) Suspension / drops Auricular (otic) Solution / drops Auricular (otic) Solution Intramuscular Solution / drops Intraocular Injection, solution; injection, suspension; kit Epidural; Intra-articular; Intracaudal; Intramuscular; Intravenous; Perineural; Topical Liquid Dental Kit Oral; Topical Injection Intramuscular; Intrasynovial; Intravenous 4 mg/mL Injection Intramuscular; Intrasynovial; Intravenous 8 mg/2mL Injection, solution Parenteral 8 MG/2ML Solution / drops Oral 2 MG/ML Solution Intra-articular; Intramuscular; Intravenous 8 mg Liquid Auricular (otic); Ophthalmic 1 mg / mL Tablet Oral .5 mg Solution Oral 2000000 mg Injection Intramuscular; Intravenous 2 mg/ml Injection 2 MG/ml Solution Parenteral 8.000 mg Tablet Oral 4.000 mg Solution / drops Auricular (otic); Ophthalmic 5 mg/5ml Syrup Oral 8 mg Solution Intravenous 8 mg/2ml Suspension / drops Ophthalmic Cream Cutaneous 0.1 g/100g Cream Topical 1 g Solution / drops Auricular (otic); Ophthalmic Cream Cutaneous Injection, solution Injection, solution 8 MG/2ML Injection, solution Intramuscular; Intravenous 4 MG/ML Injection, solution Intramuscular; Intravenous 8 MG/2ML Injection, solution 4 MG/ML Cream Topical Injection, solution Ophthalmic Injection, solution Intraocular Injection, solution Parenteral 100 MG Injection, solution Parenteral 40 MG Spray Nasal 13.5 mcg/14mL Solution Ophthalmic 1 mg/ml Ointment Ophthalmic 0.3 mg/g Solution Ophthalmic 5 ml Solution / drops Ophthalmic 0.1 % Solution Oral 0.4 MG/ML Solution Oral 2 MG/ML Solution Oral 4 MG/ML Solution Parenteral 5.25 mg Cream Topical 0.1 g Solution Intramuscular; Intravenous 800000 mg Solution Ophthalmic 1.000 mg Gel Ophthalmic 0.1 %w/w Gel Ophthalmic 0985 mg/g Solution Paste Oral 1 mg/g Paste Submucosal 1 mg/g Solution Parenteral 8 mg Solution Parenteral 4 mg Solution Intramuscular; Intravenous 10.52 mg Solution Intramuscular; Intravenous 8 mg Solution Intramuscular; Intravenous 4 mg Injection Intramuscular; Intravenous 8 mg Solution Intramuscular; Intravenous 4.3726 mg Injection, solution Intramuscular; Intravenous Tablet Oral 1.5 MG Tablet Oral 8 MG Cream Topical 0.5 mg/g Tablet Oral 20 MG Tablet Oral 40 MG Injection Solution Intra-articular; Intralesional; Intramuscular; Intravenous; Soft tissue 10 mg / mL Solution Oral 0.5 mg/5mL Solution Oral 1 mg/10mL Tablet Oral 0.5 mg/0.5mg Tablet Oral 0.5 mg/1 Tablet Oral 0.75 mg/1 Tablet Oral 0.75 mg/0.75mg Tablet Oral 1 mg/1 Tablet Oral 1.5 mg/1 Tablet Oral 2 mg/1 Tablet Oral 4 mg/1 Tablet Oral 6 mg/1 Solution, concentrate Oral 1 mg/1mL Solution Intramuscular; Intrasynovial; Intravenous 10 mg / 1 mL Liquid Intramuscular; Intrasynovial; Intravenous 10 mg / 1 mL Injection 5.45 mg Injection 6.58 mg Injection Intra-articular; Intralesional; Intramuscular; Intravenous; Soft tissue 10 mg/1mL Injection Intra-articular; Intralesional; Intramuscular; Intravenous; Soft tissue 4 mg/1mL Injection Intramuscular 10 mg/1mL Injection Intramuscular; Intravenous 10 mg/1mL Injection Intramuscular; Intravenous 100 mg/10mL Injection, emulsion Intramuscular; Intravenous 10 mg/1mL Injection, solution Intra-articular; Intralesional; Intramuscular; Intravenous; Soft tissue 4 mg/1mL Injection, solution Intramuscular 4 mg/1mL Injection, solution Intramuscular; Intravenous 10 mg/1mL Injection, solution Intramuscular; Intravenous 4 mg/1mL Injection, solution Intravenous 4 mg/1mL Injection, suspension Intra-articular; Intralesional; Intramuscular; Intravenous; Soft tissue 4 mg/1mL Solution Ophthalmic 1 mg/1mL Solution / drops Ophthalmic 1 mg/1mL Solution Topical Solution Intramuscular; Intrasynovial; Intravenous 4 mg / mL Solution Intramuscular; Intrasynovial; Intravenous 10 mg / mL Injection Intramuscular; Intravenous 4 mg/ml Solution Intra-articular; Intralesional; Intramuscular; Intravenous; Soft tissue 4 mg / mL Solution Intra-articular; Intramuscular; Intravenous 4 mg / mL Solution Intramuscular; Intravenous 10 mg / mL Liquid Intra-articular; Intralesional; Intramuscular; Intravenous; Soft tissue 4 mg / mL Liquid Auricular (otic); Ophthalmic Solution 4 mg/1ml Injection Intramuscular; Intravenous 5 mg/ml Injection 5 MG/ml Solution / drops Auricular (otic); Ophthalmic 1 MG/ML Injection Intra-articular; Intramuscular; Intravenous; Intravitreal 8 mg/2ml Kit Infiltration; Intramuscular; Intravenous; Topical Injection, solution; kit; solution; swab Epidural; Infiltration; Intra-articular; Intracaudal; Intramuscular; Intrathecal; Intravascular; Intravenous; Perineural; Topical Kit Epidural; Infiltration; Intramuscular; Intravenous; Topical Tablet 0.5 mg Syrup Oral 0.5 mg/5ml Insert Ophthalmic 0.4 mg/1 Solution Conjunctival; Ophthalmic Solution Auricular (otic); Ophthalmic Injection, suspension Intraocular 517 ug/0.005mL Kit Intramuscular; Intravenous; Topical Solution Intramuscular 100.000 mg Suspension Intra-articular; Intralesional; Intramuscular Implant Intravitreal .5 mg / unit Implant Intravitreal 0.5 mg / unit Solution / drops Ophthalmic 5 mg Gel Ophthalmic 1.5 MG/ML Solution Ophthalmic 1.140 mg Solution / drops Ophthalmic 1.5 MG/ML Solution Auricular (otic); Topical Injection, solution Intramuscular; Intravenous 100 mg/10ml Injection, solution Intramuscular; Intravenous 40 mg/5ml Injection Parenteral 100 mg Injection Parenteral 40 mg Cream Topical 200000 g Tablet Oral 20 mg/1 Injection, solution Intra-articular; Intralesional; Intramuscular; Intravenous; Soft tissue 10 mg/1mL Liquid Intramuscular; Intravenous 4 mg / mL Solution Oral 2 mg/5ml Injection 8 mg/2ml Suspension Conjunctival; Ophthalmic 1 mg Solution / drops Auricular (otic) 10 ml Cream Cutaneous 1.000 g Injection Intravenous 4 mg/ml Injection, solution; kit Intra-articular; Intralesional; Intramuscular; Intravenous; Perineural; Soft tissue Ointment Ophthalmic 2 MG/G Solution / drops Ophthalmic 2 MG/ML Kit Topical Ointment Ophthalmic 0.1 % w/w Ointment Ophthalmic 0.5 mg/1g Suspension Ophthalmic 0.1 % w/v Suspension Ophthalmic 1 mg/1mL Suspension / drops Ophthalmic 1 mg/1mL Suspension / drops Ophthalmic 0.1 % Suspension Ophthalmic 0.1 % Suspension Ophthalmic Ointment Ophthalmic 0.1 % Solution Ophthalmic 0.1 % Ointment Ophthalmic 1.000 mg Suspension Ophthalmic 1.000 mg Suspension Conjunctival; Ophthalmic 1 mg Solution Parenteral 8.00 mg Solution / drops Ophthalmic Solution Ophthalmic 0.1 % w/v Solution / drops Ophthalmic 1 mg/ml Solution Oral 20 mg Ointment Ophthalmic Solution Nasal Solution Intraocular; Ophthalmic Suspension Ophthalmic Suspension / drops Ophthalmic Suspension / drops Topical Solution Intramuscular 8.000 mg Solution Ophthalmic 3 mg Gel Conjunctival Solution Ophthalmic Solution Parenteral 200 mg Injection, solution; kit Epidural; Intracaudal; Intramuscular; Intravenous; Perineural; Topical Solution Ophthalmic; Topical Liquid Ophthalmic; Topical .1 % Solution Auricular (otic); Ophthalmic 0.1 % Ointment Conjunctival; Ophthalmic Syrup Oral Solution / drops Auricular (otic); Ophthalmic 5 ml Solution Conjunctival; Ophthalmic 1 mg Solution Ophthalmic 1 mg Implant Intraocular 700.000 mcg Implant Intravitreal 0.7 mg Implant Intravitreal 0.7 mg/1 Implant Intravitreal 700 MICROGRAMMI Implant Intravitreal 700 mcg Implant Ophthalmic 0.7 mg Intrauterine device Intraocular; Intrauterine 0.7 mg Injection 40 mg/10ml Injection 4 MG/ML Suspension Intramuscular Tablet Oral 2 mg Elixir Oral 0.5 mg / 5 mL Liquid Intramuscular; Intravenous 10 mg / mL Solution Ophthalmic 1.3 mg Solution / drops Auricular (otic); Ophthalmic .1 % Kit Intramuscular; Intravenous Solution Parenteral 8.0 mg Injection, solution Intramuscular Kit Epidural; Infiltration; Intramuscular; Intravenous; Perineural; Topical Solution / drops Auricular (otic); Ophthalmic 0.1 % Solution Intravenous 8.740 mg Ointment Auricular (otic); Ophthalmic Ointment Topical Injection Intramuscular; Intrasynovial; Intravenous 8 g Injection, solution Parenteral 4 MG/ML Ointment Ophthalmic 0.2 % Solution / drops Oral 0.2 % Spray Nasal 0.15 mg Solution Oral 0.02 % Suspension Conjunctival; Ophthalmic 2 mg Tablet Oral Solution Parenteral Suspension Conjunctival; Ophthalmic Ointment Ophthalmic 0.1 % Suspension / drops Ophthalmic 0.1 % Ointment Conjunctival; Ophthalmic 0.1 g Suspension / drops Intraocular Cream Rectal; Topical Emulsion Urethral Solution / drops Ophthalmic 0.15 % Tablet, effervescent Oral 2 MG Tablet, effervescent Oral 4 MG Tablet, effervescent Oral 8 MG Ointment Ophthalmic Solution / drops Ophthalmic Liquid Ophthalmic Capsule Liquid Auricular (otic) Injection, solution 4 mg/1ml Solution / drops Auricular (otic); Ophthalmic Syrup 0.5 mg/5ml Tablet, sugar coated Oral 0.5 mg Tablet Oral 0.25 mg Tablet, film coated 0.5 mg Solution 5 mg/1ml Tablet Oral 0.5 mg Tablet Oral 4 mg Implant Intravitreal 0.7 mg/implant - Prices
Unit description Cost Unit Ozurdex 0.7 mg implant 1554.0USD implant Maxidex 0.1% Suspension 15ml Bottle 97.96USD bottle Maxitrol 0.1-5-10000 Ointment 3.5 gm Tube 87.3USD tube Maxitrol 5-10000-0.1 Suspension 5ml Bottle 75.88USD bottle Maxidex 0.1% Suspension 5ml Bottle 53.57USD bottle Dexamethasone Sodium Phosphate 4 mg/ml Solution (1 Box = 25x1ml Vials) 41.99USD box Dexamethasone micronized powd 41.31USD g Dexamethasone powder 21.27USD g Dexamethasone Sodium Phosphate 0.1% Solution 5ml Bottle 19.99USD bottle Dexamethasone acetate powd 15.12USD g Dexamethasone sod ph powder 14.24USD g Dexamethasone Sodium Phosphate 4 mg/ml Solution 5ml Vial 13.99USD vial Dexamethasone Sodium Phosphate 10 mg/ml 4.78USD ml Dexamethasone Sodium Phosphate 4 mg/ml 1 Vial = 5ml 4.0USD ml Dexamethasone 0.1% eye drop 3.43USD ml Dexasol 0.1% eye drops 3.38USD ml Maxidex 0.1 % Ointment 2.69USD g Dexamethasone 10 mg/ml vial 2.56USD ml Maxidex 0.1% eye drops 2.36USD ml Dexamethasone Sodium Phosphate 4 mg/ml 1.77USD ml Maxidex 0.1 % Suspension 1.73USD ml Sandoz Dexamethasone Sod. Phosphate 0.1 % Solution 1.38USD ml Pms-Dexamethasone Sodium Phosp 10 mg/ml 1.34USD ml Dexamethasone 4 mg/ml vial 1.04USD ml Dexamethasone 6 mg tablet 1.01USD tablet Dexasone 4 mg Tablet 0.86USD tablet Apo-Dexamethasone 4 mg Tablet 0.8USD tablet Pms-Dexamethasone 4 mg Tablet 0.8USD tablet Ratio-Dexamethasone 4 mg Tablet 0.8USD tablet Dexamethasone 2 mg tablet 0.68USD tablet Dexamethasone 1 mg/1 ml soln 0.65USD ml Dexamethasone 4 mg tablet 0.6USD tablet Dexamethasone 1 mg tablet 0.49USD tablet Pms-Dexamethasone 0.75 mg Tablet 0.47USD tablet Pms-Dexamethasone 2 mg Tablet 0.43USD tablet Dexamethasone 0.5 mg/5ml Elixir 0.4USD ml Dexamethasone 0.75 mg tablet 0.38USD tablet Dexamethasone 1.5 mg tablet 0.35USD tablet Dexamethasone 0.5 mg tablet 0.31USD tablet Apo-Dexamethasone 0.5 mg Tablet 0.21USD tablet Pms-Dexamethasone 0.5 mg Tablet 0.2USD tablet Ratio-Dexamethasone 0.5 mg Tablet 0.18USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US8846650 No 2014-09-30 2025-06-04 US US9149486 No 2015-10-06 2022-09-13 US US6359016 No 2002-03-19 2020-08-10 US US6284804 No 2001-09-04 2020-08-10 US US6726918 No 2004-04-27 2020-10-20 US US6899717 No 2005-05-31 2023-11-01 US US8034366 No 2011-10-11 2023-01-09 US US8506987 No 2013-08-13 2023-01-09 US US9012437 No 2015-04-21 2020-10-20 US US8043628 No 2011-10-25 2020-10-20 US US8088407 No 2012-01-03 2020-10-20 US US9283178 No 2016-03-15 2020-10-20 US US9192511 No 2015-11-24 2023-01-09 US US8063031 No 2011-11-22 2020-10-20 US US7033605 No 2006-04-25 2020-10-20 US US7767223 No 2010-08-03 2021-11-28 US US8034370 No 2011-10-11 2023-01-09 US US7795316 No 2010-09-14 2028-08-03 US US8101582 No 2012-01-24 2027-12-19 US US8450287 No 2013-05-28 2027-12-19 US US9345714 No 2016-05-24 2022-09-13 US US9402805 No 2016-08-02 2022-09-13 US US9592242 No 2017-03-14 2020-10-20 US US9775849 No 2017-10-03 2020-10-20 US US6960346 No 2005-11-01 2023-07-03 US US7560120 No 2009-07-14 2022-09-05 US US10028965 No 2018-07-24 2034-05-23 US US10022502 No 2018-07-17 2020-09-12 US US10076526 No 2018-09-18 2023-01-09 US US8563027 No 2013-10-22 2030-02-12 US US8409606 No 2013-04-02 2030-05-14 US US10159683 No 2018-12-25 2034-05-23 US US9254267 No 2016-02-09 2024-09-11 US US10537585 No 2020-01-21 2037-12-18 US US10702539 No 2020-07-07 2023-01-09 US US10799642 No 2020-10-13 2032-05-11 US US11304961 No 2017-12-18 2037-12-18 US US11097061 No 2021-08-24 2039-06-23 US US11458041 No 2017-11-16 2037-11-16 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 260-264 ChemSpider water solubility 89 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 1.83 HANSCH,C ET AL. (1995) logS -3.64 ADME Research, USCD Caco2 permeability -4.75 ADME Research, USCD - Predicted Properties
Property Value Source Water Solubility 0.0505 mg/mL ALOGPS logP 1.93 ALOGPS logP 1.68 Chemaxon logS -3.9 ALOGPS pKa (Strongest Acidic) 12.42 Chemaxon pKa (Strongest Basic) -3.3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 94.83 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 102.49 m3·mol-1 Chemaxon Polarizability 40.71 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.992 Blood Brain Barrier + 0.9781 Caco-2 permeable + 0.8304 P-glycoprotein substrate Substrate 0.7862 P-glycoprotein inhibitor I Non-inhibitor 0.8112 P-glycoprotein inhibitor II Non-inhibitor 0.8134 Renal organic cation transporter Non-inhibitor 0.7971 CYP450 2C9 substrate Non-substrate 0.8733 CYP450 2D6 substrate Non-substrate 0.9115 CYP450 3A4 substrate Substrate 0.7315 CYP450 1A2 substrate Non-inhibitor 0.938 CYP450 2C9 inhibitor Non-inhibitor 0.9106 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9247 CYP450 3A4 inhibitor Non-inhibitor 0.8308 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9169 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.9399 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.1482 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9558 hERG inhibition (predictor II) Inhibitor 0.5091
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 200.5607403 predictedDarkChem Lite v0.1.0 [M-H]- 183.1403496 predictedDarkChem Lite v0.1.0 [M-H]- 193.32462 predictedDeepCCS 1.0 (2019) [M+H]+ 205.0308403 predictedDarkChem Lite v0.1.0 [M+H]+ 191.0385409 predictedDarkChem Lite v0.1.0 [M+H]+ 195.22002 predictedDeepCCS 1.0 (2019) [M+Na]+ 200.8533403 predictedDarkChem Lite v0.1.0 [M+Na]+ 203.5742586 predictedDarkChem Lite v0.1.0 [M+Na]+ 201.1668 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Receptor for glucocorticoids (GC) (PubMed:27120390, PubMed:37478846). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modulator of other transcription factors (PubMed:28139699). Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Involved in chromatin remodeling (PubMed:9590696). Plays a role in rapid mRNA degradation by binding to the 5' UTR of target mRNAs and interacting with PNRC2 in a ligand-dependent manner which recruits the RNA helicase UPF1 and the mRNA-decapping enzyme DCP1A, leading to RNA decay (PubMed:25775514). Could act as a coactivator for STAT5-dependent transcription upon growth hormone (GH) stimulation and could reveal an essential role of hepatic GR in the control of body growth (By similarity)
- Specific Function
- core promoter sequence-specific DNA binding
- Gene Name
- NR3C1
- Uniprot ID
- P04150
- Uniprot Name
- Glucocorticoid receptor
- Molecular Weight
- 85658.57 Da
References
- Warne JP, John CD, Christian HC, Morris JF, Flower RJ, Sugden D, Solito E, Gillies GE, Buckingham JC: Gene deletion reveals roles for annexin A1 in the regulation of lipolysis and IL-6 release in epididymal adipose tissue. Am J Physiol Endocrinol Metab. 2006 Dec;291(6):E1264-73. Epub 2006 Jul 11. [Article]
- Grossman R, Yehuda R, Golier J, McEwen B, Harvey P, Maria NS: Cognitive effects of intravenous hydrocortisone in subjects with PTSD and healthy control subjects. Ann N Y Acad Sci. 2006 Jul;1071:410-21. [Article]
- Funato H, Kobayashi A, Watanabe Y: Differential effects of antidepressants on dexamethasone-induced nuclear translocation and expression of glucocorticoid receptor. Brain Res. 2006 Oct 30;1117(1):125-34. Epub 2006 Sep 7. [Article]
- Vaitkuviene A, Ulinskaite A, Meskys R, Duburs G, Klusa V, Liutkevicius E: Study of the interaction of 1,4-dihydropyridine derivatives with glucocorticoid hormone receptors from the rat liver. Pharmacol Rep. 2006 Jul-Aug;58(4):551-8. [Article]
- Wang D, Zhang H, Lang F, Yun CC: Acute activation of NHE3 by dexamethasone correlates with activation of SGK1 and requires a functional glucocorticoid receptor. Am J Physiol Cell Physiol. 2007 Jan;292(1):C396-404. Epub 2006 Sep 13. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- 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
- Unknown
- Actions
- Stimulator
- General Function
- Orphan nuclear receptor. Component of a cascade required for the development of the hypothalamic-pituitary-adrenal-gonadal axis. Acts as a coregulatory protein that inhibits the transcriptional activity of other nuclear receptors through heterodimeric interactions. May also have a role in the development of the embryo and in the maintenance of embryonic stem cell pluripotency (By similarity)
- Specific Function
- AF-2 domain binding
- Gene Name
- NR0B1
- Uniprot ID
- P51843
- Uniprot Name
- Nuclear receptor subfamily 0 group B member 1
- Molecular Weight
- 51717.185 Da
References
- Gummow BM, Scheys JO, Cancelli VR, Hammer GD: Reciprocal regulation of a glucocorticoid receptor-steroidogenic factor-1 transcription complex on the Dax-1 promoter by glucocorticoids and adrenocorticotropic hormone in the adrenal cortex. Mol Endocrinol. 2006 Nov;20(11):2711-23. Epub 2006 Jul 20. [Article]
- Yu CC, Li PH: In vivo inhibition of steroidogenic acute regulatory protein expression by dexamethasone parallels induction of the negative transcription factor DAX-1. Endocrine. 2006 Dec;30(3):313-23. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Plays important roles in the innate immune response as effector of glucocorticoid-mediated responses and regulator of the inflammatory process. Has anti-inflammatory activity (PubMed:8425544). Plays a role in glucocorticoid-mediated down-regulation of the early phase of the inflammatory response (By similarity). Contributes to the adaptive immune response by enhancing signaling cascades that are triggered by T-cell activation, regulates differentiation and proliferation of activated T-cells (PubMed:17008549). Promotes the differentiation of T-cells into Th1 cells and negatively regulates differentiation into Th2 cells (PubMed:17008549). Has no effect on unstimulated T cells (PubMed:17008549). Negatively regulates hormone exocytosis via activation of the formyl peptide receptors and reorganization of the actin cytoskeleton (PubMed:19625660). Has high affinity for Ca(2+) and can bind up to eight Ca(2+) ions (By similarity). Displays Ca(2+)-dependent binding to phospholipid membranes (PubMed:2532504, PubMed:8557678). Plays a role in the formation of phagocytic cups and phagosomes. Plays a role in phagocytosis by mediating the Ca(2+)-dependent interaction between phagosomes and the actin cytoskeleton (By similarity)
- Specific Function
- cadherin binding involved in cell-cell adhesion
- Gene Name
- ANXA1
- Uniprot ID
- P04083
- Uniprot Name
- Annexin A1
- Molecular Weight
- 38713.855 Da
References
- Morand EF, Hall P, Hutchinson P, Yang YH: Regulation of annexin I in rheumatoid synovial cells by glucocorticoids and interleukin-1. Mediators Inflamm. 2006;2006(2):73835. [Article]
- John CD, Theogaraj E, Christian HC, Morris JF, Smith SF, Buckingham JC: Time-specific effects of perinatal glucocorticoid treatment on anterior pituitary morphology, annexin 1 expression and adrenocorticotrophic hormone secretion in the adult female rat. J Neuroendocrinol. 2006 Dec;18(12):949-59. [Article]
- Davies E, Omer S, Buckingham JC, Morris JF, Christian HC: Expression and externalization of annexin 1 in the adrenal gland: structure and function of the adrenal gland in annexin 1-null mutant mice. Endocrinology. 2007 Mar;148(3):1030-8. Epub 2006 Dec 7. [Article]
- Wang C, Wang J, Guo HF, Liu RY: Involvement of annexin I in the dexamethasone-mediated upregulation of A549 cells phagocytosis of apoptotic eosinophils. Immunol Lett. 2007 Aug 15;111(2):103-10. Epub 2007 Jul 2. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Negative modulator
- General Function
- Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body (PubMed:7504305, PubMed:7531687, PubMed:7544004, PubMed:7682706). In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such PTGS2/COX2 (By similarity). As component of the iNOS-S100A8/9 transnitrosylase complex involved in the selective inflammatory stimulus-dependent S-nitrosylation of GAPDH on 'Cys-247' implicated in regulation of the GAIT complex activity and probably multiple targets including ANXA5, EZR, MSN and VIM (PubMed:25417112). Involved in inflammation, enhances the synthesis of pro-inflammatory mediators such as IL6 and IL8 (PubMed:19688109)
- Specific Function
- arginine binding
- Gene Name
- NOS2
- Uniprot ID
- P35228
- Uniprot Name
- Nitric oxide synthase, inducible
- Molecular Weight
- 131116.3 Da
References
- Soderberg M, Raffalli-Mathieu F, Lang MA: Regulation of the murine inducible nitric oxide synthase gene by dexamethasone involves a heterogeneous nuclear ribonucleoprotein I (hnRNPI) dependent pathway. Mol Immunol. 2007 May;44(12):3204-10. Epub 2007 Mar 26. [Article]
- Huang H, Lavoie-Lamoureux A, Moran K, Lavoie JP: IL-4 stimulates the expression of CXCL-8, E-selectin, VEGF, and inducible nitric oxide synthase mRNA by equine pulmonary artery endothelial cells. Am J Physiol Lung Cell Mol Physiol. 2007 May;292(5):L1147-54. [Article]
- Nandi J, Saud B, Zinkievich JM, Palma DT, Levine RA: 5-aminosalicylic acid improves indomethacin-induced enteropathy by inhibiting iNOS transcription in rats. Dig Dis Sci. 2008 Jan;53(1):123-32. Epub 2007 May 15. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes
- Specific Function
- DNA-binding transcription activator activity, RNA polymerase II-specific
- Gene Name
- NR1I2
- Uniprot ID
- O75469
- Uniprot Name
- Nuclear receptor subfamily 1 group I member 2
- Molecular Weight
- 49761.245 Da
References
- Kretschmer XC, Baldwin WS: CAR and PXR: xenosensors of endocrine disrupters? Chem Biol Interact. 2005 Aug 15;155(3):111-28. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Catalyzes the conversion of biologically active 11beta-hydroxyglucocorticoids (11beta-hydroxysteroid) such as cortisol, to inactive 11-ketoglucocorticoids (11-oxosteroid) such as cortisone, in the presence of NAD(+) (PubMed:10497248, PubMed:12788846, PubMed:17314322, PubMed:22796344, PubMed:27927697, PubMed:30902677, PubMed:33387577, PubMed:7859916, PubMed:8538347). Functions as a dehydrogenase (oxidase), thereby decreasing the concentration of active glucocorticoids, thus protecting the nonselective mineralocorticoid receptor from occupation by glucocorticoids (PubMed:10497248, PubMed:12788846, PubMed:17314322, PubMed:33387577, PubMed:7859916). Plays an important role in maintaining glucocorticoids balance during preimplantation and protects the fetus from excessive maternal corticosterone exposure (By similarity). Catalyzes the oxidation of 11beta-hydroxytestosterone (11beta,17beta-dihydroxyandrost-4-ene-3-one) to 11-ketotestosterone (17beta-hydroxyandrost-4-ene-3,11-dione), a major bioactive androgen (PubMed:22796344, PubMed:27927697). Catalyzes the conversion of 11beta-hydroxyandrostenedione (11beta-hydroxyandrost-4-ene-3,17-dione) to 11-ketoandrostenedione (androst-4-ene-3,11,17-trione), which can be further metabolized to 11-ketotestosterone (PubMed:27927697). Converts 7-beta-25-dihydroxycholesterol to 7-oxo-25-hydroxycholesterol in vitro (PubMed:30902677). 7-beta-25-dihydroxycholesterol (not 7-oxo-25-hydroxycholesterol) acts as a ligand for the G-protein-coupled receptor (GPCR) Epstein-Barr virus-induced gene 2 (EBI2) and may thereby regulate immune cell migration (PubMed:30902677). May protect ovulating oocytes and fertilizing spermatozoa from the adverse effects of cortisol (By similarity)
- Specific Function
- 11-beta-hydroxysteroid dehydrogenase (NAD+) activity
- Gene Name
- HSD11B2
- Uniprot ID
- P80365
- Uniprot Name
- 11-beta-hydroxysteroid dehydrogenase type 2
- Molecular Weight
- 44126.06 Da
References
- Diederich S, Hanke B, Oelkers W, Bahr V: Metabolism of dexamethasone in the human kidney: nicotinamide adenine dinucleotide-dependent 11beta-reduction. J Clin Endocrinol Metab. 1997 May;82(5):1598-602. [Article]
- Diederich S, Hanke B, Burkhardt P, Muller M, Schoneshofer M, Bahr V, Oelkers W: Metabolism of synthetic corticosteroids by 11 beta-hydroxysteroid-dehydrogenases in man. Steroids. 1998 May-Jun;63(5-6):271-7. doi: 10.1016/s0039-128x(98)00039-7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitorInducer
- 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
- Ekins S, Bravi G, Wikel JH, Wrighton SA: Three-dimensional-quantitative structure activity relationship analysis of cytochrome P-450 3A4 substrates. J Pharmacol Exp Ther. 1999 Oct;291(1):424-33. [Article]
- Lampen A, Christians U, Guengerich FP, Watkins PB, Kolars JC, Bader A, Gonschior AK, Dralle H, Hackbarth I, Sewing KF: Metabolism of the immunosuppressant tacrolimus in the small intestine: cytochrome P450, drug interactions, and interindividual variability. Drug Metab Dispos. 1995 Dec;23(12):1315-24. [Article]
- Christians U, Schmidt G, Bader A, Lampen A, Schottmann R, Linck A, Sewing KF: Identification of drugs inhibiting the in vitro metabolism of tacrolimus by human liver microsomes. Br J Clin Pharmacol. 1996 Mar;41(3):187-90. [Article]
- Miranda SR, Meyer SA: Cytotoxicity of chloroacetanilide herbicide alachlor in HepG2 cells independent of CYP3A4 and CYP3A7. Food Chem Toxicol. 2007 May;45(5):871-7. doi: 10.1016/j.fct.2006.11.011. Epub 2006 Nov 26. [Article]
- Yamaguchi Y, Kirita S, Baba T, Aoyama J, Touchi A, Tukey RH, Guengerich FP, Matsubara T: Identification of rat and human cytochrome P450 forms involved in the metabolism of the thromboxane A2 receptor antagonist (+)-S-145. Drug Metab Dispos. 1997 Jan;25(1):75-80. [Article]
- Gomez-Lechon MJ, Donato T, Jover R, Rodriguez C, Ponsoda X, Glaise D, Castell JV, Guguen-Guillouzo C: Expression and induction of a large set of drug-metabolizing enzymes by the highly differentiated human hepatoma cell line BC2. Eur J Biochem. 2001 Mar;268(5):1448-59. [Article]
- Berson A, Wolf C, Chachaty C, Fisch C, Fau D, Eugene D, Loeper J, Gauthier JC, Beaune P, Pompon D, et al.: Metabolic activation of the nitroaromatic antiandrogen flutamide by rat and human cytochromes P-450, including forms belonging to the 3A and 1A subfamilies. J Pharmacol Exp Ther. 1993 Apr;265(1):366-72. [Article]
- McCune JS, Hawke RL, LeCluyse EL, Gillenwater HH, Hamilton G, Ritchie J, Lindley C: In vivo and in vitro induction of human cytochrome P4503A4 by dexamethasone. Clin Pharmacol Ther. 2000 Oct;68(4):356-66. doi: 10.1067/mcp.2000.110215. [Article]
- Dexamethasone monograph, Boehringer Ingelheim [Link]
- Flockhart Table of Drug Interactions [Link]
- FDA Approved Drug Products: Hemady Dexamethasone Oral Tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Controls the reversible conversion of biologically active glucocorticoids such as cortisone to cortisol, and 11-dehydrocorticosterone to corticosterone in the presence of NADP(H) (PubMed:10497248, PubMed:12460758, PubMed:14973125, PubMed:15152005, PubMed:15280030, PubMed:17593962, PubMed:21453287, PubMed:27927697, PubMed:30902677). Participates in the corticosteroid receptor-mediated anti-inflammatory response, as well as metabolic and homeostatic processes (PubMed:10497248, PubMed:12414862, PubMed:15152005, PubMed:21453287). Plays a role in the secretion of aqueous humor in the eye, maintaining a normotensive, intraocular environment (PubMed:11481269). Bidirectional in vitro, predominantly functions as a reductase in vivo, thereby increasing the concentration of active glucocorticoids (PubMed:10497248, PubMed:11481269, PubMed:12414862, PubMed:12460758). It has broad substrate specificity, besides glucocorticoids, it accepts other steroid and sterol substrates (PubMed:15095019, PubMed:15152005, PubMed:17593962, PubMed:21453287). Interconverts 7-oxo- and 7-hydroxy-neurosteroids such as 7-oxopregnenolone and 7beta-hydroxypregnenolone, 7-oxodehydroepiandrosterone (3beta-hydroxy-5-androstene-7,17-dione) and 7beta-hydroxydehydroepiandrosterone (3beta,7beta-dihydroxyandrost-5-en-17-one), among others (PubMed:17593962). Catalyzes the stereo-specific conversion of the major dietary oxysterol, 7-ketocholesterol (7-oxocholesterol), into the more polar 7-beta-hydroxycholesterol metabolite (PubMed:15095019, PubMed:15152005). 7-oxocholesterol is one of the most important oxysterols, it participates in several events such as induction of apoptosis, accumulation in atherosclerotic lesions, lipid peroxidation, and induction of foam cell formation (PubMed:15095019). Mediates the 7-oxo reduction of 7-oxolithocholate mainly to chenodeoxycholate, and to a lesser extent to ursodeoxycholate, both in its free form and when conjugated to glycine or taurine, providing a link between glucocorticoid activation and bile acid metabolism (PubMed:21453287). Catalyzes the synthesis of 7-beta-25-dihydroxycholesterol from 7-oxo-25-hydroxycholesterol in vitro, which acts as a ligand for the G-protein-coupled receptor (GPCR) Epstein-Barr virus-induced gene 2 (EBI2) and may thereby regulate immune cell migration (PubMed:30902677)
- Specific Function
- 11-beta-hydroxysteroid dehydrogenase (NADP+) activity
- Gene Name
- HSD11B1
- Uniprot ID
- P28845
- Uniprot Name
- 11-beta-hydroxysteroid dehydrogenase 1
- Molecular Weight
- 32400.665 Da
References
- Diederich S, Hanke B, Oelkers W, Bahr V: Metabolism of dexamethasone in the human kidney: nicotinamide adenine dinucleotide-dependent 11beta-reduction. J Clin Endocrinol Metab. 1997 May;82(5):1598-602. [Article]
- Diederich S, Hanke B, Burkhardt P, Muller M, Schoneshofer M, Bahr V, Oelkers W: Metabolism of synthetic corticosteroids by 11 beta-hydroxysteroid-dehydrogenases in man. Steroids. 1998 May-Jun;63(5-6):271-7. doi: 10.1016/s0039-128x(98)00039-7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInducer
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of steroid hormones and vitamins (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). 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:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Exhibits high catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes 6beta-hydroxylation of the steroid hormones testosterone, progesterone, and androstenedione (PubMed:2732228). Catalyzes the oxidative conversion 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 all trans-retinoic acid (atRA) to 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Also involved in the oxidative metabolism of xenobiotics, including calcium channel blocking drug nifedipine and immunosuppressive drug cyclosporine (PubMed:2732228)
- Specific Function
- aromatase activity
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Hukkanen J, Lassila A, Paivarinta K, Valanne S, Sarpo S, Hakkola J, Pelkonen O, Raunio H: Induction and regulation of xenobiotic-metabolizing cytochrome P450s in the human A549 lung adenocarcinoma cell line. Am J Respir Cell Mol Biol. 2000 Mar;22(3):360-6. [Article]
- Hukkanen J, Vaisanen T, Lassila A, Piipari R, Anttila S, Pelkonen O, Raunio H, Hakkola J: Regulation of CYP3A5 by glucocorticoids and cigarette smoke in human lung-derived cells. J Pharmacol Exp Ther. 2003 Feb;304(2):745-52. [Article]
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInducer
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of steroid hormones and vitamins during embryogenesis (PubMed:11093772, PubMed:12865317, PubMed:14559847, PubMed:17178770, PubMed:9555064). 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:12865317, PubMed:14559847, PubMed:17178770, PubMed:9555064). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes 3beta-hydroxyandrost-5-en-17-one (dehydroepiandrosterone, DHEA), a precursor in the biosynthesis of androgen and estrogen steroid hormones (PubMed:17178770, PubMed:9555064). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1), particularly D-ring hydroxylated estrone at the C16-alpha position (PubMed:12865317, PubMed:14559847). Mainly hydroxylates all trans-retinoic acid (atRA) to 4-hydroxyretinoate and may play a role in atRA clearance during fetal development (PubMed:11093772). Also involved in the oxidative metabolism of xenobiotics including anticonvulsants (PubMed:9555064)
- Specific Function
- all-trans retinoic acid 18-hydroxylase activity
- Gene Name
- CYP3A7
- Uniprot ID
- P24462
- Uniprot Name
- Cytochrome P450 3A7
- Molecular Weight
- 57469.95 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- A cytochrome P450 monooxygenase involved in corticoid and androgen biosynthesis (PubMed:22266943, PubMed:25301938, PubMed:27339894, PubMed:9452426). Catalyzes 17-alpha hydroxylation of C21 steroids, which is common for both pathways. A second oxidative step, required only for androgen synthesis, involves an acyl-carbon cleavage. The 17-alpha hydroxy intermediates, as part of adrenal glucocorticoids biosynthesis pathway, are precursors of cortisol (Probable) (PubMed:25301938, PubMed:9452426). Hydroxylates steroid hormones, pregnenolone and progesterone to form 17-alpha hydroxy metabolites, followed by the cleavage of the C17-C20 bond to form C19 steroids, dehydroepiandrosterone (DHEA) and androstenedione (PubMed:22266943, PubMed:25301938, PubMed:27339894, PubMed:36640554, PubMed:9452426). Has 16-alpha hydroxylase activity. Catalyzes 16-alpha hydroxylation of 17-alpha hydroxy pregnenolone, followed by the cleavage of the C17-C20 bond to form 16-alpha-hydroxy DHEA (PubMed:36640554). Also 16-alpha hydroxylates androgens, relevant for estriol synthesis (PubMed:25301938, PubMed:27339894). 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 (CPR; NADPH-ferrihemoprotein reductase) (PubMed:22266943, PubMed:25301938, PubMed:27339894, PubMed:9452426)
- Specific Function
- heme binding
- Gene Name
- CYP17A1
- Uniprot ID
- P05093
- Uniprot Name
- Steroid 17-alpha-hydroxylase/17,20 lyase
- Molecular Weight
- 57369.995 Da
References
- Trzeciak WH, LeHoux JG, Waterman MR, Simpson ER: Dexamethasone inhibits corticotropin-induced accumulation of CYP11A and CYP17 messenger RNAs in bovine adrenocortical cells. Mol Endocrinol. 1993 Feb;7(2):206-13. doi: 10.1210/mend.7.2.8385739. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- InhibitorInducer
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15041462, PubMed:15805301, 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:10681376, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15041462, PubMed:15805301, PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. 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 C15-alpha and C16-alpha positions (PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15805301). Displays different regioselectivities for polyunsaturated fatty acids (PUFA) hydroxylation (PubMed:15041462, PubMed:18577768). Catalyzes the epoxidation of double bonds of certain PUFA (PubMed:15041462, PubMed:19965576, PubMed:20972997). Converts arachidonic acid toward epoxyeicosatrienoic acid (EET) regioisomers, 8,9-, 11,12-, and 14,15-EET, that function as lipid mediators in the vascular system (PubMed:20972997). Displays an absolute stereoselectivity in the epoxidation of eicosapentaenoic acid (EPA) producing the 17(R),18(S) enantiomer (PubMed:15041462). May play an important role in all-trans retinoic acid biosynthesis in extrahepatic tissues. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195)
- Specific Function
- arachidonic acid monooxygenase activity
- Gene Name
- CYP1A1
- Uniprot ID
- P04798
- Uniprot Name
- Cytochrome P450 1A1
- Molecular Weight
- 58164.815 Da
References
- Baron JM, Holler D, Schiffer R, Frankenberg S, Neis M, Merk HF, Jugert FK: Expression of multiple cytochrome p450 enzymes and multidrug resistance-associated transport proteins in human skin keratinocytes. J Invest Dermatol. 2001 Apr;116(4):541-8. doi: 10.1046/j.1523-1747.2001.01298.x. [Article]
- Monostory K, Kohalmy K, Prough RA, Kobori L, Vereczkey L: The effect of synthetic glucocorticoid, dexamethasone on CYP1A1 inducibility in adult rat and human hepatocytes. FEBS Lett. 2005 Jan 3;579(1):229-35. doi: 10.1016/j.febslet.2004.11.080. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity
- Specific Function
- arachidonic acid epoxygenase activity
- Gene Name
- CYP2A6
- Uniprot ID
- P11509
- Uniprot Name
- Cytochrome P450 2A6
- Molecular Weight
- 56517.005 Da
References
- Onica T, Nichols K, Larin M, Ng L, Maslen A, Dvorak Z, Pascussi JM, Vilarem MJ, Maurel P, Kirby GM: Dexamethasone-mediated up-regulation of human CYP2A6 involves the glucocorticoid receptor and increased binding of hepatic nuclear factor 4 alpha to the proximal promoter. Mol Pharmacol. 2008 Feb;73(2):451-60. Epub 2007 Oct 31. [Article]
- Meunier V, Bourrie M, Julian B, Marti E, Guillou F, Berger Y, Fabre G: Expression and induction of CYP1A1/1A2, CYP2A6 and CYP3A4 in primary cultures of human hepatocytes: a 10-year follow-up. Xenobiotica. 2000 Jun;30(6):589-607. doi: 10.1080/004982500406426 . [Article]
- Waxman DJ, Chang TK: Spectrofluorometric analysis of CYP2A6-catalyzed coumarin 7-hydroxylation. Methods Mol Biol. 2006;320:91-6. doi: 10.1385/1-59259-998-2:91. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of endocannabinoids and steroids (PubMed:12865317, PubMed:21289075). 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 epoxidation of double bonds of arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:21289075). Hydroxylates steroid hormones, including testosterone at C-16 and estrogens at C-2 (PubMed:12865317, PubMed:21289075). Plays a role in the oxidative metabolism of xenobiotics, including plant lipids and drugs (PubMed:11695850, PubMed:22909231). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850)
- Specific Function
- anandamide 11,12 epoxidase activity
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Baron JM, Holler D, Schiffer R, Frankenberg S, Neis M, Merk HF, Jugert FK: Expression of multiple cytochrome p450 enzymes and multidrug resistance-associated transport proteins in human skin keratinocytes. J Invest Dermatol. 2001 Apr;116(4):541-8. doi: 10.1046/j.1523-1747.2001.01298.x. [Article]
- Wang H, Tompkins LM: CYP2B6: new insights into a historically overlooked cytochrome P450 isozyme. Curr Drug Metab. 2008 Sep;9(7):598-610. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- 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
- Raucy JL, Mueller L, Duan K, Allen SW, Strom S, Lasker JM: Expression and induction of CYP2C P450 enzymes in primary cultures of human hepatocytes. J Pharmacol Exp Ther. 2002 Aug;302(2):475-82. doi: 10.1124/jpet.102.033837. [Article]
- Scott SA, Sangkuhl K, Shuldiner AR, Hulot JS, Thorn CF, Altman RB, Klein TE: PharmGKB summary: very important pharmacogene information for cytochrome P450, family 2, subfamily C, polypeptide 19. Pharmacogenet Genomics. 2012 Feb;22(2):159-65. doi: 10.1097/FPC.0b013e32834d4962. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- 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
- Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [Article]
- Pascussi JM, Gerbal-Chaloin S, Fabre JM, Maurel P, Vilarem MJ: Dexamethasone enhances constitutive androstane receptor expression in human hepatocytes: consequences on cytochrome P450 gene regulation. Mol Pharmacol. 2000 Dec;58(6):1441-50. doi: 10.1124/mol.58.6.1441. [Article]
- Gerbal-Chaloin S, Pascussi JM, Pichard-Garcia L, Daujat M, Waechter F, Fabre JM, Carrere N, Maurel P: Induction of CYP2C genes in human hepatocytes in primary culture. Drug Metab Dispos. 2001 Mar;29(3):242-51. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of fatty acids (PubMed:10553002, PubMed:18577768). 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:10553002, PubMed:18577768). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates fatty acids specifically at the omega-1 position displaying the highest catalytic activity for saturated fatty acids (PubMed:10553002, PubMed:18577768). May be involved in the oxidative metabolism of xenobiotics (Probable)
- Specific Function
- 4-nitrophenol 2-monooxygenase activity
- Gene Name
- CYP2E1
- Uniprot ID
- P05181
- Uniprot Name
- Cytochrome P450 2E1
- Molecular Weight
- 56848.42 Da
References
- Baron JM, Holler D, Schiffer R, Frankenberg S, Neis M, Merk HF, Jugert FK: Expression of multiple cytochrome p450 enzymes and multidrug resistance-associated transport proteins in human skin keratinocytes. J Invest Dermatol. 2001 Apr;116(4):541-8. doi: 10.1046/j.1523-1747.2001.01298.x. [Article]
- Sampol E, Mirrione A, Villard PH, Piccerelle P, Scoma H, Berbis P, Barra Y, Durand A, Lacarelle B: Evidence for a tissue-specific induction of cutaneous CYP2E1 by dexamethasone. Biochem Biophys Res Commun. 1997 Jun 27;235(3):557-61. doi: 10.1006/bbrc.1997.6829. [Article]
- Monostory K, Vereczkey L: Combined action of phenobarbital and dexamethasone on the activity of rat liver P450 system. Acta Pharm Hung. 1993 Sep;63(5):296-300. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Exhibits low testosterone 6-beta-hydroxylase activity
- Specific Function
- aromatase activity
- Gene Name
- CYP3A43
- Uniprot ID
- Q9HB55
- Uniprot Name
- Cytochrome P450 3A43
- Molecular Weight
- 57669.21 Da
References
- Krusekopf S, Roots I, Kleeberg U: Differential drug-induced mRNA expression of human CYP3A4 compared to CYP3A5, CYP3A7 and CYP3A43. Eur J Pharmacol. 2003 Apr 11;466(1-2):7-12. doi: 10.1016/s0014-2999(03)01481-x. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of fatty acids and their oxygenated derivatives (oxylipins) (PubMed:10553002, PubMed:10660572, PubMed:15611369, PubMed:1739747, PubMed:7679927, PubMed:8914854). 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 (CPR; NADPH-ferrihemoprotein reductase) (PubMed:10553002, PubMed:10660572, PubMed:15611369, PubMed:1739747, PubMed:7679927, PubMed:8914854). Catalyzes predominantly the oxidation of the terminal carbon (omega-oxidation) of saturated and unsaturated fatty acids, the catalytic efficiency decreasing in the following order: dodecanoic > tetradecanoic > (9Z)-octadecenoic > (9Z,12Z)-octadecadienoic > hexadecanoic acid (PubMed:10553002, PubMed:10660572). Acts as a major omega-hydroxylase for dodecanoic (lauric) acid in liver (PubMed:15611369, PubMed:1739747, PubMed:7679927, PubMed:8914854). Participates in omega-hydroxylation of (5Z,8Z,11Z,14Z)-eicosatetraenoic acid (arachidonate) to 20-hydroxyeicosatetraenoic acid (20-HETE), a signaling molecule acting both as vasoconstrictive and natriuretic with overall effect on arterial blood pressure (PubMed:10620324, PubMed:10660572, PubMed:15611369). Can also catalyze the oxidation of the penultimate carbon (omega-1 oxidation) of fatty acids with lower efficiency (PubMed:7679927). May contribute to the degradation of saturated very long-chain fatty acids (VLCFAs) such as docosanoic acid, by catalyzing successive omega-oxidations to the corresponding dicarboxylic acid, thereby initiating chain shortening (PubMed:18182499). Omega-hydroxylates (9R,10S)-epoxy-octadecanoate stereoisomer (PubMed:15145985). Plays a minor role in omega-oxidation of long-chain 3-hydroxy fatty acids (PubMed:18065749). Has little activity toward prostaglandins A1 and E1 (PubMed:7679927)
- Specific Function
- alkane 1-monooxygenase activity
- Gene Name
- CYP4A11
- Uniprot ID
- Q02928
- Uniprot Name
- Cytochrome P450 4A11
- Molecular Weight
- 59347.31 Da
References
- Cummings BS, Lasker JM, Lash LH: Expression of glutathione-dependent enzymes and cytochrome P450s in freshly isolated and primary cultures of proximal tubular cells from human kidney. J Pharmacol Exp Ther. 2000 May;293(2):677-85. [Article]
- Savas U, Hsu MH, Johnson EF: Differential regulation of human CYP4A genes by peroxisome proliferators and dexamethasone. Arch Biochem Biophys. 2003 Jan 1;409(1):212-20. doi: 10.1016/s0003-9861(02)00499-x. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the biosynthesis of adrenal corticoids (PubMed:12530636, PubMed:1518866, PubMed:1775135, PubMed:18215163, PubMed:23322723). Catalyzes a variety of reactions that are essential for many species, including detoxification, defense, and the formation of endogenous chemicals like steroid hormones. Steroid 11beta, 18- and 19-hydroxylase with preferred regioselectivity at 11beta, then 18, and lastly 19 (By similarity). Catalyzes the hydroxylation of 11-deoxycortisol and 11-deoxycorticosterone (21-hydroxyprogesterone) at 11beta position, yielding cortisol or corticosterone, respectively, but cannot produce aldosterone (PubMed:12530636, PubMed:1518866, PubMed:1775135, PubMed:18215163, PubMed:23322723). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate for hydroxylation and reducing the second into a water molecule. Two electrons are provided by NADPH via a two-protein mitochondrial transfer system comprising flavoprotein FDXR (adrenodoxin/ferredoxin reductase) and nonheme iron-sulfur protein FDX1 or FDX2 (adrenodoxin/ferredoxin) (PubMed:18215163). Due to its lack of 18-oxidation activity, it is incapable of generating aldosterone (PubMed:23322723). Could also be involved in the androgen metabolic pathway (Probable)
- Specific Function
- corticosterone 18-monooxygenase activity
- Gene Name
- CYP11B1
- Uniprot ID
- P15538
- Uniprot Name
- Cytochrome P450 11B1, mitochondrial
- Molecular Weight
- 57572.44 Da
References
- Fardella CE, Pinto M, Mosso L, Gomez-Sanchez C, Jalil J, Montero J: Genetic study of patients with dexamethasone-suppressible aldosteronism without the chimeric CYP11B1/CYP11B2 gene. J Clin Endocrinol Metab. 2001 Oct;86(10):4805-7. doi: 10.1210/jcem.86.10.7920. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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
- Cummings DM, Larijani GE, Conner DP, Ferguson RK, Rocci ML Jr: Characterization of dexamethasone binding in normal and uremic human serum. DICP. 1990 Mar;24(3):229-31. doi: 10.1177/106002809002400301. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitorInducer
- 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
- Geick A, Eichelbaum M, Burk O: Nuclear receptor response elements mediate induction of intestinal MDR1 by rifampin. J Biol Chem. 2001 May 4;276(18):14581-7. Epub 2001 Jan 31. [Article]
- Romiti N, Tramonti G, Chieli E: Influence of different chemicals on MDR-1 P-glycoprotein expression and activity in the HK-2 proximal tubular cell line. Toxicol Appl Pharmacol. 2002 Sep 1;183(2):83-91. [Article]
- Schuetz JD, Silverman JA, Thottassery JV, Furuya KN, Schuetz EG: Divergent regulation of the class II P-glycoprotein gene in primary cultures of hepatocytes versus H35 hepatoma by glucocorticoids. Cell Growth Differ. 1995 Oct;6(10):1321-32. [Article]
- Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [Article]
- Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. [Article]
- Adachi Y, Suzuki H, Sugiyama Y: Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8. [Article]
- Yates CR, Chang C, Kearbey JD, Yasuda K, Schuetz EG, Miller DD, Dalton JT, Swaan PW: Structural determinants of P-glycoprotein-mediated transport of glucocorticoids. Pharm Res. 2003 Nov;20(11):1794-803. [Article]
- Schinkel AH, Wagenaar E, van Deemter L, Mol CA, Borst P: Absence of the mdr1a P-Glycoprotein in mice affects tissue distribution and pharmacokinetics of dexamethasone, digoxin, and cyclosporin A. J Clin Invest. 1995 Oct;96(4):1698-705. [Article]
- Matoulkova P, Pavek P, Maly J, Vlcek J: Cytochrome P450 enzyme regulation by glucocorticoids and consequences in terms of drug interaction. Expert Opin Drug Metab Toxicol. 2014 Mar;10(3):425-35. doi: 10.1517/17425255.2014.878703. Epub 2014 Jan 23. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- 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
- VanWert AL, Gionfriddo MR, Sweet DH: Organic anion transporters: discovery, pharmacology, regulation and roles in pathophysiology. Biopharm Drug Dispos. 2010 Jan;31(1):1-71. doi: 10.1002/bdd.693. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Catalyzes the transport of the major hydrophobic bile salts, such as taurine and glycine-conjugated cholic acid across the canalicular membrane of hepatocytes in an ATP-dependent manner, therefore participates in hepatic bile acid homeostasis and consequently to lipid homeostasis through regulation of biliary lipid secretion in a bile salts dependent manner (PubMed:15791618, PubMed:16332456, PubMed:18985798, PubMed:19228692, PubMed:20010382, PubMed:20398791, PubMed:22262466, PubMed:24711118, PubMed:29507376, PubMed:32203132). Transports taurine-conjugated bile salts more rapidly than glycine-conjugated bile salts (PubMed:16332456). Also transports non-bile acid compounds, such as pravastatin and fexofenadine in an ATP-dependent manner and may be involved in their biliary excretion (PubMed:15901796, PubMed:18245269)
- Specific Function
- ABC-type bile acid transporter activity
- Gene Name
- ABCB11
- Uniprot ID
- O95342
- Uniprot Name
- Bile salt export pump
- Molecular Weight
- 146405.83 Da
References
- Fardel O, Payen L, Courtois A, Vernhet L, Lecureur V: Regulation of biliary drug efflux pump expression by hormones and xenobiotics. Toxicology. 2001 Oct 5;167(1):37-46. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- ATP-dependent transporter of the ATP-binding cassette (ABC) family that binds and hydrolyzes ATP to enable active transport of various substrates including many drugs, toxicants and endogenous compound across cell membranes. Transports a wide variety of conjugated organic anions such as sulfate-, glucuronide- and glutathione (GSH)-conjugates of endo- and xenobiotics substrates (PubMed:10220572, PubMed:10421658, PubMed:11500505, PubMed:16332456). Mediates hepatobiliary excretion of mono- and bis-glucuronidated bilirubin molecules and therefore play an important role in bilirubin detoxification (PubMed:10421658). Mediates also hepatobiliary excretion of others glucuronide conjugates such as 17beta-estradiol 17-glucosiduronic acid and leukotriene C4 (PubMed:11500505). Transports sulfated bile salt such as taurolithocholate sulfate (PubMed:16332456). Transports various anticancer drugs, such as anthracycline, vinca alkaloid and methotrexate and HIV-drugs such as protease inhibitors (PubMed:10220572, PubMed:11500505, PubMed:12441801). Confers resistance to several anti-cancer drugs including cisplatin, doxorubicin, epirubicin, methotrexate, etoposide and vincristine (PubMed:10220572, PubMed:11500505)
- Specific Function
- ABC-type glutathione S-conjugate transporter activity
- Gene Name
- ABCC2
- Uniprot ID
- Q92887
- Uniprot Name
- ATP-binding cassette sub-family C member 2
- Molecular Weight
- 174205.64 Da
References
- Demeule M, Jodoin J, Beaulieu E, Brossard M, Beliveau R: Dexamethasone modulation of multidrug transporters in normal tissues. FEBS Lett. 1999 Jan 15;442(2-3):208-14. [Article]
- Schrenk D, Baus PR, Ermel N, Klein C, Vorderstemann B, Kauffmann HM: Up-regulation of transporters of the MRP family by drugs and toxins. Toxicol Lett. 2001 Mar 31;120(1-3):51-7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Broad substrate specificity ATP-dependent transporter of the ATP-binding cassette (ABC) family that actively extrudes a wide variety of physiological compounds, dietary toxins and xenobiotics from cells (PubMed:11306452, PubMed:12958161, PubMed:19506252, PubMed:20705604, PubMed:28554189, PubMed:30405239, PubMed:31003562). Involved in porphyrin homeostasis, mediating the export of protoporphyrin IX (PPIX) from both mitochondria to cytosol and cytosol to extracellular space, it also functions in the cellular export of heme (PubMed:20705604, PubMed:23189181). Also mediates the efflux of sphingosine-1-P from cells (PubMed:20110355). Acts as a urate exporter functioning in both renal and extrarenal urate excretion (PubMed:19506252, PubMed:20368174, PubMed:22132962, PubMed:31003562, PubMed:36749388). In kidney, it also functions as a physiological exporter of the uremic toxin indoxyl sulfate (By similarity). Also involved in the excretion of steroids like estrone 3-sulfate/E1S, 3beta-sulfooxy-androst-5-en-17-one/DHEAS, and other sulfate conjugates (PubMed:12682043, PubMed:28554189, PubMed:30405239). Mediates the secretion of the riboflavin and biotin vitamins into milk (By similarity). Extrudes pheophorbide a, a phototoxic porphyrin catabolite of chlorophyll, reducing its bioavailability (By similarity). Plays an important role in the exclusion of xenobiotics from the brain (Probable). It confers to cells a resistance to multiple drugs and other xenobiotics including mitoxantrone, pheophorbide, camptothecin, methotrexate, azidothymidine, and the anthracyclines daunorubicin and doxorubicin, through the control of their efflux (PubMed:11306452, PubMed:12477054, PubMed:15670731, PubMed:18056989, PubMed:31254042). In placenta, it limits the penetration of drugs from the maternal plasma into the fetus (By similarity). May play a role in early stem cell self-renewal by blocking differentiation (By similarity)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCG2
- Uniprot ID
- Q9UNQ0
- Uniprot Name
- Broad substrate specificity ATP-binding cassette transporter ABCG2
- Molecular Weight
- 72313.47 Da
References
- Elahian F, Kalalinia F, Behravan J: Evaluation of indomethacin and dexamethasone effects on BCRP-mediated drug resistance in MCF-7 parental and resistant cell lines. Drug Chem Toxicol. 2010 Apr;33(2):113-9. doi: 10.3109/01480540903390000. [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
- Kullak-Ublick GA, Fisch T, Oswald M, Hagenbuch B, Meier PJ, Beuers U, Paumgartner G: Dehydroepiandrosterone sulfate (DHEAS): identification of a carrier protein in human liver and brain. FEBS Lett. 1998 Mar 13;424(3):173-6. [Article]
- Bossuyt X, Muller M, Hagenbuch B, Meier PJ: Polyspecific drug and steroid clearance by an organic anion transporter of mammalian liver. J Pharmacol Exp Ther. 1996 Mar;276(3):891-6. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 29, 2024 18:17