Explore a selection of our essential drug information below, or:
Identification
- Summary
Econazole is a topical antifungal used to treat tinea pedis, tinea cruris, tinea corporis, cutaneous candidiasis and tinea versicolor.
- Brand Names
- Ecoza
- Generic Name
- Econazole
- DrugBank Accession Number
- DB01127
- Background
A broad spectrum antimycotic with some action against Gram positive bacteria. It is used topically in dermatomycoses also orally and parenterally.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Econazole (DB01127)
- Weight
- Average: 381.684
Monoisotopic: 380.024996233 - Chemical Formula
- C18H15Cl3N2O
- Synonyms
- (+-)-Econazole
- Econazol
- Econazole
Pharmacology
- Indication
For topical application in the treatment of tinea pedis, tinea cruris, and tinea corporis caused by Trichophyton rubrum, Trichophyton mentagrophytes, Trichophyton tonsurans, Microsporum canis, Microsporum audouini, Microsporum gypseum, and Epidermophyton floccosum, in the treatment of cutaneous candidiasis, and in the treatment of tinea versicolor.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Allergy skin Combination Product in combination with: Triamcinolone (DB00620) •••••••••••• ••••• Treatment of Balanitis candida •••••••••••• Used in combination to treat Fungal infectious disorders of the beard Combination Product in combination with: Triamcinolone (DB00620) •••••••••••• •••••••• Used in combination to treat Fungal skin infection Combination Product in combination with: Triamcinolone (DB00620) •••••••••••• •••••••••••• •••••••• ••••• Used in combination to treat Fungal skin infection Combination Product in combination with: Triamcinolone (DB00620) •••••••••••• •••••• ••••• •••••••••••• ••••••••• •••••••• - 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
Econazole is an antifungal medication related to fluconazole (Diflucan), ketoconazole (Nizoral), itraconazole (Sporanox), and clotrimazole (Lotrimin, Mycelex). Econazole prevents fungal organisms from producing vital substances required for growth and function. This medication is effective only for infections caused by fungal organisms. It will not work for bacterial or viral infections.
- Mechanism of action
Econazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Econazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis.
Target Actions Organism ALanosterol 14-alpha demethylase antagonistYeast UNuclear receptor subfamily 1 group I member 2 partial agonistHumans - Absorption
After topical application to the skin of normal subjects, systemic absorption of econazole nitrate is extremely low. Although most of the applied drug remains on the skin surface, drug concentrations were found in the stratum corneum which, by far, exceeded the minimum inhibitory concentration for dermatophytes.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hepatic.
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- 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
Overdosage of econazole in humans has not been reported to date. In mice, rats guinea pigs and dogs, the oral LD 50 values were found to be 462, 668, 272, and > 160 mg/kg, respectively.
- 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 softwareAdagrasib The serum concentration of Adagrasib can be increased when it is combined with Econazole. Alfuzosin The metabolism of Alfuzosin can be decreased when combined with Econazole. Asciminib The serum concentration of Asciminib can be increased when it is combined with Econazole. Atogepant The serum concentration of Atogepant can be increased when it is combined with Econazole. Avanafil The metabolism of Avanafil can be decreased when combined with Econazole. - Food Interactions
- No interactions found.
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 Econazole nitrate H438WYN10E 24169-02-6 DDXORDQKGIZAME-UHFFFAOYSA-N - International/Other Brands
- Ecostatin (Bristol-Myers Squibb) / Gyno-Pevaryl (Janssen) / Ifenec (Italfarmaco) / Palavale (Otsuka Pharmaceutical) / Pevaryl (Janssen)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Econasil Kit 10 mg/1g Topical PureTek Corporation 2020-03-25 2021-04-30 US 
Econazole Nitrate Cream Cream 10 mg/1g Topical Alvogen Inc. 2017-09-07 2019-09-01 US Econazole Nitrate Cream Cream 10 mg/1g Topical Lake Erie Medical DBA Quality Care Products LLC 2018-06-15 2019-10-11 US Econazole Nitrate Topical Foam, 1% Aerosol, foam 10 mg/1g Topical Xiromed Llc 2016-12-09 2017-05-02 US Ecostatin Cream 1% Cream 1 % Topical Bristol Myers Squibb 1982-12-31 2006-09-05 Canada 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Econazole Nitrate Cream 10 mg/1g Topical McKesson Corporation 2013-08-01 Not applicable US Econazole Nitrate Cream 10 mg/1g Topical Prasco Laboratories 2007-09-01 2015-02-28 US Econazole Nitrate Cream 10 mg/1g Topical bryant ranch prepack 2006-08-08 Not applicable US Econazole Nitrate Cream 10 mg/1g Topical Preferred Pharmaceuticals Inc. 2018-06-06 Not applicable US Econazole Nitrate Cream 10 mg/1g Topical Mylan Pharmaceuticals Inc. 2018-10-02 2020-01-31 US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image GYNO-PEVARYL DEPOT VAGINAL SUPPOSITORY 150 mg Suppository 150 mg Vaginal JOHNSON & JOHNSON PTE. LTD. 1989-06-05 Not applicable Singapore 
อีคอน Cream 1 %w/w Topical บริษัท เยนเนอร์ราลดรั๊กส์เฮ้าส์ จำกัด 1986-05-28 Not applicable Thailand 
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image AECORAS OINTMENT Econazole nitrate (1 %) + Triamcinolone acetonide (0.1 %) Ointment Topical DUOPHARMA (M) SDN. BHD. 2020-09-08 2022-02-08 Malaysia 
ECOCORT CREAM Econazole nitrate (1 %) + Triamcinolone acetonide (0.1 %) Cream Topical HOE PHARMACEUTICALS SDN. BHD. 2020-09-08 Not applicable Malaysia ECOCORT CREAM Econazole nitrate (1 %w/w) + Triamcinolone acetonide (0.1 %w/w) Cream Topical ZUELLIG PHARMA PTE. LTD. 1998-09-10 Not applicable Singapore ECOCORT CREAM Econazole nitrate (1 g/100g) + Triamcinolone acetonide (100 mg/100g) Cream บริษัท ซิลลิค ฟาร์มา จำกัด 2018-07-03 Not applicable Thailand Econavix Econazole nitrate (10 mg/1g) + Econazole nitrate (10 mg/1g) + Econazole nitrate (10 mg/1g) Kit Topical Primary Pharmaceuticals, Inc. 2020-12-20 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 071023 Econazole Nitrate 1% / Niacinamide 4% Econazole nitrate (1 g/100g) + Nicotinamide (4 g/100g) Cream Topical Sincerus Florida, LLC 2020-07-02 Not applicable US Econasil Econazole nitrate (10 mg/1g) Kit Topical PureTek Corporation 2020-03-25 2021-04-30 US Econazole Nitrate 1% / Niacinamide 4% Econazole nitrate (1 g/100g) + Nicotinamide (4 g/100g) Cream Topical Sincerus Florida, LLC 2019-05-20 Not applicable US PM External Econazole nitrate (10 mg/1mL) + Levomenthol (20 mg/1mL) + Lidocaine (20 mg/1mL) + Salicylic acid (100 mg/1mL) Solution Topical OASIS TRADING 2018-11-15 Not applicable US Triamazole Econazole nitrate (10 mg/1g) + Triamcinolone acetonide (1 mg/1g) Kit Topical PureTek Corporation 2020-12-15 Not applicable US
Categories
- ATC Codes
- G01AF05 — Econazole
- G01AF — Imidazole derivatives
- G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
- G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- D01AC — Imidazole and triazole derivatives
- D01A — ANTIFUNGALS FOR TOPICAL USE
- D01 — ANTIFUNGALS FOR DERMATOLOGICAL USE
- D — DERMATOLOGICALS
- G01AF — Imidazole derivatives
- G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
- G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- Drug Categories
- 14-alpha Demethylase Inhibitors
- Anti-Infective Agents
- Antifungal Agents
- Antifungal Agents (Vaginal)
- Antifungals for Dermatological Use
- Antifungals for Topical Use
- Azole Antifungals
- Cytochrome P-450 CYP2E1 Inhibitors
- Cytochrome P-450 CYP2E1 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strong)
- Cytochrome P-450 Enzyme Inhibitors
- Dermatologicals
- Enzyme Inhibitors
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Hormone Antagonists
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Imidazole and Triazole Derivatives
- Imidazole Derivatives
- Imidazoles
- P-glycoprotein inhibitors
- Steroid Synthesis Inhibitors
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzylethers
- Direct Parent
- Benzylethers
- Alternative Parents
- Dichlorobenzenes / N-substituted imidazoles / Aryl chlorides / Heteroaromatic compounds / Dialkyl ethers / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organochlorides / Hydrocarbon derivatives
- Substituents
- 1,3-dichlorobenzene / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Azole / Benzylether / Chlorobenzene / Dialkyl ether / Ether
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- imidazoles, ether, dichlorobenzene, monochlorobenzenes (CHEBI:82873)
- Affected organisms
- Yeast and other fungi
Chemical Identifiers
- UNII
- 6Z1Y2V4A7M
- CAS number
- 27220-47-9
- InChI Key
- LEZWWPYKPKIXLL-UHFFFAOYSA-N
- InChI
- InChI=1S/C18H15Cl3N2O/c19-14-3-1-13(2-4-14)11-24-18(10-23-8-7-22-12-23)16-6-5-15(20)9-17(16)21/h1-9,12,18H,10-11H2
- IUPAC Name
- 1-{2-[(4-chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole
- SMILES
- ClC1=CC=C(COC(CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=C1
References
- Synthesis Reference
Godefroi, E.F. and Heeres, J.; U.S. Patent 3,717,655; February 20,1973; assigned to Jansen Pharmaceutica NV, Belgium.
US3717655- General References
- AIFA Product Information: Pevaryl (econazole) for vaginal use [Link]
- External Links
- Human Metabolome Database
- HMDB0015259
- KEGG Drug
- D03936
- KEGG Compound
- C08068
- PubChem Compound
- 3198
- PubChem Substance
- 46508881
- ChemSpider
- 3086
- BindingDB
- 31773
- 3743
- ChEBI
- 82873
- ChEMBL
- CHEMBL808
- Therapeutic Targets Database
- DAP001269
- PharmGKB
- PA164746010
- Guide to Pharmacology
- GtP Drug Page
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Econazole
- FDA label
- Download (203 KB)
- MSDS
- Download (72.9 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 data3 Completed Treatment Tinea Pedis 3 somestatus stop reason just information to hide 2 Completed Treatment Interdigital Tinea Pedis 1 somestatus stop reason just information to hide 2 Completed Treatment Onychomycosis 1 somestatus stop reason just information to hide 2 Completed Treatment Tinea Pedis 1 somestatus stop reason just information to hide 1 Completed Other Healthy Volunteers (HV) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- DPT Laboratories Ltd.
- E. Fougera and Co.
- Medisca Inc.
- Ortho Mcneil Janssen Pharmaceutical Inc.
- Perrigo Co.
- Pharmedix
- Physicians Total Care Inc.
- Prasco Labs
- Preferred Pharmaceuticals Inc.
- Prescript Pharmaceuticals
- Rebel Distributors Corp.
- Taro Pharmaceuticals USA
- Dosage Forms
Form Route Strength Solution Vaginal Cream Topical 1 % w/w Powder Topical Emulsion Topical 1 % Insert Vaginal 150 MG Powder Topical 1 % Solution Vaginal 100 MG Kit Topical Cream Topical 10 mg/1 Cream Topical 10 mg/1g Cream Topical Aerosol, foam Topical 10 mg/1g Cream Topical 1 % Spray Topical 1 % Emulsion Topical Solution Topical 10 mg Cream Topical 10 mg/g Cream Vaginal 10 mg/g Solution Vaginal 1 MG/ML Cream Vaginal Suppository Vaginal 150 mg Cream Vaginal 1 % Gel Topical 1 % Insert Vaginal 50 MG Solution Topical 1 % Cream Topical Insert Vaginal Aerosol, foam Topical 1 % Douche Vaginal 0.3 g/100ml Cream Topical 10 mg/g Cream Topical 1 g Cream Cutaneous Emulsion Topical Solution Topical Aerosol, foam Topical Solution Topical Spray Cutaneous 1 % Ointment Topical Kit Topical 10 mg/1g Cream Topical 1 %w/w Cream - Prices
Unit description Cost Unit Econazole Nitrate 1% Cream 85 gm Tube 73.63USD tube Econazole Nitrate 1% Cream 30 gm Tube 32.16USD tube Econazole Nitrate 1% Cream 15 gm Tube 19.32USD tube Econazole nitrate powder 2.5USD g Spectazole 1% cream 1.33USD g Econazole nitrate 1% cream 0.93USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5993830 No 1999-11-30 2018-01-16 US US10071054 No 2018-09-11 2031-08-08 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 162 Godefroi, E.F. and Heeres, J.; U.S. Patent 3,717,655; February 20,1973; assigned to Jansen Pharmaceutica NV, Belgium. logP 5.5 Not Available - Predicted Properties
Property Value Source Water Solubility 0.00148 mg/mL ALOGPS logP 4.67 ALOGPS logP 5.35 Chemaxon logS -5.4 ALOGPS pKa (Strongest Basic) 6.48 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 27.05 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 98.26 m3·mol-1 Chemaxon Polarizability 37.37 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9735 Blood Brain Barrier + 0.9823 Caco-2 permeable + 0.6096 P-glycoprotein substrate Non-substrate 0.545 P-glycoprotein inhibitor I Non-inhibitor 0.7958 P-glycoprotein inhibitor II Inhibitor 0.8387 Renal organic cation transporter Inhibitor 0.6806 CYP450 2C9 substrate Non-substrate 0.8407 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.7017 CYP450 1A2 substrate Inhibitor 0.9472 CYP450 2C9 inhibitor Inhibitor 0.939 CYP450 2D6 inhibitor Inhibitor 0.9413 CYP450 2C19 inhibitor Inhibitor 0.9591 CYP450 3A4 inhibitor Inhibitor 0.8861 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.9961 Ames test Non AMES toxic 0.9133 Carcinogenicity Non-carcinogens 0.853 Biodegradation Not ready biodegradable 0.9933 Rat acute toxicity 2.8478 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5 hERG inhibition (predictor II) Inhibitor 0.8505
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 170.2619752 predictedDarkChem Lite v0.1.0 [M-H]- 182.86502 predictedDeepCCS 1.0 (2019) [M+H]+ 171.6491752 predictedDarkChem Lite v0.1.0 [M+H]+ 185.3168 predictedDeepCCS 1.0 (2019) [M+Na]+ 170.7207752 predictedDarkChem Lite v0.1.0 [M+Na]+ 193.30585 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Yeast
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Sterol 14-demethylase activity
- Specific Function
- Catalyzes C14-demethylation of lanosterol which is critical for ergosterol biosynthesis. It transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
- Gene Name
- ERG11
- Uniprot ID
- P10613
- Uniprot Name
- Lanosterol 14-alpha demethylase
- Molecular Weight
- 60674.965 Da
References
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Warrilow AG, Martel CM, Parker JE, Melo N, Lamb DC, Nes WD, Kelly DE, Kelly SL: Azole binding properties of Candida albicans sterol 14-alpha demethylase (CaCYP51). Antimicrob Agents Chemother. 2010 Oct;54(10):4235-45. doi: 10.1128/AAC.00587-10. Epub 2010 Jul 12. [Article]
- Strushkevich N, Usanov SA, Park HW: Structural basis of human CYP51 inhibition by antifungal azoles. J Mol Biol. 2010 Apr 9;397(4):1067-78. doi: 10.1016/j.jmb.2010.01.075. Epub 2010 Feb 10. [Article]
- Jackson CJ, Lamb DC, Kelly DE, Kelly SL: Bactericidal and inhibitory effects of azole antifungal compounds on Mycobacterium smegmatis. FEMS Microbiol Lett. 2000 Nov 15;192(2):159-62. [Article]
- Pietila MP, Vohra PK, Sanyal B, Wengenack NL, Raghavakaimal S, Thomas CF Jr: Cloning and characterization of CYP51 from Mycobacterium avium. Am J Respir Cell Mol Biol. 2006 Aug;35(2):236-42. Epub 2006 Mar 16. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Partial 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
- Svecova L, Vrzal R, Burysek L, Anzenbacherova E, Cerveny L, Grim J, Trejtnar F, Kunes J, Pour M, Staud F, Anzenbacher P, Dvorak Z, Pavek P: Azole antimycotics differentially affect rifampicin-induced pregnane X receptor-mediated CYP3A4 gene expression. Drug Metab Dispos. 2008 Feb;36(2):339-48. Epub 2007 Nov 12. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- A cytochrome P450 monooxygenase that catalyzes the conversion of C19 androgens, androst-4-ene-3,17-dione (androstenedione) and testosterone to the C18 estrogens, estrone and estradiol, respectively (PubMed:27702664, PubMed:2848247). Catalyzes three successive oxidations of C19 androgens: two conventional oxidations at C19 yielding 19-hydroxy and 19-oxo/19-aldehyde derivatives, followed by a third oxidative aromatization step that involves C1-beta hydrogen abstraction combined with cleavage of the C10-C19 bond to yield a phenolic A ring and formic acid (PubMed:20385561). Alternatively, the third oxidative reaction yields a 19-norsteroid and formic acid. Converts dihydrotestosterone to delta1,10-dehydro 19-nordihydrotestosterone and may play a role in homeostasis of this potent androgen (PubMed:22773874). Also displays 2-hydroxylase activity toward estrone (PubMed:22773874). 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:20385561, PubMed:22773874)
- Specific Function
- Aromatase activity
- Gene Name
- CYP19A1
- Uniprot ID
- P11511
- Uniprot Name
- Aromatase
- Molecular Weight
- 57882.48 Da
References
- Ayub M, Levell MJ: The inhibition of human prostatic aromatase activity by imidazole drugs including ketoconazole and 4-hydroxyandrostenedione. Biochem Pharmacol. 1990 Oct 1;40(7):1569-75. doi: 10.1016/0006-2952(90)90456-u. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- 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
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
- Tassaneeyakul W, Birkett DJ, Miners JO: Inhibition of human hepatic cytochrome P4502E1 by azole antifungals, CNS-active drugs and non-steroidal anti-inflammatory agents. Xenobiotica. 1998 Mar;28(3):293-301. doi: 10.1080/004982598239579 . [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- 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
- Monostory K, Hazai E, Vereczkey L: Inhibition of cytochrome P450 enzymes participating in p-nitrophenol hydroxylation by drugs known as CYP2E1 inhibitors. Chem Biol Interact. 2004 Apr 15;147(3):331-40. doi: 10.1016/j.cbi.2004.03.003. [Article]
- Godamudunage MP, Grech AM, Scott EE: Comparison of Antifungal Azole Interactions with Adult Cytochrome P450 3A4 versus Neonatal Cytochrome P450 3A7. Drug Metab Dispos. 2018 Sep;46(9):1329-1337. doi: 10.1124/dmd.118.082032. Epub 2018 Jul 10. [Article]
Drug created at June 13, 2005 13:24 / Updated at May 07, 2021 21:23