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Identification
- Summary
Oxiconazole is a topical antifungal used to treat a variety of dermatophyte infections.
- Brand Names
- Oxistat
- Generic Name
- Oxiconazole
- DrugBank Accession Number
- DB00239
- Background
Oxiconazole is an antifungal agent that is commonly found in topical formulations. It is marketed under the brand names Oxistat and Oxistat, and is used in the treatment of various skin infections such as athlete's foot, jock itch and ringworm.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Oxiconazole (DB00239)
- Weight
- Average: 429.12
Monoisotopic: 426.9812729 - Chemical Formula
- C18H13Cl4N3O
- Synonyms
- 2',4'-Dichloro-2-imidazol-1-ylacetophenone (Z)-[O-(2,4-dichlorobenzyl)oxime]
- Oxiconazol
- Oxiconazole
- Oxiconazolum
- External IDs
- Ro 13-8996
Pharmacology
- Indication
For treatment of dermal fungal infection.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Fungal skin infection •••••••••••• Treatment of Tinea corporis •••••••••••• Treatment of Tinea cruris •••••••••••• Treatment of Tinea pedis •••••••••••• Treatment of Tinea versicolor •••••••••••• - Contraindications & Blackbox Warnings
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Oxiconazole is a broad-spectrum imidazole derivative whose antifungal activity is derived primarily from the inhibition of ergosterol biosynthesis, which is critical for cellular membrane integrity. It has fungicidal or fungistatic activity in vitro against a number of pathogenic fungi including the following dermatophytes, and yeasts: T. rubrum, T. mentagrophytes, T. tonsurans, T. violaceum, E. floccosum, M. canis, M. audouini, M. gypseum, C. albicans, and M. furfur.
- Mechanism of action
Oxiconazole inhibits ergosterol biosynthesis, which is required for cytoplasmic membrane integrity of fungi. It acts to destabilize the fungal cyctochrome P450 51 enzyme (also known as Lanosterol 14-alpha demethylase). This is vital in the cell membrance structure of the fungus. Its inhibition leads to cell lysis. Oxiconazole has also been shown in inhibit DNA synthesis and suppress intracellular concentrations of ATP. Like other imidazole antifungals, Oxiconazole can increase membrane permeability to zinc, augmenting its cytotoxicity.
Target Actions Organism ALanosterol 14-alpha demethylase inhibitorYeast ALanosterol synthase inhibitorYeast UNuclear receptor subfamily 1 group I member 2 partial agonistHumans - Absorption
Systemic absorption of oxiconazole is low.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- 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
Side effects incliude pruritus, burning, irritation, erythema, stinging and allergic contact dermatitis and folliculitis, fissuring, maceration rash and nodules.
- 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 softwareCapmatinib The serum concentration of Capmatinib can be decreased when it is combined with Oxiconazole. Clindamycin The metabolism of Clindamycin can be increased when combined with Oxiconazole. Clozapine The serum concentration of Clozapine can be decreased when it is combined with Oxiconazole. Doxorubicin The serum concentration of Doxorubicin can be decreased when it is combined with Oxiconazole. Lemborexant The serum concentration of Lemborexant can be decreased when it is combined with Oxiconazole. - 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 Oxiconazole nitrate RQ8UL4C17S 64211-46-7 WVNOAGNOIPTWPT-NDUABGMUSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Oxistat Cream 10 mg/1g Topical PharmaDerm a division of Fougera Pharmaceuticals Inc. 1988-12-30 Not applicable US 
Oxistat Cream 10 mg/1g Topical Glaxosmithkline Inc 2006-02-02 2011-12-31 US Oxistat Lotion 10 mg/1mL Topical ANI Pharmaceuticals, Inc. 2022-09-12 Not applicable US Oxistat Lotion 10 mg/1g Topical Pharma Derm, A Division Of Fougera Pharmaceuticals Inc. 2006-01-25 2012-12-04 US Oxistat Lotion 10 mg/1mL Topical Glaxosmithkline Inc 2006-02-02 2011-02-11 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Oxiconazole Nitrate Cream 10 mg/1g Topical Taro Pharmaceuticals U.S.A., Inc. 2016-03-07 Not applicable US Oxiconazole Nitrate Cream 10 mg/1g Topical E. Fougera & Co. a division of Fougera Pharmaceuticals Inc. 2016-03-09 Not applicable US Oxiconazole Nitrate Cream 1% Cream 10 mg/1g Topical Welgo, Llc 2016-08-01 2017-12-31 US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Oxizole Lotion 10 mg / g Topical Stiefel Laboratories, Inc. 1998-05-21 2002-04-02 Canada 
Oxizole Cream 1 % Topical Valeo Pharma Corp. 1998-05-21 2006-07-31 Canada
Categories
- ATC Codes
- D01AC11 — Oxiconazole
- 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
- Anti-Infective Agents
- Antifungal Agents
- Antifungals for Dermatological Use
- Antifungals for Topical Use
- Azole Antifungals
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Substrates
- Dermatologicals
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Imidazole and Triazole Derivatives
- Imidazole Derivatives
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Halobenzenes
- Direct Parent
- Dichlorobenzenes
- Alternative Parents
- N-substituted imidazoles / Aryl chlorides / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organochlorides / Hydrocarbon derivatives
- Substituents
- 1,3-dichlorobenzene / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Azole / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / N-substituted imidazole
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- conazole antifungal drug, imidazoles, imidazole antifungal drug, oxime O-ether, dichlorobenzene (CHEBI:7825)
- Affected organisms
- Fungi
Chemical Identifiers
- UNII
- C668Q9I33J
- CAS number
- 64211-45-6
- InChI Key
- QRJJEGAJXVEBNE-HKOYGPOVSA-N
- InChI
- InChI=1S/C18H13Cl4N3O/c19-13-2-1-12(16(21)7-13)10-26-24-18(9-25-6-5-23-11-25)15-4-3-14(20)8-17(15)22/h1-8,11H,9-10H2/b24-18+
- IUPAC Name
- (Z)-[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethylidene][(2,4-dichlorophenyl)methoxy]amine
- SMILES
- ClC1=CC(Cl)=C(CO\N=C(/CN2C=CN=C2)C2=CC=C(Cl)C=C2Cl)C=C1
References
- Synthesis Reference
- US4124767
- General References
- Matsui H, Sakanashi Y, Oyama TM, Oyama Y, Yokota S, Ishida S, Okano Y, Oyama TB, Nishimura Y: Imidazole antifungals, but not triazole antifungals, increase membrane Zn2+ permeability in rat thymocytes Possible contribution to their cytotoxicity. Toxicology. 2008 Jun 27;248(2-3):142-50. doi: 10.1016/j.tox.2008.03.022. Epub 2008 Apr 7. [Article]
- Fromtling RA: Overview of medically important antifungal azole derivatives. Clin Microbiol Rev. 1988 Apr;1(2):187-217. [Article]
- FDA Approved Drug Products: OXISTAT (oxiconazole nitrate) topical [Link]
- External Links
- KEGG Drug
- D08313
- KEGG Compound
- C08074
- PubChem Compound
- 5353853
- PubChem Substance
- 46504752
- ChemSpider
- 4510239
- BindingDB
- 50051844
- 32638
- ChEBI
- 7825
- ChEMBL
- CHEMBL1262
- ZINC
- ZINC000003873295
- Therapeutic Targets Database
- DAP001204
- PharmGKB
- PA164754742
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Oxiconazole
- FDA label
- Download (33.7 KB)
- MSDS
- Download (24.5 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data1 Completed Treatment Tinea infections 1 somestatus stop reason just information to hide 1 Completed Treatment Tinea Pedis 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Altana inc
- Packagers
- Dispensing Solutions
- GlaxoSmithKline Inc.
- Nycomed Inc.
- Pharmaderm
- Rebel Distributors Corp.
- Dosage Forms
Form Route Strength Cream Topical 1.000 mg Spray Topical 1 % Cream Topical 10 mg/1g Lotion Topical 10 mg/1g Lotion Topical 10 mg/1mL Lotion Topical 30 mg/1g Cream Topical 1 % Lotion Topical 10 mg / g - Prices
Unit description Cost Unit Oxistat 1% Cream 60 gm Tube 157.99USD tube Oxistat 1% Lotion 30ml Bottle 93.13USD bottle Oxistat 1% Cream 30 gm Tube 90.31USD tube Oxistat 1% Cream 15 gm Tube 48.99USD tube Oxistat 1% cream 2.23USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00191 mg/mL ALOGPS logP 5.28 ALOGPS logP 5.84 Chemaxon logS -5.4 ALOGPS pKa (Strongest Basic) 6.74 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 39.41 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 105.95 m3·mol-1 Chemaxon Polarizability 40.79 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9903 Blood Brain Barrier + 0.9699 Caco-2 permeable + 0.5346 P-glycoprotein substrate Non-substrate 0.6346 P-glycoprotein inhibitor I Non-inhibitor 0.7469 P-glycoprotein inhibitor II Inhibitor 0.8492 Renal organic cation transporter Inhibitor 0.8361 CYP450 2C9 substrate Non-substrate 0.8221 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.6122 CYP450 1A2 substrate Inhibitor 0.793 CYP450 2C9 inhibitor Inhibitor 0.6532 CYP450 2D6 inhibitor Non-inhibitor 0.6844 CYP450 2C19 inhibitor Inhibitor 0.8635 CYP450 3A4 inhibitor Inhibitor 0.6477 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8414 Ames test Non AMES toxic 0.7381 Carcinogenicity Non-carcinogens 0.7601 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.5642 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.6542 hERG inhibition (predictor II) Inhibitor 0.507
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0bu3-5923000000-a7d62bf7e3c6df2ca64f Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0001900000-90c48e7e411ea8e9e5b3 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0560-9520800000-ae82942dfd9000942515 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-1111900000-00139fc6e60f7c73abf5 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9100000000-b29501993164113ac90c Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00xr-2911100000-dcc08a2fb32c3a36dca1 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9000000000-87af7e16a152620eb5e2 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 187.36497 predictedDeepCCS 1.0 (2019) [M+H]+ 189.72299 predictedDeepCCS 1.0 (2019) [M+Na]+ 196.20271 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Yeast
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Sterol 14alpha-demethylase that plays a critical role in the third module of ergosterol biosynthesis pathway, being ergosterol the major sterol component in fungal membranes that participates in a variety of functions (PubMed:10393548, PubMed:28258218, PubMed:8647850, PubMed:9559662). The third module or late pathway involves the ergosterol synthesis itself through consecutive reactions that mainly occur in the endoplasmic reticulum (ER) membrane (By similarity). In filamentous fungi, during the initial step of this module, lanosterol (lanosta-8,24-dien-3beta-ol) can be metabolized to eburicol (By similarity). Sterol 14alpha-demethylase catalyzes the three-step oxidative removal of the 14alpha-methyl group (C-32) of both these sterols in the form of formate, and converts eburicol and lanosterol to 14-demethyleburicol (4,4,24-trimethylergosta-8,14,24(28)-trienol) and 4,4-dimethyl-5alpha-cholesta-8,14,24-trien-3beta-ol, respectively, which are further metabolized by other enzymes in the pathway to ergosterol (PubMed:10393548, PubMed:28258218, PubMed:8647850, PubMed:9559662). Can also use substrates not intrinsic to fungi, such as 24,25-dihydrolanosterol (DHL), producing 4,4-dimethyl-8,14-cholestadien-3-beta-ol, but at lower rates than the endogenous substrates (By similarity).
- Specific Function
- heme binding
- Gene Name
- ERG11
- Uniprot ID
- P10613
- Uniprot Name
- Lanosterol 14-alpha demethylase
- Molecular Weight
- 60674.965 Da
References
- Carrillo-Munoz AJ, Giusiano G, Ezkurra PA, Quindos G: Antifungal agents: mode of action in yeast cells. Rev Esp Quimioter. 2006 Jun;19(2):130-9. [Article]
- Rossello A, Bertini S, Lapucci A, Macchia M, Martinelli A, Rapposelli S, Herreros E, Macchia B: Synthesis, antifungal activity, and molecular modeling studies of new inverted oxime ethers of oxiconazole. J Med Chem. 2002 Oct 24;45(22):4903-12. [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
- Yeast
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Lanosterol synthase; part of the third module of ergosterol biosynthesis pathway that includes the late steps of the pathway (PubMed:2185141, PubMed:8486282). ERG7 catalyzes the cyclization of (S)-2,3 oxidosqualene to lanosterol, a reaction that forms the sterol core (PubMed:2185141). The third module or late pathway involves the ergosterol synthesis itself through consecutive reactions that mainly occur in the endoplasmic reticulum (ER) membrane. Firstly, the squalene synthase ERG9 catalyzes the condensation of 2 farnesyl pyrophosphate moieties to form squalene, which is the precursor of all steroids. Squalene synthase is crucial for balancing the incorporation of farnesyl diphosphate (FPP) into sterol and nonsterol isoprene synthesis. Secondly, the squalene epoxidase ERG1 catalyzes the stereospecific oxidation of squalene to (S)-2,3-epoxysqualene, which is considered to be a rate-limiting enzyme in steroid biosynthesis. Then, the lanosterol synthase ERG7 catalyzes the cyclization of (S)-2,3 oxidosqualene to lanosterol, a reaction that forms the sterol core. In the next steps, lanosterol is transformed to zymosterol through a complex process involving various demethylation, reduction and desaturation reactions. The lanosterol 14-alpha-demethylase ERG11 (also known as CYP51) catalyzes C14-demethylation of lanosterol to produce 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol, which is critical for ergosterol biosynthesis. The C-14 reductase ERG24 reduces the C14=C15 double bond of 4,4-dimethyl-cholesta-8,14,24-trienol to produce 4,4-dimethyl-cholesta-8,24-dienol. 4,4-dimethyl-cholesta-8,24-dienol is substrate of the C-4 demethylation complex ERG25-ERG26-ERG27 in which ERG25 catalyzes the three-step monooxygenation required for the demethylation of 4,4-dimethyl and 4alpha-methylsterols, ERG26 catalyzes the oxidative decarboxylation that results in a reduction of the 3-beta-hydroxy group at the C-3 carbon to an oxo group, and ERG27 is responsible for the reduction of the keto group on the C-3. ERG28 has a role as a scaffold to help anchor ERG25, ERG26 and ERG27 to the endoplasmic reticulum and ERG29 regulates the activity of the iron-containing C4-methylsterol oxidase ERG25. Then, the sterol 24-C-methyltransferase ERG6 catalyzes the methyl transfer from S-adenosyl-methionine to the C-24 of zymosterol to form fecosterol. The C-8 sterol isomerase ERG2 catalyzes the reaction which results in unsaturation at C-7 in the B ring of sterols and thus converts fecosterol to episterol. The sterol-C5-desaturase ERG3 then catalyzes the introduction of a C-5 double bond in the B ring to produce 5-dehydroepisterol. The C-22 sterol desaturase ERG5 further converts 5-dehydroepisterol into ergosta-5,7,22,24(28)-tetraen-3beta-ol by forming the C-22(23) double bond in the sterol side chain. Finally, ergosta-5,7,22,24(28)-tetraen-3beta-ol is substrate of the C-24(28) sterol reductase ERG4 to produce ergosterol (Probable).
- Specific Function
- lanosterol synthase activity
- Gene Name
- ERG7
- Uniprot ID
- Q04782
- Uniprot Name
- Lanosterol synthase
- Molecular Weight
- 83713.975 Da
References
- Gebre-Hiwot A, Frommel D: The in-vitro anti-leishmanial activity of inhibitors of ergosterol biosynthesis. J Antimicrob Chemother. 1993 Dec;32(6):837-42. [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
- Unknown
- Actions
- Inducer
- 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
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position (PubMed:18577768). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:20972997). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine. Hydroxylates fenbendazole at the 4' position (PubMed:23959307)
- Specific Function
- (R)-limonene 6-monooxygenase activity
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55944.565 Da
References
- Mahajan MK, Uttamsingh V, Daniels JS, Gan LS, LeDuc BW, Williams DA: In vitro metabolism of oxymetazoline: evidence for bioactivation to a reactive metabolite. Drug Metab Dispos. 2011 Apr;39(4):693-702. doi: 10.1124/dmd.110.036004. Epub 2010 Dec 21. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 05, 2024 06:47