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Identification
- Summary
Clotrimazole is a topical broad-spectrum antifungal agent used for the treatment of a wide variety of dermatophyte infections and candidiasis.
- Brand Names
- Alevazol, Dermacinrx Therazole Pak, Lotriderm, Lotrimin, Lotrimin AF, Lotrisone, Mycelex
- Generic Name
- Clotrimazole
- DrugBank Accession Number
- DB00257
- Background
This drug is a broad spectrum antimycotic or antifungal agent. Clotrimazole's antimycotic properties were discovered in the late 1960s 2. Clotrimazole falls under the imidazole category of azole antifungals, possessing broad-spectrum antimycotic activity 2. It is available in various preparations, including creams, pessaries, and troche formulations (slowly dissolving tablets). As well as its antifungal activity, clotrimazole has become a drug of interest in treating several other diseases such as sickle cell disease, malaria and some cancers 2. The minimal side effect profile of this drug and its uncomplicated metabolic profile have led it to gain widespread acceptance for the treatment of mycotic outbreaks such as vaginal yeast infections as well as athlete's foot 3.
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Clotrimazole (DB00257)
- Weight
- Average: 344.837
Monoisotopic: 344.108026261 - Chemical Formula
- C22H17ClN2
- Synonyms
- 1-((2-Chlorophenyl)diphenylmethyl)-1H-imidazole
- 1-(o-Chloro-α,α-diphenylbenzyl)imidazole
- 1-(o-Chlorotrityl)imidazole
- 1-(α-(2-Chlorophenyl)benzhydryl)imidazole
- Clotrimazol
- Clotrimazole
- Clotrimazolum
- External IDs
- BAY 5097
- BAY-5097
Pharmacology
- Indication
Topical preparations
Clotrimazole topical cream is indicated for the topical treatment of the following dermal infections 12, 15:
Tinea pedis, tinea cruris, and tinea corporis due to Trichophyton rubrum, Trichophyton mentagrophytes, Epidermophyton floccosum
Candidiasis due to Candida albicans
Tinea versicolor due to Malassezia furfur
Diaper rash infected by Candida albicans
In some preparations, clotrimazole may be combined with betamethasone dipropionate, a corticosteroid 15.
Oral preparations
The oral troche preparation is indicated for the local treatment of oropharyngeal candidiasis Label. It is also indicated as a prophylactic drug to reduce the incidence of oropharyngeal candidiasis in patients immunocompromised by conditions such as chemotherapy, radiotherapy, or steroid therapy utilized in the treatment of leukemia, solid tumors, or renal transplantation Label. Troche preparations are not indicated for the treatment of any systemic mycoses Label.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Athlete's foot •••••••••••• ••••• Treatment of Balanitis candida ••• ••• ••••• Used in combination to treat Candidiasis Combination Product in combination with: Dexamethasone (DB01234) •••••••••••• ••••• Treatment of Dermatomycoses ••• ••• ••••• Treatment of Ear infection fungal •••••••••••• •••••••• • ••••• - Contraindications & Blackbox Warnings
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Clotrimazole is a broad-spectrum antifungal agent that inhibits the growth of pathogenic yeasts by changing the permeability of cell membranes. The action of clotrimazole is fungistatic at concentrations of drug up to 20 mcg/mL and may be fungicidal in vitro against Candida albicans and other species of the genus Candida at higher concentrations Label. Unfortunately, resistance to clotrimazole, which was rare in the past, is now common in various patient populations 2.
Clotrimazole is generally considered to be a fungistatic, and not a fungicidal drug, although this contrast is not absolute, as clotrimazole shows fungicidal properties at higher concentrations 2.
- Mechanism of action
Clotrimazole acts primarily by damaging the permeability barrier in the cell membrane of fungi. Clotrimazole causes inhibition of ergosterol biosynthesis, an essential constituent of fungal cell membranes. If ergosterol synthesis is either completely or partially inhibited, the cell is no longer able to construct an intact and functional cell membrane 12,13. Because ergosterol directly promotes the growth of fungal cells in a hormone‐like fashion, rapid onset of the above events leads to dose-dependent inhibition of fungal growth 2.
Though decreased ergosterol, due to the inhibition of lanosterol 14-demethylase (also known as CYP51) 2 is accepted to be primarily responsible for the antimycotic properties of clotrimazole, this drug also shows other pharmacological effects. These include the inhibition of sarcoplasmic reticulum Ca2+‐ATPase, depletion of intracellular calcium, and blocking of calcium‐dependent potassium channels and voltage‐dependent calcium channels 2. The action of clotrimazole on these targets accounts for other effects of this drug that are separate from its antimycotic activities 2.
Target Actions Organism AC-X-C chemokine receptor type 2 modulatorHumans ALanosterol 14-alpha demethylase antagonistinhibitorYeast AIntermediate conductance calcium-activated potassium channel protein 4 inhibitorHumans AErgosterol inhibitorCandida albicans UNuclear receptor subfamily 1 group I member 2 activatorHumans UHydroxycarboxylic acid receptor 2 partial agonistHumans - Absorption
Because clotrimazole is generally not significantly absorbed, drug interactions are not a major issue with its use 2.
- Volume of distribution
The topical form is minimally absorbed in the serum and tissues 12. Clotrimazole is a lipophilic drug 4, and has been shown to be secreted in breastmilk in animal studies 12. There are limited data available regarding the volume of distribution following oral troche administration.
- Protein binding
98% 7
- Metabolism
Hepatic (metabolized to inactive metabolites) 8.
- Route of elimination
Mainly hepatic 8.
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Symptoms of overdose include erythema, stinging, blistering, peeling, edema, pruritus, urticaria, burning, and general irritation of the skin, and cramps. As with all topical agents, skin sensitization may result 12.
Oral LD50 (rat): 708 mg/kg; Intraperitoneal LD50 (rat): 445 mg/kg; Subcutaneous LDLO (rat): 10 g/kg; Oral LD50 (mouse): 761 mg/kg; Subcutaneous LDLO (mouse): 10 g/kg; Intraperitoneal LD50 (mouse): 108 mg/kg;16
Overdose
This drug poses no risk of acute intoxication, as it is unlikely to occur following a single vaginal or dermal application of an overdose (application over a large area under conditions favorable to absorption) or accidental oral ingestion. There is no specific antidote 13.
Effects on Fertility
No human studies of the effects of clotrimazole on fertility have been conducted; however, animal studies have not shown any effects on the drug on fertility 12.
Use in Pregnancy
There are limited data regarding the use of clotrimazole in pregnant women. Animal studies do not show direct or indirect harmful effects on reproduction. Although the topical application of clotrimazole may result in very low serum and tissue levels, the use of clotrimazole topical cream by pregnant women is not recommended unless it is advised by the prescribing physician. Clotrimazole topical cream should not be used in the first trimester of pregnancy unless it is considered by the physician to be essential to patient well-being 12.
Use in Breastfeeding
Available pharmacodynamic/toxicological studies in animals have shown excretion of clotrimazole/metabolites in breastmilk. Clotrimazole should not be administered during breastfeeding. Although the topical application of clotrimazole has resulted in very low serum and tissue levels, the use of clotrimazole topical cream by lactating women is not recommended unless it recommended by the prescribing physician 12.
- 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 softwareAcenocoumarol The therapeutic efficacy of Acenocoumarol can be increased when used in combination with Clotrimazole. Capmatinib The serum concentration of Capmatinib can be decreased when it is combined with Clotrimazole. Clindamycin The metabolism of Clindamycin can be increased when combined with Clotrimazole. Dicoumarol The therapeutic efficacy of Dicoumarol can be increased when used in combination with Clotrimazole. Fluindione The therapeutic efficacy of Fluindione can be increased when used in combination with Clotrimazole. - 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.- International/Other Brands
- Canesten (Bayer) / Canifug (Dr. August Wolff) / Clotrimaderm (Taro) / Empecid (Bayer) / FemCare / Fungicip (Cipla) / Gyne-Lotrimin (Schering-Plough) / Myclo-Derm / Myclo-Gyne
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Lotrimin Solution 10 mg/1mL Topical Physicians Total Care, Inc. 2000-11-03 2005-06-30 US 
Lotrimin Cream 10 mg/1g Topical Physicians Total Care, Inc. 1994-11-28 2005-06-30 US Mycelex Troche 10 mg/1 Oral Physicians Total Care, Inc. 1983-06-17 2011-05-31 US Mycelex Troche 10 mg/1 Oral Bayer Pharmaceuticals Corp 2006-08-14 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Clotrimazole Solution 10 mg/1mL Topical Physicians Total Care, Inc. 1996-07-29 2011-06-30 US Clotrimazole Cream 10 mg/1g Topical Glenmark Pharmaceuticals Inc., USA 2010-08-04 Not applicable US Clotrimazole Solution 10 mg/1mL Topical Taro Pharmaceuticals U.S.A., Inc. 1996-07-29 Not applicable US Clotrimazole Cream 10 mg/1g Topical Proficient Rx LP 1993-08-31 Not applicable US Clotrimazole Lozenge 10 mg/1 Oral; Topical Cardinal Health 2004-07-29 2021-01-31 US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image 1MED Clotrimazole 1% Antifungal Cream Cream 1 g/100g Topical QYK BRANDS LLC 2022-01-01 Not applicable US 1MED Clotrimazole 1% Antifungal Cream Cream 1 g/100g Topical QYK BRANDS LLC 2022-01-01 Not applicable US Akin Anti-fungal Solution 10 mg/1mL Topical Southern Sales & Service, Inc. 2017-01-01 Not applicable US Alevazol Ointment 10 mg/1g Topical Capital Pharmaceutical, LLC 2014-09-01 Not applicable US Anti Fungal Liquid 1 g/100mL Topical Guangzhou Ertiantang Pharmaceutical Co.,ltd 2017-09-22 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ALERTREX Clotrimazole (1 g) + Dexamethasone acetate (0.04 g) + Neomycin (0.5 g) Cream Topical LABORATORIOS COASPHARMA S.A.S. 2017-04-24 2018-12-13 Colombia 
AMZOL FEM® Clotrimazole (100 mg) + Metronidazole (500 mg) Insert Vaginal 2015-12-02 2015-12-02 Colombia ANTIFUNGOL HEXAL 3 KOMBI Clotrimazole (200 mg) + Clotrimazole (10 mg/g) Kit Topical 2006-07-01 Not applicable Germany 
ANTIFUNGOL HEXAL 3 KOMBI Clotrimazole (200 mg) + Clotrimazole (10 mg/g) Kit Topical 2006-07-01 Not applicable Germany ANTIFUNGOL HEXAL 6 KOMBI Clotrimazole (100 mg) + Clotrimazole (10 mg/g) Kit Topical 2010-04-01 Not applicable Germany - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Alevazol Clotrimazole (10 mg/1g) Ointment Topical Capital Pharmaceutical, LLC 2014-09-01 Not applicable US Ciclomazole Clotrimazole (10 mg/1g) + Betamethasone dipropionate (0.5 mg/1g) + Ciclopirox (80 mg/1mL) Cream; Kit; Solution Topical PureTek Corporation 2020-12-17 Not applicable US DermacinRx Therazole Pak Clotrimazole (10 mg/1g) + Betamethasone dipropionate (0.5 mg/1g) + Zinc oxide (200 mg/1g) Kit Topical PureTek Corporation 2016-08-09 Not applicable US Gehwol Nail Protection Pen Clotrimazole (10 mg/1mL) Liquid Topical Eduard Gerlach Gmb H 2008-03-07 2017-04-12 US Shield and Protect Anti-Fungal Clotrimazole (1.1 g/115g) Cream Topical Gentell, Inc. 2007-01-01 Not applicable US
Categories
- ATC Codes
- D01AC01 — Clotrimazole
- D01AC — Imidazole and triazole derivatives
- D01A — ANTIFUNGALS FOR TOPICAL USE
- D01 — ANTIFUNGALS FOR DERMATOLOGICAL USE
- D — DERMATOLOGICALS
- A01AB — Antiinfectives and antiseptics for local oral treatment
- A01A — STOMATOLOGICAL PREPARATIONS
- A01 — STOMATOLOGICAL PREPARATIONS
- A — ALIMENTARY TRACT AND METABOLISM
- 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
- Anti-Infective Agents, Local
- Antifungal Agents
- Antifungal Agents (Vaginal)
- Antifungals for Dermatological Use
- Antifungals for Topical Use
- Antiinfectives and Antiseptics for Local Oral Treatment
- Azole Antifungals
- BSEP/ABCB11 Inhibitors
- BSEP/ABCB11 Substrates
- Cytochrome P-450 CYP2A6 Inhibitors
- Cytochrome P-450 CYP2A6 Inhibitors (strong)
- Cytochrome P-450 CYP2B6 Inducers
- Cytochrome P-450 CYP2B6 Inducers (strength unknown)
- Cytochrome P-450 CYP2B6 Inhibitors
- Cytochrome P-450 CYP2B6 Inhibitors (strong)
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors (moderate)
- Cytochrome P-450 CYP2C8 Inhibitors (strong)
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (moderate)
- Cytochrome P-450 CYP2C9 Inhibitors (strong)
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (moderate)
- Cytochrome P-450 CYP2E1 Inhibitors
- Cytochrome P-450 CYP2E1 Inhibitors (moderate)
- 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 (strength unknown)
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A7 Inducers
- Cytochrome P-450 CYP3A7 Inducers (strong)
- Cytochrome P-450 CYP3A7 Inducers (weak)
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Dermatologicals
- Enzyme Inhibitors
- Gynecological Antiinfectives and Antiseptics
- Hormone Antagonists
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Imidazole and Triazole Derivatives
- Imidazole Derivatives
- Imidazoles
- OATP1B1/SLCO1B1 Inhibitors
- OATP1B1/SLCO1B1 Substrates
- OATP1B3 inducers
- P-glycoprotein inducers
- P-glycoprotein inhibitors
- P-glycoprotein substrates
- Steroid Synthesis Inhibitors
- Stomatological Preparations
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as triphenyl compounds. These are aromatic compounds containing a triphenyl moiety.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Triphenyl compounds
- Sub Class
- Not Available
- Direct Parent
- Triphenyl compounds
- Alternative Parents
- Chlorobenzenes / N-substituted imidazoles / Aryl chlorides / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organochlorides / Hydrocarbon derivatives
- Substituents
- Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Azole / Chlorobenzene / Halobenzene / Heteroaromatic compound / Hydrocarbon derivative / Imidazole
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- conazole antifungal drug, imidazoles, imidazole antifungal drug, monochlorobenzenes (CHEBI:3764) / a small molecule (CPD-8926)
- Affected organisms
- Yeast and other fungi
Chemical Identifiers
- UNII
- G07GZ97H65
- CAS number
- 23593-75-1
- InChI Key
- VNFPBHJOKIVQEB-UHFFFAOYSA-N
- InChI
- InChI=1S/C22H17ClN2/c23-21-14-8-7-13-20(21)22(25-16-15-24-17-25,18-9-3-1-4-10-18)19-11-5-2-6-12-19/h1-17H
- IUPAC Name
- 1-[(2-chlorophenyl)diphenylmethyl]-1H-imidazole
- SMILES
- ClC1=CC=CC=C1C(N1C=CN=C1)(C1=CC=CC=C1)C1=CC=CC=C1
References
- Synthesis Reference
Buechel, K.H., et al; South African Patent 69/0039; January 3, 1969; assigned to Farben- Buechel, K.H., Regel, E. and Plempel, M.; US. Patent 3,660,577; May 2,1972; and U.S. fabriken Bayer AG, Germany. Patent 3,705,172; Dec. 5,1972; both assigned to Farbenfabriken Bayer A.G. (Germany).
US3705172- General References
- Ritter W: Pharmacokinetic fundamentals of vaginal treatment with clotrimazole. Am J Obstet Gynecol. 1985 Aug 1;152(7 Pt 2):945-7. [Article]
- Crowley PD, Gallagher HC: Clotrimazole as a pharmaceutical: past, present and future. J Appl Microbiol. 2014 Sep;117(3):611-7. doi: 10.1111/jam.12554. Epub 2014 Jun 30. [Article]
- S K, C S, Cs K, S W: Clotrimazole as a Cancer Drug: A Short Review. Med Chem (Los Angeles). 2014;4(11):722-724. doi: 10.4172/2161-0444.1000219. [Article]
- Hashem FM, Shaker DS, Ghorab MK, Nasr M, Ismail A: Formulation, characterization, and clinical evaluation of microemulsion containing clotrimazole for topical delivery. AAPS PharmSciTech. 2011 Sep;12(3):879-86. doi: 10.1208/s12249-011-9653-7. Epub 2011 Jul 2. [Article]
- Clotrimazole Drug Summary [Link]
- HMDB Database [Link]
- The binding of Clotrimazole to the proteins of human serum [Link]
- Clotrimazole Cream, DailyMed [Link]
- FDA Approved Drug Products: Lotrisone (clotrimazole/betamethasone dipropionate) topical cream [Link]
- Health Canada Product Monograph: Canesten (clotrimazole) for topical and/or vaginal application [Link]
- Health Canada Product Monograph: Canesten (clotrimazole 1%) topical cream [Link]
- Canesten Monograph [File]
- MedSafe NZ Data Sheet, Clotrimazole [File]
- HPLC Measurement, Bbod Distribution, and Pharmacokinetics of Oral Clotrimazole, Potentially Useful Antisickling Agent [File]
- Lotrisone FDA label [File]
- Clotrimazole SDS [File]
- External Links
- Human Metabolome Database
- HMDB0001922
- KEGG Drug
- D00282
- KEGG Compound
- C06922
- PubChem Compound
- 2812
- PubChem Substance
- 46507927
- ChemSpider
- 2710
- BindingDB
- 31774
- 2623
- ChEBI
- 3764
- ChEMBL
- CHEMBL104
- ZINC
- ZINC000003807804
- Therapeutic Targets Database
- DAP000138
- PharmGKB
- PA449057
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- CL6
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Clotrimazole
- PDB Entries
- 2xfh / 3mdv / 4xe3 / 6h1t / 6uw2 / 7axa / 7axj / 8sg5 / 8spd
- FDA label
- Download (139 KB)
- MSDS
- Download (73.8 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 data4 Completed Health Services Research Renal Failure, Chronic Renal Failure 1 somestatus stop reason just information to hide 4 Completed Treatment Bacterial Vaginosis (BV) / Candidiasis 1 somestatus stop reason just information to hide 4 Completed Treatment Vaginal Infections 1 somestatus stop reason just information to hide 4 Completed Treatment Vulvovaginal Candidiasis 2 somestatus stop reason just information to hide 4 Not Yet Recruiting Treatment Bacterial Vaginosis (BV) / Premature Delivery / Vaginal Dysbiosis 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Schering plough healthcare products inc
- Bayer pharmaceuticals corp
- Glenmark pharmaceuticals inc usa
- Nycomed us inc
- Taro pharmaceuticals usa inc
- Actavis mid atlantic llc
- Taro pharmaceuticals inc
- Schering corp sub schering plough corp
- Teva pharmaceuticals usa inc
- Bayer healthcare pharmaceuticals inc
- Teva pharmaceuticals usa
- Paddock laboratories inc
- Roxane laboratories inc
- Packagers
- Actavis Group
- Alza Corp.
- Bayer Healthcare
- Bergen Brunswig
- Cardinal Health
- CVS Pharmacy
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- E. Fougera and Co.
- H.J. Harkins Co. Inc.
- Ivax Pharmaceuticals
- Major Pharmaceuticals
- Mckesson Corp.
- McNeil Laboratories
- Medisca Inc.
- Neuman Distributors Inc.
- Novartis AG
- Nycomed Inc.
- Ortho Mcneil Janssen Pharmaceutical Inc.
- Paddock Labs
- Palmetto Pharmaceuticals Inc.
- PEDiNOL
- Pharmaceutical Utilization Management Program VA Inc.
- Pharmedix
- Physicians Total Care Inc.
- Preferred Pharmaceuticals Inc.
- Qualitest
- Rebel Distributors Corp.
- Resource Optimization and Innovation LLC
- Rite Aid Corp.
- Roxane Labs
- S&P Healthcare
- Sandhills Packaging Inc.
- Schering Corp.
- Schering-Plough Inc.
- Southwood Pharmaceuticals
- Stat Rx Usa
- Taro Pharmaceuticals USA
- Teva Pharmaceutical Industries Ltd.
- Walgreen Co.
- Warrick Pharmaceuticals Corp.
- Dosage Forms
Form Route Strength Ointment Topical 10 mg/1g Cream Oral; Topical 1 mg Liquid Topical 1 g/100mL Cream Vaginal 20 mg/g Solution Topical 1 % Cream Vaginal 10 mg/g Cream Topical 10 MG/G Solution Topical 10 MG/ML Spray Topical 10 mg/mL Cream Topical 350 mg/35g Lotion Topical 1 g/100mL Solution Cream Vaginal 1000 mg Cream Topical 1 mg Cream Topical 0.01 kg/1kg Cream Topical 1 % w/w Lotion Topical 1 % Cream Cutaneous; Vaginal 10 % w/w Liquid Auricular (otic) 10 mg/1ml Cream Topical 1 % w/w Powder Topical 1 % Powder Topical 1 % w/w Solution Auricular (otic) 1 % Solution / drops Auricular (otic) Lotion Topical 1 % w/v Solution Topical 1 % w/v Gel Vaginal Insert Vaginal Cream Topical 0.025 % w/w Lotion Topical Cream Vaginal 2.0000 g Insert Vaginal 500.0000 mg Capsule; cream Oral; Topical; Vaginal Capsule; cream Oral; Topical Cream 1 % Cream Topical Powder Topical Solution Topical Cream Vaginal 10 g Cream Vaginal 10 % w/w Cream Topical; Vaginal 2 % Suppository Vaginal 200 mg / sup Cream Topical 0.01 g/g Solution Topical 0.01 g/ml Tablet Vaginal Capsule Vaginal 0.5 g Cream; kit; tablet Vaginal Cream; kit Topical; Vaginal Cream; kit; tablet Topical; Vaginal Cream; suppository Topical; Vaginal Cream Topical 1 % Cream Topical; Vaginal 1 % Cream Topical 2 % w/w Tablet Vaginal 0.5 g Tablet Vaginal 200 mg/1 Tablet Vaginal 0.1 g Liquid Topical 1 % Cream Topical 1 g/100g Capsule Vaginal 500 mg Insert Vaginal 500.000 mg Suppository Vaginal 100 mg / sup Cream Topical 100000 g Suppository Vaginal 100 mg/1 Kit Topical 20 G Suppository Vaginal 200 mg/1 Lotion Topical 1 g Cream; kit; solution Topical Solution Topical 10 mg/g Spray Topical 10 mg/g Cream Cutaneous 1 g Solution Topical 1 % w/w Cream Vaginal 2 g Cream Vaginal 2 % w/w Cream Vaginal 1 % w/w Capsule; cream; kit Oral; Topical Cream Topical 0.2 g/1g Suspension Topical 1 g Cream Vaginal 10 MG Solution Topical 1 g Solution Topical 100000 g Insert Vaginal 100 mg Cream Vaginal 200000 g Cream Vaginal 2 % Tablet Vaginal 100 mg/1 Capsule Vaginal 1 g Cream Topical 1000 MG Solution Topical 1000 mg Cream Vaginal 100000 g Cream Topical 1 g/100g Cream Topical 10 mg/1g Cream Topical 50 mg/1g Cream Vaginal 1 g/100g Cream Vaginal 10 mg/1g Cream Vaginal 100 g/1g Liquid Topical 1 mg/1mL Lozenge Oral 10 mg/1 Lozenge Oral; Topical 10 mg/1 Solution Topical 1 g/1mL Solution Topical 10 mg/1mL Cream Topical Cream Vaginal 1 % Capsule Vaginal Cream Topical 10 mg Suppository Vaginal 100 mg Cream Topical 1.00 % w/w Capsule, liquid filled Vaginal 500 mg Cream Vaginal 2 g/100g Solution Topical 1 mg/1mL Cream Topical 1.000 g Cream Topical 1 g Cream Topical 0.01 g/1g Powder Topical Aerosol, spray Topical 1 mL/100mL Aerosol, foam Topical 1 g/100g Liquid Topical 10 g/1000g Gel Topical 0.01 kg/1kg Solution Topical 1 g/100mL Liquid Topical 10 mg/1mL Powder Topical 1 g Liquid Topical 1 mg/100mL Gel Topical 10 mg/1g Solution Topical 0.001 g Spray Topical 4 mg/1mL Powder Topical 1.0 g/100g Gel Topical Cream Cutaneous Cream Topical 6 mg/1mL Solution Oral 10 mg Spray Topical 10 mg Tablet Oral 100 mg Tablet Vaginal Cream Vaginal Capsule Vaginal Insert Vaginal 500 mg Tablet Vaginal 10000000 mg Aerosol Topical 1 g Cream Topical 10 g/1g Ointment Topical 1 mg/100g Ointment Topical 1 g/100g Paste Topical 10 mg/g Insert Vaginal 200 mg Gel Topical 1 g/100g Cream Topical 420 mg/42g Cream Cutaneous 1.000 g Capsule Vaginal 200 mg Lotion Topical Cream Vaginal 2.000 mg Cream Vaginal Insert Vaginal Solution Vaginal Cream Cream Topical 2 g Cream Topical 1.007 g Troche Oral 10 mg/1 Cream Vaginal 50 mg / 5 g Liquid Topical 10 mg / mL Suppository Vaginal 100 mg / tab Cream Topical 10 mg / g Solution Topical 10 mg / mL Cream Topical; Vaginal 10 mg / g Spray Topical 1 % Cream Vaginal 1 g Kit Topical 25 G Cream Topical 0.5 mg/g Cream Vaginal 10000 g Suppository Vaginal 500 mg Aerosol, foam Topical 10 mg/1g Cream Topical 1 g/100mL Solution Oral 10 mg/ml Cream Topical 1.0 g/100g Ointment Topical 2.0 g/100g Cream Topical; Vaginal 1 g Oil Topical 10 mg/1mL Cream Topical 10 mg/1mL Cream Cutaneous 2.000 g Cream Topical 0.01 mg/10g Cream Topical 0.64 mg/g Cream Topical 1.1 g/115g Spray Extracorporeal 0.06 mg/30mL Cream Cutaneous 1.000 g Cream Topical 1 g/1g Cream Vaginal 2.000 g Solution Topical Ointment Topical 1.0 g/100g Kit Topical Cream Cutaneous 1 % w/w Spray Topical Cream Topical 0.02 % Capsule, liquid filled Vaginal Insert Vaginal 200.000 mg Cream Topical 10 mg/100g Tablet Vaginal 200 mg Tablet Vaginal 100 mg Lozenge Oral 10 mg Tablet Vaginal 500 mg Cream Topical 1 %w/w Ointment Topical 1 %w/w - Prices
Unit description Cost Unit Clotrimazole 70 10 mg Troche Bottle 117.04USD bottle Clotrimazole 1% Cream 45 gm Tube 49.99USD tube Clotrimazole 1% Cream 30 gm Tube 35.99USD tube Clotrimazole 1% Solution 30ml Bottle 24.99USD bottle Clotrimazole 1% Cream 15 gm Tube 17.99USD tube Clotrimazole 1% Solution 10ml Bottle 17.99USD bottle Clotrimazole powder 5.2USD g Mycelex 10 mg troche 1.85USD troche Clotrimazole 10 mg troche 1.61USD troche Mycelex-7 100 mg vaginal tablet 1.33USD tablet Lotrimin 1% cream 1.28USD g Gyne-lotrimin insert 1.03USD insert Mycelex 1% cream 0.9USD g Clotrimazole insert 0.86USD insert Lotrimin ultra 1% cream 0.68USD g Clotrimazole 1% cream 0.53USD g Clotrimazole 3 2% cream 0.5USD g Ra clotrimazole 3 cream 0.46USD g Ra athlete's 1% foot cream 0.37USD g Desenex 1% cream 0.33USD g CVS Pharmacy clotrimazole 1% cream 0.32USD g Antifungal 1% cream 0.27USD g Sm antifungal 1% cream 0.25USD g Ra clotrimazole af cream 0.24USD g Clotrim 1% vaginal cream 0.18USD g Lotrimin af 2% spray powder 0.05USD g Lotrimin af 2% liquid spray 0.04USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 148 MSDS water solubility 0.49 mg/L http://www.ijpsonline.com/articles/improvement-of-solubility-and-dissolution-properties-of-clotrimazole-by-solid-dispersions-and-inclusion-complexes.pdf logP 6.1 https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6749186/ pKa 4.1 http://www.ijpsonline.com/articles/improvement-of-solubility-and-dissolution-properties-of-clotrimazole-by-solid-dispersions-and-inclusion-complexes.pdf - Predicted Properties
Property Value Source Water Solubility 0.00147 mg/mL ALOGPS logP 5.48 ALOGPS logP 5.84 Chemaxon logS -5.4 ALOGPS pKa (Strongest Basic) 6.26 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 17.82 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 103.76 m3·mol-1 Chemaxon Polarizability 36.25 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9725 Blood Brain Barrier + 0.9837 Caco-2 permeable + 0.6858 P-glycoprotein substrate Non-substrate 0.7185 P-glycoprotein inhibitor I Non-inhibitor 0.6612 P-glycoprotein inhibitor II Non-inhibitor 0.7884 Renal organic cation transporter Non-inhibitor 0.5854 CYP450 2C9 substrate Non-substrate 0.7898 CYP450 2D6 substrate Non-substrate 0.9149 CYP450 3A4 substrate Non-substrate 0.6262 CYP450 1A2 substrate Inhibitor 0.9106 CYP450 2C9 inhibitor Inhibitor 0.8948 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Inhibitor 0.8994 CYP450 3A4 inhibitor Inhibitor 0.8478 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.9799 Ames test Non AMES toxic 0.7428 Carcinogenicity Non-carcinogens 0.9018 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.7194 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9659 hERG inhibition (predictor II) Inhibitor 0.6779
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 184.5859505 predictedDarkChem Lite v0.1.0 [M-H]- 184.9006505 predictedDarkChem Lite v0.1.0 [M-H]- 176.18741 predictedDeepCCS 1.0 (2019) [M+H]+ 185.4075505 predictedDarkChem Lite v0.1.0 [M+H]+ 185.5582505 predictedDarkChem Lite v0.1.0 [M+H]+ 178.54541 predictedDeepCCS 1.0 (2019) [M+Na]+ 185.1093505 predictedDarkChem Lite v0.1.0 [M+Na]+ 185.3247505 predictedDarkChem Lite v0.1.0 [M+Na]+ 185.62465 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Modulator
- General Function
- Receptor for interleukin-8 which is a powerful neutrophil chemotactic factor (PubMed:1891716). Binding of IL-8 to the receptor causes activation of neutrophils. This response is mediated via a G-protein that activates a phosphatidylinositol-calcium second messenger system (PubMed:8662698). Binds to IL-8 with high affinity. Also binds with high affinity to CXCL3, GRO/MGSA and NAP-2
- Specific Function
- C-c chemokine binding
- Gene Name
- CXCR2
- Uniprot ID
- P25025
- Uniprot Name
- C-X-C chemokine receptor type 2
- Molecular Weight
- 40758.735 Da
References
- 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
- AntagonistInhibitor
- 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
- 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]
- Gachotte D, Pierson CA, Lees ND, Barbuch R, Koegel C, Bard M: A yeast sterol auxotroph (erg25) is rescued by addition of azole antifungals and reduced levels of heme. Proc Natl Acad Sci U S A. 1997 Oct 14;94(21):11173-8. [Article]
- Henry KW, Nickels JT, Edlind TD: Upregulation of ERG genes in Candida species by azoles and other sterol biosynthesis inhibitors. Antimicrob Agents Chemother. 2000 Oct;44(10):2693-700. [Article]
- Lorenz RT, Parks LW: Physiological effects of fenpropimorph on wild-type Saccharomyces cerevisiae and fenpropimorph-resistant mutants. Antimicrob Agents Chemother. 1991 Aug;35(8):1532-7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Forms a voltage-independent potassium channel that is activated by intracellular calcium (PubMed:26148990). Activation is followed by membrane hyperpolarization which promotes calcium influx. Required for maximal calcium influx and proliferation during the reactivation of naive T-cells (PubMed:17157250, PubMed:18796614). Plays a role in the late stages of EGF-induced macropinocytosis (PubMed:24591580)
- Specific Function
- Calcium-activated potassium channel activity
- Gene Name
- KCNN4
- Uniprot ID
- O15554
- Uniprot Name
- Intermediate conductance calcium-activated potassium channel protein 4
- Molecular Weight
- 47695.12 Da
References
- Brugnara C, Gee B, Armsby CC, Kurth S, Sakamoto M, Rifai N, Alper SL, Platt OS: Therapy with oral clotrimazole induces inhibition of the Gardos channel and reduction of erythrocyte dehydration in patients with sickle cell disease. J Clin Invest. 1996 Mar 1;97(5):1227-34. [Article]
- Wu SN, Li HF, Jan CR, Shen AY: Inhibition of Ca2+-activated K+ current by clotrimazole in rat anterior pituitary GH3 cells. Neuropharmacology. 1999 Jul;38(7):979-89. [Article]
- Rufo PA, Jiang L, Moe SJ, Brugnara C, Alper SL, Lencer WI: The antifungal antibiotic, clotrimazole, inhibits Cl- secretion by polarized monolayers of human colonic epithelial cells. J Clin Invest. 1996 Nov 1;98(9):2066-75. doi: 10.1172/JCI119012. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Activator
- 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
- Faucette SR, Wang H, Hamilton GA, Jolley SL, Gilbert D, Lindley C, Yan B, Negishi M, LeCluyse EL: Regulation of CYP2B6 in primary human hepatocytes by prototypical inducers. Drug Metab Dispos. 2004 Mar;32(3):348-58. [Article]
- Smith CM, Faucette SR, Wang H, LeCluyse EL: Modulation of UDP-glucuronosyltransferase 1A1 in primary human hepatocytes by prototypical inducers. J Biochem Mol Toxicol. 2005;19(2):96-108. [Article]
- 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]
- Dring AM, Anderson LE, Qamar S, Stoner MA: Rational quantitative structure-activity relationship (RQSAR) screen for PXR and CAR isoform-specific nuclear receptor ligands. Chem Biol Interact. 2010 Dec 5;188(3):512-25. doi: 10.1016/j.cbi.2010.09.018. Epub 2010 Oct 20. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Partial agonist
- General Function
- Acts as a high affinity receptor for both nicotinic acid (also known as niacin) and (D)-beta-hydroxybutyrate and mediates increased adiponectin secretion and decreased lipolysis through G(i)-protein-mediated inhibition of adenylyl cyclase. This pharmacological effect requires nicotinic acid doses that are much higher than those provided by a normal diet. Mediates nicotinic acid-induced apoptosis in mature neutrophils. Receptor activation by nicotinic acid results in reduced cAMP levels which may affect activity of cAMP-dependent protein kinase A and phosphorylation of target proteins, leading to neutrophil apoptosis. The rank order of potency for the displacement of nicotinic acid binding is 5-methyl pyrazole-3-carboxylic acid = pyridine-3-acetic acid > acifran > 5-methyl nicotinic acid = acipimox >> nicotinuric acid = nicotinamide
- Specific Function
- Nicotinic acid receptor activity
- Gene Name
- HCAR2
- Uniprot ID
- Q8TDS4
- Uniprot Name
- Hydroxycarboxylic acid receptor 2
- Molecular Weight
- 41849.08 Da
References
- Kanno Y, Inouye Y: A consecutive three alanine residue insertion mutant of human CAR: a novel CAR ligand screening system in HepG2 cells. J Toxicol Sci. 2010 Aug;35(4):515-25. [Article]
- Auerbach SS, Ramsden R, Stoner MA, Verlinde C, Hassett C, Omiecinski CJ: Alternatively spliced isoforms of the human constitutive androstane receptor. Nucleic Acids Res. 2003 Jun 15;31(12):3194-207. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- 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
- Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. [Article]
- Ong CE, Coulter S, Birkett DJ, Bhasker CR, Miners JO: The xenobiotic inhibitor profile of cytochrome P4502C8. Br J Clin Pharmacol. 2000 Dec;50(6):573-80. doi: 10.1046/j.1365-2125.2000.00316.x. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitorInducer
- Curator comments
- Several studies provide conflicting evidence of Clotrimazole inducing or inhibiting CYP3A4. The references have been included.
- 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
- Bjornsson TD, Callaghan JT, Einolf HJ, Fischer V, Gan L, Grimm S, Kao J, King SP, Miwa G, Ni L, Kumar G, McLeod J, Obach SR, Roberts S, Roe A, Shah A, Snikeris F, Sullivan JT, Tweedie D, Vega JM, Walsh J, Wrighton SA: The conduct of in vitro and in vivo drug-drug interaction studies: a PhRMA perspective. J Clin Pharmacol. 2003 May;43(5):443-69. [Article]
- 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]
- Shord SS, Chan LN, Camp JR, Vasquez EM, Jeong HY, Molokie RE, Baum CL, Xie H: Effects of oral clotrimazole troches on the pharmacokinetics of oral and intravenous midazolam. Br J Clin Pharmacol. 2010 Feb;69(2):160-6. doi: 10.1111/j.1365-2125.2009.03559.x. [Article]
- Choy M: Tacrolimus interaction with clotrimazole: a concise case report and literature review. P T. 2010 Oct;35(10):568-9. [Article]
- 16, 29. (2008). In Stockley's Drug Interactions (8th ed., pp. 598, 1071-1072). RPS Publishing. [ISBN:085369754X]
- Effects of oral clotrimazole troches on the pharmacokinetics of oral and intravenous midazolam [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- InhibitorInducer
- 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
- Walsky RL, Astuccio AV, Obach RS: Evaluation of 227 drugs for in vitro inhibition of cytochrome P450 2B6. J Clin Pharmacol. 2006 Dec;46(12):1426-38. [Article]
- Faucette SR, Wang H, Hamilton GA, Jolley SL, Gilbert D, Lindley C, Yan B, Negishi M, LeCluyse EL: Regulation of CYP2B6 in primary human hepatocytes by prototypical inducers. Drug Metab Dispos. 2004 Mar;32(3):348-58. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, 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) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
- Specific Function
- Anandamide 11,12 epoxidase activity
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- Data for this enzyme action is based on one in vitro study.
- 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
- Draper AJ, Madan A, Parkinson A: Inhibition of coumarin 7-hydroxylase activity in human liver microsomes. Arch Biochem Biophys. 1997 May 1;341(1):47-61. doi: 10.1006/abbi.1997.9964. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)
- Specific Function
- (r)-limonene 6-monooxygenase activity
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Sweeney BP, Bromilow J: Liver enzyme induction and inhibition: implications for anaesthesia. Anaesthesia. 2006 Feb;61(2):159-77. doi: 10.1111/j.1365-2044.2005.04462.x. [Article]
- Miners JO, Birkett DJ: Cytochrome P4502C9: an enzyme of major importance in human drug metabolism. Br J Clin Pharmacol. 1998 Jun;45(6):525-38. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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
- 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]
- 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
- Unknown
- Actions
- Inducer
- Curator comments
- Enzyme action based on data from one in vitro study
- 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
- Usui T, Saitoh Y, Komada F: Induction of CYP3As in HepG2 cells by several drugs. Association between induction of CYP3A4 and expression of glucocorticoid receptor. Biol Pharm Bull. 2003 Apr;26(4):510-7. doi: 10.1248/bpb.26.510. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- InhibitorInducer
- 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]
- Schuetz EG, Beck WT, Schuetz JD: Modulators and substrates of P-glycoprotein and cytochrome P4503A coordinately up-regulate these proteins in human colon carcinoma cells. Mol Pharmacol. 1996 Feb;49(2):311-8. [Article]
- Ekins S, Kim RB, Leake BF, Dantzig AH, Schuetz EG, Lan LB, Yasuda K, Shepard RL, Winter MA, Schuetz JD, Wikel JH, Wrighton SA: Three-dimensional quantitative structure-activity relationships of inhibitors of P-glycoprotein. Mol Pharmacol. 2002 May;61(5):964-73. [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]
- Bain LJ, LeBlanc GA: Interaction of structurally diverse pesticides with the human MDR1 gene product P-glycoprotein. Toxicol Appl Pharmacol. 1996 Nov;141(1):288-98. [Article]
- Interaction of Cytochrome P450 3A Inhibitors with P-Glycoprotein [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [Article]
- Zhang J, He K, Cai L, Chen YC, Yang Y, Shi Q, Woolf TF, Ge W, Guo L, Borlak J, Tong W: Inhibition of bile salt transport by drugs associated with liver injury in primary hepatocytes from human, monkey, dog, rat, and mouse. Chem Biol Interact. 2016 Aug 5;255:45-54. doi: 10.1016/j.cbi.2016.03.019. Epub 2016 Mar 19. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Mediates the Na(+)-independent uptake of organic anions (PubMed:10358072, PubMed:15159445, PubMed:17412826). Shows broad substrate specificity, can transport both organic anions such as bile acid taurocholate (cholyltaurine) and conjugated steroids (dehydroepiandrosterone 3-sulfate, 17-beta-glucuronosyl estradiol, and estrone 3-sulfate), as well as eicosanoids (prostaglandin E2, thromboxane B2, leukotriene C4, and leukotriene E4), and thyroid hormones (T4/L-thyroxine, and T3/3,3',5'-triiodo-L-thyronine) (PubMed:10358072, PubMed:10601278, PubMed:10873595, PubMed:11159893, PubMed:12196548, PubMed:12568656, PubMed:15159445, PubMed:15970799, PubMed:16627748, PubMed:17412826, PubMed:19129463, PubMed:26979622). Can take up bilirubin glucuronides from plasma into the liver, contributing to the detoxification-enhancing liver-blood shuttling loop (PubMed:22232210). Involved in the clearance of endogenous and exogenous substrates from the liver (PubMed:10358072, PubMed:10601278). Transports coproporphyrin I and III, by-products of heme synthesis, and may be involved in their hepatic disposition (PubMed:26383540). May contribute to regulate the transport of organic compounds in testes across the blood-testis-barrier (Probable). Can transport HMG-CoA reductase inhibitors (also known as statins), such as pravastatin and pitavastatin, a clinically important class of hypolipidemic drugs (PubMed:10601278, PubMed:15159445, PubMed:15970799). May play an important role in plasma and tissue distribution of the structurally diverse chemotherapeutic drug methotrexate (PubMed:23243220). May also transport antihypertension agents, such as the angiotensin-converting enzyme (ACE) inhibitor prodrug enalapril, and the highly selective angiotensin II AT1-receptor antagonist valsartan, in the liver (PubMed:16624871, PubMed:16627748). Shows a pH-sensitive substrate specificity towards prostaglandin E2 and T4 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)
- Specific Function
- Bile acid transmembrane transporter activity
- Gene Name
- SLCO1B1
- Uniprot ID
- Q9Y6L6
- Uniprot Name
- Solute carrier organic anion transporter family member 1B1
- Molecular Weight
- 76447.99 Da
References
- Kalliokoski A, Niemi M: Impact of OATP transporters on pharmacokinetics. Br J Pharmacol. 2009 Oct;158(3):693-705. doi: 10.1111/j.1476-5381.2009.00430.x. Epub 2009 Sep 25. [Article]
- Gui C, Miao Y, Thompson L, Wahlgren B, Mock M, Stieger B, Hagenbuch B: Effect of pregnane X receptor ligands on transport mediated by human OATP1B1 and OATP1B3. Eur J Pharmacol. 2008 Apr 14;584(1):57-65. doi: 10.1016/j.ejphar.2008.01.042. Epub 2008 Feb 8. [Article]
- Identification, Ki determination and CoMFA analysis of nuclear receptor ligands as competitive inhibitors of OATP1B1-mediated estradiol-17β-glucuronide transport [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Mediates the Na(+)-independent uptake of organic anions (PubMed:10779507, PubMed:15159445, PubMed:17412826). Shows broad substrate specificity, can transport both organic anions such as bile acid taurocholate (cholyltaurine) and conjugated steroids (17-beta-glucuronosyl estradiol, dehydroepiandrosterone sulfate (DHEAS), and estrone 3-sulfate), as well as eicosanoid leukotriene C4, prostaglandin E2 and L-thyroxine (T4) (PubMed:10779507, PubMed:11159893, PubMed:12568656, PubMed:15159445, PubMed:17412826, PubMed:19129463). Hydrogencarbonate/HCO3(-) acts as the probable counteranion that exchanges for organic anions (PubMed:19129463). Shows a pH-sensitive substrate specificity towards sulfated steroids, taurocholate and T4 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). Involved in the clearance of bile acids and organic anions from the liver (PubMed:22232210). Can take up bilirubin glucuronides from plasma into the liver, contributing to the detoxification-enhancing liver-blood shuttling loop (PubMed:22232210). Transports coproporphyrin I and III, by-products of heme synthesis, and may be involved in their hepatic disposition (PubMed:26383540). May contribute to regulate the transport of organic compounds in testes across the blood-testis-barrier (Probable). Can transport HMG-CoA reductase inhibitors (also known as statins) such as pitavastatin, a clinically important class of hypolipidemic drugs (PubMed:15159445). May play an important role in plasma and tissue distribution of the structurally diverse chemotherapeutic drugs methotrexate and paclitaxel (PubMed:23243220). May also transport antihypertension agents, such as the angiotensin-converting enzyme (ACE) inhibitor prodrug enalapril, and the highly selective angiotensin II AT1-receptor antagonist valsartan, in the liver (PubMed:16624871, PubMed:16627748)
- Specific Function
- Bile acid transmembrane transporter activity
- Gene Name
- SLCO1B3
- Uniprot ID
- Q9NPD5
- Uniprot Name
- Solute carrier organic anion transporter family member 1B3
- Molecular Weight
- 77402.175 Da
References
- Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P: Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions. J Med Chem. 2012 May 24;55(10):4740-63. doi: 10.1021/jm300212s. Epub 2012 May 15. [Article]
- Gui C, Miao Y, Thompson L, Wahlgren B, Mock M, Stieger B, Hagenbuch B: Effect of pregnane X receptor ligands on transport mediated by human OATP1B1 and OATP1B3. Eur J Pharmacol. 2008 Apr 14;584(1):57-65. doi: 10.1016/j.ejphar.2008.01.042. Epub 2008 Feb 8. [Article]
Drug created at June 13, 2005 13:24 / Updated at September 07, 2024 14:25