Clotrimazole

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
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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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofAthlete's foot•••••••••••••••••
Treatment ofBalanitis candida••• ••••••••
Used in combination to treatCandidiasisCombination Product in combination with: Dexamethasone (DB01234)•••••••••••••••••
Treatment ofDermatomycoses••• ••••••••
Treatment ofEar infection fungal•••••••••••••••••••• • •••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

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.

TargetActionsOrganism
ACytochrome P450 51
antagonist
inhibitor
Yeast
AIntermediate conductance calcium-activated potassium channel protein 4
inhibitor
Humans
AErgosterol
inhibitor
Candida albicans
UNuclear receptor subfamily 1 group I member 2
activator
Humans
UHydroxycarboxylic acid receptor 2
partial agonist
Humans
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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Toxicity

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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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.
DrugInteraction
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be increased when used in combination with Clotrimazole.
CapmatinibThe serum concentration of Capmatinib can be decreased when it is combined with Clotrimazole.
ClindamycinThe metabolism of Clindamycin can be increased when combined with Clotrimazole.
DicoumarolThe therapeutic efficacy of Dicoumarol can be increased when used in combination with Clotrimazole.
FluindioneThe therapeutic efficacy of Fluindione can be increased when used in combination with Clotrimazole.
Food Interactions
No interactions found.

Products

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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
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
LotriminCream10 mg/1gTopicalPhysicians Total Care, Inc.1994-11-282005-06-30US flag
LotriminSolution10 mg/1mLTopicalPhysicians Total Care, Inc.2000-11-032005-06-30US flag
MycelexTroche10 mg/1OralPhysicians Total Care, Inc.1983-06-172011-05-31US flag
MycelexTroche10 mg/1OralBayer Pharmaceuticals Corp2006-08-14Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ClotrimazoleCream10 mg/1gTopicalProficient Rx LP1993-08-31Not applicableUS flag
ClotrimazoleLozenge10 mg/1Oral; TopicalCardinal Health2004-07-292021-01-31US flag
ClotrimazoleLozenge10 mg/1Oral; TopicalHikma Pharmacuticals USA USA Inc.2004-07-29Not applicableUS flag
ClotrimazoleLozenge10 mg/1OralPadagis US LLC2005-12-01Not applicableUS flag
ClotrimazoleSolution10 mg/1mLTopicalTeva1996-07-102017-09-30US flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
1MED Clotrimazole 1% Antifungal CreamCream1 g/100gTopicalQYK BRANDS LLC2022-01-01Not applicableUS flag
1MED Clotrimazole 1% Antifungal CreamCream1 g/100gTopicalQYK BRANDS LLC2022-01-01Not applicableUS flag
Akin Anti-fungalSolution10 mg/1mLTopicalSouthern Sales & Service, Inc.2017-01-01Not applicableUS flag
AlevazolOintment10 mg/1gTopicalCapital Pharmaceutical, LLC2014-09-01Not applicableUS flag
Anti FungalLiquid1 g/100mLTopicalGuangzhou Ertiantang Pharmaceutical Co.,ltd2017-09-22Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ALERTREXClotrimazole (1 g) + Dexamethasone acetate (0.04 g) + Neomycin (0.5 g)CreamTopicalLABORATORIOS COASPHARMA S.A.S.2017-04-242018-12-13Colombia flag
AMZOL FEM®Clotrimazole (100 mg) + Metronidazole (500 mg)InsertVaginal2015-12-022015-12-02Colombia flag
ANTIFUNGOL HEXAL 3 KOMBIClotrimazole (200 mg) + Clotrimazole (10 mg/g)KitTopical2006-07-01Not applicableGermany flag
ANTIFUNGOL HEXAL 3 KOMBIClotrimazole (200 mg) + Clotrimazole (10 mg/g)KitTopical2006-07-01Not applicableGermany flag
ANTIFUNGOL HEXAL 6 KOMBIClotrimazole (100 mg) + Clotrimazole (10 mg/g)KitTopical2010-04-01Not applicableGermany flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AlevazolClotrimazole (10 mg/1g)OintmentTopicalCapital Pharmaceutical, LLC2014-09-01Not applicableUS flag
CiclomazoleClotrimazole (10 mg/1g) + Betamethasone dipropionate (0.5 mg/1g) + Ciclopirox (80 mg/1mL)Cream; Kit; SolutionTopicalPureTek Corporation2020-12-17Not applicableUS flag
DermacinRx Therazole PakClotrimazole (10 mg/1g) + Betamethasone dipropionate (0.5 mg/1g) + Zinc oxide (200 mg/1g)KitTopicalPureTek Corporation2016-08-09Not applicableUS flag
Gehwol Nail Protection PenClotrimazole (10 mg/1mL)LiquidTopicalEduard Gerlach Gmb H2008-03-072017-04-12US flag
Shield and Protect Anti-FungalClotrimazole (1.1 g/115g)CreamTopicalGentell, Inc.2007-01-01Not applicableUS flag

Categories

ATC Codes
D01AC01 — ClotrimazoleA01AB18 — ClotrimazoleG01AF02 — ClotrimazoleG01AF20 — Combinations of imidazole derivatives
Drug Categories
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
  1. Ritter W: Pharmacokinetic fundamentals of vaginal treatment with clotrimazole. Am J Obstet Gynecol. 1985 Aug 1;152(7 Pt 2):945-7. [Article]
  2. 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]
  3. 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]
  4. 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]
  5. Clotrimazole Drug Summary [Link]
  6. HMDB Database [Link]
  7. The binding of Clotrimazole to the proteins of human serum [Link]
  8. Clotrimazole Cream, DailyMed [Link]
  9. FDA Approved Drug Products: Lotrisone (clotrimazole/betamethasone dipropionate) topical cream [Link]
  10. Health Canada Product Monograph: Canesten (clotrimazole) for topical and/or vaginal application [Link]
  11. Health Canada Product Monograph: Canesten (clotrimazole 1%) topical cream [Link]
  12. Canesten Monograph [File]
  13. MedSafe NZ Data Sheet, Clotrimazole [File]
  14. HPLC Measurement, Bbod Distribution, and Pharmacokinetics of Oral Clotrimazole, Potentially Useful Antisickling Agent [File]
  15. Lotrisone FDA label [File]
  16. Clotrimazole SDS [File]
Human Metabolome Database
HMDB0001922
KEGG Drug
D00282
KEGG Compound
C06922
PubChem Compound
2812
PubChem Substance
46507927
ChemSpider
2710
BindingDB
31774
RxNav
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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
4CompletedHealth Services ResearchRenal Failure, Chronic Renal Failure1
4CompletedTreatmentBacterial Vaginosis (BV) / Candidiasis1
4CompletedTreatmentVaginal Infections1
4CompletedTreatmentVulvovaginal Candidiasis2
4RecruitingTreatmentRecurrent Vulvovaginal Candidiasis1

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
FormRouteStrength
OintmentTopical10 mg/1g
LiquidTopical1 g/100mL
CreamVaginal20 mg/g
SolutionTopical1 %
CreamVaginal10 mg/g
CreamTopical10 MG/G
SolutionTopical10 MG/ML
SprayTopical10 mg/mL
CreamTopical350 mg/35g
LotionTopical1 g/100mL
Solution
CreamVaginal1000 mg
CreamTopical1 mg
CreamTopical0.01 kg/1kg
CreamTopical1 % w/w
LotionTopical1 %
CreamCutaneous; Vaginal10 % w/w
LiquidAuricular (otic)10 mg/1ml
CreamTopical1 % w/w
PowderTopical1 % w/w
SolutionAuricular (otic)1 %
Solution / dropsAuricular (otic)
SolutionTopical1 % w/v
GelVaginal
InsertVaginal
CreamCutaneous
CreamTopical0.025 % w/w
LotionTopical
CreamVaginal2.0000 g
InsertVaginal500.0000 mg
Capsule; creamOral; Topical; Vaginal
Capsule; creamOral; Topical
Cream1 %
CreamTopical
PowderTopical
SolutionTopical
CreamVaginal10 g
CreamVaginal10 % w/w
CreamTopical; Vaginal2 %
SuppositoryVaginal200 mg / sup
CreamTopical0.01 g/g
SolutionTopical0.01 g/ml
TabletVaginal
CapsuleVaginal0.5 g
Cream; kit; tabletVaginal
Cream; kitTopical; Vaginal
Cream; kit; tabletTopical; Vaginal
Cream; suppositoryTopical; Vaginal
CreamTopical1 %
CreamTopical; Vaginal1 %
CreamTopical2 % w/w
TabletVaginal0.5 g
TabletVaginal200 mg/1
TabletVaginal0.1 g
LiquidTopical1 %
CreamTopical1 g/100g
InsertVaginal500.000 mg
SuppositoryVaginal100 mg / sup
CreamTopical100000 g
SuppositoryVaginal100 mg/1
KitTopical20 G
SuppositoryVaginal200 mg/1
LotionTopical1 g
Cream; kit; solutionTopical
SolutionTopical10 mg/g
SprayTopical10 mg/g
CreamCutaneous1 g
CreamVaginal2 g
PowderTopical1 g
CreamVaginal2 % w/w
CreamVaginal1 % w/w
Capsule; cream; kitOral; Topical
CreamTopical0.2 g/1g
SuspensionTopical1 g
CreamVaginal10 MG
SolutionTopical1 g
SolutionTopical100000 g
InsertVaginal100 mg
CreamVaginal200000 g
CreamVaginal2 %
TabletVaginal100 mg/1
CapsuleVaginal1 g
CreamTopical1000 MG
SolutionTopical1000 mg
CreamVaginal100000 g
CreamTopical1 g/100g
CreamTopical10 mg/1g
CreamTopical50 mg/1g
CreamVaginal1 g/100g
CreamVaginal10 mg/1g
CreamVaginal100 g/1g
LiquidTopical1 mg/1mL
LozengeOral10 mg/1
LozengeOral; Topical10 mg/1
SolutionTopical1 g/1mL
SolutionTopical10 mg/1mL
CreamTopical
CreamVaginal1 %
CreamTopical10 mg
SuppositoryVaginal
CreamTopical1.00 % w/w
Capsule, liquid filledVaginal500 mg
CreamVaginal2 g/100g
SolutionTopical1 mg/1mL
CreamTopical1.000 g
CreamTopical1 g
CreamTopical0.01 g/1g
PowderTopical
Aerosol, sprayTopical1 mL/100mL
Aerosol, foamTopical1 g/100g
LiquidTopical10 g/1000g
GelTopical0.01 kg/1kg
SolutionTopical1 g/100mL
LiquidTopical10 mg/1mL
LiquidTopical1 mg/100mL
GelTopical10 mg/1g
SolutionTopical0.001 g
SprayTopical4 mg/1mL
PowderTopical1.0 g/100g
GelTopical
CreamTopical6 mg/1mL
SolutionOral10 mg
SprayTopical10 mg
TabletOral100 mg
TabletVaginal
CreamVaginal
SuppositoryVaginal500 mg
CapsuleVaginal
TabletVaginal10000000 mg
AerosolTopical1 g
CreamTopical10 g/1g
OintmentTopical1 mg/100g
OintmentTopical1 g/100g
PasteTopical10 mg/g
InsertVaginal200 mg
InsertVaginal500 mg
GelTopical1 g/100g
CreamTopical420 mg/42g
CapsuleVaginal
CapsuleVaginal200 mg
LotionTopical
CreamVaginal2.000 mg
CreamVaginal
InsertVaginal
SolutionVaginal
Cream
CreamTopical2 g
CreamTopical1.007 g
CreamVaginal2000 mg
TrocheOral10 mg/1
CreamVaginal50 mg / 5 g
LiquidTopical10 mg / mL
SuppositoryVaginal100 mg / tab
CreamTopical10 mg / g
SolutionTopical10 mg / mL
CreamTopical; Vaginal10 mg / g
SprayTopical1 %
CreamVaginal1 g
KitTopical25 G
CreamTopical0.5 mg/g
CreamVaginal10000 g
Aerosol, foamTopical10 mg/1g
CreamTopical1 g/100mL
SolutionOral10 mg/ml
CreamTopical1.0 g/100g
OintmentTopical2.0 g/100g
CreamTopical; Vaginal1 g
OilTopical10 mg/1mL
CreamTopical10 mg/1mL
CreamCutaneous2.000 g
CreamTopical0.01 mg/10g
CreamTopical0.64 mg/g
CreamTopical1.1 g/115g
SprayExtracorporeal0.06 mg/30mL
CreamCutaneous1.000 g
CreamTopical1 g/1g
CreamVaginal2.000 g
SolutionTopical
OintmentTopical1.0 g/100g
KitTopical
CreamCutaneous1 % w/w
SprayTopical
CreamTopical40 mg
CreamTopical0.02 %
Capsule, liquid filledVaginal
InsertVaginal200.000 mg
CreamTopical10 mg/100g
TabletVaginal200 mg
TabletVaginal100 mg
LozengeOral10 mg
TabletVaginal500 mg
CreamTopical1 %w/w
OintmentTopical1 %w/w
Prices
Unit descriptionCostUnit
Clotrimazole 70 10 mg Troche Bottle117.04USD bottle
Clotrimazole 1% Cream 45 gm Tube49.99USD tube
Clotrimazole 1% Cream 30 gm Tube35.99USD tube
Clotrimazole 1% Solution 30ml Bottle24.99USD bottle
Clotrimazole 1% Cream 15 gm Tube17.99USD tube
Clotrimazole 1% Solution 10ml Bottle17.99USD bottle
Clotrimazole powder5.2USD g
Mycelex 10 mg troche1.85USD troche
Clotrimazole 10 mg troche1.61USD troche
Mycelex-7 100 mg vaginal tablet1.33USD tablet
Lotrimin 1% cream1.28USD g
Gyne-lotrimin insert1.03USD insert
Mycelex 1% cream0.9USD g
Clotrimazole insert0.86USD insert
Lotrimin ultra 1% cream0.68USD g
Clotrimazole 1% cream0.53USD g
Clotrimazole 3 2% cream0.5USD g
Ra clotrimazole 3 cream0.46USD g
Ra athlete's 1% foot cream0.37USD g
Desenex 1% cream0.33USD g
CVS Pharmacy clotrimazole 1% cream0.32USD g
Antifungal 1% cream0.27USD g
Sm antifungal 1% cream0.25USD g
Ra clotrimazole af cream0.24USD g
Clotrim 1% vaginal cream0.18USD g
Lotrimin af 2% spray powder0.05USD g
Lotrimin af 2% liquid spray0.04USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)148MSDS
water solubility0.49 mg/Lhttp://www.ijpsonline.com/articles/improvement-of-solubility-and-dissolution-properties-of-clotrimazole-by-solid-dispersions-and-inclusion-complexes.pdf
logP6.1https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6749186/
pKa4.1http://www.ijpsonline.com/articles/improvement-of-solubility-and-dissolution-properties-of-clotrimazole-by-solid-dispersions-and-inclusion-complexes.pdf
Predicted Properties
PropertyValueSource
Water Solubility0.00147 mg/mLALOGPS
logP5.48ALOGPS
logP5.84Chemaxon
logS-5.4ALOGPS
pKa (Strongest Basic)6.26Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area17.82 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity103.76 m3·mol-1Chemaxon
Polarizability36.25 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9725
Blood Brain Barrier+0.9837
Caco-2 permeable+0.6858
P-glycoprotein substrateNon-substrate0.7185
P-glycoprotein inhibitor INon-inhibitor0.6612
P-glycoprotein inhibitor IINon-inhibitor0.7884
Renal organic cation transporterNon-inhibitor0.5854
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateNon-substrate0.9149
CYP450 3A4 substrateNon-substrate0.6262
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorInhibitor0.8948
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorInhibitor0.8478
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9799
Ames testNon AMES toxic0.7428
CarcinogenicityNon-carcinogens0.9018
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7194 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9659
hERG inhibition (predictor II)Inhibitor0.6779
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0059-6090000000-3cccc4c11a7c5a63573d
Mass Spectrum (Electron Ionization)MSsplash10-004i-1490000000-442fa75d6a2d80321e36
MS/MS Spectrum - Quattro_QQQ 10V, N/ALC-MS/MSsplash10-004i-0090000000-9ac001e37a55e61bc916
MS/MS Spectrum - Quattro_QQQ 25V, N/ALC-MS/MSsplash10-004i-0290000000-6285150b307e50af52c7
MS/MS Spectrum - Quattro_QQQ 40V, N/ALC-MS/MSsplash10-016u-0690000000-5814802384fae84ca3df
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0090000000-23b69c41217f6b148307
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-016r-0960000000-5b3632c056ca1c0fa601
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-016r-0950000000-bcb189995c8cdcd62304
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0090000000-f1d5f44ac74388f9bf4f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-1490000000-1ed188e9911ad62a7fc7
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-0390000000-c2f0490842646cf25d56
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014l-3970000000-0cf80068015e539b67c9
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00or-0391000000-e8d9d4c77703a87fdcd8
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0090000000-a24f529f8c94a798b11a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0009000000-e3f5c68b94f06e90a5ca
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0090000000-ef4662c5d72f76f82bbe
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0009000000-340565dce8487aba92f0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0091000000-5f7a762f68216b214b21
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014u-1097000000-b95c382b8a97a5e1d534
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-184.5859505
predicted
DarkChem Lite v0.1.0
[M-H]-184.9006505
predicted
DarkChem Lite v0.1.0
[M-H]-176.18741
predicted
DeepCCS 1.0 (2019)
[M+H]+185.4075505
predicted
DarkChem Lite v0.1.0
[M+H]+185.5582505
predicted
DarkChem Lite v0.1.0
[M+H]+178.54541
predicted
DeepCCS 1.0 (2019)
[M+Na]+185.1093505
predicted
DarkChem Lite v0.1.0
[M+Na]+185.3247505
predicted
DarkChem Lite v0.1.0
[M+Na]+185.62465
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Yeast
Pharmacological action
Yes
Actions
Antagonist
Inhibitor
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
  1. 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]
  2. 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]
  3. 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]
  4. 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
Protein phosphatase binding
Specific 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. Requi...
Gene Name
KCNN4
Uniprot ID
O15554
Uniprot Name
Intermediate conductance calcium-activated potassium channel protein 4
Molecular Weight
47695.12 Da
References
  1. 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]
  2. 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]
  3. 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
Small molecule
Organism
Candida albicans
Pharmacological action
Yes
Actions
Inhibitor
References
  1. Haller I: Mode of action of clotrimazole: implications for therapy. Am J Obstet Gynecol. 1985 Aug 1;152(7 Pt 2):939-44. [Article]
  2. Canesten Monograph [File]
  3. MedSafe NZ Data Sheet, Clotrimazole [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
General Function
Zinc ion binding
Specific 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 an...
Gene Name
NR1I2
Uniprot ID
O75469
Uniprot Name
Nuclear receptor subfamily 1 group I member 2
Molecular Weight
49761.245 Da
References
  1. 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]
  2. 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]
  3. 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]
  4. 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
Nicotinic acid receptor activity
Specific 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)-protei...
Gene Name
HCAR2
Uniprot ID
Q8TDS4
Uniprot Name
Hydroxycarboxylic acid receptor 2
Molecular Weight
41849.08 Da
References
  1. 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]
  2. 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
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. 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]
  2. 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]
Details
2. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
Curator comments
Several studies provide conflicting evidence of Clotrimazole inducing or inhibiting CYP3A4. The references have been included.
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. 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]
  2. 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]
  3. 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]
  4. Choy M: Tacrolimus interaction with clotrimazole: a concise case report and literature review. P T. 2010 Oct;35(10):568-9. [Article]
  5. 16, 29. (2008). In Stockley's Drug Interactions (8th ed., pp. 598, 1071-1072). RPS Publishing. [ISBN:085369754X]
  6. Effects of oral clotrimazole troches on the pharmacokinetics of oral and intravenous midazolam [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. 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]
  2. 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
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Zhang W, Ramamoorthy Y, Kilicarslan T, Nolte H, Tyndale RF, Sellers EM: Inhibition of cytochromes P450 by antifungal imidazole derivatives. Drug Metab Dispos. 2002 Mar;30(3):314-8. [Article]
  2. Genetic Polymorphism of CYP2D6 [File]
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
Steroid hydroxylase activity
Specific 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. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. 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
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. 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]
  2. 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
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. 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]
  2. 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
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. 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

Details
1. P-glycoprotein 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. Interaction of Cytochrome P450 3A Inhibitors with P-Glycoprotein [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. 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]
  2. 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
Substrate
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. 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]
  2. 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]
  3. 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
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
Gene Name
SLCO1B3
Uniprot ID
Q9NPD5
Uniprot Name
Solute carrier organic anion transporter family member 1B3
Molecular Weight
77402.175 Da
References
  1. 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]
  2. 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 February 20, 2024 23:55