Identification

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Name
Clotrimazole
Accession Number
DB00257  (APRD00244)
Type
Small Molecule
Groups
Approved, Vet approved
Description

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.

Structure
Thumb
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
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
LotriminSolution10 mg/1mLTopicalPhysicians Total Care, Inc.2000-11-032005-06-30Us
LotriminCream10 mg/1gTopicalPhysicians Total Care, Inc.1994-11-282005-06-30Us
MycelexTroche10 mg/1OralPhysicians Total Care, Inc.1983-06-172011-05-31Us
MycelexTroche10 mg/1OralBayer Pharmaceuticals Corp2006-08-14Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ClotrimazoleCream10 mg/1gTopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2008-09-02Not applicableUs
ClotrimazoleCream10 mg/1gTopicalGlenmark Pharmaceuticals Inc., USA2010-08-04Not applicableUs
ClotrimazoleCream10 mg/1gTopicalLake Erie Medical Dba Quality Care Produts Llc2010-08-04Not applicableUs
ClotrimazoleSolution10 mg/1mLTopicalPhysicians Total Care, Inc.1996-07-292011-06-30Us
ClotrimazoleLozenge10 mg/1OralPaddock Laboratories, LLC2005-12-01Not applicableUs
ClotrimazoleLozenge10 mg/1OralRemedy Repack2012-07-202014-02-19Us
ClotrimazoleCream10 mg/1gTopicalStat Rx USA1993-08-31Not applicableUs
ClotrimazoleSolution10 mg/1mLTopicalRpk Pharmaceuticals, Inc.1996-07-29Not applicableUs
ClotrimazoleLozenge10 mg/1Oral; TopicalWest-Ward Pharmaceuticals Corp.2004-07-29Not applicableUs
ClotrimazoleLozenge10 mg/1OralPhysicians Total Care, Inc.2009-07-23Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Akin Anti-FungalSolution10 mg/1mLTopicalSouthern Sales & Service, Inc.2017-01-01Not applicableUs
AlevazolOintment10 mg/1gTopicalCapital Pharmaceutical2014-09-01Not applicableUs
Anti FungalLiquid1 g/100mLTopicalGuangzhou Ertiantang Pharmaceutical Co.,ltd2017-09-22Not applicableUs
Anti-FungalCream10 mg/1gTopicalMPM Medical, Inc.2002-10-14Not applicableUs
AntifungalCream1 g/100gTopicalSafeway2008-11-202017-04-14Us
AntifungalCream1 g/100gTopicalGalentic Pharma (India) Private Limited2013-08-07Not applicableUs
AntifungalCream10 mg/1gTopicalRite Aid2011-04-15Not applicableUs
Antifungal FootCream1 g/100gTopicalHyvee2015-11-28Not applicableUs
Aptrimazole 1.0% Antifungal CreamCream1 g/100gTopicalA P J Laboratories Limited2013-04-27Not applicableUs
Aspiera Anti-FungalOintment1.0 g/100gTopicalAidance Skincare & Topical Solutions, LLC2012-05-31Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Betamethasone ClotrimazoleClotrimazole (10 mg/1) + Betamethasone dipropionate (0.64 mg/1)CreamTopicalStat Rx USA2002-08-02Not applicableUs
Canesoral CombiClotrimazole (1 %) + Fluconazole (150 mg)Capsule; CreamOral; Topical; VaginalBayer2010-03-10Not applicableCanada
Canesoral Combi 1 DayClotrimazole (2 %) + Fluconazole (150 mg)Capsule; CreamOral; TopicalBayerNot applicableNot applicableCanada
Canesten 1 Vaginal Tablet Combi-pakClotrimazole (1 %) + Clotrimazole (500 mg)Cream; SuppositoryTopical; VaginalBayer Inc Consumer Care1995-12-312007-08-02Canada
Canesten 1 Vaginal Tablet Combi-pakClotrimazole (1 %) + Clotrimazole (500 mg)Cream; SuppositoryTopical; VaginalBayer Inc Consumer Care1995-12-312007-08-02Canada
Canesten 3 Vaginal Tablet Combi-pakClotrimazole (1 %) + Clotrimazole (200 mg)Cream; SuppositoryTopical; VaginalBayer Inc Consumer Care1995-12-312007-08-02Canada
Canesten 3 Vaginal Tablet Combi-pakClotrimazole (1 %) + Clotrimazole (200 mg)Cream; SuppositoryTopical; VaginalBayer Inc Consumer Care1995-12-312007-08-02Canada
Canesten Combi 1 Day Comfortab + External CreamClotrimazole (500 mg) + Clotrimazole (1 %)Cream; Kit; TabletTopical; VaginalBayer2006-05-12Not applicableCanada
Canesten Combi 1 Day Comfortab + External CreamClotrimazole (500 mg) + Clotrimazole (1 %)Cream; Kit; TabletTopical; VaginalBayer2006-05-12Not applicableCanada
Canesten Combi 1 Day Internal + External CreamsClotrimazole (1 %) + Clotrimazole (10 %)Cream; KitTopical; VaginalBayer1997-06-11Not applicableCanada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Gehwol Nail Protection PenClotrimazole (10 mg/1mL)LiquidTopicalEduard Gerlach Gmb H2008-03-072017-04-12Us
Shield and Protect Anti-FungalClotrimazole (1.1 g/115g)CreamTopicalGentell, Inc.2007-01-01Not applicableUs
Terbinafine HCl Chlortimazole and TolnaftateClotrimazole (1 g/100mL) + Terbinafine hydrochloride (1 g/100mL) + Tolnaftate (1 g/100mL)SolutionTopicalDr Marc's Manufacturing And Sales2018-01-302018-04-18Us
International/Other Brands
Canesten (Bayer) / Canifug (Dr. August Wolff) / Clotrimaderm (Taro) / Empecid (Bayer) / FemCare / Fungicip (Cipla) / Gyne-Lotrimin (Schering-Plough) / Myclo-Derm / Myclo-Gyne
Categories
UNII
G07GZ97H65
CAS number
23593-75-1
Weight
Average: 344.837
Monoisotopic: 344.108026261
Chemical Formula
C22H17ClN2
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

Pharmacology

Indication

Topical preparations

Clotrimazole topical cream is indicated for the topical treatment of the following dermal infections 9, 12:

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 12.

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.

Associated Conditions
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 9,10. 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
UNuclear receptor subfamily 1 group I member 2
activator
Humans
UHydroxycarboxylic acid receptor 2
partial agonist
Humans
AErgosterol
inhibitor
Candida albicans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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 9. Clotrimazole is a lipophilic drug 4, and has been shown to be secreted in breastmilk in animal studies 9. 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
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 9.

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;13

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 10.

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 9.

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 9.

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 9.

Affected organisms
  • Yeast and other fungi
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.
DrugInteraction
4-hydroxycoumarinThe therapeutic efficacy of 4-hydroxycoumarin can be increased when used in combination with Clotrimazole.
ClorindioneThe therapeutic efficacy of Clorindione can be increased when used in combination with Clotrimazole.
CoumarinThe therapeutic efficacy of Coumarin can be increased when used in combination with Clotrimazole.
DicoumarolThe therapeutic efficacy of Dicoumarol can be increased when used in combination with Clotrimazole.
DiphenadioneThe therapeutic efficacy of Diphenadione can be increased when used in combination with Clotrimazole.
Ethyl biscoumacetateThe therapeutic efficacy of Ethyl biscoumacetate can be increased when used in combination with Clotrimazole.
FluindioneThe therapeutic efficacy of Fluindione can be increased when used in combination with Clotrimazole.
PhenindioneThe therapeutic efficacy of Phenindione can be increased when used in combination with Clotrimazole.
PhenprocoumonThe therapeutic efficacy of Phenprocoumon can be increased when used in combination with Clotrimazole.
SirolimusThe serum concentration of Sirolimus can be increased when it is combined with Clotrimazole.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

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. [PubMed:4025444]
  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. [PubMed:24863842]
  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. [PubMed:26819835]
  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. [PubMed:21725708]
  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. Canesten Monograph [File]
  10. MedSafe NZ Data Sheet, Clotrimazole [File]
  11. HPLC Measurement, Bbod Distribution, and Pharmacokinetics of Oral Clotrimazole, Potentially Useful Antisickling Agent [File]
  12. Lotrisone FDA label [File]
  13. 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
ChEBI
3764
ChEMBL
CHEMBL104
Therapeutic Targets Database
DAP000138
PharmGKB
PA449057
Guide to Pharmacology
GtP Drug Page
HET
CL6
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Clotrimazole
ATC Codes
D01AC01 — ClotrimazoleA01AB18 — ClotrimazoleG01AF02 — ClotrimazoleG01AF20 — Combinations of imidazole derivatives
AHFS Codes
  • 84:04.08.08 — Azoles
PDB Entries
2xfh / 3mdv / 4xe3 / 6h1t
FDA label
Download (139 KB)
MSDS
Download (73.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedOtherLeukemia Acute Myeloid Leukemia (AML)1
1CompletedPreventionHIV- Prevention1
1CompletedTreatmentTinea Pedis3
1TerminatedTreatmentInterdigital Tinea Pedis1
1, 2CompletedTreatmentKidney Diseases / Transplantation, Kidney1
1, 2CompletedTreatmentSickle Cell Disorders1
1, 2RecruitingTreatmentVulvovaginal Candidiasis1
1, 2SuspendedTreatmentIleitis / Inflammatory Bowel Diseases (IBD) / Pouchitis / Ulcerative Colitis (UC)1
2CompletedTreatmentOral Candidiasis / Stomatitis, Denture1
2RecruitingTreatmentKeratotic Nodular Size1
2RecruitingTreatmentNeoplasms1
2, 3CompletedTreatmentVulvovaginal Candidiasis (VVC)1
2, 3RecruitingTreatmentInfections, Fungal1
2, 3SuspendedTreatmentFolliculitis1
3CompletedPreventionCandidiasis infection / Human Immunodeficiency Virus (HIV) Infections / Mycoses1
3CompletedTreatmentBacterial Vaginosis (BV) / Candidiasis infection / Vaginal Inflammation1
3CompletedTreatmentClotrimazole / Ovulen / Vulvovaginal Candidiasis1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentOral Candidiasis1
3CompletedTreatmentOtomycosis1
3RecruitingTreatmentTinea infections1
3Unknown StatusTreatmentInfections, Fungal / Tinea Corporis / Tinea Cruris / Tinea Pedis1
3WithdrawnTreatmentSexual Active Women / Vaginal Discharge1
3WithdrawnTreatmentVulvovaginal Candidiasis1
4CompletedHealth Services ResearchChronic Renal Failure (CRF)1
4CompletedTreatmentBacterial Vaginosis (BV) / Candidiasis infection1
4CompletedTreatmentVaginal Infections1
4CompletedTreatmentVulvovaginal Candidiasis2
4TerminatedTreatmentAtopic Dermatitis (AD) / Skin Diseases, Eczematous1
4Unknown StatusTreatmentMelasma1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Oral Candidiasis1
Not AvailableCompletedTreatmentOtomycosis1
Not AvailableCompletedTreatmentSickle Cell Disorders1
Not AvailableNo Longer AvailableNot AvailableType 1 Insulin-Dependent Diabetes Mellitus1
Not AvailableRecruitingNot AvailableVaginal Candida1
Not AvailableUnknown StatusTreatmentMycotic Corneal Ulcer1

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
CreamTopical350 mg/35g
LotionTopical1 g/100mL
Capsule; creamOral; Topical; Vaginal
Capsule; creamOral; Topical
CreamTopical; Vaginal
Cream; kitTopical; Vaginal
Cream; kit; tabletTopical; Vaginal
Cream; suppositoryTopical; Vaginal
TabletVaginal
CreamTopical
LiquidTopical
SuppositoryVaginal
CreamTopical1 g/1g
Capsule; cream; kitOral; Topical
CreamTopical1 g/100g
CreamTopical10 mg/1g
CreamTopical50 mg/1g
CreamVaginal1 g/100g
CreamVaginal10 mg/1g
LiquidTopical1 mg/1mL
LozengeOral10 mg/1
LozengeOral; Topical10 mg/1
SolutionTopical1 g/1mL
SolutionTopical10 mg/1mL
CreamTopical
CreamVaginal
CreamVaginal2 g/100g
SolutionTopical1 mg/1mL
CreamTopical0.01 g/1g
Aerosol, sprayTopical1 mL/100mL
Aerosol, foamTopical1 g/100g
LiquidTopical10 g/1000g
SolutionTopical1 g/100mL
GelTopical10 mg/1g
LiquidTopical1 mg/100mL
LiquidTopical10 mg/1mL
SprayTopical4 mg/1mL
PowderTopical1.0 g/100g
CreamTopical6 mg/1mL
CreamTopical10 g/1g
OintmentTopical1 mg/100g
GelTopical1 g/100g
CreamTopical420 mg/42g
LotionTopical
TrocheOral10 mg/1
SolutionTopical
Aerosol, foamTopical10 mg/1g
CreamTopical1.0 g/100g
OintmentTopical2.0 g/100g
OilTopical10 mg/1mL
CreamTopical10 mg/1mL
CreamTopical0.01 mg/10g
CreamTopical1.1 g/115g
SolutionTopical
OintmentTopical1.0 g/100g
KitTopical
CreamTopical10 mg/100g
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
logP0.5https://www.researchgate.net/publication/262605568_Clotrimazole_as_a_pharmaceutical_Past_present_and_future
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)6.62ChemAxon
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-MSNot Available
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
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
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

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
Triphenyl compound / Chlorobenzene / Halobenzene / Aryl chloride / Aryl halide / Monocyclic benzene moiety / N-substituted imidazole / Azole / Heteroaromatic compound / Imidazole
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
conazole antifungal drug, imidazoles, imidazole antifungal drug, monochlorobenzenes (CHEBI:3764) / a small molecule (CPD-8926)

Targets

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. [PubMed:20625155]
  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. [PubMed:9326581]
  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. [PubMed:10991846]
  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. [PubMed:1929324]
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. [PubMed:8636434]
  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. [PubMed:10428416]
  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. [PubMed:8903326]
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. [PubMed:14977870]
  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. [PubMed:15849716]
  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. [PubMed:17998298]
  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. [PubMed:20869355]
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. [PubMed:20686338]
  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. [PubMed:12799447]
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. [PubMed:3895959]
  2. Canesten Monograph [File]
  3. MedSafe NZ Data Sheet, Clotrimazole [File]

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. [PubMed:15601807]
  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. [PubMed:11136296]
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. [PubMed:12751267]
  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. [PubMed:15135088]
  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. [PubMed:20233179]
  4. Choy M: Tacrolimus interaction with clotrimazole: a concise case report and literature review. P T. 2010 Oct;35(10):568-9. [PubMed:21037909]
  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. [PubMed:17101742]
  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. [PubMed:14977870]
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. [PubMed:11854151]
  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. [PubMed:9143352]
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. [PubMed:16430569]
  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. [PubMed:9663807]
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. [PubMed:15135088]
  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 . [PubMed:9574817]
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. [PubMed:12673034]

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. [PubMed:11297522]
  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. [PubMed:8632764]
  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. [PubMed:11961113]
  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. [PubMed:12699389]
  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. [PubMed:8917702]
  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. [PubMed:24014644]
  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. [PubMed:27000539]
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. [PubMed:19785645]
  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. [PubMed:18321482]
  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. [PubMed:22541068]
  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. [PubMed:18321482]

Drug created on June 13, 2005 07:24 / Updated on October 17, 2019 21:18