U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
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Details

Stereochemistry ACHIRAL
Molecular Formula C22H17ClN2
Molecular Weight 344.837
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLOTRIMAZOLE

SMILES

ClC1=CC=CC=C1C(N2C=CN=C2)(C3=CC=CC=C3)C4=CC=CC=C4

InChI

InChIKey=VNFPBHJOKIVQEB-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018052Orig1s032lbl.pdf

Clotrimazole is an anti-fungal medicine indicated for the treatment of vaginal yeast infections and tinea. It can be used either in combination with other drugs (betamethasone dipropionate) or alone, in form of topical or vaginal cream. The drug exerts its action by inhibiting lanosterol demethylase thereby affecting the growth of fungi.

Originator

Curator's Comment: # Bayer

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
19.7 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
GYNE-LOTRIMIN

Approved Use

To treat vaginal yeast infections.

Launch Date

1976
Curative
LOTRISONE

Approved Use

LOTRISONE cream contains a combination of clotrimazole, an azole antifungal, and betamethasone dipropionate, a corticosteroid, and is indicated for the topical treatment of symptomatic inflammatory tinea pedis, tinea cruris, and tinea corporis due to Epidermophyton floccosum, Trichophyton mentagrophytes, and Trichophyton rubrum in patients 17 years and older.

Launch Date

1984
Curative
LOTRISONE

Approved Use

LOTRISONE cream contains a combination of clotrimazole, an azole antifungal, and betamethasone dipropionate, a corticosteroid, and is indicated for the topical treatment of symptomatic inflammatory tinea pedis, tinea cruris, and tinea corporis due to Epidermophyton floccosum, Trichophyton mentagrophytes, and Trichophyton rubrum in patients 17 years and older.

Launch Date

1984
Curative
LOTRISONE

Approved Use

LOTRISONE cream contains a combination of clotrimazole, an azole antifungal, and betamethasone dipropionate, a corticosteroid, and is indicated for the topical treatment of symptomatic inflammatory tinea pedis, tinea cruris, and tinea corporis due to Epidermophyton floccosum, Trichophyton mentagrophytes, and Trichophyton rubrum in patients 17 years and older.

Launch Date

1984
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.4 μM
1 g single, oral
dose: 1 g
route of administration: Oral
experiment type: SINGLE
co-administered:
CLOTRIMAZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
4.98 ng/mL
10 mg single, buccal
dose: 10 mg
route of administration: Buccal
experiment type: SINGLE
co-administered:
CLOTRIMAZOLE serum
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
12.59 μM × h
1 g single, oral
dose: 1 g
route of administration: Oral
experiment type: SINGLE
co-administered:
CLOTRIMAZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.99 h
1 g single, oral
dose: 1 g
route of administration: Oral
experiment type: SINGLE
co-administered:
CLOTRIMAZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
4.25 h
500 mg single, vaginal
dose: 500 mg
route of administration: Vaginal
experiment type: SINGLE
co-administered:
CLOTRIMAZOLE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: FEMALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
10 mg 5 times / day multiple, oral
Recommended
Dose: 10 mg, 5 times / day
Route: oral
Route: multiple
Dose: 10 mg, 5 times / day
Sources:
unhealthy, 33 years (range: 22 - 43 years)
Health Status: unhealthy
Age Group: 33 years (range: 22 - 43 years)
Sex: M+F
Sources:
Disc. AE: Nausea, Taste abnormality...
AEs leading to
discontinuation/dose reduction:
Nausea (2 patients)
Taste abnormality (2 patients)
Sources:
500 mg single, vaginal
Highest studied dose
unhealthy, adult
Disc. AE: Vulvovaginal pruritus...
AEs leading to
discontinuation/dose reduction:
Vulvovaginal pruritus (1 patient)
Sources:
500 mg single, vaginal
Highest studied dose
unhealthy, adult
Disc. AE: Vulvovaginal burning sensation...
AEs leading to
discontinuation/dose reduction:
Vulvovaginal burning sensation (1 patient)
Sources:
50 mg 1 times / day multiple, vaginal
Dose: 50 mg, 1 times / day
Route: vaginal
Route: multiple
Dose: 50 mg, 1 times / day
Sources:
unhealthy, adult
Disc. AE: Vaginal irritation, Spotting vaginal...
AEs leading to
discontinuation/dose reduction:
Vaginal irritation (1 patient)
Spotting vaginal (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Nausea 2 patients
Disc. AE
10 mg 5 times / day multiple, oral
Recommended
Dose: 10 mg, 5 times / day
Route: oral
Route: multiple
Dose: 10 mg, 5 times / day
Sources:
unhealthy, 33 years (range: 22 - 43 years)
Health Status: unhealthy
Age Group: 33 years (range: 22 - 43 years)
Sex: M+F
Sources:
Taste abnormality 2 patients
Disc. AE
10 mg 5 times / day multiple, oral
Recommended
Dose: 10 mg, 5 times / day
Route: oral
Route: multiple
Dose: 10 mg, 5 times / day
Sources:
unhealthy, 33 years (range: 22 - 43 years)
Health Status: unhealthy
Age Group: 33 years (range: 22 - 43 years)
Sex: M+F
Sources:
Vulvovaginal pruritus 1 patient
Disc. AE
500 mg single, vaginal
Highest studied dose
unhealthy, adult
Vulvovaginal burning sensation 1 patient
Disc. AE
500 mg single, vaginal
Highest studied dose
unhealthy, adult
Spotting vaginal 1 patient
Disc. AE
50 mg 1 times / day multiple, vaginal
Dose: 50 mg, 1 times / day
Route: vaginal
Route: multiple
Dose: 50 mg, 1 times / day
Sources:
unhealthy, adult
Vaginal irritation 1 patient
Disc. AE
50 mg 1 times / day multiple, vaginal
Dose: 50 mg, 1 times / day
Route: vaginal
Route: multiple
Dose: 50 mg, 1 times / day
Sources:
unhealthy, adult
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
yes [IC50 0.00315 uM]
yes [IC50 0.00822 uM]
yes [IC50 0.1 uM]
yes [IC50 0.745 uM]
yes [IC50 2.3 uM]
yes [IC50 >10 uM]
yes [IC50 >10 uM]
yes [IC50 >10 uM]
yes [IC50 >10 uM]
yes [IC50 >10 uM]
yes [IC50 >10 uM]
yes [IC50 >10 uM]
yes
yes
yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
[Vulvovaginal candidiasis in childhood--diagnostic and therapeutic results].
2001
Topical treatment for vaginal candidiasis (thrush) in pregnancy.
2001
A double-blind randomized comparative trial: eberconazole 1% cream versus clotrimazole 1% cream twice daily in Candida and dermatophyte skin infections.
2001
Drug sensitivity of Candida yeast isolated from patients with allergic diseases.
2001 Apr
Liquid chromatographic determination of ketoconazole, a potent inhibitor of CYP3A4-mediated metabolism.
2001 Apr 5
Application of capillary zone electrophoresis with off-line solid-phase extraction to in vitro metabolism studies of antifungals.
2001 Aug
A systematic review of the effectiveness of antifungal drugs for the prevention and treatment of oropharyngeal candidiasis in HIV-positive patients.
2001 Aug
State-dependent block of rabbit vascular smooth muscle delayed rectifier and Kv1.5 channels by inhibitors of cytochrome P450-dependent enzymes.
2001 Aug
Suppression of transient outward potassium currents in mouse ventricular myocytes by imidazole antimycotics and by glybenclamide.
2001 Aug
Regulation of anion secretion by nitric oxide in human airway epithelial cells.
2001 Aug
Delineation of the clotrimazole/TRAM-34 binding site on the intermediate conductance calcium-activated potassium channel, IKCa1.
2001 Aug 24
Inhibition and stimulation of phospholipid scrambling activity. Consequences for lipid asymmetry, echinocytosis, and microvesiculation of erythrocytes.
2001 Aug 7
Effects of clotrimazole on transport mediated by multidrug resistance associated protein 1 (MRP1) in human erythrocytes and tumour cells.
2001 Dec
Regulation of K(+) current in human airway epithelial cells by exogenous and autocrine adenosine.
2001 Dec
Toward a novel metal-based chemotherapy against tropical diseases. 6. Synthesis and characterization of new copper(II) and gold(I) clotrimazole and ketoconazole complexes and evaluation of their activity against Trypanosoma cruzi.
2001 Dec 31
A novel drug-regulated gene expression system based on the nuclear receptor constitutive androstane receptor (CAR).
2001 Feb
Therapeutic strategies for prevention of sickle cell dehydration.
2001 Jan-Feb
Development of a mucoadhesive dosage form for vaginal administration.
2001 Jul
In vitro metabolism of 14C-moxidectin by hepatic microsomes from various species.
2001 Jul
Evaluation of two self-care treatments for prevention of vaginal candidiasis in women with HIV.
2001 Jul-Aug
[Therapeutic efficacy of a topical tolnaftate preparation in guinea pig model of tinea pedis].
2001 Jun
An investigation into the pathogenesis of vulvo-vaginal candidosis.
2001 Jun
A neuronal isoform of nitric oxide synthase expressed in pancreatic beta-cells controls insulin secretion.
2001 Jun
Clotrimazole is a selective and potent inhibitor of rat cytochrome P450 3A subfamily-related testosterone metabolism.
2001 Jun
Azole-antifungal binding to a novel cytochrome P450 from Mycobacterium tuberculosis: implications for treatment of tuberculosis.
2001 Jun 15
In vitro activity of sertaconazole, fluconazole, ketoconazole, fenticonazole, clotrimazole and itraconazole against pathogenic vaginal yeast isolates.
2001 Mar
Comparison of in vitro activities of amphotericin, clotrimazole, econazole, miconazole, and nystatin against Fusarium oxysporum.
2001 May
What happens in cidal and static action?
2001 May
Substantivity of topically applied antifungals on dermatophytic toe webs.
2001 May
Optimization of the separation of a group of antifungals by capillary zone electrophoresis.
2001 May 11
Intracellular signalling involved in activation of the volume-sensitive K+ current in Ehrlich ascites tumour cells.
2001 Oct
[How I treat ... sickle cell anemia: current therapies].
2001 Oct
In vitro activity of 6 antifungal agents on candida species isolated as causative agents from vaginal and other clinical specimens.
2001 Oct
Novel effects of minocycline on Ca(2+)-dependent Cl(-) secretion in human airway epithelial Calu-3 cells.
2001 Oct 15
Angiotensin II type AT(2) receptor mRNA expression and renal vasodilatation are increased in renal failure.
2001 Sep
Conservation of signaling pathways of xenobiotic-sensing orphan nuclear receptors, chicken xenobiotic receptor, constitutive androstane receptor, and pregnane X receptor, from birds to humans.
2001 Sep
Use of topical clotrimazole in human keratomycosis.
2001 Sep-Oct
Activation of ion secretion via proteinase-activated receptor-2 in human colon.
2002 Feb
Characterization of basolateral K+ channels underlying anion secretion in the human airway cell line Calu-3.
2002 Feb 1
Modulation of mouse Paneth cell alpha-defensin secretion by mIKCa1, a Ca2+-activated, intermediate conductance potassium channel.
2002 Feb 1
Arginine supplementation of sickle transgenic mice reduces red cell density and Gardos channel activity.
2002 Feb 15
Clotrimazole binds to heme and enhances heme-dependent hemolysis: proposed antimalarial mechanism of clotrimazole.
2002 Feb 8
Comparison of two methods for antifungal susceptibility testing of Trichophyton rubrum.
2002 Jan
Development of a topical suspension containing three active ingredients.
2002 Jan
Spectrofluorimetric determination of vigabatrin and gabapentin in urine and dosage forms through derivatization with fluorescamine.
2002 Jan 1
Differential pulse polarographic determination of clotrimazole after derivatization with Procion Red HE-3B.
2002 Jan 1
Clotrimazole/betamethasone diproprionate: a review of costs and complications in the treatment of common cutaneous fungal infections.
2002 Jan-Feb
K+ currents generated by NMDA receptor activation in rat hippocampal pyramidal neurons.
2002 Jun
Effect of antifungal azoles on the heme detoxification system of malarial parasite.
2002 Mar
Inhibition of vascular smooth muscle cell migration by cytochrome p450 epoxygenase-derived eicosanoids.
2002 May 17
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018052Orig1s032lbl.pdf
Vaginal 1% cream: insert an applicator full of cream into the vagina at bedtime for 7 days. External 1% cream for vaginal yeast infections: apply to the skin outside the vagina 2 times daily for up to 7 days. Topical 1% cream: apply a thin layer to the affected area twice daily for 2 weeks (tinea pedis) or 1 week (tinea cruris and tinea corporis).
Route of Administration: Topical
In vitro antifungal activity indicated Clotrimazole (MIC 16 and 8 microg/ml) effective against 68 (70%) of Candida SPP.
Name Type Language
LOTRISONE COMPONENT CLOTRIMAZOLE
Preferred Name English
CLOTRIMAZOLE
EP   GREEN BOOK   HSDB   INCI   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN   INCI  
Official Name English
CLOTRIMAZOLE [GREEN BOOK]
Common Name English
SVT-15652
Code English
CLOTRIMAZOLE [ORANGE BOOK]
Common Name English
GNF-PF-3499
Code English
CLOTRIMAZOLE [USP IMPURITY]
Common Name English
TRIVAGIZOLE
Brand Name English
clotrimazole [INN]
Common Name English
CLOTRIMAZOLE [MART.]
Common Name English
CLOTRIMAZOLE [JAN]
Common Name English
Clotrimazole [WHO-DD]
Common Name English
GYNIX
Brand Name English
BAY-5097
Code English
LOTRIMIN
Brand Name English
CLOTRIMAZOLE [MI]
Common Name English
GYNE-LOTRIMIN
Brand Name English
CLOTRIMAZOLE [EP IMPURITY]
Common Name English
BAY 5097
Code English
1-(2-CHLOROTRITYL)IMIDAZOLE
Systematic Name English
CLOTRIMAZOLE [USP MONOGRAPH]
Common Name English
MYCELEX
Brand Name English
CLOTRIMAZOLE [EP MONOGRAPH]
Common Name English
NSC-257473
Code English
1-(O-CHLORO-.ALPHA.,.ALPHA.-DIPHENYLBENZYL)IMIDAZOLE
Common Name English
CLOTRIMAZOLE [VANDF]
Common Name English
1-((2-CHLOROPHENYL)DIPHENYLMETHYL)-1H-IMIDAZOLE
Systematic Name English
CLOTRIMAZOLE [USAN]
Common Name English
1H-IMIDAZOLE, 1-((2-CHLOROPHENYL)DIPHENYLMETHYL)-
Systematic Name English
CLOTRIMAZOLE [USP-RS]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 524.1044G
Created by admin on Mon Mar 31 17:45:54 GMT 2025 , Edited by admin on Mon Mar 31 17:45:54 GMT 2025
FDA ORPHAN DRUG 204005
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WHO-VATC QJ02AB90
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WHO-VATC QG01AF02
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NDF-RT N0000008217
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WHO-ESSENTIAL MEDICINES LIST 6.3
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CFR 21 CFR 524.450
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FDA ORPHAN DRUG 216705
Created by admin on Mon Mar 31 17:45:54 GMT 2025 , Edited by admin on Mon Mar 31 17:45:54 GMT 2025
WHO-VATC QA01AB18
Created by admin on Mon Mar 31 17:45:54 GMT 2025 , Edited by admin on Mon Mar 31 17:45:54 GMT 2025
FDA ORPHAN DRUG 88094
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WHO-VATC QD01AC01
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LIVERTOX NBK548320
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WHO-ATC D01AC01
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NDF-RT N0000175487
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WHO-ATC G01AF02
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NCI_THESAURUS C514
Created by admin on Mon Mar 31 17:45:54 GMT 2025 , Edited by admin on Mon Mar 31 17:45:54 GMT 2025
WHO-ATC A01AB18
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CFR 21 CFR 333.210
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CFR 21 CFR 524.1044H
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FDA ORPHAN DRUG 520516
Created by admin on Mon Mar 31 17:45:54 GMT 2025 , Edited by admin on Mon Mar 31 17:45:54 GMT 2025
Code System Code Type Description
MESH
D003022
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PRIMARY
IUPHAR
2330
Created by admin on Mon Mar 31 17:45:54 GMT 2025 , Edited by admin on Mon Mar 31 17:45:54 GMT 2025
PRIMARY
WIKIPEDIA
CLOTRIMAZOLE
Created by admin on Mon Mar 31 17:45:54 GMT 2025 , Edited by admin on Mon Mar 31 17:45:54 GMT 2025
PRIMARY
ECHA (EC/EINECS)
245-764-8
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PRIMARY
INN
2912
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PRIMARY
MERCK INDEX
m3671
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PRIMARY Merck Index
EPA CompTox
DTXSID7029871
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PRIMARY
EVMPD
SUB06777MIG
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PRIMARY
DAILYMED
G07GZ97H65
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PRIMARY
HSDB
3266
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PRIMARY
RXCUI
2623
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PRIMARY RxNorm
NSC
257473
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PRIMARY
SMS_ID
100000092074
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PRIMARY
DRUG BANK
DB00257
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PRIMARY
CHEBI
3764
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PRIMARY
ALANWOOD
clotrimazole
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PRIMARY
ChEMBL
CHEMBL104
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PRIMARY
PUBCHEM
2812
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PRIMARY
NCI_THESAURUS
C381
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PRIMARY
CAS
23593-75-1
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PRIMARY
LACTMED
Clotrimazole
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PRIMARY
RS_ITEM_NUM
1141002
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PRIMARY
DRUG CENTRAL
719
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PRIMARY
FDA UNII
G07GZ97H65
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PRIMARY