Chemical: Drug
clotrimazole

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PharmGKB contains no Clinical Variants that meet the highest level of criteria.

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Overview

Generic Names
  • Chlotrimazole
  • Clotrimazol
Trade Names
  • Canesten
  • Canesten 1-Day Cream Combi-Pak
  • Canesten 1-Day Therapy
  • Canesten 3-Day Therapy
  • Canesten 6-Day Therapy
  • Canesten Combi-Pak 1-Day Therapy
  • Canesten Combi-Pak 3-Day Therapy
  • Canesten Cream
  • Canesten Solution
  • Canestine
  • Canifug
  • Cimitidine
  • Clotrimaderm
  • Empecid
  • FemCare
  • Gyne lotrimin
  • Gyne-Lotrimin 3
  • Gyne-Lotrimin 3 Combination Pack
  • Gyne-Lotrimin Combination Pack
  • Gyne-lotrimin
  • Gynix
  • Lotrimin
  • Lotrimin AF Cream
  • Lotrimin AF Jock-Itch Cream
  • Lotrimin AF Lotion
  • Lotrimin AF Solution
  • Lotrimin Af
  • Lotrimin Cream
  • Lotrimin Lotion
  • Lotrimin Solution
  • Mono-baycuten
  • Mycelax
  • Mycelex
  • Mycelex 7
  • Mycelex Cream
  • Mycelex G
  • Mycelex Solution
  • Mycelex Troches
  • Mycelex Twin Pack
  • Mycelex-7
  • Mycelex-7 Combination Pack
  • Mycelex-G
  • Myclo Cream
  • Myclo Solution
  • Myclo Spray Solution
  • Myclo-Gyne
  • Mycosporin
  • Mykosporin
  • Neo-Zol Cream
  • Trimysten
  • Trivagizole 3
  • Veltrim
Brand Mixture Names
  • Lotrisone (clotrimazole + betamethasone)

PharmGKB Accession Id

PA449057

Type(s):

Drug

Description

An imidazole derivative with a broad spectrum of antimycotic activity. It inhibits biosynthesis of the sterol ergostol, an important component of fungal cell membranes. Its action leads to increased membrane permeability and apparent disruption of enzyme systems bound to the membrane.

Source: Drug Bank

Indication

For the local treatment of oropharyngeal candidiasis and vaginal yeast infections, also used in fungal infections of the skin such as ringworm, athlete's foot, and jock itch.

Source: Drug Bank

Other Vocabularies

Information pulled from DrugBank has not been reviewed by PharmGKB.

Pharmacology, Interactions, and Contraindications

Mechanism of Action

Clotrimazole interacts with yeast 14-alpha demethylase, a cytochrome P-450 enzyme that converts lanosterol to ergosterol, an essential component of the membrane. In this way, clotrimazole inhibits ergosterol synthesis, resulting in increased cellular permeability. Clotrimazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms and the uptake of purine, impair triglyceride and/or phospholipid biosynthesis, and inhibit the movement of calcium and potassium ions across the cell membrane by blocking the ion transport pathway known as the Gardos channel.

Source: Drug Bank

Pharmacology

Clotrimazole, an imidazole derivative with a broad spectrum of antimycotic activity, inhibits biosynthesis of the sterol ergostol, an important component of fungal cell membranes. Its action leads to increased membrane permeability and apparent disruption of enzyme systems bound to the membrane. Betamethasone and clotrimazole are used together to treat cutaneous tinea infections. In studies in fungal cultures, the minimum fungicidal concentration of clotrimazole caused leakage of intracellular phosphorous compounds into the ambient medium with concomitant breakdown of cellular nucleic acids, and accelerated potassium etflux. Both of these events began rapidly and extensively after addition of the drug to the cultures. The primary action of clotrimazole is against dividing and growing organisms.

Source: Drug Bank

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Hepatic (metabolized to inactive metabolites)

Source: Drug Bank

Protein Binding

90%

Source: Drug Bank

Absorption

Poorly and erratically absorbed orally, minimal vaginal or topical absorption.

Source: Drug Bank

Half-Life

2 hours

Source: Drug Bank

Toxicity

Symptoms of overdose include erythema, stinging, blistering, peeling, edema, pruritus, urticaria, burning, and general irritation of the skin, and cramps.

Source: Drug Bank

Chemical Properties

Chemical Formula

C22H17ClN2

Source: Drug Bank

Isomeric SMILES

c1ccc(cc1)C(c2ccccc2)(c3ccccc3Cl)n4ccnc4

Source: OpenEye

Canonical SMILES

ClC1=CC=CC=C1C(N1C=CN=C1)(C1=CC=CC=C1)C1=CC=CC=C1

Source: Drug Bank

Average Molecular Weight

344.837

Source: Drug Bank

Monoisotopic Molecular Weight

344.108026261

Source: Drug Bank

SMILES

ClC1=CC=CC=C1C(N1C=CN=C1)(C1=CC=CC=C1)C1=CC=CC=C1

Source: Drug Bank

InChI String

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

Source: Drug Bank

Genes that are associated with this drug in PharmGKB's database based on (1) variant annotations, (2) literature review, (3) pathways or (4) information automatically retrieved from DrugBank, depending on the "evidence" and "source" listed below.

Curated Information ?

Drug Targets

Gene Description
CYP51A1 (source: Drug Bank)
KCNN4 (source: Drug Bank)

Drug Interactions

Interaction Description
tamsulosin - clotrimazole Clotrimazole, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Clotrimazole is initiated, discontinued, or dose changed. (source: Drug Bank)
tamsulosin - clotrimazole Clotrimazole, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Clotrimazole is initiated, discontinued, or dose changed. (source: Drug Bank)
tolterodine - clotrimazole Clotrimazole may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity. (source: Drug Bank)
tolterodine - clotrimazole Clotrimazole may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity. (source: Drug Bank)
tramadol - clotrimazole Clotrimazole may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance. (source: Drug Bank)
trazodone - clotrimazole The CYP3A4 inhibitor, Clotrimazole, may increase Trazodone efficacy/toxicity by decreasing Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Clotrimazole is initiated, discontinued or dose changed. (source: Drug Bank)
trazodone - clotrimazole The CYP3A4 inhibitor, Clotrimazole, may increase Trazodone efficacy/toxicity by decreasing Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Clotrimazole is initiated, discontinued or dose changed. (source: Drug Bank)

Curated Information ?

Relationships from National Drug File - Reference Terminology (NDF-RT)

May Treat
May Prevent
Contraindicated With

Publications related to clotrimazole: 13

No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available VIP No VIP available
Very important pharmacogene summary: ABCB1 (MDR1, P-glycoprotein). Pharmacogenetics and genomics. 2011. Hodges Laura M, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Structure, function and regulation of P-glycoprotein and its clinical relevance in drug disposition. Xenobiotica; the fate of foreign compounds in biological systems. 2008. Zhou S-F. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Effect of pregnane X receptor ligands on transport mediated by human OATP1B1 and OATP1B3. European journal of pharmacology. 2008. Gui Chunshan, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Azole antimycotics differentially affect rifampicin-induced pregnane X receptor-mediated CYP3A4 gene expression. Drug metabolism and disposition: the biological fate of chemicals. 2008. Svecova Lucie, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
The induction of cytochrome P450 3A5 (CYP3A5) in the human liver and intestine is mediated by the xenobiotic sensors pregnane X receptor (PXR) and constitutively activated receptor (CAR). The Journal of biological chemistry. 2004. Burk Oliver, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Human extrahepatic cytochromes P450: function in xenobiotic metabolism and tissue-selective chemical toxicity in the respiratory and gastrointestinal tracts. Annual review of pharmacology and toxicology. 2003. Ding Xinxin, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
CYP3A4 induction by drugs: correlation between a pregnane X receptor reporter gene assay and CYP3A4 expression in human hepatocytes. Drug metabolism and disposition: the biological fate of chemicals. 2002. Luo Gang, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Orphan nuclear receptors constitutive androstane receptor and pregnane X receptor share xenobiotic and steroid ligands. The Journal of biological chemistry. 2000. Moore L B, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
The pregnane X receptor: a promiscuous xenobiotic receptor that has diverged during evolution. Molecular endocrinology (Baltimore, Md.). 2000. Jones S A, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Identification of a human nuclear receptor defines a new signaling pathway for CYP3A induction. Proceedings of the National Academy of Sciences of the United States of America. 1998. Bertilsson G, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
The human orphan nuclear receptor PXR is activated by compounds that regulate CYP3A4 gene expression and cause drug interactions. The Journal of clinical investigation. 1998. Lehmann J M, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Inhibition of human hepatic cytochrome P4502E1 by azole antifungals, CNS-active drugs and non-steroidal anti-inflammatory agents. Xenobiotica; the fate of foreign compounds in biological systems. 1998. Tassaneeyakul W, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Effects of imidazole derivatives on cytochromes P450 from human hepatocytes in primary culture. The FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 1992. Maurice M, et al. PubMed

LinkOuts

Web Resource:
Wikipedia
National Drug Code Directory:
54868-5463-0
DrugBank:
DB00257
ChEBI:
3764
KEGG Compound:
C06922
KEGG Drug:
D00282
PubChem Compound:
2812
PubChem Substance:
174033
46507927
IUPHAR Ligand:
2330
Drugs Product Database (DPD):
2229380
BindingDB:
31774
ChemSpider:
2710
Therapeutic Targets Database:
DAP000138
FDA Drug Label at DailyMed:
eacf7456-5f44-483d-8b5f-c2c273f46e76

Clinical Trials

These are trials that mention clotrimazole and are related to either pharmacogenetics or pharmacogenomics.

No trials found.

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Sources for PharmGKB drug information: DrugBank, PubChem.