Drug/Small Molecule:
clotrimazole

2D structure

Overview

Generic Names: Chlotrimazole; Clotrimazol
IUPAC Name: 1-[(2-chlorophenyl)-di(phenyl)methyl]imidazole
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 Mixtures: Lotrisone (clotrimazole + betamethasone)
PharmGKB Accession Id: PA449057

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. [PubChem]

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.

ATC Therapeutic Categories

  • A01AB:Antiinfectives and antiseptics for local oral treatment
  • D01AC:Imidazole and triazole derivatives
  • G01AF:Imidazole derivatives

Pharmacology and Interactions

Mechanism Of Action

Clotrimazole interacts with yeast 14-α 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.

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.

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Hepatic (metabolized to inactive metabolites)

Protein Binding

90%

Absorption

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

Half Life

2 hours

Toxicity

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

Chemical Properties

Chemical Formula:

C22H17ClN2

SMILES Code:

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

(Format: OpenEye Isomeric)

Molecular Weight ( average / monoisotopic )

344.837 / 344.108

Curated Information

The following genes are in curated knowledge about this drug.

  Gene Relationship Evidence
Phenotype data available Genotype Data Available Literature annotations available Has annotations
ABCB1
  •   
  •   
  •   
  • FA
  •   
Publications
No phenotype data Genotype Data Available Literature annotations available Not annotated
CYP2E1
  •   
  •   
  • PK
  •   
  •   
Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
CYP3A4
  •   
  •   
  • PK
  • FA
  •   
Publications
No phenotype data Genotype Data Available Literature annotations available Has annotations
SLCO1B1
  •   
  •   
  • PK
  • FA
  •   
Publications

Non-Curated Information

A list of non-curated publications that mention this drug along with other genes is available.

Metabolizing Enzymes

Drug Targets

Non-Curated Information

A list of non-curated publications that mention this drug along with other drugs is available.

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

Additional Datasets

These datasets are minimally curated and are sorted alphabetically by title.

  1. The Connectivity Map: using gene-expression signatures to connect small molecules, genes, and disease

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00257
ChEBI ID:
3764
KEGG Compound ID:
C06922
KEGG Drug ID:
D00282
PubChem Compound ID:
2812
PubChem Substance ID:
174033

Common Searches

Search PubMed
Search Medline Plus
Search PubChem
Search CTD

Non-Curated Publications

A list of non-curated publications that mention this drug is available.

PharmGKB integrates drug information from different sources: DrugBank, Open Eye Scientific Software.
The PharmGKB is financially supported by the NIH/ NIGMS and is managed at Stanford University (U01GM61374).
©2001-2010 PharmGKB.