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 | |
|---|---|---|---|
|
ABCB1 |
|
Publications |
|
CYP2E1 |
|
Publications |
|
|
CYP3A4 |
|
Publications |
|
|
SLCO1B1 |
|
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.
LinkOuts
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.