SynCED: Clotrimazole

Record Information

Version

1.0

Creation Date

2009-07-21 20:26:25 UTC

Update Date

2026-05-14 16:24:59 UTC

Accession Number

CHEM002155

Identification

Common Name

Clotrimazole

Class

Small Molecule

Description

Clotrimazole is 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. There is the potential for drug interactions with Clotrimazole if taken orally, as it is a potent, specific inhibitor of cytochrome P450 oxidase enzymes and so may alter the metabolism of other drugs. Clotrimazole is an antifungal medication commonly used in the treatment of fungal infections of both humans and animals such as vaginal yeast infections and ringworm. 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. Clotrimazole is a potent, specific inhibitor of cytochrome P450 oxidase enzymes. Hence, it may alter the metabolism of other drugs particularly if taken orally. Clotrimazole is an antifungal medication commonly used in the treatment of fungal infections of both humans and animals such as vaginal yeast infections and ringworm. It also used to treat athlete's foot and jock itch.

Contaminant Sources

FooDB Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

14-alpha Demethylase Inhibitor
Amine
Anti-Infective Agent, Local
Antifungal Agent
Drug
Food Toxin
Growth Inhibitor
Metabolite
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF 3D SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
1-((2-Chlorophenyl)diphenylmethyl)-1H-imidazole	ChEBI
1-(alpha-(2-Chlorophenyl)benzhydryl)imidazole	ChEBI
1-(O-Chloro-alpha,alpha-diphenylbenzyl)imidazole	ChEBI
1-(O-Chlorotrityl)imidazole	ChEBI
Lotrimin	ChEBI
Mycelex	ChEBI
1-(a-(2-Chlorophenyl)benzhydryl)imidazole	Generator
1-(Α-(2-chlorophenyl)benzhydryl)imidazole	Generator
1-(O-Chloro-a,a-diphenylbenzyl)imidazole	Generator
1-(O-Chloro-α,α-diphenylbenzyl)imidazole	Generator
(Chlorotrityl)imidazole	HMDB
Canesten	HMDB
Canesten 1-day cream combi-pak	HMDB
Canesten 1-day therapy	HMDB
Canesten 3-day therapy	HMDB
Canesten 6-day therapy	HMDB
Canesten combi-pak 1-day therapy	HMDB
Canesten combi-pak 3-day therapy	HMDB
Canesten cream	HMDB
Canesten solution	HMDB
Canestine	HMDB
Chlotrimazole	HMDB
Clotrimaderm	HMDB
Clotrimaderm cream	HMDB
Clotrimazol	HMDB
Clotrimazolum	HMDB
Desamix F	HMDB
Empecid	HMDB
Fem care	HMDB
FemCare	HMDB
Gyne lotrimin	HMDB
Gyne-lotrimin	HMDB
Gyne-lotrimin 3	HMDB
Gyne-lotrimin 3 combination pack	HMDB
Gyne-lotrimin combination pack	HMDB
Gyne-lotrimin3	HMDB
Gyne-lotrimin3 combination pack	HMDB
Gynix	HMDB
Lopac-C-6019	HMDB
Lotrimax	HMDB
Lotrimin af	HMDB
Lotrimin af cream	HMDB
Lotrimin af jock-itch cream	HMDB
Lotrimin af lotion	HMDB
Lotrimin af solution	HMDB
Lotrimin cream	HMDB
Lotrimin lotion	HMDB
Lotrimin solution	HMDB
Lotrisone	HMDB
mono-Baycuten	HMDB
Monobaycuten	HMDB
Mycelax	HMDB
Mycelex 7	HMDB
Mycelex cream	HMDB
Mycelex g	HMDB
Mycelex otc	HMDB
Mycelex solution	HMDB
Mycelex troches	HMDB
Mycelex twin pack	HMDB
Mycelex-7	HMDB
Mycelex-7 combination pack	HMDB
Mycelex-g	HMDB
Mycelex: mycosporinrimazole	HMDB
Myclo cream	HMDB
Myclo solution	HMDB
Myclo spray solution	HMDB
Myclo-gyne	HMDB
Mycosporin	HMDB
Mykosporin	HMDB
Neo-zol cream	HMDB
Otomax	HMDB
Pedisafe	HMDB
Prestwick_120	HMDB
Rimazole	HMDB
Tibatin	HMDB
Trimysten	HMDB
Trivagizole 3	HMDB
Veltrim	HMDB
Klotrimazole	HMDB
Schering brand OF clotrimazole	HMDB
Bayer brand 1 OF clotrimazole	HMDB
Bayer brand 2 OF clotrimazole	HMDB
FB b 5097	HMDB
Bay b 5097	HMDB
Clotrimazole schering brand	HMDB
Kanesten	HMDB

Chemical Formula

C₂₂H₁₇ClN₂

Average Molecular Mass

344.837 g/mol

Monoisotopic Mass

344.108 g/mol

CAS Registry Number

23593-75-1

IUPAC Name

1-[(2-chlorophenyl)diphenylmethyl]-1H-imidazole

Traditional Name

clotrimazole

SMILES

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

InChI Identifier

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

InChI Key

VNFPBHJOKIVQEB-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Substituents

Triphenyl compound
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
N-substituted imidazole
Azole
Heteroaromatic compound
Imidazole
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organochloride
Organohalogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

conazole antifungal drug (CHEBI:3764 )
imidazoles (CHEBI:3764 )
imidazole antifungal drug (CHEBI:3764 )
monochlorobenzenes (CHEBI:3764 )
a small molecule (CPD-8926 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Skin

Pathways

Not Available

Applications

Biological Roles

fungicide

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	154-156°C
Boiling Point	Not Available
Solubility	29.84 mg/mL

Predicted Properties

Property	Value	Source
Water Solubility	0.0015 g/L	ALOGPS
logP	5.48	ALOGPS
logP	5.84	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Basic)	6.62	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.82 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	103.76 m³·mol⁻¹	ChemAxon
Polarizability	36.25 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Toxicity Profile

Route of Exposure

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

Mechanism of Toxicity

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.

Metabolism

Hepatic (metabolized to inactive metabolites) Half Life: 2 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

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.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

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

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00257

HMDB ID

HMDB0001922

FooDB ID

FDB022740

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

1897

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

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).

MSDS

Link

General References

1. Lucker PW, Beubler E, Kukovetz WR, Ritter W: Retention time and concentration in human skin of bifonazole and clotrimazole. Dermatologica. 1984;169 Suppl 1:51-5.

2. Schmidt A, Ruhl-Horster B: In vitro susceptibility of Malassezia furfur against azole compounds. Mycoses. 1996 Jul-Aug;39(7-8):309-12.

3. Schmook FP, Meingassner JG, Billich A: Comparison of human skin or epidermis models with human and animal skin in in-vitro percutaneous absorption. Int J Pharm. 2001 Mar 14;215(1-2):51-6.

4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18728240

5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24892421

Clotrimazole (CHEM002155)

Structure for CHEM002155: Clotrimazole