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Substance Name: Clotrimazole [USAN:USP:INN:BAN:JAN]
RN: 23593-75-1
UNII: G07GZ97H65
InChIKey: VNFPBHJOKIVQEB-UHFFFAOYSA-N

Note

  • 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.

Molecular Formula

  • C22-H17-Cl-N2

Molecular Weight

  • 344.843
 

Classification Codes

  • 14-alpha Demethylase Inhibitors
  • Anti-Infective Agents
  • Anti-Infective Agents, Local
  • Antifungal
  • Antifungal Agents
  • Cytochrome P-450 Enzyme Inhibitors
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Hormone Antagonists
  • Hormones, Hormone Substitutes, and Hormone Antagonists
  • Human Data
  • Reproductive Effect
  • Steroid Synthesis Inhibitors

Names and Synonyms

Name of Substance

  • Clotrimazole
  • Clotrimazole [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Clotrimazole

Synonyms

  • (2-Chlorophenyl)diphenyl-1-imidazolylmethane
  • (Chlorotrityl)imidazole
  • 1-((2-Chlorophenyl)diphenylmethyl)-1H-imidazole
  • 1-((o-Chloro-phenyl)diphenylmethyl)imidazole
  • 1-(alpha-(2-Chlorophenyl)benzhydryl)imidazole
  • 1-(o-Chloro-alpha,alpha-diphenylbenzyl)imidazole
  • 1-(o-Chlorophenyldiphenylmethyl)imidazole
  • 1-(o-Chlorotrityl)imidazole
  • 1H-Imidazole, 1-((2-chlorophenyl)diphenylmethyl)-
  • 5-23-04-00291 (Beilstein Handbook Reference)
  • B 5097
  • BAY 5097
  • BAY b 5097
  • Bay-B 5097
  • Bis-fenil-(2-clorofenil)-1-imidazolil-metano
  • Bis-fenil-(2-clorofenil)-1-imidazolil-metano [Italian]
  • Bis-phenyl-(2-chlorophenyl)(1-imidazoyl)methane
  • Bisphenyl-(2-chlorphenyl)-1-imidazolyl-methan
  • Bisphenyl-(2-chlorphenyl)-1-imidazolyl-methan [German]
  • BRN 0622318
  • Canesten
  • Canestene
  • Canifug
  • CCRIS 6245
  • Chlotrimazole
  • Clomatin
  • Clotrimazol
  • Clotrimazol [INN-Spanish]
  • Clotrimazole
  • Clotrimazolum
  • Clotrimazolum [INN-Latin]
  • Cutistad
  • Desamix F
  • Diphenyl(2-chlorophenyl)(1-imidazolyl)methane
  • Diphenyl-(2-chlorophenyl)-1-imidazolylmethane
  • DRG-0072
  • EINECS 245-764-8
  • Empecid
  • Esparol
  • FB 5097
  • Fem Care
  • Gino-Lotremine
  • Gyne lotrimin
  • Gyne-Lotrimin
  • Gyne-lotrimin 3
  • Gyne-lotrimin 3 Combination Pack
  • Gyne-lotrimin Combination Pack
  • Gynix
  • HSDB 3266
  • Jidesheng
  • Lotrimin
  • Lotrimin AF
  • Lotrimin AF Cream
  • Lotrimin AF Jock-Itch Cream
  • Lotrimin AF Solution
  • Methane, bis-phenyl-(2-chlorophenyl)-1-imidazolyl-
  • Mono-Baycuten
  • Monobaycuten
  • Mycelex
  • Mycelex 7
  • Mycelex G
  • Mycelex OTC
  • Mycelex Troches
  • Mycelex-7
  • Mycelex-7 Combination Pack
  • Mycelex-G
  • Mycofug
  • Mycosporin
  • Mykosporin
  • Nalbix
  • NSC 257473
  • Pan-Fungex
  • Pedisafe
  • Rimazole
  • Stiemazol
  • Tibatin
  • Trimysten
  • Trivagizole 3
  • UNII-G07GZ97H65
  • Veltrim

Systematic Names

  • 1-((2-Chlorophenyl)diphenylmethyl)-1H-imidazole (9CI)
  • 1H-Imidazole, 1-((2-chlorophenyl)diphenylmethyl)-
  • Clotrimazole
  • Imidazole, 1-(o-chloro-alpha,alpha-diphenylbenzyl)-

Mixture Names

  • Lotrimax
  • Lotrisone
  • Otomax (Veterinary)

Registry Numbers

CAS Registry Number

  • 23593-75-1

FDA UNII

  • G07GZ97H65

Other Registry Number

  • 117829-71-7

System Generated Number

  • 0023593751

Structure Descriptors

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

InChIKey

VNFPBHJOKIVQEB-UHFFFAOYSA-N

Smiles

C(c1c(cccc1)Cl)(n1ccnc1)(c1ccccc1)c1ccccc1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 oral > 1gm/kg (1000mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1272, 1972.
dog LD50 oral > 2gm/kg (2000mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1272, 1972.
mammal (species unspecified) LD50 oral 750mg/kg (750mg/kg)   Antimicrobial Agents and Chemotherapy Vol. -, Pg. 271, 1969.
mouse LD50 intraperitoneal 108mg/kg (108mg/kg)   Drug and Chemical Toxicology. Vol. 13, Pg. 195, 1990.
mouse LD50 intravenous 198mg/kg (198mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967.
mouse LD50 oral 761mg/kg (761mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1272, 1972.
mouse LDLo subcutaneous 10gm/kg (10000mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 1333, 1973.
rabbit LD50 oral > 1gm/kg (1000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: MUSCLE WEAKNESS
Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1272, 1972.
rat LD50 intraperitoneal 445mg/kg (445mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 1333, 1973.
rat LD50 oral 708mg/kg (708mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1272, 1972.
rat LDLo subcutaneous 10gm/kg (10000mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 1333, 1973.
women TDLo intravaginal 28mg/kg/7D (28mg/kg) SKIN AND APPENDAGES (SKIN): PRIMARY IRRITATION: AFTER TOPICAL EXPOSURE Clinical Toxicology. Vol. 18, Pg. 41, 1981.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 148 deg C   EXP
log P (octanol-water) 6.260 (none)   EST
Atmospheric OH Rate Constant 4.62E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.