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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
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
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
- Human Data
- Metabolic Side Effects of Drugs and Substances
- Reproductive Effect
- Steroid Synthesis Inhibitors
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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
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/h1-17HInChIKey
VNFPBHJOKIVQEB-UHFFFAOYSA-NSmiles
Clc1ccccc1C(c2ccccc2)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.