C6019

Clotrimazole

98.5-100.5% (dry basis), powder, Ca²⁺-activated K⁺ channels inhibitor

• Synonym(s): 1-(o-Chloro-α,α-diphenylbenzyl)imidazole, 1-(o-Chlorotrityl)imidazole, 1-[(2-Chlorophenyl)diphenylmethyl]-1H-imidazole
• Empirical Formula (Hill Notation): C₂₂H₁₇ClN₂
• CAS Number: 23593-75-1
• Molecular Weight: 344.84
• EC Number: 245-764-8
• MDL number: MFCD00057220
• UNSPSC Code: 12352200
• PubChem Substance ID: 24278327
• NACRES: NA.77

Properties

• product name: Clotrimazole,
• form: powder
• antibiotic activity spectrum: fungi
• Mode of action: cell membrane | interferes; protein synthesis | interferes
• originator: Schering Plough
• SMILES string: Clc1ccccc1C(c2ccccc2)(c3ccccc3)n4ccnc4
• 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
• Gene Information: human ... ABCB1(5243) , CYP17A1(1586) , CYP3A4(1576) ; mouse ... Abcb1a(18671) , Abcb1b(18669)

Description

General description

Chemical structure: imidazole

Application

Clotrimazole has been used:

• to study the upregulation of the gene ERG11 that codes for an azole target enzyme lanosterol demethylase, in Candida species, upon treatment with azole antibiotics
• to study the development of resistance in Candida species isolated from patients undergoing prolonged antifungal treatment
• to induce stress granules via mitochondrial stress
• for the inhibition of in vitro formation of high density sickle cells induced by treatment with 1-chloro-2,4-dinitrobenzene (CDNB)
• to inhibit cytochrome P450 enzyme in cell cultures

Biochem/physiol Actions

Clotrimazole is a specific inhibitor of Ca²⁺-activated K⁺ channels. It is an antifungal azole. Clotrimazole is a derivative of imidazole and has similar antimicrobial action and activity to ketoconazole. It inhibits cytochrome P450-dependent 14α-demethylase, which is critical to ergosterol biosynthesis. The accumulated 14α-methylated sterols change the membrane structure of sensitive fungi, altering cell membrane permeability.

Features and Benefits

This compound is featured on the Potassium Channels page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

This compound was developed by Schering Plough. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Safety Information

• Pictograms: GHS07,GHS09
• Signal Word: Warning
• Hazard Statements: H302,H315,H319,H410
• Precautionary Statements: P264 - P270 - P273 - P301 + P312 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Skin Irrit. 2
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves