C6019

Clotrimazole

Name: Clotrimazole
Brand: SIGMA

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

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About This Item

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

Key Documents

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Product Name

Clotrimazole,

form

powder

Quality Level

200

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)

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.

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