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C6019

Sigma-Aldrich

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

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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

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)

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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.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H315,H319,H410

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Nancy Kedersha et al.
The Journal of cell biology, 169(6), 871-884 (2005-06-22)
Stress granules (SGs) are cytoplasmic aggregates of stalled translational preinitiation complexes that accumulate during stress. GW bodies/processing bodies (PBs) are distinct cytoplasmic sites of mRNA degradation. In this study, we show that SGs and PBs are spatially, compositionally, and functionally
A Shartava et al.
American journal of hematology, 62(1), 19-24 (1999-09-01)
Clotrimazole, a specific inhibitor of the Ca(2+) activated potassium (Gardos) channel, and the antioxidant N-acetylcysteine were found to inhibit the in vitro formation of high-density sickle cells induced by treatment with 1-chloro-2,4-dinitrobenzene (CDNB). The CDNB induced leakage of K(+) can
P Fan-Havard et al.
Antimicrobial agents and chemotherapy, 35(11), 2302-2305 (1991-11-01)
The impact of prolonged antifungal therapy on the development of resistance was examined in 61 patients with oropharyngeal thrush. Fifty-nine patients had symptomatic human immunodeficiency virus infection, one had lung cancer, and one had metastatic prostate cancer. Cultures of pharyngeal
K W Henry et al.
Antimicrobial agents and chemotherapy, 44(10), 2693-2700 (2000-09-19)
Infections due to Candida albicans are usually treated with azole antifungals such as fluconazole, but treatment failure is not uncommon especially in immunocompromised individuals. Relatedly, in vitro studies demonstrate that azoles are nonfungicidal, with continued growth at strain-dependent rates even
Martindale: The Extra Pharmacopoeia, 403-403 (1996)
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