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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

NACRES:

NA.77

PubChem Substance ID:

24278327

UNSPSC Code:

12352200

EC Number:

245-764-8

MDL number:

MFCD00057220

Form:

powder

Quality level:

200

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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)

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Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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

GHS07,GHS09

signalword

Warning

hcodes

H302,H315,H319,H410

pcodes

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

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number

0000527329

0000521835

0000515506

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Upregulation of ERG genes in Candida species by azoles and other sterol biosynthesis inhibitors.

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

Human-relevant concentrations of the antifungal drug clotrimazole disrupt maternal and fetal steroid hormone profiles in rats.

Monica Kam Draskau et al.

Toxicology and applied pharmacology, 422, 115554-115554 (2021-04-29)

Clotrimazole is a non-prescription and broad-spectrum antifungal drug sold under brand names such as Canesten® and Lotrimin®. It is used to treat different types of fungal infections, from oral thrush to athlete's foot and vaginal mycosis. The level of exposure

Martindale: The Extra Pharmacopoeia, 403-403 (1996)

N-acetylcysteine and clotrimazole inhibit sickle erythrocyte dehydration induced by 1-chloro-2,4-dinitrobenzene.

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

Stress granules and processing bodies are dynamically linked sites of mRNP remodeling.

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

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Global Trade Item Number

SKU	GTIN
C6019-25G	04061833503041
C6019-5G	04061833503058
C6019-100G	04061835374724

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