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C6019

Sigma-Aldrich

Clotrimazole

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

Sinónimos:

1-(o-Chloro-α,α-diphenylbenzyl)imidazole, 1-(o-Chlorotrityl)imidazole, 1-[(2-Chlorophenyl)diphenylmethyl]-1H-imidazole

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About This Item

Fórmula empírica (notación de Hill):
C22H17ClN2
Número de CAS:
23593-75-1
Peso molecular:
344.84
Número CE:
245-764-8
Número MDL:
MFCD00057220
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
24278327
NACRES:
NA.77

Nombre del producto

Clotrimazole,

Formulario

powder

Nivel de calidad

200

espectro de actividad antibiótica

fungi

Modo de acción

cell membrane | interferes
protein synthesis | interferes

emisor

Schering Plough

cadena SMILES

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

Clave InChI

VNFPBHJOKIVQEB-UHFFFAOYSA-N

Información sobre el gen

human ... ABCB1(5243) , CYP17A1(1586) , CYP3A4(1576)
mouse ... Abcb1a(18671) , Abcb1b(18669)

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Descripción general

Chemical structure: imidazole

Aplicación

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

Acciones bioquímicas o fisiológicas

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.

Características y beneficios

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.

Pictogramas

Exclamation markEnvironment
GHS07,GHS09

Palabra de señalización

Warning

Frases de peligro

H302,H315,H319,H410

Clasificaciones de peligro

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Skin Irrit. 2

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
0000395321
0000388531
0000368628
0000388531
0000368628

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Visite la Librería de documentos

Martindale: The Extra Pharmacopoeia, 403-403 (1996)
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
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
B S Jensen et al.
Current drug targets, 2(4), 401-422 (2001-12-06)
This review discusses the Ca2+-activated K+ channels of intermediate conductance (IK channels), and their historical discovery in erythrocytes, their classical biophysical characteristics, physiological function, molecular biology as well as their role as possible molecular targets for pharmacological intervention in various
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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