Merck
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C6019

Sigma-Aldrich

Clotrimazole

Todas as fotos(1)
Sinônimo(s):
1-[(2-Chlorophenyl)diphenylmethyl]-1H-imidazole, 1-(o-Chlorotrityl)imidazole, 1-(o-Chloro-α,α-diphenylbenzyl)imidazole
Empirical Formula (Hill Notation):
C22H17ClN2
Número CAS:
23593-75-1
Peso molecular:
344.84
Número EC:
245-764-8
Número MDL:
MFCD00057220
ID de substância PubChem:
24278327
NACRES:
NA.77

forma

powder

Nível de qualidade

200

espectro de atividade do antibiótico

fungi

Modo de ação

cell membrane | interferes
protein synthesis | interferes

originador

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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Descrição geral

Chemical structure: imidazole

Aplicação

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

Ações bioquímicas/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 e benefícios

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

Pictogramas

Exclamation markEnvironment
GHS07,GHS09

Palavra indicadora

Warning

Classificações de perigo

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

Código de classe de armazenamento

11 - Combustible Solids

WGK

WGK 3

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

Certificado de análise

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Certificado de origem

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Product Information Sheet

Product Information Sheet - C6019

Mais documentos

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Structure Search

Quotes and Ordering

Bulk Quote-Order Product
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)
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
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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