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Documentos Principais

C6019

Sigma-Aldrich

Clotrimazole

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

Sinônimo(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

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

Nome do produto

Clotrimazole,

Formulário

powder

espectro de atividade do antibiótico

fungi

Modo de ação

cell membrane | interferes
protein synthesis | interferes

originador

Schering Plough

cadeia de caracteres 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

chave InChI

VNFPBHJOKIVQEB-UHFFFAOYSA-N

Informações sobre genes

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 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

Palavra indicadora

Warning

Frases de perigo

H302,H315,H319,H410

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

Classe de risco de água (WGK)

WGK 3

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análise (COA)

Lot/Batch Number
039M4777V
039M4778V
118M4880V
128M4765V
047M4830V

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Voriconazole ≥98% (HPLC)

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