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Merck

C6019

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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Fórmula empírica (notación de Hill):
C22H17ClN2
Número CAS:
23593-75-1
Peso molecular:
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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Nombre del producto

Clotrimazole,

InChI key

VNFPBHJOKIVQEB-UHFFFAOYSA-N

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

SMILES string

Clc1ccccc1C(c2ccccc2)(c3ccccc3)n4ccnc4

form

powder

antibiotic activity spectrum

fungi

mode of action

cell membrane | interferes, protein synthesis | interferes

originator

Schering Plough

Quality Level

200

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

signalword

Warning

Hazard Classifications

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

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
0000521835
0000521835
0000515506
0000515506
0000485115

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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
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)
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
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