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C6019

Clotrimazole

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:
Molecular Weight:
344.84
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
EC Number:
245-764-8
MDL number:
Form:
powder
Quality level:
Pricing and availability is not currently available.
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Product Name

Clotrimazole,

form

powder

Quality Level

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

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[1]
  • to study the development of resistance in Candida species isolated from patients undergoing prolonged antifungal treatment[2]
  • to induce stress granules via mitochondrial stress[3][4]
  • for the inhibition of in vitro formation of high density sickle cells induced by treatment with 1-chloro-2,4-dinitrobenzene (CDNB)[5]
  • to inhibit cytochrome P450 enzyme in cell cultures[6]

Biochem/physiol Actions

Clotrimazole is a specific inhibitor of Ca2+-activated K+ channels.[7] It is an antifungal azole. Clotrimazole is a derivative of imidazole and has similar antimicrobial action and activity to ketoconazole.[8] 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.

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1 of 1

This Item
C24300001141002BP379
form

powder

form

-

form

-

form

solid

Quality Level

200

Quality Level

-

Quality Level

-

Quality Level

-

originator

Schering Plough

originator

-

originator

-

originator

-

antibiotic activity spectrum

fungi

antibiotic activity spectrum

-

antibiotic activity spectrum

-

antibiotic activity spectrum

-

mode of action

cell membrane | interferes, protein synthesis | interferes

mode of action

-

mode of action

-

mode of action

-

Gene Information

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

Gene Information

-

Gene Information

-

Gene Information

-


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Warning

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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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
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



Global Trade Item Number

SKUGTIN
C6019-25G04061833503041
C6019-5G04061833503058
C6019-100G04061835374724

Questions

  1. Please provide the absorption molecular coefficient of clotrimazole and the solvent used to quantify my clotrimazole solutions.

    1 answer
    1. C6019 is supplied in powder form. It is soluble in Chloroform at 50.0 - 52.0 mg/ml. But the information on the absorption molecular coefficient of clotrimazole is currently unavailable. However, I conducted an extensive literature search and found some relevant information. Clotrimazole showed absorption maxima (λ max) at 263 nm, and linearity was obtained by concentration versus absorbance for clotrimazole with a correlation coefficient of r = 0.999.

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