C6019
Clotrimazole
98.5-100.5% (dry basis), powder, Ca²⁺-activated K⁺ channels inhibitor
동의어(들):
1-(o-Chloro-α,α-diphenylbenzyl)imidazole, 1-(o-Chlorotrityl)imidazole, 1-[(2-Chlorophenyl)diphenylmethyl]-1H-imidazole
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크기 선택
제품정보 (DICE 배송 시 비용 별도)
실험식(Hill 표기법):
C22H17ClN2
CAS 번호:
Molecular Weight:
344.84
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
EC Number:
245-764-8
MDL number:
Form:
powder
Quality level:
제품 이름
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
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.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Skin Irrit. 2
저장 등급
11 - Combustible Solids
wgk
WGK 3
ppe
dust mask type N95 (US), Eyeshields, Gloves
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
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)
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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