Merck
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UC280

Sigma-Aldrich

Ketoconazole

Sinônimo(s):
(±)-cis-1-Acetyl-4-(4-[(2-[2,4-dichlorophenyl]-2-[1H-imidazol-1-ylmethyl]-1,3-dioxolan-4-yl)-methoxy]phenyl)piperazine
Empirical Formula (Hill Notation):
C26H28Cl2N4O4
Número CAS:
Peso molecular:
531.43
Número EC:
Número MDL:
ID de substância PubChem:
NACRES:
NA.77

teor

≥99% (HPLC)

forma

solid

cor

white to light yellow

solubilidade

DMSO: soluble

espectro de atividade do antibiótico

fungi
yeast

Modo de ação

enzyme | inhibits

originador

Johnson & Johnson

temperatura de armazenamento

2-8°C

SMILES string

CC(=O)N1CCN(CC1)c2ccc(OC[C@H]3CO[C@@](Cn4ccnc4)(O3)c5ccc(Cl)cc5Cl)cc2

InChI

1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3/t23-,26-/m0/s1

InChI key

XMAYWYJOQHXEEK-OZXSUGGESA-N

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Aplicação

Ketoconazole has been used as a cytochrome P450 (CYP) inhibitor to study its functions in embryonic testes of rats. Ketoconazole has also been used for the screening of antimicrobial agents against nonreplicating M. tuberculosis. Furthermore, studies have used ketoconazole for antifungal susceptibility testing and also as a standard antifungal agent.
CYP3A4 inhibitor

Embalagem

5, 10 mg in glass bottle
Bottomless glass bottle. Contents are inside inserted fused cone.

Ações bioquímicas/fisiológicas

Ketoconazole is an imidazole derivative. It plays an important role in inhibiting the conversion of lanosterol to ergosterol in the cell wall of fungi. Ketoconazole has therapeutic effects against dermatophytosis, superficial candidiasis, and paracoccidioidomycosis.
Antifungal agent

Características e benefícios

This compound was developed by Johnson & Johnson. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.
This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Nota de preparo

Ketoconazole is soluble in DMSO.

Palavra indicadora

Danger

Classificações de perigo

Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Repr. 1B - STOT RE 2

Código de classe de armazenamento

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Ponto de fulgor (ºF)

Not applicable

Ponto de fulgor (ºC)

Not applicable

Equipamento de proteção individual

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificado de análise

Insira o número de lote para pesquisar o Certificado de análise (COA).

Certificado de origem

Insira o número de lote para pesquisar o Certificado de origem (COO).

Mais documentos

Quotes and Ordering

Ketoconazole.
Hay, R.
British Medical Journal (Clinical Research ed.), 285(6342), 584-584 (1982)
Gökalp Işcan et al.
Journal of agricultural and food chemistry, 50(14), 3943-3946 (2002-06-27)
Essential oils of peppermint Mentha piperita L. (Lamiaceae), which are used in flavors, fragrances, and pharmaceuticals, were investigated for their antimicrobial properties against 21 human and plant pathogenic microorganisms. The bioactivity of the oils menthol and menthone was compared using
Po-Ren Hsueh et al.
Antimicrobial agents and chemotherapy, 49(2), 512-517 (2005-01-28)
The susceptibilities of nonduplicate isolates to six antifungal agents were determined for 391 blood isolates of seven Candida species, 70 clinical isolates (from blood or cerebrospinal fluid) of Cryptococcus neoformans, and 96 clinical isolates of four Aspergillus species, which were
Ketoconazole and other imidazole derivatives as inhibitors of steroidogenesis
Feldman, David
Endocrine Reviews, 7(4), 409-420 (1986)
Ketoconazole and other imidazole derivatives as inhibitors of steroidogenesis.
D Feldman
Endocrine reviews, 7(4), 409-420 (1986-11-01)

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