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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

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About This Item

Fórmula empírica (Notação de Hill):
C26H28Cl2N4O4
Número CAS:
65277-42-1
Peso molecular:
531.43
Número CE:
265-667-4
Número MDL:
MFCD00058579
Código UNSPSC:
12161501
ID de substância PubChem:
24724652
NACRES:
NA.77

Ensaio

≥99% (HPLC)

Formulário

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

cadeia de caracteres SMILES

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

chave InChI

XMAYWYJOQHXEEK-OZXSUGGESA-N

Informações sobre genes

human ... ABCB1(5243) , CYP11B1(1584) , CYP11B2(1585) , CYP17A1(1586) , CYP19A1(1588) , CYP1A2(1544) , CYP24A1(1591) , CYP26A1(1592) , CYP3A4(1576) , CYP51A1(1595) , KCNH1(3756)
mouse ... Abcb1a(18671) , Abcb1b(18669)
rat ... Alox5(25290) , Cyp17a1(25146) , Cyp51(25427) , Cyp7a1(25428)

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Aplicação

CYP3A4 inhibitor
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.

Ações bioquímicas/fisiológicas

Antifungal agent
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.

Características e benefícios

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.
This compound was developed by Johnson & Johnson. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Embalagem

Bottomless glass bottle. Contents are inside inserted fused cone.

Nota de preparo

Ketoconazole is soluble in DMSO.

Palavra indicadora

Danger

Frases de perigo

H301,H360F,H373,H410

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

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

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

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Certificados de análise (COA)

Lot/Batch Number
BCBH0425V
SI/610/28A
BCBD3641V
BCBD3640V
BCBC0673

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Sigma-Aldrich

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