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K1003

Sigma-Aldrich

Ketoconazole

99.0-101.0% (EP, titration)

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:
51101500
ID de substância PubChem:
24278176
NACRES:
NA.85

descrição

Specific Optical Rotation (EP): (−0.10) ∼ +0.10 °

Ensaio

99.0-101.0% (EP, titration)

forma

powder

cor

white to off-white

espectro de atividade do antibiótico

Gram-positive bacteria
fungi
yeast

Modo de ação

enzyme | inhibits

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)

Procurando produtos similares? Visita Guia de comparação de produtos

Categorias relacionadas

Descrição geral

Chemical structure: imidazole

Aplicação

Ketoconazole is a broad spectrum antifungal agent used to treat candidiasis, chronic mucocutaneous candidiasis, oral thrush, candiduria, blastomycosis, coccidioidomycosis, histoplasmosis, chromomycosis, and paracoccidioidomycosis. It is used to identify p-glycoprotein/CYP3A-limited bioavailability in the monkey model, to study interleukin 1 mediated antitumor effects, and drug interactions in vivo
CYP3A4 inhibitor

Ações bioquímicas/fisiológicas

Ketoconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme that is necessary for the conversion of lanosterol to ergosterol. This interaction inhibits ergosterol synthesis and results in increased fungal cellular permeability. Other possible mechanisms of action are the inhibition of endogenous respiration, interaction with membrane phospholipids, inhibition of yeast transformation to mycelial forms, inhibition of purine uptake, and impairment of triglyceride and/or phospholipid biosynthesis. Ketoconazole inhibits the synthesis of thromboxane and sterols such as aldosterone, cortisol, and testosterone .
Antifungal agent

Aplicação

Nº do produto
Descrição
Preços

produto relacionado

Nº do produto
Descrição
Preços

UC280

Ketoconazole

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

Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “Lot” ou “Batch”.

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Sigma-Aldrich

UC166

Sulfaphenazole

Ketoconazole impurity standard British Pharmacopoeia (BP) Reference Standard

BP1170

Ketoconazole impurity standard

(±)-Miconazole nitrate salt imidazole antibiotic

Sigma-Aldrich

M3512

(±)-Miconazole nitrate salt

Ticlopidine hydrochloride analytical standard, for drug analysis

Supelco

T6654

Ticlopidine hydrochloride

vibrant-m

M1880000

Miconazole

(+)-N-3-Benzylnirvanol ≥98% (HPLC), powder

Sigma-Aldrich

B8686

(+)-N-3-Benzylnirvanol

Keith W Ward et al.
Drug metabolism and disposition: the biological fate of chemicals, 32(2), 172-177 (2004-01-28)
The effect of P-glycoprotein (Pgp) and/or CYP3A on the disposition of xenobiotics has been extensively investigated and is often of interest during drug discovery lead optimization. We have previously described a monkey pharmacokinetic screen to rapidly estimate absorption and first-pass
Flor Soriano-Agatón et al.
Journal of natural products, 68(11), 1581-1587 (2005-11-29)
Zanthoxylum chiloperone var. angustifolium was investigated. Alkaloids 1-3 from the canthin-6-one series were characterized. Derivatives 7-28 were prepared by hemisynthesis or total synthesis. All compounds were tested for in vitro antifungal activities against five pathogenic fungal strains. Analogues of canthin-6-one
P G Braunschweiger et al.
Cancer research, 50(15), 4709-4717 (1990-08-01)
In the present studies, the regulatory role of adrenal hormones on the antitumor activity of recombinant human interleukin 1 alpha (IL-1 alpha) was investigated. Ketoconazole, a potent but transient inhibitor of adrenal steroid hormone biosynthesis, inhibited IL-1 alpha induced increases
Francisco M Garibotto et al.
Bioorganic & medicinal chemistry, 18(1), 158-167 (2009-12-05)
The synthesis, in vitro evaluation, and conformational study of a new series of small-size peptides acting as antifungal agents are reported. In a first step of our study we performed a conformational analysis using Molecular Mechanics calculations. The electronic study
L L von Moltke et al.
The Journal of pharmacology and experimental therapeutics, 268(3), 1278-1283 (1994-03-01)
Biotransformation of the tricyclic antidepressant desipramine (DMI) to its metabolite 2-hydroxy-desipramine (2-OH-DMI) was studied in vitro using microsomal preparations from human, monkey, mouse and rat liver. In all species 2-OH-DMI was the principal identified metabolite. Mean (+/- S.E.) reaction parameters
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