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K1003

Sigma-Aldrich

Ketoconazole

99.0-101.0% (EP, titration)

Sinónimos:

(±)-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 (notación de Hill):
C26H28Cl2N4O4
Número de CAS:
65277-42-1
Peso molecular:
531.43
Número CE:
265-667-4
Número MDL:
MFCD00058579
Código UNSPSC:
51101500
ID de la sustancia en PubChem:
24278176
NACRES:
NA.85

descripción

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

Nivel de calidad

200

Análisis

99.0-101.0% (EP, titration)

formulario

powder

color

white to off-white

espectro de actividad antibiótica

Gram-positive bacteria
fungi
yeast

Modo de acción

enzyme | inhibits

temp. de almacenamiento

2-8°C

cadena 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

Clave InChI

XMAYWYJOQHXEEK-OZXSUGGESA-N

Información sobre el gen

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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Descripción general

Chemical structure: imidazole

Aplicación

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

Acciones bioquímicas o 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

Aplicación

Referencia del producto
Descripción
Precios

Producto relacionado

Referencia del producto
Descripción
Precios

UC280

Ketoconazole

Palabra de señalización

Danger

Frases de peligro

H301,H360F,H373,H410

Clasificaciones de peligro

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

Código de clase de almacenamiento

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

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Wendy W J van de Sande et al.
Antimicrobial agents and chemotherapy, 54(6), 2738-2740 (2010-03-31)
Eumycetoma caused by Madurella mycetomatis is treated surgically and with high doses of ketoconazole. Therapeutic responses are poor, and recurrent infections are common. In search of therapeutic alternatives in the treatment of mycetoma, we determined the in vitro susceptibilities of
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
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
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
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