K1003

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
• 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

Propiedades

• descripción: Specific Optical Rotation (EP): (−0.10) ∼ +0.10 °
• Nivel de calidad: 200
• Ensayo: 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)

Descripción

Descripción general

Chemical structure: imidazole

Aplicación

CYP3A4 inhibitor

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

Acciones bioquímicas o fisiológicas

Antifungal agent

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 .

Información de seguridad

• Pictogramas: GHS06,GHS08,GHS09
• Palabra de señalización: Danger
• Frases de peligro: H301,H360F,H373,H410
• Consejos de prudencia: P202 - P260 - P264 - P273 - P280 - P301 + P310
• 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