K1003

Ketoconazol

99.0-101.0% (EP, titration)

• Synonym(e): (±)-cis-1-Acetyl-4-{4-{[2-(2,4-dichlorphenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]-methoxy}-phenyl}-piperazin
• Empirische Formel (Hill-System): C₂₆H₂₈Cl₂N₄O₄
• CAS-Nummer: 65277-42-1
• Molekulargewicht: 531.43
• EG-Nummer: 265-667-4
• MDL-Nummer: MFCD00058579
• UNSPSC-Code: 51101500
• PubChem Substanz-ID: 24278176
• NACRES: NA.85

Eigenschaften

• Beschreibung: Specific Optical Rotation (EP): (−0.10) ∼ +0.10 °
• Assay: 99.0-101.0% (EP, titration)
• Form: powder
• Farbe: white to off-white
• Wirkungsspektrum von Antibiotika: Gram-positive bacteria; fungi; yeast
• Wirkungsweise: enzyme | inhibits
• Lagertemp.: 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
• InChIKey: XMAYWYJOQHXEEK-OZXSUGGESA-N
• Angaben zum 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)

Beschreibung

Allgemeine Beschreibung

Chemical structure: imidazole

Anwendung

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[1], to study interleukin 1 mediated antitumor effects[2], and drug interactions in vivo[3]

Biochem./physiol. Wirkung

Antifungales Mittel

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 .

Sicherheitshinweise

• Piktogramme: GHS06,GHS08,GHS09
• Signalwort: Danger
• H-Sätze: H301,H360F,H373,H410
• P-Sätze: P202 - P260 - P264 - P273 - P280 - P301 + P310
• Gefahreneinstufungen: Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Repr. 1B - STOT RE 2
• Lagerklassenschlüssel: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges