K1003

Ketoconazole

99.0-101.0% (EP, titration)

• Synonyme(s) : (±)-cis-1-Acetyl-4-(4-[(2-[2,4-dichlorophenyl]-2-[1H-imidazol-1-ylmethyl]-1,3-dioxolan-4-yl)-methoxy]phenyl)piperazine
• Formule empirique (notation de Hill): C₂₆H₂₈Cl₂N₄O₄
• Numéro CAS: 65277-42-1
• Poids moléculaire : 531.43
• Numéro CE : 265-667-4
• Numéro MDL: MFCD00058579
• Code UNSPSC : 51101500
• ID de substance PubChem : 24278176
• Nomenclature NACRES : NA.85

Propriétés

• Description: Specific Optical Rotation (EP): (−0.10) ∼ +0.10 °
• Niveau de qualité: 200
• Essai: 99.0-101.0% (EP, titration)
• Forme: powder
• Couleur: white to off-white
• Spectre d'activité de l'antibiotique: Gram-positive bacteria; fungi; yeast
• Mode d’action: enzyme | inhibits
• Température de stockage: 2-8°C
• Chaîne 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
• Clé InChI: XMAYWYJOQHXEEK-OZXSUGGESA-N
• Informations sur le gène: 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)

Description

Description générale

Chemical structure: imidazole

Application

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]

CYP3A4 inhibitor

Actions biochimiques/physiologiques

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

Informations sur la sécurité

• Pictogrammes: GHS06,GHS08,GHS09
• Mention d'avertissement: Danger
• Mentions de danger: H301,H360F,H373,H410
• Conseils de prudence: P202 - P260 - P264 - P273 - P280 - P301 + P310
• Classification des risques: Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Repr. 1B - STOT RE 2
• Code de la classe de stockage: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges