Ketoconazole

• Catalog No.: K1003
• CAS Number: 65277-42-1
• M. F.: C26H28Cl2N4O4
• M. W.: 531.43092
• Purity: ≥98% (HPLC)

SYNONYMS

• IUPAC name: 1-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one
• IUPAC Traditional name: (2R,4S)-ketoconazole
• Synonyms: (±)-cis-1-Acetyl-4-(4-[(2-[2,4-dichlorophenyl]-2-[1H-imidazol-1-ylmethyl]-1,3-dioxolan-4-yl)-methoxy]phenyl)piperazine

DATABASE IDS

• PubChem SID: 24278176
• CAS Number: 65277-42-1
• MDL Number: MFCD00058579
• EC Number: 265-667-4

PROPERTIES

• Purity: ≥98% (HPLC)
• Quality Level: PREMIUM
• Gene Information: 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)
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H360F-H373-H410
• European Hazard Symbols: Toxic (T)
• European Hazard Symbols: Nature polluting (N)
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• GHS Precautionary statements: P201-P273-P301 + P310-P308 + P313-P501
• RID/ADR: UN 2811 6.1/PG 3
• Risk Statements: 60-25-48/22-50/53
• RTECS: TK7912300
• Safety Statements: 53-45-60-61
• Storage Temperature: 2-8°C
• Hazard Class: 6.1
• UN Number: 2811
• Packing Group: 3
• German water hazard class: 3

DETAILS

Description (English)

Application
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 model1, to study interleukin 1 mediated antitumor effects2, and drug interactions in vivo3
Biochem/physiol Actions
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 .
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information