Itraconazole

• Catalog No.: I6657
• CAS Number: 84625-61-6
• M. F.: C35H38Cl2N8O4
• M. W.: 705.63342
• Purity: ≥98% (TLC)

SYNONYMS

• IUPAC name: 1-(butan-2-yl)-4-{4-[4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-4,5-dihydro-1H-1,2,4-triazol-5-one
• IUPAC Traditional name: itraconazole
• Synonyms: Oriconazole; R51211; Sporanox

DATABASE IDS

• CAS Number: 84625-61-6
• MDL Number: MFCD00870168

PROPERTIES

• Empirical Formula (Hill Notation): C35H38Cl2N8O4
• Purity: ≥98% (TLC)
• Solubility: chloroform: soluble50 mg/mL, clear, colorless
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• European Hazard Symbols: Irritant (Xi)
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• GHS Precautionary statements: P261-P305 + P351 + P338
• Risk Statements: 36/37/38
• RTECS: XZ5481000
• Safety Statements: 22-26-36
• Storage Temperature: 2-8°C
• German water hazard class: 3

DETAILS

Description (简体中文)

Application
Itraconazole is a triazole antifungal agent. It is used to inhibit cytochrome P-450-dependent enzymes and ergosterol synthesis. It has been used against histoplasmosis, blastomycosis, cryptococcal meningitis, and aspergillosis. It′s different formulations are used to study Candida strains in murine invasive infections1. It has been used to study proliferative changes of the forestomach mucosa in alloxan-induced diabetic rats2.
Biochem/physiol Actions
Itraconazole inhibits cytochrome P-450-dependent enzymes which results in the inhibition of ergosterol synthesis. It does so by interacting with 14-α demethylase, which is a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. Ergosterol is a crucial compenent of fungal cell membranes. Therefore, it′s inhibition results in increased cellular permeability causing leakage of cellular contents. Itraconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and phospholipid biosynthesis.

Description (English)

Application
Itraconazole is a triazole antifungal agent. It is used to inhibit cytochrome P-450-dependent enzymes and ergosterol synthesis. It has been used against histoplasmosis, blastomycosis, cryptococcal meningitis, and aspergillosis. It′s different formulations are used to study Candida strains in murine invasive infections1. It has been used to study proliferative changes of the forestomach mucosa in alloxan-induced diabetic rats2.
Biochem/physiol Actions
Itraconazole inhibits cytochrome P-450-dependent enzymes which results in the inhibition of ergosterol synthesis. It does so by interacting with 14-α demethylase, which is a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. Ergosterol is a crucial compenent of fungal cell membranes. Therefore, it′s inhibition results in increased cellular permeability causing leakage of cellular contents. Itraconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and phospholipid biosynthesis.