I6657

Itraconazole

≥98% (HPLC)

• Synonym(s): Oriconazole, R51211, Sporanox
• Empirical Formula (Hill Notation): C₃₅H₃₈Cl₂N₈O₄
• CAS Number: 84625-61-6
• Molecular Weight: 705.63
• MDL number: MFCD00870168
• UNSPSC Code: 51102829
• PubChem Substance ID: 329815394
• NACRES: NA.85

Properties

• Quality Level: 200
• assay: ≥98% (HPLC)
• color: white
• solubility: chloroform: 50 mg/mL, clear, colorless
• antibiotic activity spectrum: fungi
• mode of action: enzyme | inhibits
• storage temp.: 2-8°C
• SMILES string: CCC(C)N1N=CN(C1=O)c2ccc(cc2)N3CCN(CC3)c4ccc(OCC5COC(Cn6cncn6)(O5)c7ccc(Cl)cc7Cl)cc4
• InChI: 1S/C35H38Cl2N8O4/c1-3-25(2)45-34(46)44(24-40-45)29-7-5-27(6-8-29)41-14-16-42(17-15-41)28-9-11-30(12-10-28)47-19-31-20-48-35(49-31,21-43-23-38-22-39-43)32-13-4-26(36)18-33(32)37/h4-13,18,22-25,31H,3,14-17,19-21H2,1-2H3
• InChI key: VHVPQPYKVGDNFY-UHFFFAOYSA-N

Description

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 infections. It has been used to study proliferative changes of the forestomach mucosa in alloxan-induced diabetic rats.

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.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H302,H315,H319,H335
• pcodes: P261 - P264 - P271 - P301 + P312 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Faceshields, Gloves