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Itraconazole

SIGMA/I6657 - ≥98% (HPLC)

Synonym: Oriconazole; R51211; Sporanox

CAS Number: 84625-61-6
Empirical Formula (Hill Notation): C35H38Cl2N8O4
Molecular Weight: 705.63
MDL Number: MFCD00870168
Linear Formula: C35H38Cl2N8O4
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-I6657-100MG 100 mg
 $181.00
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antibiotic activity spectrum fungi
assay ≥98% (HPLC)
color white
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
mode of action enzyme | inhibits
Quality Level 200 
SMILES string CCC(C)N1N=CN(C1=O)c2ccc(cc2)N3CCN(CC3)c4ccc(OCC5COC(Cn6cncn6)(O5)c7ccc(Cl)cc7Cl)cc4
solubility chloroform: 50 mg/mL, clear, colorless
storage temp. 2-8°C
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.
Biochem/physiol Actions: Synthetic broad-spectrum triazole antifungal agent. Mode of action: Inhibits cytochrome P450 dependent enzymes including 14α-demethylase. The inhibition results in prevention of the biosynthesis of ergosterol, a critical fungal cell wall component.
Packaging: 100 mg in poly bottle
Purity ≥98% (HPLC)
Storage Temp. 2-8°C
UNSPSC 51102829

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