Itraconazole

(CC) Image: David E. Volk Itraconazole, a triazole-based antifungal agent.
itraconazole
IUPAC name: 2-butan-2-yl-4-[4-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one Synonyms: itraconazol, itraconazolum Formula: C35H38Cl2N8O4
Uses:	antifungal drug
Properties:	triazole compound
Hazards:	see drug interactions
Mass (g/mol): CAS #: 705.6334 84625-61-6

Itraconazole is an azole-based antifungal drug containing three azoles, like fluconazole. It inhibits cytochrom P450-dependent enzymes and impairs the biosynthesis of ergosterol. It can be used to treate apergillosis, blasoplasmosis, cryptococcal meningitis, histoplasmosis and onychomycosis.

Mechanism of action

Like other azole-based antifungal agents, itraconazole interacts with 14-$\alpha$-demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol, an essential component of fungal cell membranes, by stopping sterol C-14 $\alpha$-demethylation. 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/or phospholipid biosynthesis.

Drug interactions

The azole-based antifungal agents have many drug interactions and some can be sever. This section is under construction, see ketoconazole for a partial list of drug interactions.

Chemical information

The IUPAC name for itraconazole is 2-butan-2-yl-4-[4-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one, and its chemical formula, C₃₅H₃₈C_l2N₈O₄, gives a molecular mass of 705.6334 g/mol.

Synonyms

• ITC
• ITCZ
• ITR
• Itraconazol
• Itraconazolum
• ITZ

Brand names

• Itrizole®
• Oriconazole®
• Sporal®
• Sporanos®
• Sporanox®
• Sporonox®
• Triasporn®