Itraconazole is a triazole antifungal agent used to treat various fungal infections, such as blastomycosis and onychomycosis. It is a 1:1:1:1 racemic mixture of four diastereomers, made up of two enantiomeric pairs, each possessing three chiral centers.
- Mechanism
- Curator reviewed · 7 references
Itraconazole mediates its antifungal activity by inhibiting 14α-demethylase, a fungal cytochrome P450 enzyme that converts lanosterol to ergosterol, a vital component of fungal cell membranes. The azole nitrogen atoms in the chemical structure of itraconazole form a complex with the active site, or the haem iron, of the fungal enzyme to impede its function. The accumulation of lanosterol and 14-methylated sterols results in increased permeability of the fungal cell membrane, and modified membrane-bound enzyme activity, and dysregulated chitin synthesis. Other proposed mechanisms of action of itraconazole include the inhibition of fungal cytochrome c oxidative and peroxidative enzymes that also lead to the disruption of fungal cell membranes.
- Primary indication
- Itraconazole is indicated for the treatment of the following fungal infections in immunocompromised and non-immunocompromised patients: - Blastomycosis, pulmonary and extrapulmonary - Histoplasmosis, including chronic cavitary pulmonary disease and disseminated, nonmeningeal histoplasmosis, and - Aspergillosis,...Curator reviewed · 19 structured indications
- Formula / weight
- C35H38Cl2N8O4 · 705.633 g/mol (avg)
- First approval
- Canada, 1997 · United States, 1992
- Also known as
- (±)-1-SEC-BUTYL-4-(P-(4-(P-(((2R*,4S*)-2-(2,4-DICHLOROPHENYL)-2-(1H-1,2,4-TRIAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL)METHOXY)PHENYL)-1-PIPERAZINYL)PHENYL)-.DELTA.(SUP 2)-1,2,4-TRIAZOLIN-5-ONE · 3H-1,2,4-TRIAZOL-3-ONE, 4-(4-(4-(4-((2-(2,4-DICHLOROPHENYL)-2-(1H-1,2,4-TRIAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL)METHOXY)PHENYL)-1-PIPERAZINYL)PHENYL)-2,4-DIHYDRO-2-(1-METHYLPROPYL)- · ITRACONAZOLE COMPONENT OF SUBA-ITRACONAZOLE · Oriconazole
- Code names
- NSC-759239 · R-51211
- Brand names
Resolves to
VHVPQPYKVGDNFY-ZPGVKDDISA-NSMILESCCC(C)N1N=CN(C1=O)C1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(OC[C@H]2CO[C@@](CN3C=NC=N3)(O2)C2=C(Cl)C=C(Cl)C=C2)C=C1What you can answer from here — as of September 23, 2026
Which drugs share a target with Itraconazole, and which of those have an active Phase 3 trial?
Create a free account or log in to explore the full data card.
Create Account