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You are here: Home » eGM Resources » Health Information & Resources Portal|Home » RX Drug List (listed alphabetically) » Drug Reference (i's) » Itraconazole



DESCRIPTION

WARNING

Coadministration of terfenadine with itraconazole is contraindicated. Serious cardiovascular adverse events, including death, ventricular tachycardia, and torsades de pointes have occurred in patients taking itraconazole concomitantly with terfenadine. This is due to elevated terfenadine concentrations caused by itraconazole. See CONTRAINDICATIONS, WARNINGS and PRECAUTIONS sections.

Another oral azole antifungal, ketoconazole, inhibits the metabolism of astemizole, resulting in elevated plasma concentrations of astemizole and its active metabolite desmethylastemizole, which may prolong QT intervals. Based on results of an in vitro study and the chemical resemblance of itraconazole and ketoconazole, coadministration of astemizole and itraconazole is contraindicated. See CONTRAINDICATIONS, WARNINGS and PRECAUTIONS sections.

Coadministration of cisapride with itraconazole is contraindicated. Serious cardiovascular adverse events including death, ventricular tachycardia, and torsades de pointes have occurred in patients taking itraconazole concomitantly with cisapride. See CONTRAINDICATIONS, WARNINGS and PRECAUTIONS sections.


Sporanox is the brand name of itraconazole, a synthetic triazole antifungal agent. Itraconazole is a 1:1:1:1 racemic mixture of four diastereomers (two enantiomeric pairs), each possessing three chiral centers. It may be represented by the following nomenclature:

(±)-1-[(R*)-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]-delta2-1,2,4-triazolin-5-one mixture with (±)-1-[(R*)-sec-butyl]-4-[p-[4-[p- [[(2S*4R*)-2-(2,4,-dichlorophenyl)-2-(1H-1,2,4- triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-delta2-1,2,4-triazolin-5-one

or

(±)-1-[(RS)-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]-delta2-1,2,4-triazolin-5-one

Itraconazole has a molecular formula of C35H38Cl2N8O4 and a molecular weight of 705.64. It is a white to slightly yellowish powder. It is insoluble in water, very slightly soluble in alcohols, and freely soluble in dichloromethane. It has a pKa of 3.70 (based on extrapolation of values obtained from methanolic solutions) and a log (n-octanol/water) partition coefficient of 5.66 at pH 8.1.

Sporanox contains 100 mg of itraconazole coated on sugar spheres. Inactive ingredients are gelatin, hydroxypropyl methylcellulose, polyethylene glycol (PEG) 20,000, starch, sucrose, titanium dioxide, FD&C Blue No. 1, FD&C Blue No. 2, D&C Red No. 22 and D&C Red No. 28.

CATEGORIES, BRAND NAMES

CATEGORIES: Aspergillosis; Blastomycosis; Histoplasmosis; Infection, Fungal; Infection, HIV; Pregnancy Category C; FDA Class 1P (Priority Review); FDA Approved 1992 Sep

FDA Drug Class: Antifungals

BRAND NAMES: Isox; Itranax; Sopranox; Sporacid; Sporal; Sporanox; Sporanox 15 D
(Foreign brand names outside U.S. in italics)

COST OF THERAPY: $1,142.28 (Histoplasmosis; Capsule; 100 mg; 2/day; 90 days)





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