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QuickView for Voriconazole (compound)


PubChem
Name: voriconazole
PubChem Compound ID: 5231054
Molecular formula: C16H14F3N5O
Molecular weight: 349.311 g/mol
DrugBank
Identification
Name: voriconazole
Name (isomeric): DB00582
Drug Type: small molecule
Synonyms:
VCZ
Brand: Vfend
Category: Antifungal Agents, Antifungals
CAS number: 137234-62-9
Pharmacology
Indication: For the treatment of esophageal candidiasis, invasive pulmonary aspergillosis, and serious fungal infections caused by <i>Scedosporium apiospermum</i> and <i>Fusarium</i> spp.
Pharmacology:
Voriconazole is a triazole antifungal agent indicated for use in the treatment of fungal infections including invasive aspergillosis, esophageal candidiasis, and serious fungal infections caused by Scedosporium apiospermum (asexual form of Pseudallescheria boydii) and Fusarium spp. including Fusarium solani. Fungal plasm...
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Mechanism of Action: Voriconazole binds and inhibits ergosterol synthesis by inhibiting CYP450-dependent 14-alpha sterol demethylase. The inhibition of 14-alpha sterol demethylase results in a depletion of ergosterol in fungal cell membrane.
Absorption: The oral bioavailability is estimated to be 96% (CV 13%).
Protein binding: 58%
Biotransformation: Hepatic. The major metabolite of voriconazole is the N-oxide, which accounts for 72% of the circulating radiolabelled metabolites in plasma. Since this metabolite has minimal antifungal activity, it does not contribute to the overall efficacy of voriconazole.
Route of elimination: Voriconazole is eliminated via hepatic metabolism with less than 2% of the dose excreted unchanged in the urine.
Toxicity: The minimum lethal oral dose in mice and rats was 300 mg/kg (equivalent to 4 and 7 times the recommended maintenance dose (RMD), based on body surface area). At this dose, clinical signs observed in both mice and rats included salivation, mydriasis, titubation (loss of balance while moving), depressed behavior, prostration, partially closed eyes, and dyspnea. Other signs in mice were convulsions, corneal opacification and swollen abdomen.
Affected organisms: Yeast and other fungi
Interactions
Drug interaction:
ZopicloneVoriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of zopiclone by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zopiclone if voriconazole is initiated, discontinued or dose changed.
KetoconazoleKetoconazole, a strong CYP2C9 inhibitor, may increase the serum concentration of voriconazole by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of voriconazole if ketoconazole is initiated, discontinued or dose changed.
MethadoneVoriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of methadone by decreasing its metabolism. Additive QTc prolongation may also occur. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of methadone if voriconazole is initiated, discontinued or dose changed.
PhencyclidineVoriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of phencyclidine by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of phencyclidine if voriconazole is initiated, discontinued or dose changed.
IndomethacinIndomethacin, a strong CYP2C9 inhibitor, may increase the serum concentration of voriconazole by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of voriconazole if indomethacin is initiated, discontinued or dose changed.
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