ABSTRACT
Itraconazole (Sporanox) is a synthetic triazole drug developed in the 1980s as the first orally bioavailable triazole agent. Similar to posaconazole (see Chapter 157, Posaconazole), it contains a piperazine-phenyl-triazole side chain (Figure 154.1). Available preparations include a 100-mg capsule and an oral solution (10 mg/ml complexed with 400 mg/ml hydroxypropyl-β-cyclodextrin). Although not currently available, itraconazole has also been formulated for intravenous administration. Itraconazole was the first orally active agent against aspergillosis and sporotrichosis and currently has US Food and Drug Administration (FDA) approval for the treatment of aspergillosis, blastomycosis, histoplasmosis, mucosal candidiasis, febrile neutropenia, and onychomycosis. Itraconazole has the chemical name (±)-1-[(RS)-sec-butyl]-4-[p-[4-[p-[[(2R,4S)-2-(2,4-dichloro-phenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]-phenyl]-1-piperazrnyl]phenyl]-A2-1,2,4-triazolin-5-one and is a racemic mixture of four diastereomers (two enantiomeric pairs). Chemical structure of itraconazole. https://s3-euw1-ap-pe-df-pch-content-public-p.s3.eu-west-1.amazonaws.com/9781315152110/08d8042d-9481-4a8d-8c27-9bd589f6de6b/content/fig154_1.tif" xmlns:xlink="https://www.w3.org/1999/xlink"/>
