Oxidative degradation pathways of beclabuvir hydrochloride mediated by hydrogen peroxide and UV/Vis light

Abstract Beclabuvir hydrochloride (BCV) is a marketed product for the treatment of hepatitis C viral infection. It contains functional groups such as indole, tertiary amine and amides. Forced degradation studies of BCV revealed different degradation profiles under photo and hydrogen peroxide oxidative conditions. Under the photo-oxidative degradation conditions, the tertiary amine on the piperazine ring was oxidized to form the degradants as the hydroxyl and des-methyl analogs of beclabuvir. However, under the oxidative condition using hydrogen peroxide, the indole ring was oxidized to form a typical kynuric degradant and two unexpected cyclohexyl rearranged diastereomeric degradants. The plausible mechanisms for the photo and hydrogen peroxide mediated oxidative degradation of beclabuvir hydrochloride are proposed.