4-Amino-3-(3'-methoxycarbonyl-2'-thioureido)benzophenone, a prodrug of mebendazole

Abstract

The compound 4-amino-3-(3'-methoxycarbonyl-2'-thioureido) benzophenone has shown promise as a prodrug of the anthelmintic mebendazole. The compound is stable in acid and neutral media and is rapidly hydrolysed in base. An HPLC assay procedure for mebendazole, the prodrug and their known or expected metabolites and degradation products in aqueous media and rat blood has been developed. The prodrug administrated orally to rats is rapidly converted to mebendazole. The area under the blood level versus time curve of mebendazole, in rats dosed with the prodrug, is more than twice that obtained after dosing rats with an equimolar amount of mebendazole. Only the prodrug, mebendazole and known metabolites of mebendazole are detected in rats dosed with the prodrug.