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N4-Benzoyl-2',3'-dideoxy-2',3'-didehydrocytidine (Bz-DDCN) was synthesized as a novel prodrug of 2',3'-dideoxy-2',3'-didehydrocytidine (DDCN), which is a reverse transcriptase inhibitor and is considered to be a potential anti-acquired immunodeficiency syndrome agent. Chemical and enzymatic regeneration of DDCN from the prodrug has been investigated in both in vitro and in vivo experiments. Bz-DDCN regenerated DDCN under basic conditions (greater than pH 8), while cleavage of the N-glycosidic linkage and production of N4-benzoylcytosine were observed under acidic conditions (less than pH 6). DDCN was enzymatically regenerated from the prodrug in the presence of several enzyme preparations, including human plasma. DDCN and Bz-DDCN were intravenously administered to mice and the plasma concentrations of DDCN and the prodrug were measured. Though DDCN levels following direct DDCN administration decreased exponentially with a half-life of 14.5 min, the plasma levels of DDCN following the prodrug administration were sustained above 2 microM for over 3 h.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

Studies on 2',3'-dideoxy-2',3'-didehydropyrimidine nucleosides. II. N4-benzoyl-2',3'-dideoxy-2',3'-didehydrocytidine as a prodrug of 2',3'-dideoxy-2',3'-didehydrocytidine(DDCN).