Prodrugs for Compounds Containing Carbonyl Groups Schiff Bases and Oximes Schiff bases and oximes formed from ketones or aldehydes with amines or hydroxyl amines are chemically reversible under acidic or basic conditions. They could be used as prodrugs of compounds containing either an amine or carbonyl functionality.

Oximes of enones (98, 100, and 101) have been used as prodrugs of contraceptive norethindrone (97) and levonorgestrel (99). The oximes are highly bioavailable and are converted in vivo through chemical hydrolysis to their corresponding active drugs.56,57

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