Indomethacin suffers from the general side effects of NSAIDs. The study aimed to retard the adverse effects of gastrointestinal (GI) origin. Two conjugates of indomethacin were synthesized by esterification with flavonoids namely, naringenin and hespertin. Purified synthesized mutual prodrugs were characterized by m.p., TLC, elemental analyzes, FTIR, NMR and MS. Synthesized conjugates were subjected for antiinflammatory, analgesic and antiulcer activity. These conjugates showed retention of antiinflammatory activity with reduced ulcerogenic side effects. These results indicated that indomethacin–flavonoid conjugates have the potential to be developed as safer NSAIDs.