All NSAIDs are suffering from deadlier GIT toxicity. The free carboxylic group is thought to be responsible for this toxicity. The main aim of the present study was to develop new chemical entities as prodrug of potential antiinflammatory agents with no gastric toxicity. Various substituted derivatives of Mefenamic acid were synthesized in good yield by esterification. All structures of the newly synthesized compounds were elucidated by elemental analyses, spectral data like infrared, proton magnetic resonance and mass spectroscopy. Prodrugs were also characterized by solubility studies, partition coefficient and hydrolytic studies. The synthesized derivatives are screened for their anti-inflammatory and Ulcerogenic study which show retention of anti-inflammatory activity with reduced Ulcerogenicity.