Abstract: Ketorolac (Non-steroidal anti-inflammatory drugs) is associated with gastric ulceration and irritation due to presence of free carboxylic group. The current investigation reports mutual amide prodrug synthesis of ketorolac with Glucosamine, a nutrional supplement for arthritis. The current investigation reports synthesis of mutual amide prodrug of ketorolac by masking free carboxylic group with Glucosamine, a nutrional supplement for treatment of arthritis. Confirmation and characterization of the structure of the synthesized prodrug done by elemental and spectroscopy analysis, m.p., determination of migration parameters (Rf, RM and Rt) by using TLC and HPLC, respectively. Partition coefficient and solubility study confirms its lipophilic character so can be suitable candidate for controlled release delivery. In vitro hydrolytic studies of prodrug confirms good rate of hydrolysis in blood plasma, fecal matter and simulated intestinal fluid while stable in gastric simulated fluid. In vivo pharmacological screening performed on animals. Prodrug with respect to etodolac shows good analgesic, antiinflammatory and antiarthritic activity. The prodrug was assessed for their probable damaging effects by ulcerogeniticity and histopathological analysis. Less ulceration in the gastric region during histopathological study was found when treated with prodrug. The data proves better action of prodrug as compared to ketorolac and are profitable in having less gastrointestinal side effects.