Purpose: To carry out computational and pharmacological evaluation of two stevioside derivatives in order to develop more effective candidates for analgesia and inflammation.Methods: Primarily, compounds were docked against targets of nociception and inflammation such as cyclooxygenase-1, cyclooxygenase-2, 5-lypooxygenase 12-lypooxygenase, 15-lypooxygenase, prostaglandin synthase, leukotrienes C4 synthase, mu, kappa, and delta receptors to obtain their possible binding modes. Test compounds were then screened in animal model of nociception and inflammation.Results: The results of docking show that IO possesses good affinity when compared to ID. IO showed two hydrogen bonds against COX-1 and COX-2. IO also demonstrated good binding against 5-LOX, 12- LOX and 15-LOX, exhibited four, one and two hydrogen bonds respectively. Against PG synthase and LTC4, both IO and ID produced moderate binding. IO also showed significant binding against opoid receptors (p < 0.05). IO and ID significantly decrease the number of writhes to 21.20 ± 2.1 and 27.0 ± 2.12 at 10 mg/kg in acetic acid mediated pain test respectively. In hot plate method, IO and ID increase the latency period of mice to 14.14 ± 0.40 and 10.50 ± 0.34 s, respectively. IO and ID significantly reduced the paw edema to 1.69 ± 0.14 and 1.94 ± 0.14 mL, respectively, in acute inflammation (p < 0.05). In chronic inflammatory model, IO and ID decreased paw volume to 3.26 ± 0.38 and 4.20 ± 0.38 mL, respectively.Conclusion: The results show that IO is a promising candidate for further development as analgesic and anti-inflammatory agents. However, their pharmacokinetic and pharmacodynamic profiles need to be investigated. Keywords: Computational, Stevioside, Docking, Analgesic, Anti-inflammatory