Drug repositioning involves the investigation of existing drugs for new therapeutic purposes such as type 2 diabetes. This disease affects the health and quality of life for individuals around the world. Sitagliptin, a highly selective dipeptidyl peptidase-4 (DPP-4) inhibitor, is used to treat type 2 diabetes mellitus by effective fasting and improved glycemic control. Despite this advantage, serious hypersensitivity reactions have been acknowledged for patients receiving sitagliptin. In this context, new drugs with enhanced profile and targeting DPP-4 are necessary to be developed. Sitagliptin, ((2R)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihidro[1,2,4]triazolo[4,3-A] pirazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine), was used as a query in a 3D similarity search (ROCS, OpenEye) on the approved DrugBank. Based on the TanimotoCombo parameter, the first 10 approved DrugBank drugs were docked using FRED from OpenEye package in the 4FFW active site to identify effective anti-diabetic effects for possible repurposable drugs marketed with other indications.