(-)-Sitagliptin (phosphate)

(-)-Sitagliptin is a potent inhibitor of dipeptidyl peptidase 4 (DPP-4, IC50 = 18 nM). It is selective for DPP-4 over DPP-8 (IC50 = 48 µM) as well as several other peptidases, including DPP-9, DPP-2, and amino peptidase P. (-)-Sitagliptin improves glucose tolerance in insulin-resistant Zucker fatty and high-fat diet fed rats as well as ob/ob and high-fat diet fed mice. It also reduces hyperglycemia in mice fed a high-fat diet with diabetes induced by streptozotocin (Cay-13104). Formulations containing (-)-sitagliptin have been used in the treatment of type 2 diabetes mellitus.Formal Name: (3R)-3-amino-1-[5,6-dihydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)-1-butanone, monophosphate. CAS Number: 654671-78-0. Synonyms: INN, MK-431, ONO-5435, (R)-Sitagliptin. Molecular Formula: C16H15F6N5O . H3PO4. Formula Weight: 505.3. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 0.25 mg/ml, DMSO: 5 mg/ml, PBS (pH 7.2): 5 mg/ml. lambdamax: 267 nm. SMILES: FC1=CC(C[C@@H](N)CC(N2CC3=NN=C(C(F)(F)F)N3CC2)=O)=C(F)C=C1F.O=P(O)(O)O. InChi Code: InChI=1S/C16H15F6N5O.H3O4P/c17-10-6-12(19)11(18)4-8(10)3-9(23)5-14(28)26-1-2-27-13(7-26)24-25-15(27)16(20,21)22,1-5(2,3)4/h4,6,9H,1-3,5,7,23H2,(H3,1,2,3,4)/t9-,/m1./s1. InChi Key: IQFYVLUXQXSJJN-SBSPUUFOSA-N.