Alogliptin benzoate (SYR-322)

Description: Alogliptin benzoate (SYR-322 benzoate) is a novel, potent, orally bioavailable, and selective inhibitor of DPP-4 (serine protease dipeptidyl peptidase IV) with IC50 value of 2.6 nM, it exhibits greater than 10, 000-fold selectivity for DPP-4 over the closely related DPP-8 and DPP-9. It is an anti-diabetic drug marketed in Japan since 2010; and in 2013, the FDA approved the drug in three formulations: as a stand-alone with the brand-name Nesina, combined with metformin using the name Kazano, and when combined with pioglitazone as Oseni. Like other medications for the treatment of Type 2 diabetes, alogliptin does not decrease the risk of heart attack and stroke. Alogliptin and other gliptins are commonly used in combination with metformin in patients whose diabetes cannot adequately be controlled with metformin alone.

References: J Med Chem. 2007 May 17; 50(10):2297-300; Life Sci. 2009 Jul 17; 85(3-4):122-6.

Related CAS#: 850649-61-5 (free base); 850649-62-6 (benzoate); 1246817-18-4 Alogliptin (13CD3

Chemical Name: (R)-2-((6-(3-aminopiperidin-1-yl)-3-methyl-2, 4-dioxo-3, 4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile benzoate

InChi Key: KEJICOXJTRHYAK-XFULWGLBSA-N

InChi Code: InChI=1S/C18H21N5O2.C7H6O2/c1-21-17(24)9-16(22-8-4-7-15(20)12-22)23(18(21)25)11-14-6-3-2-5-13(14)10-19; 8-7(9)6-4-2-1-3-5-6/h2-3, 5-6, 9, 15H, 4, 7-8, 11-12, 20H2, 1H3; 1-5H, (H, 8, 9)/t15-; /m1./s1

SMILES Code: O=C(O)C1=CC=CC=C1.N#CC2=CC=CC=C2CN(C(N3C)=O)C(N4C[CH](N)CCC4)=CC3=O