Linagliptin

Description: Linagliptin (formerly known as BI-1356; trade names Tradjenta and Trajenta) is a xanthine-based, highly potent, selective, and competitive DPP-4 inhibitor with potential anti-diabetic activity. It inhibits DPP-4 with an IC50 of 1 nM. DPP-4 plays a major role in the degradation of incretins such as GLP-1 which is of great importance in the process of glucose metabolism. Under physiological conditions, GLP-1 is truncated by DPP-4 rapidly, which is located on the capillary endothelium proximal to the L-cells where GLP-1 is secreted in the ileum. On 2 May 2011, Linagliptin was approved by the FDA fortreatment of type II diabetes. It is being marketed by BoehringerIngelheim and Lilly.

References: J Med Chem. 2007 Dec 27; 50(26):6450-3; J Pharmacol Exp Ther. 2008 Apr; 325(1):175-82.

Chemical Name: 8-[(3R)-3-aminopiperidin-1-yl]-7-(but-2-yn-1-yl)-3- methyl-1-[(4-methylquinazolin-2-yl)methyl]-3, 7-dihydro-1H-purine-2, 6-dione

InChi Key: LTXREWYXXSTFRX-QGZVFWFLSA-N

InChi Code: InChI=1S/C25H28N8O2/c1-4-5-13-32-21-22(29-24(32)31-12-8-9-17(26)14-31)30(3)25(35)33(23(21)34)15-20-27-16(2)18-10-6-7-11-19(18)28-20/h6-7, 10-11, 17H, 8-9, 12-15, 26H2, 1-3H3/t17-/m1/s1

SMILES Code: O=C(N1CC2=NC(C)=C3C=CC=CC3=N2)N(C)C4=C(N(CC#CC)C(N5C[CH](N)CCC5)=N4)C1=O