linagliptin   Click here for help

GtoPdb Ligand ID: 6318

Synonyms: BI-1356 | Tradjenta®
Approved drug PDB Ligand
linagliptin is an approved drug (EMA & FDA (2011))
Compound class: Synthetic organic
Comment: Linagliptin is a once-daily, oral dipeptidyl peptidase-4 (DPP-4) inhibitor class anti-diabetic drug.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 116.86
Molecular weight 472.23
XLogP 3.92
No. Lipinski's rules broken 0
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Canonical SMILES CC#CCn1c(nc2c1c(=O)n(Cc1nc(C)c3c(n1)cccc3)c(=O)n2C)N1CCCC(C1)N
Isomeric SMILES CC#CCn1c(nc2c1c(=O)n(Cc1nc(C)c3c(n1)cccc3)c(=O)n2C)N1CCC[C@H](C1)N
InChI 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
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Summary of Clinical Use Click here for help
Used in the management of type 2 diabetes.
Linagliptin was assessed in a combination therapy with the SGLT-2 inhibitor, empagliflozin with ID NCT01734785. In February 2015, this translated to US FDA approval for the fixed dose formulation Glyxambi® (empagliflozin and linagliptin) for the treatment of type 2 diabetes.
In July 2016, the FDA approved a once-daily, extended release DPP-4 inhibitor/biguanide combination (Jentadueto XR®: linagliptin and metformin hydrochloride) as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Competitively and reversibly inhibits dipeptidyl peptidase, the enzyme which catalyses the breakdown of GLP-1. The resulting elevation of GLP-1 levels leads to increased production and release of insulin from pancreatic beta cells and decreased release of glucagon from pancreatic alpha cell. This leads to a decrease in glucose production in the liver and an increase of insulin.
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