Small-molecule inhibitor: dabigatran

Name

Common name: dabigatran
Other names: BIBR 1048; BIBR-953ZW prodrug; dabigatran etexilate; HY023016 (prodrug); Pradaxa; Rendix

History: The X-ray crystal structure of the peptide-like thrombin inhibitor NAPAP in complex with bovine thrombin led to the design of the very polar, zwitterionic molecule of compound BIBR 953. This was converted into a double-prodrug, BIBR 1048, that showed strong oral activity in animals (Hauel et al., 2002).
Peptidases inhibited: Thrombin. There is much weaker inhibition of coagulation factor Xa and trypsin (Hauel et al., 2002).
Mechanism: This is a tight-binding, reversible inhibitor of thrombin.
Pharmaceutical relevance: Dabigatran etexilate is the orally-active prodrug form of a direct thrombin inhibitor that has been under investigation for use as an anticoagulant (Baetz & Spinler, 2008).

CID at PubChem: 216210
ChEBI: 175302
Structure
Chemical/biochemical name: 3-({2-[(4-Carbamimidoyl-phenylamino)-methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}-pyridin-2-yl-amino)-propionic acid
Formula weight: 472