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Dabigatran (Molecule of the Month for May 2008)

Pradaxa, anticoagulant

Dabigatran is an anticoagulant from the class of the direct thrombin inhibitors. It is being studied for various clinical indications, for some of which it may replace warfarin as the preferred anticoagulant. It is orally administered as the prodrug dabigatran etexilate (marketed as Pradaxa since April in European countries and Pradax in Canada). It was developed by pharmaceutical company Boehringer-Ingelheim.

Dabigatran (then compound BIBR 953) was discovered from a panel of chemicals with similar structure to benzamidine-based thrombin inhibitor α-NAPAP (N-alpha-(2-naphthylsulfonylglycyl)-4-amidinophenylalanine piperidide), which had been known since the 1980s as a powerful inhibitor of various serine proteases, specifically thrombin but also trypsin.

The National Health Service in Britain have authorised the use of dabigatran for use in preventing blood clots in hip and knee surgery patients. Charities, including the British Heart Foundation are campaigning for the drug to be widely prescribed in place of Warfarin, which has the down side of having to be taken for at least one month, and heparin, which is administered intravenously or subcutaneously in its low molecular weight form.

Formal Chemical Name (IUPAC)
Ethyl 3-{[(2-{[(4-{N'-[(hexyloxy)carbonyl] carbamimidoyl}phenyl)amino]methyl}-1-methyl-1H-benzimidazol-5-yl)carbonyl] (2-pyridinyl)amino}propanoate




Picture of Dabigatran 3D model

click on the picture of  Dabigatran above to interact
with the 3D model of the
Dabigatran structure
(this will open a new browser window)

Picture of Dabigatran


Update by Karl Harrison
(Molecule of the Month for May 2008 )

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