2797. Dabigatran
Nomenclature
CAS number: 211914-51-1
N-[[2-[[[4-(Aminoiminomethyl)phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-2-pyridinyl-β-alanine; 3-[[2-[(4-carbamimidoylphenylamino)methyl]-1-methyl-1H-benzoimidazole-5-carbonyl]pyridin-2-ylamino]propionic
acid; BIBR-953. C25H25N7O3; mol wt 471.51.
C 63.68%, H 5.34%, N 20.79%, O 10.18%.
Description and references
Nonpeptide, direct thrombin inhibitor. Prepn and crystal structure of complex with thrombin: N. Hauel et al., WO 9837075; eidem, US 6087380 (1998, 2000 both to Boehringer, Ing.); eidem, J. Med. Chem. 45, 1757 (2002) DOI PubMed. Review of pharmacology: D. Mungall, Curr. Opin. Investig. Drugs 3, 905-907 (2002) PubMed. Clinical pharmacokinetics: J. Stangier et al., J. Clin. Pharmacol. 45, 555 (2005) DOI PubMed. Clinical evaluations in joint replacement: B. I. Eriksson et al., J. Thromb. Haemost. 2, 1573 (2004) DOI PubMed; idem et al., ibid. 3, 103 (2005).
Properties
White crystals, mp 276-277°. Log P (n-octanol/buffer, pH 7.4): -2.4.Derivative
Etexilate.Nomenclature
CAS number: 211915-06-9
N-[[2-[[[4-[[[(Hexyloxy)carbonyl]amino]iminomethyl]phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-2-pyridinyl-β-alanine
ethyl ester; ethyl 3-[[[2-[[[4-[[[(hexyloxy)carbonyl]amino]iminomethyl]phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl](pyridin-2-yl)amino]propanoate; BIBR-1048; Pradaxa (Boehringer, Ing.); Rendix (Boehringer, Ing.). C34H41N7O5; mol wt 627.73.
C 65.05%, H 6.58%, N 15.62%, O 12.74%.
Properties
Colorless crystals, mp 128-129°. Log P (n-octanol/buffer, pH 7.4): 2.6.Therapeutic Category
Antithrombotic.
Keywords
Antithrombotic