13-05606. Lotrafiban [Archived]

Nomenclature

CAS number: 171049-14-2
(2S)-7-([4,4′-Bipiperidin]-1-ylcarbonyl)-2,3,4,5-tetrahydro-4-methyl-3-oxo-1H-1,4-benzodiazepine-2-acetic acid; SB-214857.
C23H32N4O4; mol wt 428.52.
C 64.47%, H 7.53%, N 13.07%, O 14.93%.

Description and references

Specific nonpeptide platelet fibrinogen receptor (GPIIb/IIIa) antagonist. Prepn: W. E. Bondinell et al., WO 9518619; W. E. Bondinell, J. M. Samanen, US 6117866 (1995, 2000 both to SmithKline Beecham). Enantiospecific synthesis: W. H. Miller et al., Tetrahedron Lett. 36, 9433 (1995). Structure-activity study: J. M. Samanen et al., J. Med. Chem. 39, 4867 (1996). Binding study: A. Wong et al., J. Pharmacol. Exp. Ther. 285, 228 (1998). Clinical evaluation in patients with coronary or cerebral atherosclerosis: R. A. Harrington et al., Circulation 102 728 (2000). Clinical trial in cerebrovascular and coronary artery disease: E. J. Topol et al., Circulation 108, 399 (2003).

Chemical structure

Properties

Zwitterionic. [α]D 200.1° (c = 0.5 in methanol).

Therapeutic Category

Antithrombotic.

Keywords

Fibrinogen Receptor Antagonist; Antithrombotic

Status

This monograph has been retired and is no longer subject to revision or update.