5349. Lamifiban

Nomenclature

CAS number: 144412-49-7
(S)-[[1-[2-[[4-(Aminoiminomethyl)benzoyl]amino]-3-(4-hydroxyphenyl)-1-oxopropyl]-4-piperidinyl]oxy]acetic acid; [[1-[N-(p-amidinobenzoyl)-l-tyrosyl]-4-piperidinyl]oxy]acetic acid; Ro-44-9883.
C24H28N4O6; mol wt 468.50.
C 61.53%, H 6.02%, N 11.96%, O 20.49%.

Description and references

Specific nonpeptide platelet fibrinogen receptor (GPIIb/IIIa) antagonist. Prepn: L. Alig et al., EP 505868; eidem, US 5378712 (1992, 1995 both to Hoffmann-La Roche); L. Alig et al., J. Med. Chem. 35, 4393 (1992). Pharmacology: J.-P. Carteaux et al., Thromb. Haemostasis 70, 817 (1993); Y. Takiguchi et al., ibid. 73, 683 (1995).

Chemical structure

Properties

Crystals (zwitterionic form) from water, mp above 200° (dec). [α]D20 +29.8° (c = 0.86 in 1N HCl).

Derivative

Trifluoroacetate salt.

Nomenclature

CAS number: 144412-50-0
C24H28N4O6.C2HF3O2; mol wt 582.53.
C 53.61%, H 5.02%, N 9.62%, O 21.97%, F 9.78%.

Properties

mp 125-130° (dec). LD50 i.v. in mice: 250 mg/kg (Alig, 1995).

Therapeutic Category

Antithrombotic.

Keywords

Antithrombotic; Fibrinogen Receptor Antagonist