Tirofiban
Title: Tirofiban
CAS Registry Number: 144494-65-5
CAS Name: N-(Butylsulfonyl)-O-[4-(4-piperidinyl)butyl]-L-tyrosine
Additional Names: N-(butylsulfonyl)-4-[4-(4-piperidyl)butoxy]-L-phenylalanine; 2-S-(n-butylsulfonylamino)-3-[4-(piperidin-4-yl)butyloxyphenyl]propionic acid
Molecular Formula: C22H36N2O5S
Molecular Weight: 440.60
Percent Composition: C 59.97%, H 8.24%, N 6.36%, O 18.16%, S 7.28%
Literature References: Specific nonpeptide platelet fibrinogen receptor (GPIIb/IIIa) antagonist. Prepn: M. S. Egbertson et al., EP 478363; M. E. Duggan et al., US 5292756 (1992, 1994 both to Merck & Co.); J. Y. L. Chung et al., Tetrahedron 49, 5767 (1993). Physicochemical properties: J. A. McCauley et al., J. Phys. D: Appl. Phys. 26, B85 (1993). Pharmacology: J. J. Lynch et al., J. Pharmacol. Exp. Ther. 272, 20 (1995). Clinical pharmacokinetics and pharmacodynamics: J. S. Barrett et al., Clin. Pharmacol. Ther. 56, 377 (1994). Clinical trials in angina: P. Théroux et al., N. Engl. J. Med. 338, 1488 (1998); H. D. White et al., ibid. 1498. Clinical comparison with abciximab, q.v., in coronary revascularization: D. J. Moliterno et al., Lancet 360, 355 (2002).
Properties: White solid, mp 223-225°.
Melting point: mp 223-225°
 
Derivative Type: Hydrochloride monohydrate
CAS Registry Number: 150915-40-5; 142373-60-2 (hydrochloride)
Manufacturers' Codes: MK-383
Trademarks: Aggrastat (Merck & Co.)
Molecular Formula: C22H36N2O5S.HCl.H2O
Molecular Weight: 495.07
Percent Composition: C 53.37%, H 7.94%, N 5.66%, O 19.39%, S 6.48%, Cl 7.16%
Properties: Solid, mp 131-132°. [a]D25 -14.4° (c = 0.92 in methanol).
Melting point: mp 131-132°
Optical Rotation: [a]D25 -14.4° (c = 0.92 in methanol)
 
Therap-Cat: Antithrombotic; in treatment of unstable angina.
Keywords: Antithrombotic; Fibrinogen Receptor Antagonist.

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