TIROFIBAN HYDROCHLORIDE MONOHYDRATE Chemical Properties

Melting point:

83-87oC

solubility 

Methanol (Slightly)

form 

Solid

color 

White

CAS DataBase Reference

142373-60-2

TIROFIBAN HYDROCHLORIDE MONOHYDRATE Usage And Synthesis

Description

Tirofiban was launched as Aggrastat in Switzerland and the US for patients with unstable angina or non-Q-wave myocardial infarction to prevent cardiac ischemic events. Tirofiban is synthesized from (S)-tyrosine by a fourstep process. Tirofiban is a novel highly potent antiplatelet agent that inhibits the interaction of fibrinogen with GPⅡb/Ⅲa, an activated platelet membrane-bound glycoprotein complex. It prevents arterial thrombus formation in a dosedependent manner. Clinical efficacy was highly significant with an absolute and relative risk reduction. In these studies, treatment with tirofiban was well tolerated, without significant adverse effects.

Originator

Sibutramine (Sibutramine)

Uses

Aggrastat (Millot Laboratories, France).

Uses

Tirofiban Hydrochloride is a selective nonpeptide platelet glycoprotein IIb/IIIa antagonist.

Manufacturing Process

The synthesis of tirofiban starts by reaction of tyrosine with bis-trimethylsilyl trifluoraceramide to give a derivative in which both functions -OH and COOH_x0002_are protected. Treatment of this intermediate with butylsulfonyl chloride gives the corresponding sulfonamide derivative; the quite labile silyl groups are then removed under mildly acidic conditions to give N-butylsulfonyl-tyrosine. In a parallel scheme, 4-picoline is converted to its anion by means of butyl lithium; this gives 4-(4-chlorobutyl)-pyridine on alkylation with 1-bromo-3- chloropropane. The reaction of this compound with N-butylsulfonyl-tyrosine in presence of NaOH gives the ether 2-butylsulfonyaminol-3-[4-pyridin-4-ylbutoxy-phenyl]propionic acid. Hydrogenation over palladium on charcoal then reduce the pyridine ring to a piperidine to afford the fibrinogen receptor antagonist tirofiban.

brand name

Tirofiban is INN and BAN.

Therapeutic Function

Fibrinogen receptor antagonist

TIROFIBAN HYDROCHLORIDE MONOHYDRATE(142373-60-2)Related Product Information

• Tirofiban hydrochloride monohydrate
• L-N-BUTYLSULFONYL-P-HYDROXYPHENYLALANINE
• Tirofiban IMpurity (4,4'-Dipyridyl-1,5-Pentane)
• tirofiban
• N-Butylsulfonyl-O-(4-(4-pyridinyl)butyl)-L-tyrosine
• 4-PYRIDIN-4-YL-BUTAN-1-OL
• 1-Butanesulfonic acid methyl ester
• 4-PYRIDIN-4-YL-BUTYRIC ACID
• Sodium 1-butanesulfonate
• 1-Methylethyl 1-butanesulfonate
• METHYL N-BUTYLSULFONYL-L-P-HYDROXYPHENYLALANINE
• tirofiban
• tirofiban
• 1-Butanesulfonyl chloride
• 4-(4-Piperidyl)-1-butanol
• 2-butyl-4-methylpyridine
• 4,4'-Dimethyl-2,2'-bipyridyl
• 4-Chloro-1-butanol