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TIROFIBAN HYDROCHLORIDE MONOHYDRATE

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TIROFIBAN HYDROCHLORIDE MONOHYDRATE Basic information
TIROFIBAN HYDROCHLORIDE MONOHYDRATE Chemical Properties
TIROFIBAN HYDROCHLORIDE MONOHYDRATE Usage And Synthesis
  • DescriptionTirofiban 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.
  • OriginatorSibutramine (Sibutramine)
  • UsesAggrastat (Millot Laboratories, France).
  • Manufacturing ProcessThe 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 nameTirofiban is INN and BAN.
  • Therapeutic FunctionFibrinogen receptor antagonist
TIROFIBAN HYDROCHLORIDE MONOHYDRATE(142373-60-2)Related Product Information
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