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| TIROFIBAN HYDROCHLORIDE MONOHYDRATE Basic information |
| Product Name: | TIROFIBAN HYDROCHLORIDE MONOHYDRATE | | Synonyms: | L 700462;L-Tyrosine, N-(butylsulfonyl)-o-(4-(4-piperidinyl)butyl)-, monohydrochloride;N-(Butylsulfonyl)-o-(4-(4-piperidinyl)butyl)-L-tyrosine monohydrochloride;2-(butylsulfonaMido)-3-(4-(4-(piperidin-4-yl)butoxy)phenyl)propanoic acid;L-Tyrosine,N-(butylsulfonyl)-O-[4-(4-piperidinyl)butyl]-, hydrochloride (1:1);-3-(4-(4-(piperidin-4-yl);butoxy);N-(Butylsulfonyl)-O-[4-(4-piperidinyl)butyl]-L-tyrosine hydrochloride | | CAS: | 142373-60-2 | | MF: | C22H39ClN2O6S | | MW: | 495.07 | | EINECS: | | Product Categories: | | Mol File: | 142373-60-2.mol |
| 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 Preparation Products And Raw materials |
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