Tirofiban

Bezeichnung:Tirofiban

CAS-Nr144494-65-5

Englisch Name:Tirofiban

CBNumberCB9169083

SummenformelC22H36N2O5S

Molgewicht440.6

MOL-Datei144494-65-5.mol

Tirofiban physikalisch-chemischer Eigenschaften

Schmelzpunkt	223-225°
Siedepunkt	611.7±65.0 °C(Predicted)
Dichte	1.154±0.06 g/cm3(Predicted)
storage temp.	Keep in dark place,Sealed in dry,Store in freezer, under -20°C
Löslichkeit	Limited solubility
Aggregatzustand	Solid
pka	3.37±0.10(Predicted)
Farbe	White to off-white
BRN	6182267
CAS Datenbank	144494-65-5(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26
WGK Germany	3
RTECS-Nr.	YP2364100
Giftige Stoffe Daten	144494-65-5(Hazardous Substances Data)

Gefahreninformationscode (GHS)

Tirofiban Chemische Eigenschaften,Einsatz,Produktion Methoden

Chemische Eigenschaften
Tirofiban is an Off-White to Pale Yellow Solid. It is soluble in organic solvents such as ethanol, DMSO, and dimethyl formamide, which should be purged with an inert gas. The solubility of tirofiban in these solvents is approximately 30 mg/ml.
Originator
Aggrastat,Merck and Co., Inc.
Verwenden
Tirofiban (Aggrastatt, MK-0383; L-700,462) is a parenteral, highly specific, and potent GPIIb/IIIa antagonist that was approved for patient use in 1998 for the treatment of unstable angina and non-Q-wave myocardial infarction.
Tirofiban is a nonpeptide GP IIb/IIIa antagonist that binds reversibly to IIb/IIIa receptors. Tirofiban is a non-peptide reversible antagonist of the platelet integrin glycoprotein (GP) IIbIIIa receptor used as an antiplatelet drug.
Tirofiban is a small molecule inhibitor of the protein-protein interaction between fibrinogen and the platelet integrin receptor GP IIb/IIIa and is the first drug candidate whose origins can be traced to a pharmacophore-based virtual screening lead.
Definition
ChEBI: Tirofiban is a member of the class of piperidines that is L-tyrosine in which a hydrogen attached to the amino group is replaced by a butylsulfonyl group and in which the hydrogen attached to the phenolic hydroxy group is replaced by a 4-(piperidin-4-yl)butyl group. It has a role as a fibrin modulating drug, a platelet glycoprotein-IIb/IIIa receptor antagonist and an anticoagulant. It is a member of piperidines, a sulfonamide and a L-tyrosine derivative.
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.
Therapeutic Function
Fibrinogen receptor antagonist
Allgemeine Beschreibung
Tirofiban is a nonpeptide that appears unrelatedchemically to eptifibatide, but actually has many similarities.The chemical architecture incorporates a systemthat is mimicking the RGD moiety that is present in eptifibatide.This can be seen in the distance between the nitrogenof the piperidine ring, which mimics the basic nitrogen ofarginine in the RGD sequence, and the carboxylic acid,which mimics the acid of aspartate in the RGD sequence.The basic nitrogen and the carboxylic acid of tirofiban areseparated by approximately 15 to 17? (16–18 atoms). Thisis the optimum distance seen in the RGD sequence of theplatelet receptor. Tirofiban is useful in treating non–Q wavemyocardial infarction and unstable angina.
Clinical Use
Tirofiban is a member of a new class of antithrombotic agents known as the “ fibans”. These compounds have a structural similarity to disintegrin, which was originally isolated from snake venoms. The location of the –COO- and NH3+ in the fibans is identical to the distance between the same functional groups of the RGD loop of disintegrin, and as a result, the fibans are able to effectively block the binding of fibrinogen to the GPIIb/IIIa receptor in an reversible manor.
Arzneimittelwechselwirkung
Potentially hazardous interactions with other drugs
Iloprost: increased risk of bleeding.
Heparin: increased risk of bleeding
Stoffwechsel
Tirofiban is eliminated largely unchanged in the urine, with some biliary excretion in the faeces.
Mode of action
Tirofiban is a reversible antagonist that inhibits platelet aggregation by reversibly binding to the receptor glycoprotein (GP) IIb/IIIa of human platelets, thus preventing the binding of fibrinogen. Inhibition of platelet aggregation occurs in a dose- and concentrationdependent manner.?

Tirofiban Upstream-Materialien And Downstream Produkte

Tirofiban Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

144494-65-5, Tirofiban Verwandte Suche:

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