Prasugrel

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Warnung

• Gefahrenhinweise

  H302：Gesundheitsschädlich bei Verschlucken.

  H315：Verursacht Hautreizungen.

  H319：Verursacht schwere Augenreizung.

  H335：Kann die Atemwege reizen.

• Sicherheit

  P261：Einatmen von Staub vermeiden.

  P305+P351+P338：BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.

Prasugrel Chemische Eigenschaften,Einsatz,Produktion Methoden

• Beschreibung

  Prasugrel is a third-generation thienopyridine that has been developed and launched for the prevention of atherothrombotic events in patients with ACS or following PCI. While the second-generation agent clopidogrel was an improvement over the first-generation ticlopidine, which suffered from gastrointestinal adverse effects and the risk of neutropenia with prolonged use, its delayed onset of action and considerable interpatient variability prompted the search for the next-generation thienopyridine. The mechanism of action of these platelet inhibitors involves initial biological activation to a sulfhydryl metabolite that irreversibly binds to the P2γ₁₂ receptor on platelets via disulfide formation, thereby preventing platelet activation and aggregation by the endogenous agonist adenosine diphosphate (ADP). The advantage of prasugrel over its predecessors is its more efficient and consistent absorption and rapid conversion to its active metabolite. Co-administration of thienopyridines with acetylsalicylic acid (aspirin), an inhibitor of the synthesis of the platelet aggregation mediator thromboxane A2, is an effective antiplatelet strategy and joins antagonists of glycoprotein IIb/IIIa, which target the final step in platelet aggregation, in the medical arsenal combating atherothrombotic events.

• Originator

  Daiichi Sankyo (Japan)

• Verwenden

  Inhibits platelet aggregation (platelet ADPP 2Y12 antagonist).

• Verwenden

  Prasugrel is a platelet inhibitor that reduces aggregation of platelets by being a P2Y12(ADP receptor) inhibitor.

• Definition

  ChEBI: 5-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate is a member of the class of thienopyridines that is 2-acetoxy-4,5,6,7-tetrahydrothieno[3,2-c]pyridine in which the amino hydrogen is replaced by a 2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl group. It is an acetate ester, a member of cyclopropanes, a ketone, a member of monofluorobenzenes, a tertiary amino compound and a thienopyridine.

• Trademarks

  Effient

• Clinical Use

  Prasugrel is a platelet inhibitor developed by Daiichi Sankyo Co. and is marketed in the United States in cooperation with Eli Lilly and Company for acute coronary syndromes planned for percutaneous coronary intervention (PCI). Prasugrel was approved for use in Europe in February 2009, and is currently available in the UK. In the U.S. prasugrel is also approved for the reduction of thrombotic cardiovascular events, including stent thrombosis, in patients with acute coronary syndrome who are to be managed with PCI. Prasugrel is a member of the thienopyridine class of ADP receptor inhibitors, and irreversibly binds to P2Y12 receptors.

• Nebenwirkungen

  In addition to the hemorrhagic side effect, other serious adverse events included AF, bradycardia, leucopenia, severe thrombocytopenia, angiodema, anemia, and abnormal hepatic function with hypertension, headache, back pain, dyspnea, nausea, dizziness, and diarrhea as less severe complaints. Prasugrel is contraindicated in patients with active pathological bleeding, such as peptic ulcers or intracranial hemorrhage, and in patients with a history of prior transient ischemic attack or stroke. In addition, in patients 75 years old, <60 kg, or likely to undergo urgent coronary artery bypass graft surgery, the risk may not outweigh the benefit. When possible, prasugrel treatment should be discontinued at least 7 days prior to any surgery. While warfarin and non-steroidal antiinflammatory drugs (NSAIDS) may increase the risk of bleeding with coadministration of prasugrel, no drug interactions are anticipated with concomitant use of drugs that are inducers or inhibitors of the cytochrome P450 enzymes. Prasugrel may also be administered with aspirin (75-325 mg per day), heparin, GP IIb/IIIa inhibitors, statins, digoxin, and drugs that elevate gastric pH, including PPIs and H2 blockers.

• Synthese

  The synthesis of prasugrel begins with the preparation of the a-ketocyclopropane 102 which is prepared as summarized in the scheme. Conversion of 1-(bromomethyl)-2-fluorobenzene (99) to the corresponding Grignard reagent through reaction with magnesium followed by condensation with nitrile 100 resulted in ketone 101 in 72% yield. Chlorination of ketone 101 with CuCl2 resulted in the key prasugrel coupling component 102 in 92% yield. The piperidine coupling partner was prepared by treating thiolactone 103 with TBDMSCl and triethylamine to give thiophene 104 in 91% yield. Treatment of piperidine 104 with a-chloroketone 102 resulted in enol silane 105 in 65% yield. Reaction of silylenol ether 105 with acetic anhydride in the presence of triethylamine and catalytic DMAP resulted in the preparation of prasugrel (XVII) in 60% yield.

  

• Arzneimittelwechselwirkung

  Potentially hazardous interactions with other drugs
  Anticoagulants: enhanced anticoagulant effect with coumarins and phenindione.

• Stoffwechsel

  Prasugrel is a prodrug and is rapidly metabolised in the liver by various cytochrome P450 enzymes to an active metabolite and inactive metabolites. The active metabolite is further metabolised to 2 inactive compounds which are excreted in the urine and faeces; about 68% of a dose is excreted in urine and about 27% in faeces.

• Lager

  Store at +4°C

Prasugrel Upstream-Materialien And Downstream Produkte

Prasugrel Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global(378)Suppliers

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