Prasugrel

Prasugrel
(IUPAC) ime
	(RS)-5-[2-ciklopropil-1-(2-fluorofenil)-2-oksoetil]-4,5,6,7-; tetrahidrotieno[3,2-c]piridin-2-il acetat
Klinički podaci
Robne marke	Effient, Efient
AHFS/Drugs.com	Monografija
MedlinePlus	a609027
Identifikatori
CAS broj	150322-43-3
ATC kod	B01AC22
PubChem	6918456
DrugBank	DB06209
ChemSpider	5293653
UNII	34K66TBT99
KEGG	D05597
ChEMBL	CHEMBL1201772
Hemijski podaci
Formula	C20H20FNO3S
Mol. masa	373,442 g/mol
SMILES	eMolekuli & PubHem
InChI
	InChI=1S/C20H20FNO3S/c1-12(23)25-18-10-14-11-22(9-8-17(14)26-18)19(20(24)13-6-7-13)15-4-2-3-5-16(15)21/h2-5,10,13,19H,6-9,11H2,1H3 ; Key: DTGLZDAWLRGWQN-UHFFFAOYSA-N
Farmakokinetički podaci
Bioraspoloživost	≥79%
Vezivanje za proteine plazme	Aktivni metabolit: ~98%
Metabolizam	Brz intestinalni i serumski metabolizam
Poluvreme eliminacije	~7 sati (opseg 2-15 sata)
Izlučivanje	Urin (~68% neaktivni metaboliti); izmet (27% neaktivni metaboliti)
Farmakoinformacioni podaci
Licenca	EU EMEA:link, US FDA:link
Trudnoća	B(US)
Pravni status	POM (UK) ℞-only (SAD)
Način primene	Oralno

Prasugrel (Effient, Efient) je antitrombotik koji je razvila kompanija Daiichi Sankyo Co. On je u prodaji za akutne koronarne sindrome usled perkutane koronarne intervencije (PCI). Prasugrel je odobren za upotrebu u Evropi februara 2009. Iste godine je FDA odobrila upotrebu ovog leka za redukciju učestalosti trombotičkih kardiovaskularnih događaja (uključujući stent trombozu) kod pacijenata sa akutnim koronarnim sindromom.^[6]

Farmakologija

Reakcija prasugrela (gore levo) do njegovog aktivnog metabolita (gore desno). Za razliku od srodnog leka klopidogrela, aktivacija prasugrela ne obuhvata oksidaciju enzimom CYP2C19, jer je relevantni kiseonik (u tiofenskom prstenu) već prisutan u proleku.

Prasugrel je član tienopiridinske klase inhibitora ADP receptora, poput tiklopidina (Tiklida) i klopidogrela (Plaviksa). Ti agensi redukuju agregaciju (gzrušavanje) trombocita putem ireversizibilnog vezivanja za P2Y₁₂ receptore. U poređenju sa klopidogrelom, prasugrel brže i konzistentnije inhibira adenozin difosfatom indukovanu agregaciju trombocita. On proizvodi taj efekat u većoj meri nego standardne i povišene doze klopidogrela kod zdravih volontera i pacijenata sa koronarnom arterijskom bolešću, uključujući pacijenate koji su bili podvrgnuti perkutanoj koronarnoj intervenciji.^[7]^[8]^[9]^[10]

Reference

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.
↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit
↑ Baker WL, White CM. Role of Prasugrel, a Novel P2Y12 Receptor Antagonist, in the Management of Acute Coronary Syndromes. American Journal of Cardiovascular Drugs Aug 1, 2009; 9 (4): 213-229. Link text Arhivirano 2012-02-24 na Wayback Machine-u
↑ Wiviott SD, Braunwald E, McCabe CH i dr.. (2007). „Prasugrel versus clopidogrel in patients with acute coronary syndromes”. The New England Journal of Medicine 357 (20): 2001–15. DOI:10.1056/NEJMoa0706482.
↑ "FDA Announces New Boxed Warning on Plavix: Alerts patients, health care professionals to potential for reduced effectiveness" (Press release). Food and Drug Administration (United States). 2010-03-12. Retrieved 2010-03-12.
↑ „FDA Drug Safety Communication: Reduced effectiveness of Plavix (clopidogrel) in patients who are poor metabolizers of the drug”. Drug Safety and Availability. Food and Drug Administration (United States). 12. 3. 2010.. Pristupljeno 13. 3. 2010.
↑ Silvano M, et al. (2011). „A case of resistance to clopidogrel and prasugrel after percutaneous coronary angioplasty.”. J Thromb Thrombolysis 31(2): 233–4. PMID 21088983.

Spoljašnje veze

	Portal Medicina
	Portal Hemija

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[2] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[3] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[4] Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.

[5] Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit

[6] Baker WL, White CM. Role of Prasugrel, a Novel P2Y12 Receptor Antagonist, in the Management of Acute Coronary Syndromes. American Journal of Cardiovascular Drugs Aug 1, 2009; 9 (4): 213-229. Link text Arhivirano 2012-02-24 na Wayback Machine-u

[Wiviott2007-7] Wiviott SD, Braunwald E, McCabe CH i dr.. (2007). „Prasugrel versus clopidogrel in patients with acute coronary syndromes”. The New England Journal of Medicine 357 (20): 2001–15. DOI:10.1056/NEJMoa0706482.

[8] "FDA Announces New Boxed Warning on Plavix: Alerts patients, health care professionals to potential for reduced effectiveness" (Press release). Food and Drug Administration (United States). 2010-03-12. Retrieved 2010-03-12.

[9] „FDA Drug Safety Communication: Reduced effectiveness of Plavix (clopidogrel) in patients who are poor metabolizers of the drug”. Drug Safety and Availability. Food and Drug Administration (United States). 12. 3. 2010.. Pristupljeno 13. 3. 2010.

[10] Silvano M, et al. (2011). „A case of resistance to clopidogrel and prasugrel after percutaneous coronary angioplasty.”. J Thromb Thrombolysis 31(2): 233–4. PMID 21088983.

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