elinogrel

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = N-[(5-Chlorothiophen-2-yl)sulfonyl]-N′-{4-[6-fluoro-7-(methylamino)-2,4-dioxo-1,4-dihydroquinazolin-3(2H)-yl]phenyl}urea

| image = Elinogrel skeletal.svg

| width = 275

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status = Development terminated

| routes_of_administration = By mouth, IV

| bioavailability =

| protein_bound =

| metabolism = Mainly unchanged, ~15% N-demethylation{{cite journal | vauthors = Siller-Matula JM, Krumphuber J, Jilma B | title = Pharmacokinetic, pharmacodynamic and clinical profile of novel antiplatelet drugs targeting vascular diseases | journal = British Journal of Pharmacology | volume = 159 | issue = 3 | pages = 502–17 | date = February 2010 | pmid = 20050853 | pmc = 2828016 | doi = 10.1111/j.1476-5381.2009.00555.x }}

| elimination_half-life =

| excretion = Urine, faeces

| CAS_number = 936500-94-6

| ATC_prefix = None

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| PubChem = 16066663

| DrugBank =

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 915Y8E749J

| KEGG = D09607

| synonyms = PRT-060128

| ChemSpiderID = 17226246

| chemical_formula =

| C=20 | H=15 | Cl=1 | F=1 | N=5 | O=5 | S=2

| smiles = CNC1=C(C=C2C(=C1)NC(=O)N(C2=O)C3=CC=C(C=C3)NC(=O)NS(=O)(=O)C4=CC=C(S4)Cl)F

| StdInChI = 1S/C20H15ClFN5O5S2/c1-23-15-9-14-12(8-13(15)22)18(28)27(20(30)25-14)11-4-2-10(3-5-11)24-19(29)26-34(31,32)17-7-6-16(21)33-17/h2-9,23H,1H3,(H,25,30)(H2,24,26,29)

| StdInChIKey = LGSDFTPAICUONK-UHFFFAOYSA-N

}}

Elinogrel (INN,{{cite web | title = International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names: List 63 | url =https://www.who.int/medicines/publications/druginformation/innlists/RL63.pdf | publisher = World Health Organization | access-date = 1 December 2016 | pages = 50–1}} USAN) was an experimental antiplatelet drug acting as a P2Y12 inhibitor. Similarly to ticagrelor and in contrast to clopidogrel, elinogrel was a reversible inhibitor that acted fast and short (for about 12 hours), and it was not a prodrug but pharmacologically active itself. The substance was used in form of its potassium salt, intravenously for acute treatment and orally for long-term treatment.{{cite journal | vauthors = Gurbel PA, Kereiakes D, Tantry US | title = Elinogrel potassium: Receptor antagonist antiplatelet therapy. | journal = Drugs of the Future | date = November 2010 | volume = 35 | issue = 11 | pages = 885–92 | doi = 10.1358/dof.2010.35.11.1529823 | s2cid = 79785538 }} Development was terminated in 2012.

History

The substance was originally developed by Portola Pharmaceuticals, with Phase II clinical trials conducted around 2008–2011.{{cite journal | vauthors = Michelson AD | title = Advances in antiplatelet therapy | journal = Hematology. American Society of Hematology. Education Program | volume = 2011 | pages = 62–9 | year = 2011 | pmid = 22160013 | doi = 10.1182/asheducation-2011.1.62 | doi-access = free }} In February 2009, Novartis bought worldwide rights to develop it further, intending to conduct Phase III studies and commercialise the drug.{{cite web | work = Insciences | url = http://insciences.org/article.php?article_id=2259 | title = Novartis gains worldwide rights to elinogrel, a Phase II anti-clotting compound with potential to reduce risk of heart attack | archive-url = https://web.archive.org/web/20140714144305/http://insciences.org/article.php?article_id=2259 | archive-date=2014-07-14 }} The development of the drug was terminated in January 2012 by Novartis.{{cite web | work = BioPortfolio | url = http://www.bioportfolio.com/news/article/918579/Novartis-Drops-Elinogrel-Outright.html | title = Novartis drops elinogrel outright | archive-url = https://archive.today/20120729224358/http://www.bioportfolio.com/news/article/918579/Novartis-Drops-Elinogrel-Outright.html | archive-date=2012-07-29 }}

References

{{Reflist}}

{{Antithrombotics}}

{{Purinergics}}

Category:Abandoned drugs

Category:Adenosine diphosphate receptor inhibitors

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