Elinogrel

Elinogrel

Systematic (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
Clinical data
Pregnancy category	N/A
Routes of administration	Oral, intravenous
Legal status	Investigational
Pharmacokinetic data
Metabolism	Mainly unchanged, ca. 15% N-demethylation[1]
Excretion	Urine, faeces
Identifiers
CAS Number	936500-94-6
ATC code	none
PubChem	CID 16066663
ChemSpider	17226246
UNII	915Y8E749J
KEGG	D09607
Synonyms	PRT-060128
Chemical data
Formula	C20H15ClFN5O5S2
Molar mass	523.945 g/mol
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
InChI InChI=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) Key:LGSDFTPAICUONK-UHFFFAOYSA-N

Elinogrel (INN,^[2] 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.^[3] Development was terminated in 2012.

History

The substance was originally developed by Portola Pharmaceuticals, with Phase II clinical trials conducted around 2008–2011.^[4] In February 2009, Novartis bought worldwide rights to develop it further, intending to conduct Phase III studies and commercialise the drug.^[5] The development of the drug was terminated in January 2012 by Novartis.^[6]

References

1. Siller-Matula, J. M.; Krumphuber, J.; Jilma, B. (2010). "Pharmacokinetic, pharmacodynamic and clinical profile of novel antiplatelet drugs targeting vascular diseases". British Journal of Pharmacology 159 (3): 502–517. doi:10.1111/j.1476-5381.2009.00555.x. PMC 2828016. PMID 20050853.
2. International Nonproprietary Names for Pharmaceutical Substances (INN): Proposed INN List 101
3. Gurbel, P.A.; Kereiakes, D.; Tantry, U.S. (2010). "Elinogrel potassium". Drugs Fut 35 (11): 885.
4. Michelson, A. D. (2011). "Advances in Antiplatelet Therapy". Hematology 2011: 62–69. doi:10.1182/asheducation-2011.1.62. PMID 22160013.
5. Insciences: Novartis gains worldwide rights to elinogrel, a Phase II anti-clotting compound with potential to reduce risk of heart attack
6. BioPortfolio: Novartis drops elinogrel outright