Darapladib

Darapladib

Systematic (IUPAC) name
N-(2-diethylaminoethyl)-2-[2-[(4-fluorophenyl)methylsulfanyl]-4-oxo-6,7-dihydro-5H-cyclopenta[d]pyrimidin-1-yl]-N-[[4-[4-(trifluoromethyl)phenyl]phenyl]methyl]acetamide
Clinical data
Routes of administration	Oral
Legal status	Investigational
Identifiers
CAS Number	356057-34-6
ATC code	none
PubChem	CID 9939609
IUPHAR/BPS	6696
ChemSpider	8115230
UNII	UI1U1MYH09
ChEMBL	CHEMBL204021
Synonyms	SB-480848
Chemical data
Formula	C36H38F4N4O2S
Molar mass	666.77 g/mol
SMILES FC(F)(F)c1ccc(cc1)c2ccc(cc2)CN(C(=O)CN\4C(\SCc3ccc(F)cc3)=N/C(=O)/C5=C/4CCC5)CCN(CC)CC
InChI InChI=1S/C36H38F4N4O2S/c1-3-42(4-2)20-21-43(22-25-8-12-27(13-9-25)28-14-16-29(17-15-28)36(38,39)40)33(45)23-44-32-7-5-6-31(32)34(46)41-35(44)47-24-26-10-18-30(37)19-11-26/h8-19H,3-7,20-24H2,1-2H3 Key:WDPFJWLDPVQCAJ-UHFFFAOYSA-N
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Darapladib is an inhibitor lipoprotein-associated phospholipase A2 (Lp-PLA₂) that is in development as a drug for treatment of atherosclerosis.^[1]

It was discovered by Human Genome Sciences in collaboration with GlaxoSmithKline (GSK).^[2]

In November 2013, GSK announced that the drug had failed to meet Phase III endpoints in a trial of 16,000 patients with acute coronary syndrome.^[3] An additional trial of 13,000 patients (SOLID-TIMI 52) finished in May 2014. The study failed to reduce the risk of coronary heart disease death, MI, and urgent coronary revascularization compared with placebo in acute coronary syndrome (ACS) patients treated with standard medical care.^[4]

References

1. Thompson PL et al. Targeting the unstable plaque in acute coronary syndromes. Clin Ther. 2013 Aug;35(8):1099-107. PMID 23973042
2. Reuters. 12 April 2007 Spotlight on Glaxo Heart Drug as Others Fail
3. http://www.fiercebiotech.com/story/glaxosmithkline-loses-its-first-big-phiii-bet-heart-drug-darapladib/2013-11-12
4. http://www.gsk.com/media/press-releases/2014/gsk-announces-phase-iii-study-with-darapladib-did-not-meet-prima.html