Darapladib

Darapladib
Clinical data
Synonyms	SB-480848
Routes of; administration	By mouth
ATC code	None;
Legal status
Legal status	Investigational;
Identifiers
	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;
CAS Number	356057-34-6 ;
PubChem CID	9939609;
IUPHAR/BPS	6696;
ChemSpider	8115230 ;
UNII	UI1U1MYH09;
KEGG	D03650 ;
ChEMBL	CHEMBL204021 ;
PDB ligand	5HV (PDBe, RCSB PDB);
ECHA InfoCard	100.130.738
Chemical and physical data
Formula	C36H38F4N4O2S
Molar mass	666.77 g/mol
3D model (JSmol)	Interactive image;
	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 (ACS).^[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, myocardial infarction, and urgent coronary revascularization compared with placebo in acute coronary syndrome patients treated with standard medical care.^[4]

References

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

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[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] ttp://www.fiercebiotech.com/story/glaxosmithkline-loses-its-first-big-phiii-bet-heart-drug-darapladib/2013-11-12

[4] ttp://www.gsk.com/media/press-releases/2014/gsk-announces-phase-iii-study-with-darapladib-did-not-meet-prima.html

Clinical data

Synonyms	SB-480848
Routes of administration	By mouth
ATC code	None
Legal status
Legal status	Investigational
Identifiers
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
CAS Number	356057-34-6^Y
PubChem CID	9939609
IUPHAR/BPS	6696
ChemSpider	8115230^N
UNII	UI1U1MYH09
KEGG	D03650^N
ChEMBL	CHEMBL204021^N
PDB ligand	5HV (PDBe, RCSB PDB)
ECHA InfoCard	100.130.738
Chemical and physical data
Formula	C₃₆H₃₈F₄N₄O₂S
Molar mass	666.77 g/mol
3D model (JSmol)	Interactive image
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^N Key:WDPFJWLDPVQCAJ-UHFFFAOYSA-N^N
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