U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C36H38F4N4O2S
Molecular Weight 666.771
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DARAPLADIB

SMILES

CCN(CC)CCN(CC1=CC=C(C=C1)C2=CC=C(C=C2)C(F)(F)F)C(=O)CN3C4=C(CCC4)C(=O)N=C3SCC5=CC=C(F)C=C5

InChI

InChIKey=WDPFJWLDPVQCAJ-UHFFFAOYSA-N
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

HIDE SMILES / InChI
Molecular Formula C36H38F4N4O2S
Molecular Weight 666.771
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including http://www.fiercebiotech.com/r-d/updated-glaxosmithkline-loses-its-first-big-phiii-bet-on-heart-drug-darapladib

Darapladib (SB-435495), as reversible inhibitors of lipoprotein-associated phospholipase A(2) (Lp-PLA(2) has been developed and studies for the potential treatment of atherosclerosis. 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.

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 0.25 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
665
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
17.9 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26465780
160 mg single, oral
dose: 160 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DARAPLADIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
34.4 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26465780
160 mg 1 times / day multiple, oral
dose: 160 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DARAPLADIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
645 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26465780
160 mg single, oral
dose: 160 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DARAPLADIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
519 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26465780
160 mg 1 times / day multiple, oral
dose: 160 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DARAPLADIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
39.2 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26465780
160 mg single, oral
dose: 160 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DARAPLADIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
116 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26465780
160 mg 1 times / day multiple, oral
dose: 160 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DARAPLADIB plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
Doses

Doses

DosePopulationAdverse events​
160 mg 1 times / day multiple, oral
Studied dose
Dose: 160 mg, 1 times / day
Route: oral
Route: multiple
Dose: 160 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/26465780
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
https://pubmed.ncbi.nlm.nih.gov/26465780
Sources:
https://pubmed.ncbi.nlm.nih.gov/26465780
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P003PPF
https://www.1pchem.com/search?query=1P003PPF
Aceschem
ACF022796
https://www.aceschem.com/catalog/search.do?q=ACF022796
AChemBlock
C-2941
http://www.achemblock.com/catalogsearch/result/?q=C-2941
AK Scientific
SYN5724
https://aksci.com/item_detail.php?cat=SYN5724
AK Scientific
X5943
https://aksci.com/item_detail.php?cat=X5943
Angene
AGN-PC-0RB47J
http://www.angenechemical.com/productshow/AGN-PC-0RB47J.html
AOBIOUS INC
AOB87381
http://aobious.com/aobious/search?search_query=AOB87381
ApexBio Technology
A3349
https://www.apexbt.com/catalogsearch/result/?q=A3349
AstaTech
FD5008
http://astatechinc.com/CPSResult.php?CRNO=FD5008
BLD Pharm
BD301648
http://www.bldpharm.com/search/Search.html?keyword=BD301648
BOC Sciences
356057-34-6
http://www.bocsci.com/description.asp?cas=356057-34-6
Cayman Chemical
16429
http://www.caymanchem.com/app/template/Product.vm/catalog/16429
Chem Scene
CS-1035
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-1035
ChemShuttle
113947
https://www.chemshuttle.com/catalogsearch/result/?q=113947
Combi-Blocks
QM-5328
http://www.combi-blocks.com/cgi-bin/find.cgi?QM-5328
eMolecules
43367244
https://orderbb.emolecules.com/search/#?query=43367244
eNovation Chemicals
D498184
https://www.enovationchem.com/Products.asp?SEARCHTEXT=D498184&searchbtn.x=0&searchbtn.y=0
Excenen
EX-A2245
http://www.excenen.com/searchresultlist.php?id=EX-A2245
KeyOrganics
AS-17025
http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-17025
Lab Seeker
SC-94293
http://www.labseeker.com/search.php?keywords=SC-94293&category=0
LabSeeker
SC-94293
http://www.labseeker.com/search.php?keywords=SC-94293&category=0
Matrix Scientific
147917
http://www.matrixscientific.com/147917.html
mcule
MCULE-4205270723
https://mcule.com/MCULE-4205270723/
MedChem Express
HY-10521
https://www.medchemexpress.com/search.html?q=HY-10521&ft=&fa=&fp=
Molnova
M14219
https://www.molnova.com/en/serch-list.html?keywords=M14219
MolPort
MolPort-019-996-296
https://www.molport.com/shop/molecule-link/MolPort-019-996-296
MuseChem
I003299
https://www.musechem.com/product/I003299.html
Selleck Chemicals
S7520
http://www.selleckchem.com/search.html?searchDTO.searchParam=S7520
ShangHai Biochempartner
BCP000587
http://www.biochempartner.com/search_BCP000587
ShangHai Biochempartner
BCP04908
http://www.biochempartner.com/search_BCP04908
Synthonix
1602
https://synthonix.com/catalogsearch/result/?q=1602
TargetMol
T6109
https://www.targetmol.com/search?keyword=T6109
Tetrahedron
TS90555
http://www.thsci.com/search.do?q=TS90555
PubMed

PubMed

TitleDatePubMed
Phospholipase A2 inhibition and atherosclerotic vascular disease: prospects for targeting secretory and lipoprotein-associated phospholipase A2 enzymes.
2010-12
Study design and rationale for the clinical outcomes of the STABILITY Trial (STabilization of Atherosclerotic plaque By Initiation of darapLadIb TherapY) comparing darapladib versus placebo in patients with coronary heart disease.
2010-10
Phospholipase A2s: developing drug targets for atherosclerosis.
2010-10
Darapladib: an emerging therapy for atherosclerosis.
2010-08
Trial watch: a boost for GSK's first-in-class heart drug?
2010-07
Editorial: why inhibition of lipoprotein-associated phospholipase A2 has the potential to improve patient outcomes.
2010-07
Association of carotid plaque Lp-PLA(2) with macrophages and Chlamydia pneumoniae infection among patients at risk for stroke.
2010-06-09
Impact of analyzing less image frames per segment for radiofrequency-based volumetric intravascular ultrasound measurements in mild-to-moderate coronary atherosclerosis.
2010-06
Extracellular phospholipases in atherosclerosis.
2010-06
Lipoprotein-associated phospholipase A(2) and risk of coronary disease, stroke, and mortality: collaborative analysis of 32 prospective studies.
2010-05-01
Lipoprotein-associated phospholipase A2 activity and incident coronary heart disease among men and women with type 2 diabetes.
2010-05
A new method to measure necrotic core and calcium content in coronary plaques using intravascular ultrasound radiofrequency-based analysis.
2010-04
Lipoprotein-associated phospholipase A2: a new therapeutic target.
2010-03
Lipoprotein-associated phospholipase A2: role in atherosclerosis and utility as a cardiovascular biomarker.
2010-03
Lp-PLA2: A new target for statin therapy.
2010-01
Darapladib.
2010-01
Impact of medical therapy on atheroma volume measured by different cardiovascular imaging modalities.
2010
Darapladib, a reversible lipoprotein-associated phospholipase A2 inhibitor, for the oral treatment of atherosclerosis and coronary artery disease.
2009-10
Phospholipase A2 inhibitors in the treatment of atherosclerosis: a new approach moves forward in the clinic.
2009-10
Lipoprotein-associated phospholipase A(2) and atherosclerosis.
2009-10
Darapladib and atherosclerotic plaque: should lipoprotein-associated phospholipase A2 be a therapeutic target?
2009-09
Update on patented cholesterol absorption inhibitors.
2009-08
Phospholipase A2 inhibitors.
2009-08
Lipoprotein-associated phospholipase A2 as a biomarker of coronary heart disease and a therapeutic target.
2009-07
Phospholipase A2 inhibitors in atherosclerosis: the race is on.
2009-02-21
Low and high density lipoprotein--cholesterol and coronary atherothrombosis.
2009
Gateways to clinical trials. July-August 2008.
2008-10-14
Inhibition of lipoprotein-associated phospholipase A2 reduces complex coronary atherosclerotic plaque development.
2008-10
Inhibition of lipoprotein-associated phospholipase activity by darapladib: shifting gears in cardiovascular drug development: are antiinflammatory drugs the next frontier?
2008-09-09
Effects of the direct lipoprotein-associated phospholipase A(2) inhibitor darapladib on human coronary atherosclerotic plaque.
2008-09-09
The effect of darapladib on plasma lipoprotein-associated phospholipase A2 activity and cardiovascular biomarkers in patients with stable coronary heart disease or coronary heart disease risk equivalent: the results of a multicenter, randomized, double-blind, placebo-controlled study.
2008-04-29
Gateways to clinical trials.
2008-04
Gateways to clinical trials.
2006-09
The identification of clinical candidate SB-480848: a potent inhibitor of lipoprotein-associated phospholipase A2.
2003-03-24
Patents

Patents

WO2015114479 A1
1

Sample Use Guides

In Vivo Use Guide
Single daily oral tablet
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Wed Apr 02 06:53:05 GMT 2025
Edited
by admin
on Wed Apr 02 06:53:05 GMT 2025
Record UNII
UI1U1MYH09
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SB-480848
Preferred Name English
DARAPLADIB
INN   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
Darapladib [WHO-DD]
Common Name English
N-(2-(DIETHYLAMINO)ETHYL)-2-(2-(4-FLUOROBENZYLSULPHANYL)-4-OXO-4,5,6,7-TETRAHYDROCYCLOPENTAPYRIMIDIN-1-YL)-N-(4'-TRIFLUOROMETHYLBIPHENYL-4-YLMETHYL)ACETAMIDE
Systematic Name English
DARAPLADIB [USAN]
Common Name English
1H-CYCLOPENTAPYRIMIDINE-1-ACETAMIDE, N-(2-(DIETHYLAMINO)ETHYL)-2-(((4-FLUOROPHENYL)METHYL)THIO)-4,5,6,7-TETRAHYDRO-4-OXO-N-((4'-(TRIFLUOROMETHYL)(1,1'-BIPHENYL)-4-YL)METHYL)-
Systematic Name English
DARAPLADIB [MI]
Common Name English
darapladib [INN]
Common Name English
DARAPLADIB [JAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29703
Created by admin on Wed Apr 02 06:53:05 GMT 2025 , Edited by admin on Wed Apr 02 06:53:05 GMT 2025
Code System Code Type Description
FDA UNII
UI1U1MYH09
Created by admin on Wed Apr 02 06:53:05 GMT 2025 , Edited by admin on Wed Apr 02 06:53:05 GMT 2025
PRIMARY
EVMPD
SUB32277
Created by admin on Wed Apr 02 06:53:05 GMT 2025 , Edited by admin on Wed Apr 02 06:53:05 GMT 2025
PRIMARY
MESH
C529040
Created by admin on Wed Apr 02 06:53:05 GMT 2025 , Edited by admin on Wed Apr 02 06:53:05 GMT 2025
PRIMARY
CAS
356057-34-6
Created by admin on Wed Apr 02 06:53:05 GMT 2025 , Edited by admin on Wed Apr 02 06:53:05 GMT 2025
PRIMARY
INN
8703
Created by admin on Wed Apr 02 06:53:05 GMT 2025 , Edited by admin on Wed Apr 02 06:53:05 GMT 2025
PRIMARY
MERCK INDEX
m4094
Created by admin on Wed Apr 02 06:53:05 GMT 2025 , Edited by admin on Wed Apr 02 06:53:05 GMT 2025
PRIMARY Merck Index
WIKIPEDIA
Darapladib
Created by admin on Wed Apr 02 06:53:05 GMT 2025 , Edited by admin on Wed Apr 02 06:53:05 GMT 2025
PRIMARY
USAN
RR-57
Created by admin on Wed Apr 02 06:53:05 GMT 2025 , Edited by admin on Wed Apr 02 06:53:05 GMT 2025
PRIMARY
SMS_ID
100000124361
Created by admin on Wed Apr 02 06:53:05 GMT 2025 , Edited by admin on Wed Apr 02 06:53:05 GMT 2025
PRIMARY
ChEMBL
CHEMBL204021
Created by admin on Wed Apr 02 06:53:05 GMT 2025 , Edited by admin on Wed Apr 02 06:53:05 GMT 2025
PRIMARY
PUBCHEM
9939609
Created by admin on Wed Apr 02 06:53:05 GMT 2025 , Edited by admin on Wed Apr 02 06:53:05 GMT 2025
PRIMARY
NCI_THESAURUS
C72985
Created by admin on Wed Apr 02 06:53:05 GMT 2025 , Edited by admin on Wed Apr 02 06:53:05 GMT 2025
PRIMARY
EPA CompTox
DTXSID70189073
Created by admin on Wed Apr 02 06:53:05 GMT 2025 , Edited by admin on Wed Apr 02 06:53:05 GMT 2025
PRIMARY
DRUG BANK
DB06311
Created by admin on Wed Apr 02 06:53:05 GMT 2025 , Edited by admin on Wed Apr 02 06:53:05 GMT 2025
PRIMARY
Related Record Type Details
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TARGET -> INHIBITOR
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TARGET ORGANISM->INHIBITOR
Related Record Type Details
Structure of DARAPLADIB
ACTIVE MOIETY
NIH
NCATS
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