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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
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 0.25 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
656
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
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
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
Page: p.10
healthy, ADULT
n = 24
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: FED
Population Size: 24
Sources:
https://pubmed.ncbi.nlm.nih.gov/26465780
Page: p.10
Sources:
https://pubmed.ncbi.nlm.nih.gov/26465780
Page: p.10
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P003PPF
https://www.1pchem.com/search?query=1P003PPF
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
AOBIOUS INC
AOB87381
http://aobious.com/aobious/search?search_query=AOB87381
Aceschem
ACF022796
https://www.aceschem.com/catalog/search.do?q=ACF022796
Angene
AGN-PC-0RB47J
http://www.angenechemical.com/productshow/AGN-PC-0RB47J.html
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
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
MedChem Express
HY-10521
https://www.medchemexpress.com/search.html?q=HY-10521&ft=&fa=&fp=
MolPort
MolPort-019-996-296
https://www.molport.com/shop/molecule-link/MolPort-019-996-296
Molnova
M14219
https://www.molnova.com/en/serch-list.html?keywords=M14219
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
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
mcule
MCULE-4205270723
https://mcule.com/MCULE-4205270723/
PubMed

PubMed

TitleDatePubMed
Gateways to clinical trials.
2006 Sep
Gateways to clinical trials. July-August 2008.
2008 Jul-Aug
Inhibition of lipoprotein-associated phospholipase A2 reduces complex coronary atherosclerotic plaque development.
2008 Oct
Low and high density lipoprotein--cholesterol and coronary atherothrombosis.
2009
Phospholipase A2 inhibitors in the treatment of atherosclerosis: a new approach moves forward in the clinic.
2009 Oct
Impact of medical therapy on atheroma volume measured by different cardiovascular imaging modalities.
2010
Lp-PLA2: A new target for statin therapy.
2010 Jan
Impact of analyzing less image frames per segment for radiofrequency-based volumetric intravascular ultrasound measurements in mild-to-moderate coronary atherosclerosis.
2010 Jun
Lipoprotein-associated phospholipase A2: role in atherosclerosis and utility as a cardiovascular biomarker.
2010 Mar
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 Sat Dec 16 15:51:33 UTC 2023
Edited
by admin
on Sat Dec 16 15:51:33 UTC 2023
Record UNII
UI1U1MYH09
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DARAPLADIB
INN   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
SB-480848
Code 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 Sat Dec 16 15:51:33 UTC 2023 , Edited by admin on Sat Dec 16 15:51:33 UTC 2023
Code System Code Type Description
FDA UNII
UI1U1MYH09
Created by admin on Sat Dec 16 15:51:33 UTC 2023 , Edited by admin on Sat Dec 16 15:51:33 UTC 2023
PRIMARY
EVMPD
SUB32277
Created by admin on Sat Dec 16 15:51:33 UTC 2023 , Edited by admin on Sat Dec 16 15:51:33 UTC 2023
PRIMARY
MESH
C529040
Created by admin on Sat Dec 16 15:51:33 UTC 2023 , Edited by admin on Sat Dec 16 15:51:33 UTC 2023
PRIMARY
CAS
356057-34-6
Created by admin on Sat Dec 16 15:51:33 UTC 2023 , Edited by admin on Sat Dec 16 15:51:33 UTC 2023
PRIMARY
INN
8703
Created by admin on Sat Dec 16 15:51:33 UTC 2023 , Edited by admin on Sat Dec 16 15:51:33 UTC 2023
PRIMARY
MERCK INDEX
m4094
Created by admin on Sat Dec 16 15:51:33 UTC 2023 , Edited by admin on Sat Dec 16 15:51:33 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
Darapladib
Created by admin on Sat Dec 16 15:51:33 UTC 2023 , Edited by admin on Sat Dec 16 15:51:33 UTC 2023
PRIMARY
USAN
RR-57
Created by admin on Sat Dec 16 15:51:33 UTC 2023 , Edited by admin on Sat Dec 16 15:51:33 UTC 2023
PRIMARY
SMS_ID
100000124361
Created by admin on Sat Dec 16 15:51:33 UTC 2023 , Edited by admin on Sat Dec 16 15:51:33 UTC 2023
PRIMARY
ChEMBL
CHEMBL204021
Created by admin on Sat Dec 16 15:51:33 UTC 2023 , Edited by admin on Sat Dec 16 15:51:33 UTC 2023
PRIMARY
PUBCHEM
9939609
Created by admin on Sat Dec 16 15:51:33 UTC 2023 , Edited by admin on Sat Dec 16 15:51:33 UTC 2023
PRIMARY
NCI_THESAURUS
C72985
Created by admin on Sat Dec 16 15:51:33 UTC 2023 , Edited by admin on Sat Dec 16 15:51:33 UTC 2023
PRIMARY
EPA CompTox
DTXSID70189073
Created by admin on Sat Dec 16 15:51:33 UTC 2023 , Edited by admin on Sat Dec 16 15:51:33 UTC 2023
PRIMARY
DRUG BANK
DB06311
Created by admin on Sat Dec 16 15:51:33 UTC 2023 , Edited by admin on Sat Dec 16 15:51:33 UTC 2023
PRIMARY
Related Record Type Details
PLATELET-ACTIVATING FACTOR ACETYLHYDROLASE
TARGET -> INHIBITOR
SARS-COV2
TARGET ORGANISM->INHIBITOR
Related Record Type Details
Structure of DARAPLADIB
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