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Details

Stereochemistry ACHIRAL
Molecular Formula C29H46N2O3S
Molecular Weight 502.752
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GW-7647

SMILES

CC(C)(SC1=CC=C(CCN(CCCCC2CCCCC2)C(=O)NC3CCCCC3)C=C1)C(O)=O

InChI

InChIKey=PKNYXWMTHFMHKD-UHFFFAOYSA-N
InChI=1S/C29H46N2O3S/c1-29(2,27(32)33)35-26-18-16-24(17-19-26)20-22-31(28(34)30-25-14-7-4-8-15-25)21-10-9-13-23-11-5-3-6-12-23/h16-19,23,25H,3-15,20-22H2,1-2H3,(H,30,34)(H,32,33)

HIDE SMILES / InChI

Molecular Formula C29H46N2O3S
Molecular Weight 502.752
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 https://www.ncbi.nlm.nih.gov/pubmed/14557369

GW7647 is a potent and highly selective PPARα agonist (EC50 values are 6, 1100 and 6200 nM for human PPARα, PPARγ and PPARδ receptors respectively). GW7647 has being shown to protect the heart from ischemia/reperfusion injury in mouse model. GW7647 attenuated ischemia/reperfusion-induced release of multiple proinflammatory cytokines and inhibited neutrophil accumulation and myocardial expression of matrix metalloproteinases-9 and -2. Furthermore, GW7647 inhibited nuclear factor-kappaB activation in the heart, accompanied by enhanced levels of inhibitor-kappaBalpha.

CNS Activity

Curator's Comment: GW 7647 reduced nocifensive behaviors elicited in mice by intraplantar (i.pl.) injection of formalin or i.p. injection of magnesium sulfate.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
6.0 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Peroxisome proliferator-activated receptor-alpha regulates fatty acid utilization in primary human skeletal muscle cells.
2002 Apr
Activation of peroxisome proliferator-activated receptor-alpha protects the heart from ischemia/reperfusion injury.
2003 Nov 11
Patents

Sample Use Guides

Mice: GW7647, was administered by mouth for 2 days, and the third dose was given 1 hour before ischemia. GW7647 at 1 and 3 mg x kg(-1) x d(-1) reduced infarct size by 28% and 35%, respectively
Route of Administration: Oral
In mature human myotubes, 48-h treatment with 10-1,000 nmol/l GW7647 increased oleate oxidation dose-dependently, up to threefold.
Substance Class Chemical
Created
by admin
on Sat Dec 16 18:52:39 GMT 2023
Edited
by admin
on Sat Dec 16 18:52:39 GMT 2023
Record UNII
NTL2A9CAZ7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GW-7647
Code English
GW7647
Code English
PROPANOIC ACID, 2-((4-(2-(((CYCLOHEXYLAMINO)CARBONYL)(4-CYCLOHEXYLBUTYL)AMINO)ETHYL)PHENYL)THIO)-2-METHYL-
Systematic Name English
GW-7647X
Code English
2-(4-(2-(1-CYCLOHEXANEBUTYL)-3-CYCLOHEXYLUREIDO)ETHYL) PHENYL THIO)-2-METHYL PROPIONIC ACID
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID1040748
Created by admin on Sat Dec 16 18:52:39 GMT 2023 , Edited by admin on Sat Dec 16 18:52:39 GMT 2023
PRIMARY
CAS
265129-71-3
Created by admin on Sat Dec 16 18:52:39 GMT 2023 , Edited by admin on Sat Dec 16 18:52:39 GMT 2023
PRIMARY
PUBCHEM
3392731
Created by admin on Sat Dec 16 18:52:39 GMT 2023 , Edited by admin on Sat Dec 16 18:52:39 GMT 2023
PRIMARY
FDA UNII
NTL2A9CAZ7
Created by admin on Sat Dec 16 18:52:39 GMT 2023 , Edited by admin on Sat Dec 16 18:52:39 GMT 2023
PRIMARY