GW-0742

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H17F4NO3S2
Molecular Weight	471.488
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=C(CSC2=CC(C)=C(OCC(O)=O)C=C2)SC(=N1)C3=CC=C(C(F)=C3)C(F)(F)F

InChI

InChIKey=HWVNEWGKWRGSRK-UHFFFAOYSA-N

InChI=1S/C21H17F4NO3S2/c1-11-7-14(4-6-17(11)29-9-19(27)28)30-10-18-12(2)26-20(31-18)13-3-5-15(16(22)8-13)21(23,24)25/h3-8H,9-10H2,1-2H3,(H,27,28)

HIDE SMILES / InChI

Molecular Formula	C21H17F4NO3S2
Molecular Weight	471.488
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12699745 | https://www.ncbi.nlm.nih.gov/pubmed/25592770
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26508837 | https://www.ncbi.nlm.nih.gov/pubmed/21270242

GW0742, also known as GW610742, is a potent and highly selective PPARβ/δ agonist, with IC50 of 1 nM, with 1000-fold selectivity over hPPARα and hPPARγ. GW0742 treatment has a prominent anti-inflammatory effect in 5XFAD mice and suggests that PPARδ agonists may have therapeutic utility in treating AD. GW0742 has the ability to improve glucose homeostasis in diabetic rats through activation of PPAR-δ. Therefore, PPAR-δ is a good target for the development of antidiabetic drugs in the future.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Peroxisome proliferator-activated receptor delta 29 Target ID: CHEMBL3979 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12699745	Agonist 2678		1.0 nM [EC50]

Conditions

Condition	Modality	Highest Phase	Product
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25592770 https://www.ncbi.nlm.nih.gov/pubmed/26864581 http://adisinsight.springer.com/drugs/800019062	Primary	Preclinical	Unknown Approved Use Unknown
Diabetes mellitus 91 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26508837 http://adisinsight.springer.com/drugs/800019062 https://www.ncbi.nlm.nih.gov/pubmed/22683600 https://www.ncbi.nlm.nih.gov/pubmed/22464549	Primary	Preclinical	Unknown Approved Use Unknown
Lipid metabolism disorders 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18627005 http://adisinsight.springer.com/drugs/800019062 https://www.ncbi.nlm.nih.gov/pubmed/23803968 https://www.ncbi.nlm.nih.gov/pubmed/22824914	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Novel selective small molecule agonists for peroxisome proliferator-activated receptor delta (PPARdelta)--synthesis and biological activity.	2003 May 5	12699745
Development of PPAR-agonist GW0742 as antidiabetic drug: study in animals.	2015	26508837
Activation of the nuclear receptor PPARδ is neuroprotective in a transgenic mouse model of Alzheimer's disease through inhibition of inflammation.	2015 Jan 16	25592770
PPARδ agonist GW0742 ameliorates Aβ1-42-induced hippocampal neurotoxicity in mice.	2016 Jun	26864581

Patents

Sample Use Guides

In Vivo Use Guide

Mice: GW0742 (30 mg/kg) significantly decreases protein and mRNA levels of the pro-inflammatory cytokines IL-6, IL-1beta and TNFalpha in bronchial alveolar lavage fluid of mice.

Route of Administration: Oral

In Vitro Use Guide

GW0742 (0.2 uM and 1 uM) treatment results in significant increases in reporter activity of PPARβ/δ in N/TERT-1 keratinocytes. GW0742 (1 uM) results in significant inhibition in the average number of N/TERT-1 keratinocytes. GW0742 (1 uM) results in an increase in the number of cells in the G1 phase and a decrease in the number of cells in the S phase.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 09:41:11 GMT 2023` Edited by `admin` on `Sat Dec 16 09:41:11 GMT 2023`
Record UNII	4PZK9FJC4Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GW-0742

Common Name

English

GW0742

Common Name

English

(4-(((2-(3-FLUORO-4-(TRIFLUOROMETHYL)PHENYL)-4-METHYL-1,3-THIAZOL-5-YL)METHYL)SULFANYL)-2-METHYLPHENOXY)ACETIC ACID

Systematic Name

English

Code System Code Type Description

WIKIPEDIA

GW0742