GW-9508

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H21NO3
Molecular Weight	347.407
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)CCC1=CC=C(NCC2=CC=CC(OC3=CC=CC=C3)=C2)C=C1

InChI

InChIKey=DGENZVKCTGIDRZ-UHFFFAOYSA-N

InChI=1S/C22H21NO3/c24-22(25)14-11-17-9-12-19(13-10-17)23-16-18-5-4-8-21(15-18)26-20-6-2-1-3-7-20/h1-10,12-13,15,23H,11,14,16H2,(H,24,25)

HIDE SMILES / InChI

Molecular Formula	C22H21NO3
Molecular Weight	347.407
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/16702987
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24758921 | https://www.ncbi.nlm.nih.gov/pubmed/21593768 | https://www.ncbi.nlm.nih.gov/pubmed/24349089 | https://www.ncbi.nlm.nih.gov/pubmed/23341496

GW-9508 is a small-molecule agonist of the fatty acid receptors GPR40 and GPR120. GW-9508 exerts wide-range activity in animal models: anti-depressant, anti-inflammatory, anti-diabetic and analgetic actions.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Free fatty acid receptor 1 11 Target ID: CHEMBL4422 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16702987	Agonist 2752		7.32 null [pEC50]
G-protein coupled receptor 120 1 Target ID: CHEMBL5339 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16702987	Agonist 2752		5.46 null [pEC50]

Conditions

Condition	Modality	Highest Phase	Product
Depression 240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24758921	Primary	Basic research	Unknown Approved Use Unknown
Inflammation 105 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21593768	Primary	Basic research	Unknown Approved Use Unknown
Pain 619 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24349089 https://www.ncbi.nlm.nih.gov/pubmed/22137657	Primary	Basic research	Unknown Approved Use Unknown
Diabetes mellitus 93 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23341496	Primary	Basic research	Unknown Approved Use Unknown
Alzheimer’s disease 278 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26976092	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Involvement of the long-chain fatty acid receptor GPR40 in depression-related behavior.	2014	24758921
Discovery of TUG-770: A Highly Potent Free Fatty Acid Receptor 1 (FFA1/GPR40) Agonist for Treatment of Type 2 Diabetes.	2013-05-09	23687558
Activation of FFA1 mediates GLP-1 secretion in mice. Evidence for allosterism at FFA1.	2013-04-30	23403053
Hypothalamic GPR40 signaling activated by free long chain fatty acids suppresses CFA-induced inflammatory chronic pain.	2013	24349089
Identification and pharmacological characterization of multiple allosteric binding sites on the free fatty acid 1 receptor.	2012-11	22859723
Free fatty acid receptors and drug discovery.	2008-10	18827341
Uncovering the pharmacology of the G protein-coupled receptor GPR40: high apparent constitutive activity in guanosine 5'-O-(3-[35S]thio)triphosphate binding studies reflects binding of an endogenous agonist.	2007-04	17200419
Pharmacological regulation of insulin secretion in MIN6 cells through the fatty acid receptor GPR40: identification of agonist and antagonist small molecules.	2006-07	16702987

Patents

Sample Use Guides

In Vivo Use Guide

mice: 30-100 uM GW9508 topically to the skin in the challenging phase suppressed ear swelling in a repeated hapten application model and contact hypersensitivity with downregulation of CCL5 and CXCL10, respectively. mice: 50 mg/kg ip GW-9508 enhanced glucose-induced plasma insulin levels significantly and thus decreased glucose injection-induced hyperglycemia. mice: 1 ug icv GW-9508 for 5 days may regulate depression-related behavior.

Route of Administration: Other

In Vitro Use Guide

GW9508 (10-40 μM) did not influence basal insulin levels at 2 mM glucose, but it (above 20 μM) significantly inhibited 5 and 15 mM glucose-stimulated insulin secretion in rat islet β-cells

Substance Class	Chemical Created by `admin` on `Mon Mar 31 23:24:35 GMT 2025` Edited by `admin` on `Mon Mar 31 23:24:35 GMT 2025`
Record UNII	4T77GYP2CS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BENZENEPROPANOIC ACID, 4-(((3-PHENOXYPHENYL)METHYL)AMINO)-

Preferred Name

English

GW-9508

Common Name

English

Code System Code Type Description

CAS

885101-89-3

Created by admin on Mon Mar 31 23:24:35 GMT 2025 , Edited by admin on Mon Mar 31 23:24:35 GMT 2025

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FDA UNII

4T77GYP2CS

Created by admin on Mon Mar 31 23:24:35 GMT 2025 , Edited by admin on Mon Mar 31 23:24:35 GMT 2025

PRIMARY

EPA CompTox

DTXSID70237088

Created by admin on Mon Mar 31 23:24:35 GMT 2025 , Edited by admin on Mon Mar 31 23:24:35 GMT 2025

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PUBCHEM

11595431

Created by admin on Mon Mar 31 23:24:35 GMT 2025 , Edited by admin on Mon Mar 31 23:24:35 GMT 2025

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					4T77GYP2CS

GW-9508

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CNS Activity

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PubMed

Patents

Sample Use Guides