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 10 Target ID: CHEMBL4422 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16702987	Agonist 2678		7.32 null [pEC50]
G-protein coupled receptor 120 1 Target ID: CHEMBL5339 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16702987	Agonist 2678		5.46 null [pEC50]

Conditions

Condition	Modality	Highest Phase	Product
Depression 235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24758921	Primary	Basic research	Unknown Approved Use Unknown
Inflammation 102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21593768	Primary	Basic research	Unknown Approved Use Unknown
Pain 614 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 91 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23341496	Primary	Basic research	Unknown Approved Use Unknown
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26976092	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
		252160653
Pharmacological regulation of insulin secretion in MIN6 cells through the fatty acid receptor GPR40: identification of agonist and antagonist small molecules.	2006 Jul	16702987
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 Apr	17200419
Free fatty acid receptors and drug discovery.	2008 Oct	18827341
Identification and pharmacological characterization of multiple allosteric binding sites on the free fatty acid 1 receptor.	2012 Nov	22859723
Hypothalamic GPR40 signaling activated by free long chain fatty acids suppresses CFA-induced inflammatory chronic pain.	2013	24349089
Activation of FFA1 mediates GLP-1 secretion in mice. Evidence for allosterism at FFA1.	2013 Apr 30	23403053
Discovery of TUG-770: A Highly Potent Free Fatty Acid Receptor 1 (FFA1/GPR40) Agonist for Treatment of Type 2 Diabetes.	2013 May 9	23687558
Involvement of the long-chain fatty acid receptor GPR40 in depression-related behavior.	2014	24758921

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 `Sat Dec 16 10:44:08 GMT 2023` Edited by `admin` on `Sat Dec 16 10:44:08 GMT 2023`
Record UNII	4T77GYP2CS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GW-9508

Common Name

English

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

Systematic Name

English

Code System Code Type Description

CAS

885101-89-3

Created by admin on Sat Dec 16 10:44:08 GMT 2023 , Edited by admin on Sat Dec 16 10:44:08 GMT 2023

PRIMARY

FDA UNII

4T77GYP2CS

Created by admin on Sat Dec 16 10:44:08 GMT 2023 , Edited by admin on Sat Dec 16 10:44:08 GMT 2023

PRIMARY

EPA CompTox

DTXSID70237088

Created by admin on Sat Dec 16 10:44:08 GMT 2023 , Edited by admin on Sat Dec 16 10:44:08 GMT 2023

PRIMARY

PUBCHEM

11595431

Created by admin on Sat Dec 16 10:44:08 GMT 2023 , Edited by admin on Sat Dec 16 10:44:08 GMT 2023

PRIMARY

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					4T77GYP2CS

GW-9508

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PubMed

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Sample Use Guides