GW-501516

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H18F3NO3S2
Molecular Weight	453.498
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=YDBLKRPLXZNVNB-UHFFFAOYSA-N

InChI=1S/C21H18F3NO3S2/c1-12-9-16(7-8-17(12)28-10-19(26)27)29-11-18-13(2)25-20(30-18)14-3-5-15(6-4-14)21(22,23)24/h3-9H,10-11H2,1-2H3,(H,26,27)

HIDE SMILES / InChI

Molecular Formula	C21H18F3NO3S2
Molecular Weight	453.498
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/16625823
Curator's Comment: description was created based on several sources, including: http://adisinsight.springer.com/drugs/800015062 | https://en.wikipedia.org/wiki/GW501516

GW-501516 is a peroxisome proliferator-activator receptor-delta agonist for the potential treatment of dyslipidemia, hyperlipidemia, metabolic diseases and cardiovascular diseases. GW501516 treatment is associated with significant improvements in multiple lipid profile components (TG, LDL-C, HDL-C, free fatty acids and apoB, apoA-I and apoA-II) and a shift in LDL particle size from small dense to larger, less dense particles. Despite these promising early results, the further investigation and development of GW501516 was discontinued after observations in animal studies of its association with the rapid induction of cancers in several organs (liver, stomach, tongue, skin, bladder, ovaries, womb and testes).

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/16625823	Agonist 2678		1.1 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Dyslipidemia 30 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18808307 https://clinicaltrials.gov/ct2/show/NCT00158899	Primary	Phase II 1132	Unknown Approved Use Unknown
Obesity 203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21816786	Primary	Phase IV 63	Unknown Approved Use Unknown
Metabolic syndrome 32 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22814748	Primary	Phase II 1132	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
PPAR delta: an uncompletely known nuclear receptor.	2005 Feb	15803109
Gene expression profiling of potential peroxisome proliferator-activated receptor (PPAR) target genes in human hepatoblastoma cell lines inducibly expressing different PPAR isoforms.	2005 Oct 3	16197558
Ligand activation of peroxisome proliferator-activated receptor-beta/delta inhibits cell proliferation in human HaCaT keratinocytes.	2008 Nov	18687807
Inflammatory pathways are activated during cardiomyocyte hypertrophy and attenuated by peroxisome proliferator-activated receptors PPARalpha and PPARdelta.	2008 Oct 24	18701451
Regulation of peroxisome proliferator-activated receptor-alpha by MDM2.	2009 Mar	19103650
Cross-talk between vitamin D receptor (VDR)- and peroxisome proliferator-activated receptor (PPAR)-signaling in melanoma cells.	2009 Sep	19667161
GW501516, a PPARδ agonist, ameliorates tubulointerstitial inflammation in proteinuric kidney disease via inhibition of TAK1-NFκB pathway in mice.	2011	21966476
Activation of PPARδ prevents endothelial dysfunction induced by overexpression of amyloid-β precursor protein.	2012 Dec 1	22886847
In vitro toxicological characterization of perfluorinated carboxylic acids with different carbon chain lengths.	2013 Apr 12	23391484

Patents

Sample Use Guides

In Vivo Use Guide

12 weeks of treatment with 2.5 mg, 5.0 mg or 5,0 mg, 10 mg

Route of Administration: Oral

In Vitro Use Guide

In 1BR3N human skin fibroblasts, the 1 uM of GW501516 produced a 3.4-fold increase in ABCA1 expression and a 2-fold increase in apoA1-specific cholesterol efflux. In FHS74 human intestinal cells, the 1 uM of GW501516 produced a 2.1-fold increase in ABCA1 expression.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:34:31 GMT 2023` Edited by `admin` on `Fri Dec 15 15:34:31 GMT 2023`
Record UNII	7I2HA1NU22
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GW-501516

Common Name

English

CARDARINE

Common Name

English

GSK-516

Code

English

GW-1516

Code

English

(2-METHYL-4-(((4-METHYL-2-(4-(TRIFLUOROMETHYL)PHENYL)-1,3-THIAZOL-5-YL)METHYL)THIO)PHENOXY)ACETIC ACID

Systematic Name

English

GW501516

Code

English

Classification Tree Code System Code

DSLD

3989 (Number of products:9)