Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C21H18F3NO3S2 |
| Molecular Weight | 453.5007 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cc1cc(ccc1OCC(=O)O)SCc2c(C)nc(-c3ccc(cc3)C(F)(F)F)s2
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)
| Molecular Formula | C21H18F3NO3S2 |
| Molecular Weight | 453.5007 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment:: description was created based on several sources, including:
http://adisinsight.springer.com/drugs/800015062 | https://en.wikipedia.org/wiki/GW501516
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).
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| A selective peroxisome proliferator-activated receptor delta agonist promotes reverse cholesterol transport. | 2001 Apr 24 |
|
| PPAR delta: an uncompletely known nuclear receptor. | 2005 Feb |
|
| Nanomolar and micromolar effects of 15-deoxy-delta 12,14-prostaglandin J2 on amnion-derived WISH epithelial cells: differential roles of peroxisome proliferator-activated receptors gamma and delta and nuclear factor kappa B. | 2005 Jul |
|
| Rosiglitazone induces interleukin-1 receptor antagonist in interleukin-1beta-stimulated rat synovial fibroblasts via a peroxisome proliferator-activated receptor beta/delta-dependent mechanism. | 2005 Mar |
|
| Statins and PPARalpha agonists induce myotoxicity in differentiated rat skeletal muscle cultures but do not exhibit synergy with co-treatment. | 2005 Nov 1 |
|
| 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 |
|
| Effects of bezafibrate, PPAR pan-agonist, and GW501516, PPARdelta agonist, on development of steatohepatitis in mice fed a methionine- and choline-deficient diet. | 2006 Apr 24 |
|
| Niacin induces PPARgamma expression and transcriptional activation in macrophages via HM74 and HM74a-mediated induction of prostaglandin synthesis pathways. | 2006 Feb 28 |
|
| Role of AMP kinase and PPARdelta in the regulation of lipid and glucose metabolism in human skeletal muscle. | 2007 Jul 6 |
|
| Indomethacin induces apoptosis in 786-O renal cell carcinoma cells by activating mitogen-activated protein kinases and AKT. | 2007 Jun 1 |
|
| PPARdelta, but not PPARalpha, activates PGC-1alpha gene transcription in muscle. | 2007 Mar 23 |
|
| The PPARdelta agonist, GW501516, promotes fatty acid oxidation but has no direct effect on glucose utilisation or insulin sensitivity in rat L6 skeletal muscle cells. | 2007 Oct 2 |
|
| In vivo imaging reveals selective peroxisome proliferator activated receptor modulator activity of the synthetic ligand 3-(1-(4-chlorobenzyl)-3-t-butylthio-5-isopropylindol-2-yl)-2,2-dimethylpropanoic acid (MK-886). | 2008 May |
|
| Ligand activation of peroxisome proliferator-activated receptor-beta/delta inhibits cell proliferation in human HaCaT keratinocytes. | 2008 Nov |
|
| Inflammatory pathways are activated during cardiomyocyte hypertrophy and attenuated by peroxisome proliferator-activated receptors PPARalpha and PPARdelta. | 2008 Oct 24 |
|
| On the mechanism for PPAR agonists to enhance ABCA1 gene expression. | 2009 Aug |
|
| Regulation of peroxisome proliferator-activated receptor-alpha by MDM2. | 2009 Mar |
|
| Cross-talk between vitamin D receptor (VDR)- and peroxisome proliferator-activated receptor (PPAR)-signaling in melanoma cells. | 2009 Sep |
|
| Rosiglitazone activation of PPARgamma suppresses fractalkine signaling. | 2010 Feb |
|
| Synthesis of isosteric selenium analog of the PPARbeta/delta agonist GW501516 and comparison of biological activity. | 2010 Jul 15 |
|
| Peroxisome proliferator-activated receptor delta regulation of miR-15a in ischemia-induced cerebral vascular endothelial injury. | 2010 May 5 |
|
| Cellular and pharmacological selectivity of the peroxisome proliferator-activated receptor-beta/delta antagonist GSK3787. | 2010 Sep |
|
| GW501516, a PPARδ agonist, ameliorates tubulointerstitial inflammation in proteinuric kidney disease via inhibition of TAK1-NFκB pathway in mice. | 2011 |
|
| Dual acting and pan-PPAR activators as potential anti-diabetic therapies. | 2011 |
|
| Functional characterization of peroxisome proliferator-activated receptor-β/δ expression in colon cancer. | 2011 Nov |
|
| A cardiac-specific robotized cellular assay identified families of human ligands as inducers of PGC-1α expression and mitochondrial biogenesis. | 2012 |
|
| Activation of PPARδ prevents endothelial dysfunction induced by overexpression of amyloid-β precursor protein. | 2012 Dec 1 |
|
| Role of Peroxisome Proliferator-Activated Receptor β/δ and B-Cell Lymphoma-6 in Regulation of Genes Involved in Metastasis and Migration in Pancreatic Cancer Cells. | 2013 |
|
| In vitro toxicological characterization of perfluorinated carboxylic acids with different carbon chain lengths. | 2013 Apr 12 |
|
| Phthalates efficiently bind to human peroxisome proliferator activated receptor and retinoid X receptor α, β, γ subtypes: an in silico approach. | 2014 Jul |
Patents
Sample Use Guides
12 weeks of treatment with 2.5 mg, 5.0 mg or 5,0 mg, 10 mg
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 23:39:46 UTC 2021
by
admin
on
Fri Jun 25 23:39:46 UTC 2021
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| Record UNII |
7I2HA1NU22
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| Record Status |
Validated (UNII)
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| Record Version |
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3989 (Number of products:9)
Created by
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DSLD |
3986 (Number of products:12)
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admin on Fri Jun 25 23:39:46 UTC 2021 , Edited by admin on Fri Jun 25 23:39:46 UTC 2021
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| Code System | Code | Type | Description | ||
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7I2HA1NU22
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GW501516
Created by
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9803963
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DB05416
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317318-70-0
Created by
admin on Fri Jun 25 23:39:46 UTC 2021 , Edited by admin on Fri Jun 25 23:39:46 UTC 2021
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| Related Record | Type | Details | ||
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TARGET -> AGONIST |
| Related Record | Type | Details | ||
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ACTIVE MOIETY |
