GW 501516

  • CAT Number: I003133
  • CAS Number: 317318-70-0
  • Molecular Formula: C21H18F3NO3S2
  • Molecular Weight: 453.5
  • Purity: ≥95%
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GW501516 (Cat No.: I003133), also known as Endurobol or GSK-516, is a PPARδ receptor agonist with an EC50 value of 1.1 nM.

Catalog Number I003133
CAS Number 317318-70-0
Synonyms

GW501516; GW-501516; GW 501516; GW1516; GW 1516; GW-1516; GSK-516; GSK 516; GSK516; Endurobol.

Molecular Formula

C21H18F3NO3S2

Purity 95%
Target PPAR
Solubility 10 mM in DMSO
Storage Store at -20°C
Overview of Clinical Research

<span style=”color:#000000;”><span style=”font-family:arial,helvetica,sans-serif;”><span style=”font-size:12px;”>GW501516 is p<span style=”font-variant-ligatures: normal; orphans: 2; widows: 2;”>eroxisome proliferator-activated receptor delta agonist. The&nbsp;</span><span style=”font-variant-ligatures: normal; orphans: 2; widows: 2;”>Phase-II clinical trials in Hyperlipidaemia in USA started in 2003.</span></span></span></span>

IC50 1 nM(EC50)
IUPAC Name 2-[2-methyl-4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid
InChI 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)
InChIKey YDBLKRPLXZNVNB-UHFFFAOYSA-N
SMILES OC(COC1=CC=C(SCC2=C(C)N=C(C3=CC=C(C(F)(F)F)C=C3)S2)C=C1C)=O
Reference

1. Bioorg Med Chem. 2011 Dec 1;19(23):6982-8. doi: 10.1016/j.bmc.2011.10.020. Epub 2011 Oct 17.<br />
Synthesis, molecular modeling studies and biological evaluation of fluorine substituted analogs of GW 501516.<br />
Ciocoiu CC(1), Ravna AW, Sylte I, Rustan AC, Hansen TV.<br />
Author information:<br />
(1)School of Pharmacy, Department of Pharmaceutical Chemistry, University of Oslo, PO BOX 1068, Blindern, N-0316 Oslo, Norway.<br />
(&plusmn;)-2-Fluoro-2-(2-methyl-4-(((4-methyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl) methyl)thio)phenoxy)acetic acid (2a) has been prepared and subjected to biological testing against all three subtypes of the PPARs. This compound exhibited agonist effects with EC(50) values of 560 and 55 nM against PPAR&alpha; and PPAR&delta;, respectively, in a luciferase assay. Moreover, compound (&plusmn;)-2a also exhibited potent ability to induce oleic acid oxidation in a human myotube cell assay with EC(50)=3.7 nM. Compound (&plusmn;)-2a can be classified as a dual PPAR&alpha;/&delta; agonist with a 10-fold higher potency against the PPAR&delta; receptor than against the PPAR&alpha; receptor. Molecular modeling studies revealed that both enantiomers of 2a bind to the PPAR&delta; receptor with similar binding energies.<br />
2. Am J Physiol Endocrinol Metab. 2006 Apr;290(4):E607-11. Epub 2005 Nov 8.<br />
PPARdelta activator GW-501516 has no acute effect on glucose transport in skeletal muscle.<br />
Terada S(1), Wicke S, Holloszy JO, Han DH.<br />
Author information:<br />
(1)Division of Geriatrics and Nutritional Sciences, Department of Medicine, Washington University School of Medicine, St. Louis, Missouri 63110, USA.<br />
It has been reported that treatment of cultured human skeletal muscle myotubes with the peroxisome proliferator-activated receptor-delta (PPARdelta) activator GW-501516 directly stimulates glucose transport and enhances insulin action. Cultured myotubes are minimally responsive to insulin stimulation of glucose transport and are not a good model for studying skeletal muscle glucose transport. The purpose of this study was to evaluate the effect of GW-501516 on glucose transport to determine whether the findings on cultured myotubes have relevance to skeletal muscle. Rat epitrochlearis and soleus muscles were treated for 6 h with 10, 100, or 500 nM GW-501516, followed by measurement of 2-deoxyglucose uptake. GW-501516 had no effect on glucose uptake. There was no effect on insulin sensitivity or responsiveness. Also, in contrast to findings on myotubes, treatment of muscles with GW-501516 did not result in increased phosphorylation or increased expression of AMP-activated protein kinase (AMPK) or p38 mitogen-activated protein kinase (MAPK). Treatment of epitrochlearis muscles with GW-501516 for 24 h induced a threefold increase in uncoupling protein-3 mRNA, providing evidence that the GW-501516 compound that we used gets into and is active in skeletal muscle. In conclusion, our results show that, in contrast to myotubes in culture, skeletal muscle does not respond to GW-501516 with 1) an increase in AMPK or p38 MAPK phosphorylation or expression or 2) direct stimulation of glucose transport or enhanced insulin action.<br />

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