Endurobol
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MedKoo CAT#: 319593

CAS#: 317318-70-0

Description: Endurobol, also known as GW501516 and GSK-516, is a PPARδ receptor agonist. Endurobol was entered into clinical development as a drug candidate for metabolic diseases and cardiovascular diseases, and was abandoned in 2007 because animal testing showed that the drug caused cancer to develop rapidly in several organs.

Chemical Structure

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Endurobol
CAS# 317318-70-0
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 319593
Name: Endurobol
CAS#: 317318-70-0
Chemical Formula: C21H18F3NO3S2
Exact Mass: 453.07
Molecular Weight: 453.494
Elemental Analysis: C, 55.62; H, 4.00; F, 12.57; N, 3.09; O, 10.58; S, 14.14

Price and Availability

Size Price Availability Quantity
250mg USD 350 2 weeks
1g USD 550 2 weeks
5g USD 950 2 weeks
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Synonym: GW501516; GW-501516; GW 501516; GW1516; GW 1516; GW-1516; GSK-516; GSK 516; GSK516; Endurobol.

IUPAC/Chemical Name: {4-[({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)sulfanyl]-2-methylphenoxy}acetic acid

InChi Key: YDBLKRPLXZNVNB-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: O=C(O)COC1=CC=C(SCC2=C(C)N=C(C3=CC=C(C(F)(F)F)C=C3)S2)C=C1C

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: GW 501516 (GW 1516) is a PPARδ agonist with an EC50 of 1.1 nM.
In vitro activity: To further corroborate this, this study compared the expression level of these miRNAs in GW501516-treated C666-1 cells at the in vitro level. Figure 1B indicates, when compared to that of the control NP69 cells, that the content of miR-206 and miR-29c in the C666-1 NPC cells were diminished prominently (p < 0.01 for both), whereas miR-21’s expression was markedly higher than that in the NP69 cells (p < 0.01) (Fig. 1B). Consistent with the result from xenograft samples, GW501516 treatment was found to be associated with an apparent elevation on the expression of miR-206, while the elevated miR-21’s expression was also partially suppressed simultaneously (Fig. 1B). Correspondingly, this study found that the promoting effect of GW501516 on the expression of miR-206 could be antagonized by the PPARβ/δ selective antagonist GSK378721, signifying the specificity of PPARβ/δ activation on the suppression of miR-206 (Fig. 1C). Reference: Oncol Res. 2019; 27(8): 923–933. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7848406/
In vivo activity: FBG and FINS in each group were examined when GDM rats were treated with GW501516 on 3rd, 10th, an 17th day, as shown in Figure 1, this study found that compared with the control group, the level of FBG, FINS and HOMA-IR in GDM rats increased and the level of ISI decreased significantly; Compared with the GDM group, the levels of FBG, FINS and HOMA-IR in rats treated with GW501516 decreased in dose dependence, while the levels of ISI increased significantly. Reference: Diabetes Metab Syndr Obes. 2020; 13: 2307–2316. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7335770/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 63.8 140.77
DMF 25.0 55.13
DMF:PBS (pH 7.2) (1:2) 0.5 1.10
Ethanol 17.3 38.24

Preparing Stock Solutions

The following data is based on the product molecular weight 453.49 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Gu L, Shi Y, Xu W, Ji Y. PPARβ/δ Agonist GW501516 Inhibits Tumorigenesis and Promotes Apoptosis of the Undifferentiated Nasopharyngeal Carcinoma C666-1 Cells by Regulating miR-206. Oncol Res. 2019 Aug 8;27(8):923-933. doi: 10.3727/096504019X15518706875814. Epub 2019 Apr 8. PMID: 30982495; PMCID: PMC7848406. 2. Kim WJ, Lee W, Jung Y, Jang HJ, Kim YK, Kim SN. PPARβ/δ agonist GW501516 inhibits TNFα-induced repression of adiponectin and insulin receptor in 3T3-L1 adipocytes. Biochem Biophys Res Commun. 2019 Mar 19;510(4):621-628. doi: 10.1016/j.bbrc.2019.02.013. Epub 2019 Feb 8. PMID: 30739791. 3. Zhou J, Zhe R, Guo X, Chen Y, Zou Y, Zhou L, Wang Z. The Role of PPARδ Agosnist GW501516 in Rats with Gestational Diabetes Mellitus. Diabetes Metab Syndr Obes. 2020 Jun 30;13:2307-2316. doi: 10.2147/DMSO.S251491. PMID: 32669864; PMCID: PMC7335770. 4. Idrees M, Xu L, El Sheikh M, Sidrat T, Song SH, Joo MD, Lee KL, Kong IK. The PPARδ Agonist GW501516 Improves Lipolytic/Lipogenic Balance through CPT1 and PEPCK during the Development of Pre-Implantation Bovine Embryos. Int J Mol Sci. 2019 Dec 2;20(23):6066. doi: 10.3390/ijms20236066. PMID: 31810173; PMCID: PMC6928732.
In vitro protocol: 1. Gu L, Shi Y, Xu W, Ji Y. PPARβ/δ Agonist GW501516 Inhibits Tumorigenesis and Promotes Apoptosis of the Undifferentiated Nasopharyngeal Carcinoma C666-1 Cells by Regulating miR-206. Oncol Res. 2019 Aug 8;27(8):923-933. doi: 10.3727/096504019X15518706875814. Epub 2019 Apr 8. PMID: 30982495; PMCID: PMC7848406. 2. Kim WJ, Lee W, Jung Y, Jang HJ, Kim YK, Kim SN. PPARβ/δ agonist GW501516 inhibits TNFα-induced repression of adiponectin and insulin receptor in 3T3-L1 adipocytes. Biochem Biophys Res Commun. 2019 Mar 19;510(4):621-628. doi: 10.1016/j.bbrc.2019.02.013. Epub 2019 Feb 8. PMID: 30739791.
In vivo protocol: 1. Zhou J, Zhe R, Guo X, Chen Y, Zou Y, Zhou L, Wang Z. The Role of PPARδ Agosnist GW501516 in Rats with Gestational Diabetes Mellitus. Diabetes Metab Syndr Obes. 2020 Jun 30;13:2307-2316. doi: 10.2147/DMSO.S251491. PMID: 32669864; PMCID: PMC7335770. 2. Idrees M, Xu L, El Sheikh M, Sidrat T, Song SH, Joo MD, Lee KL, Kong IK. The PPARδ Agonist GW501516 Improves Lipolytic/Lipogenic Balance through CPT1 and PEPCK during the Development of Pre-Implantation Bovine Embryos. Int J Mol Sci. 2019 Dec 2;20(23):6066. doi: 10.3390/ijms20236066. PMID: 31810173; PMCID: PMC6928732.

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1: Chen W, Gao R, Xie X, Zheng Z, Li H, Li S, Dong F, Wang L. A metabolomic study of the PPARδ agonist GW501516 for enhancing running endurance in Kunming mice. Sci Rep. 2015 May 6;5:9884. doi: 10.1038/srep09884. PubMed PMID: 25943561; PubMed Central PMCID: PMC4421799.

2: Magliano DC, Penna-de-Carvalho A, Vazquez-Carrera M, Mandarim-de-Lacerda CA, Aguila MB. Short-term administration of GW501516 improves inflammatory state in white adipose tissue and liver damage in high-fructose-fed mice through modulation of the renin-angiotensin system. Endocrine. 2015 Nov;50(2):355-67. doi: 10.1007/s12020-015-0590-1. Epub 2015 Apr 9. PubMed PMID: 25854303.

3: Wang X, Sng MK, Foo S, Chong HC, Lee WL, Tang MB, Ng KW, Luo B, Choong C, Wong MT, Tong BM, Chiba S, Loo SC, Zhu P, Tan NS. Early controlled release of peroxisome proliferator-activated receptor β/δ agonist GW501516 improves diabetic wound healing through redox modulation of wound microenvironment. J Control Release. 2015 Jan 10;197:138-47. doi: 10.1016/j.jconrel.2014.11.001. Epub 2014 Nov 7. PubMed PMID: 25449811.

4: Pokrywka A, Cholbinski P, Kaliszewski P, Kowalczyk K, Konczak D, Zembron-Lacny A. Metabolic modulators of the exercise response: doping control analysis of an agonist of the peroxisome proliferator-activated receptor δ (GW501516) and 5-aminoimidazole-4-carboxamide ribonucleotide (AICAR). J Physiol Pharmacol. 2014 Aug;65(4):469-76. Review. PubMed PMID: 25179079.

5: Mosti MP, Stunes AK, Ericsson M, Pullisaar H, Reseland JE, Shabestari M, Eriksen EF, Syversen U. Effects of the peroxisome proliferator-activated receptor (PPAR)-δ agonist GW501516 on bone and muscle in ovariectomized rats. Endocrinology. 2014 Jun;155(6):2178-89. doi: 10.1210/en.2013-1166. Epub 2014 Apr 7. PubMed PMID: 24708238.

6: Su X, Zhou G, Wang Y, Yang X, Li L, Yu R, Li D. The PPARβ/δ agonist GW501516 attenuates peritonitis in peritoneal fibrosis via inhibition of TAK1-NFκB pathway in rats. Inflammation. 2014 Jun;37(3):729-37. doi: 10.1007/s10753-013-9791-z. PubMed PMID: 24337677.

7: Liu G, Li X, Li Y, Tang X, Xu J, Li R, Hao P, Sun Y. PPARδ agonist GW501516 inhibits PDGF-stimulated pulmonary arterial smooth muscle cell function related to pathological vascular remodeling. Biomed Res Int. 2013;2013:903947. doi: 10.1155/2013/903947. Epub 2013 Mar 27. PubMed PMID: 23607100; PubMed Central PMCID: PMC3625582.

8: Kostadinova R, Montagner A, Gouranton E, Fleury S, Guillou H, Dombrowicz D, Desreumaux P, Wahli W. GW501516-activated PPARβ/δ promotes liver fibrosis via p38-JNK MAPK-induced hepatic stellate cell proliferation. Cell Biosci. 2012 Oct 10;2(1):34. doi: 10.1186/2045-3701-2-34. PubMed PMID: 23046570; PubMed Central PMCID: PMC3519722.

9: Santhanam AV, d'Uscio LV, He T, Katusic ZS. PPARδ agonist GW501516 prevents uncoupling of endothelial nitric oxide synthase in cerebral microvessels of hph-1 mice. Brain Res. 2012 Nov 5;1483:89-95. doi: 10.1016/j.brainres.2012.09.012. Epub 2012 Sep 13. PubMed PMID: 22982594; PubMed Central PMCID: PMC3474319.

10: Olson EJ, Pearce GL, Jones NP, Sprecher DL. Lipid effects of peroxisome proliferator-activated receptor-δ agonist GW501516 in subjects with low high-density lipoprotein cholesterol: characteristics of metabolic syndrome. Arterioscler Thromb Vasc Biol. 2012 Sep;32(9):2289-94. doi: 10.1161/ATVBAHA.112.247890. Epub 2012 Jul 19. PubMed PMID: 22814748.

11: Terada M, Araki M, Ashibe B, Motojima K. GW501516 acts as an efficient PPARα activator in the mouse liver. Drug Discov Ther. 2011 Aug;5(4):176-80. PubMed PMID: 22466297.

12: Serrano-Marco L, Barroso E, El Kochairi I, Palomer X, Michalik L, Wahli W, Vázquez-Carrera M. The peroxisome proliferator-activated receptor (PPAR) β/δ agonist GW501516 inhibits IL-6-induced signal transducer and activator of transcription 3 (STAT3) activation and insulin resistance in human liver cells. Diabetologia. 2012 Mar;55(3):743-51. doi: 10.1007/s00125-011-2401-4. Epub 2011 Dec 17. PubMed PMID: 22179221.

13: Yang X, Kume S, Tanaka Y, Isshiki K, Araki S, Chin-Kanasaki M, Sugimoto T, Koya D, Haneda M, Sugaya T, Li D, Han P, Nishio Y, Kashiwagi A, Maegawa H, Uzu T. GW501516, a PPARδ agonist, ameliorates tubulointerstitial inflammation in proteinuric kidney disease via inhibition of TAK1-NFκB pathway in mice. PLoS One. 2011;6(9):e25271. doi: 10.1371/journal.pone.0025271. Epub 2011 Sep 22. PubMed PMID: 21966476; PubMed Central PMCID: PMC3178624.

14: Lee J, Chung WY. The role played by the peroxisome proliferator-activated receptor-β/δ (PPARβ/δ) activator, GW501516, in control of fatty acid metabolism: a new potential therapeutic target for treating metabolic syndrome. Endocrinology. 2011 May;152(5):1742-4. doi: 10.1210/en.2011-0211. PubMed PMID: 21511987.

15: Barroso E, Rodríguez-Calvo R, Serrano-Marco L, Astudillo AM, Balsinde J, Palomer X, Vázquez-Carrera M. The PPARβ/δ activator GW501516 prevents the down-regulation of AMPK caused by a high-fat diet in liver and amplifies the PGC-1α-Lipin 1-PPARα pathway leading to increased fatty acid oxidation. Endocrinology. 2011 May;152(5):1848-59. doi: 10.1210/en.2010-1468. Epub 2011 Mar 1. PubMed PMID: 21363937.

16: Barroso E, Eyre E, Palomer X, Vázquez-Carrera M. The peroxisome proliferator-activated receptor β/δ (PPARβ/δ) agonist GW501516 prevents TNF-α-induced NF-κB activation in human HaCaT cells by reducing p65 acetylation through AMPK and SIRT1. Biochem Pharmacol. 2011 Feb 15;81(4):534-43. doi: 10.1016/j.bcp.2010.12.004. Epub 2010 Dec 10. PubMed PMID: 21146504.

17: Sharma AK, Sk UH, He P, Peters JM, Amin S. Synthesis of isosteric selenium analog of the PPARbeta/delta agonist GW501516 and comparison of biological activity. Bioorg Med Chem Lett. 2010 Jul 15;20(14):4050-2. doi: 10.1016/j.bmcl.2010.05.094. Epub 2010 May 27. PubMed PMID: 20542425.

18: Coll T, Alvarez-Guardia D, Barroso E, Gómez-Foix AM, Palomer X, Laguna JC, Vázquez-Carrera M. Activation of peroxisome proliferator-activated receptor-{delta} by GW501516 prevents fatty acid-induced nuclear factor-{kappa}B activation and insulin resistance in skeletal muscle cells. Endocrinology. 2010 Apr;151(4):1560-9. doi: 10.1210/en.2009-1211. Epub 2010 Feb 25. PubMed PMID: 20185762.

19: Defaux A, Zurich MG, Braissant O, Honegger P, Monnet-Tschudi F. Effects of the PPAR-beta agonist GW501516 in an in vitro model of brain inflammation and antibody-induced demyelination. J Neuroinflammation. 2009 May 7;6:15. doi: 10.1186/1742-2094-6-15. PubMed PMID: 19422681; PubMed Central PMCID: PMC2687435.

20: Thevis M, Beuck S, Thomas A, Kortner B, Kohler M, Rodchenkov G, Schänzer W. Doping control analysis of emerging drugs in human plasma - identification of GW501516, S-107, JTV-519, and S-40503. Rapid Commun Mass Spectrom. 2009 Apr;23(8):1139-46. doi: 10.1002/rcm.3987. PubMed PMID: 19280612.