GW0742
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MedKoo CAT#: 522547

CAS#: 317318-84-6

Description: GW0742, also known as GW610742 and GW0742X is a PPARδ/β agonist. GW0742 Induces Early Neuronal Maturation of Cortical Post-Mitotic Neurons. GW0742 prevents hypertension, vascular inflammatory and oxidative status, and endothelial dysfunction in diet-induced obesity. GW0742 has direct protective effects on right heart hypertrophy.GW0742 may enhance lipid metabolism in heart both in vivo and in vitro.

Chemical Structure

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GW0742
CAS# 317318-84-6
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 522547
Name: GW0742
CAS#: 317318-84-6
Chemical Formula: C21H17F4NO3S2
Exact Mass: 471.06
Molecular Weight: 471.485
Elemental Analysis: C, 53.50; H, 3.63; F, 16.12; N, 2.97; O, 10.18; S, 13.60

Price and Availability

Size Price Availability Quantity
25mg USD 150
50mg USD 250
100mg USD 450
200mg USD 750 2 Weeks
500mg USD 1250 2 Weeks
1g USD 2250 2 Weeks
2g USD 3250 2 Weeks
5g USD 4650 2 Weeks
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Synonym: GW0742; GW-0742; GW 0742; GW0742X; GW-0742X; GW 0742X; GW610742; GW-610742; GW 610742.

IUPAC/Chemical Name: [4-[[[2-[3-fluoro-4-(trifluoromethyl)phenyl]-4-methyl-5-thiazolyl]methyl]thio]-2-methyl phenoxy]-acetic acid

InChi Key: HWVNEWGKWRGSRK-UHFFFAOYSA-N

InChi Code: InChI=1S/C21H17F4NO3S2/c1-11-7-14(4-6-17(11)29-9-19(27)28)30-10-18-12(2)26-20(31-18)13-3-5-15(16(22)8-13)21(23,24)25/h3-8H,9-10H2,1-2H3,(H,27,28)

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

Appearance: Solid powder

Purity: >95% (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:
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Biological target: GW0742 is a potent PPARβ and PPARδ agonist, with an IC50 of 1 nM for human PPARδ in binding assay, and EC50s of 1 nM, 1.1 μM and 2 μM for human PPARδ, PPARα, and PPARγ, respectively.
In vitro activity: Treatment with 10 µmol/L of GW0742 significantly reduced expression of TXNIP (Figure 6C,D, P < 0.01), which was accompanied by decreased expression of secreted pro‐inflammatory cytokines IL‐1β and TNF‐α (Figure 6C,D, P < 0.05), suggesting that GW0742 can reduce inflammation in PC12 cells subjected to OGD. Reference: J Cell Mol Med. 2020 Nov;24(21):12318-12330. https://pubmed.ncbi.nlm.nih.gov/33034416/
In vivo activity: Since neural stem cells have been shown to use FAO to support neurogenic activity, and neurogenesis is linked with amelioration of cognitive deficits, this study assessed whether GW0742 treatment enhanced the production of newborn neurons as detected by DCX staining in the hippocampi of the GW0742 treated APP/PS1 mice. Although the number of DCX positive cells was very low in the 12-month-old APP/PS1 mice, it was slightly, yet significantly, increased in the treated mice compared to their vehicle treated controls (t(15) = 2.3, p = .04, unpaired t test, Figure 4a,b). Reference: Glia. 2019 Jan;67(1):146-159. https://pubmed.ncbi.nlm.nih.gov/30453390/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 30.0 63.63
DMF:PBS (pH 7.2) (1:10) 0.1 0.21
DMSO 50.4 106.84
Ethanol 26.1 55.31

Preparing Stock Solutions

The following data is based on the product molecular weight 471.48 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. Gamdzyk M, Doycheva DM, Kang R, Tang H, Travis ZD, Tang J, Zhang JH. GW0742 activates miR-17-5p and inhibits TXNIP/NLRP3-mediated inflammation after hypoxic-ischaemic injury in rats and in PC12 cells. J Cell Mol Med. 2020 Nov;24(21):12318-12330. doi: 10.1111/jcmm.15698. Epub 2020 Oct 9. PMID: 33034416; PMCID: PMC7686982. 2. Konttinen H, Gureviciene I, Oksanen M, Grubman A, Loppi S, Huuskonen MT, Korhonen P, Lampinen R, Keuters M, Belaya I, Tanila H, Kanninen KM, Goldsteins G, Landreth G, Koistinaho J, Malm T. PPARβ/δ-agonist GW0742 ameliorates dysfunction in fatty acid oxidation in PSEN1ΔE9 astrocytes. Glia. 2019 Jan;67(1):146-159. doi: 10.1002/glia.23534. Epub 2018 Nov 19. PMID: 30453390; PMCID: PMC7526864. 3. Ozawa C, Horiguchi M, Akita T, Oiso Y, Abe K, Motomura T, Yamashita C. Pulmonary Administration of GW0742, a High-Affinity Peroxisome Proliferator-Activated Receptor Agonist, Repairs Collapsed Alveoli in an Elastase-Induced Mouse Model of Emphysema. Biol Pharm Bull. 2016;39(5):778-85. doi: 10.1248/bpb.b15-00909. PMID: 27150147.
In vitro protocol: 1. Gamdzyk M, Doycheva DM, Kang R, Tang H, Travis ZD, Tang J, Zhang JH. GW0742 activates miR-17-5p and inhibits TXNIP/NLRP3-mediated inflammation after hypoxic-ischaemic injury in rats and in PC12 cells. J Cell Mol Med. 2020 Nov;24(21):12318-12330. doi: 10.1111/jcmm.15698. Epub 2020 Oct 9. PMID: 33034416; PMCID: PMC7686982.
In vivo protocol: 1. Konttinen H, Gureviciene I, Oksanen M, Grubman A, Loppi S, Huuskonen MT, Korhonen P, Lampinen R, Keuters M, Belaya I, Tanila H, Kanninen KM, Goldsteins G, Landreth G, Koistinaho J, Malm T. PPARβ/δ-agonist GW0742 ameliorates dysfunction in fatty acid oxidation in PSEN1ΔE9 astrocytes. Glia. 2019 Jan;67(1):146-159. doi: 10.1002/glia.23534. Epub 2018 Nov 19. PMID: 30453390; PMCID: PMC7526864. 2. Ozawa C, Horiguchi M, Akita T, Oiso Y, Abe K, Motomura T, Yamashita C. Pulmonary Administration of GW0742, a High-Affinity Peroxisome Proliferator-Activated Receptor Agonist, Repairs Collapsed Alveoli in an Elastase-Induced Mouse Model of Emphysema. Biol Pharm Bull. 2016;39(5):778-85. doi: 10.1248/bpb.b15-00909. PMID: 27150147.

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1: Niu HS, Ku PM, Niu CS, Cheng JT, Lee KS. Development of PPAR-agonist GW0742 as antidiabetic drug: study in animals. Drug Des Devel Ther. 2015 Oct 14;9:5625-32. doi: 10.2147/DDDT.S95045. eCollection 2015. PubMed PMID: 26508837; PubMed Central PMCID: PMC4610778.

2: Benedetti E, Di Loreto S, D'Angelo B, Cristiano L, d'angelo M, Antonosante A, Fidoamore A, Golini R, Cinque B, Cifone MG, Ippoliti R, Giordano A, Cimini A. The PPARβ/δ Agonist GW0742 Induces Early Neuronal Maturation of Cortical Post-Mitotic Neurons: Role of PPARβ/δ in Neuronal Maturation. J Cell Physiol. 2016 Mar;231(3):597-606. doi: 10.1002/jcp.25103. PubMed PMID: 26206209.

3: Toral M, Gómez-Guzmán M, Jiménez R, Romero M, Zarzuelo MJ, Utrilla MP, Hermenegildo C, Cogolludo Á, Pérez-Vizcaíno F, Gálvez J, Duarte J. Chronic peroxisome proliferator-activated receptorβ/δ agonist GW0742 prevents hypertension, vascular inflammatory and oxidative status, and endothelial dysfunction in diet-induced obesity. J Hypertens. 2015 Sep;33(9):1831-44. doi: 10.1097/HJH.0000000000000634. PubMed PMID: 26147382.

4: Teske K, Nandhikonda P, Bogart JW, Feleke B, Sidhu P, Yuan N, Preston J, Goy R, Arnold LA. Modulation of Transcription mediated by the Vitamin D Receptor and the Peroxisome Proliferator-Activated Receptor δ in the presence of GW0742 analogs. J Biomol Res Ther. 2014;3(1). pii: 1000111. PubMed PMID: 25485183; PubMed Central PMCID: PMC4255951.

5: Kojonazarov B, Luitel H, Sydykov A, Dahal BK, Paul-Clark MJ, Bonvini S, Reed A, Schermuly RT, Mitchell JA. The peroxisome proliferator-activated receptor β/δ agonist GW0742 has direct protective effects on right heart hypertrophy. Pulm Circ. 2013 Dec;3(4):926-35. doi: 10.1086/674755. Erratum in: Pulm Circ. 2014 Jun;4(2):352. PubMed PMID: 25006409; PubMed Central PMCID: PMC4070821.

6: Galatou E, Kelly T, Lazou A. The PPARβ/δ agonist GW0742 modulates signaling pathways associated with cardiac myocyte growth via a non-genomic redox mechanism. Mol Cell Biochem. 2014 Oct;395(1-2):145-54. doi: 10.1007/s11010-014-2120-5. Epub 2014 Jun 18. PubMed PMID: 24939361.

7: Wepler M, Hafner S, Scheuerle A, Reize M, Gröger M, Wagner F, Simon F, Matallo J, Gottschalch F, Seifritz A, Stahl B, Matejovic M, Kapoor A, Möller P, Calzia E, Georgieff M, Wachter U, Vogt JA, Thiemermann C, Radermacher P, McCook O. Effects of the PPAR-β/δ agonist GW0742 during resuscitated porcine septic shock. Intensive Care Med Exp. 2013 Dec;1(1):28. doi: 10.1186/2197-425X-1-9. Epub 2013 Oct 29. PubMed PMID: 26266797.

8: Kuo SC, Ku PM, Chen LJ, Niu HS, Cheng JT. Activation of receptors δ (PPARδ) by agonist (GW0742) may enhance lipid metabolism in heart both in vivo and in vitro. Horm Metab Res. 2013 Nov;45(12):880-6. doi: 10.1055/s-0033-1348317. Epub 2013 Jun 26. PubMed PMID: 23803968.

9: Nandhikonda P, Yasgar A, Baranowski AM, Sidhu PS, McCallum MM, Pawlak AJ, Teske K, Feleke B, Yuan NY, Kevin C, Bikle DD, Ayers SD, Webb P, Rai G, Simeonov A, Jadhav A, Maloney D, Arnold LA. Peroxisome proliferation-activated receptor δ agonist GW0742 interacts weakly with multiple nuclear receptors, including the vitamin D receptor. Biochemistry. 2013 Jun 18;52(24):4193-203. doi: 10.1021/bi400321p. Epub 2013 Jun 10. PubMed PMID: 23713684; PubMed Central PMCID: PMC3724348.

10: Schnegg CI, Greene-Schloesser D, Kooshki M, Payne VS, Hsu FC, Robbins ME. The PPARδ agonist GW0742 inhibits neuroinflammation, but does not restore neurogenesis or prevent early delayed hippocampal-dependent cognitive impairment after whole-brain irradiation. Free Radic Biol Med. 2013 Aug;61:1-9. doi: 10.1016/j.freeradbiomed.2013.03.002. Epub 2013 Mar 14. PubMed PMID: 23499837; PubMed Central PMCID: PMC3884086.

11: Sobolevsky T, Dikunets M, Sukhanova I, Virus E, Rodchenkov G. Detection of PPARδ agonists GW1516 and GW0742 and their metabolites in human urine. Drug Test Anal. 2012 Oct;4(10):754-60. doi: 10.1002/dta.1413. Epub 2012 Sep 13. PubMed PMID: 22977012.

12: Paterniti I, Mazzon E, Riccardi L, Galuppo M, Impellizzeri D, Esposito E, Bramanti P, Cappellani A, Cuzzocrea S. Peroxisome proliferator-activated receptor β/δ agonist GW0742 ameliorates cerulein- and taurocholate-induced acute pancreatitis in mice. Surgery. 2012 Jul;152(1):90-106. doi: 10.1016/j.surg.2012.02.004. Epub 2012 Apr 21. PubMed PMID: 22521259.

13: Esposito E, Paterniti I, Meli R, Bramanti P, Cuzzocrea S. GW0742, a high-affinity PPAR-δ agonist, mediates protection in an organotypic model of spinal cord damage. Spine (Phila Pa 1976). 2012 Jan 15;37(2):E73-8. doi: 10.1097/BRS.0b013e3182276d88. PubMed PMID: 21685825.

14: Galuppo M, Di Paola R, Mazzon E, Esposito E, Paterniti I, Kapoor A, Thiemermann C, Cuzzocrea S. GW0742, a high affinity PPAR-β/δ agonist reduces lung inflammation induced by bleomycin instillation in mice. Int J Immunopathol Pharmacol. 2010 Oct-Dec;23(4):1033-46. PubMed PMID: 21244753.

15: Di Paola R, Esposito E, Mazzon E, Paterniti I, Galuppo M, Cuzzocrea S. GW0742, a selective PPAR-beta/delta agonist, contributes to the resolution of inflammation after gut ischemia/reperfusion injury. J Leukoc Biol. 2010 Aug;88(2):291-301. doi: 10.1189/jlb.0110053. Epub 2010 Apr 29. PubMed PMID: 20430778.

16: Di Paola R, Crisafulli C, Mazzon E, Esposito E, Paterniti I, Galuppo M, Genovese T, Thiemermann C, Cuzzocrea S. GW0742, a high-affinity PPAR -beta/delta agonist, inhibits acute lung injury in mice. Shock. 2010 Apr;33(4):426-35. doi: 10.1097/SHK.0b013e3181b8f2fb. PubMed PMID: 20407409.

17: Harrington LS, Moreno L, Reed A, Wort SJ, Desvergne B, Garland C, Zhao L, Mitchell JA. The PPARbeta/delta agonist GW0742 relaxes pulmonary vessels and limits right heart hypertrophy in rats with hypoxia-induced pulmonary hypertension. PLoS One. 2010 Mar 4;5(3):e9526. doi: 10.1371/journal.pone.0009526. PubMed PMID: 20209098; PubMed Central PMCID: PMC2831997.

18: Briand F, Naik SU, Fuki I, Millar JS, Macphee C, Walker M, Billheimer J, Rothblat G, Rader DJ. Both the peroxisome proliferator-activated receptor delta agonist, GW0742, and ezetimibe promote reverse cholesterol transport in mice by reducing intestinal reabsorption of HDL-derived cholesterol. Clin Transl Sci. 2009 Apr;2(2):127-33. PubMed PMID: 20169010; PubMed Central PMCID: PMC2823289.

19: Haskova Z, Hoang B, Luo G, Morgan LA, Billin AN, Barone FC, Shearer BG, Barton ME, Kilgore KS. Modulation of LPS-induced pulmonary neutrophil infiltration and cytokine production by the selective PPARbeta/delta ligand GW0742. Inflamm Res. 2008 Jul;57(7):314-21. doi: 10.1007/s00011-007-7157-4. PubMed PMID: 18622687.

20: Faiola B, Falls JG, Peterson RA, Bordelon NR, Brodie TA, Cummings CA, Romach EH, Miller RT. PPAR alpha, more than PPAR delta, mediates the hepatic and skeletal muscle alterations induced by the PPAR agonist GW0742. Toxicol Sci. 2008 Oct;105(2):384-94. doi: 10.1093/toxsci/kfn130. Epub 2008 Jun 30. PubMed PMID: 18593727.