GW-7647
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MedKoo CAT#: 526871

CAS#: 265129-71-3

Description: GW-7647 is a potent, selective agonist of human and murine PPARα4 It activates human PPARα, PPARγ, and PPARδ with EC50 values of 0.006, 1.1 and 6.2 µM, respectively.

Chemical Structure

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GW-7647
CAS# 265129-71-3
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 526871
Name: GW-7647
CAS#: 265129-71-3
Chemical Formula: C29H46N2O3S
Exact Mass: 502.32
Molecular Weight: 502.760
Elemental Analysis: C, 69.28; H, 9.22; N, 5.57; O, 9.55; S, 6.38

Price and Availability

Size Price Availability Quantity
5mg USD 90 Ready to ship
10mg USD 150 Ready to ship
25mg USD 250 Ready to ship
50mg USD 450 Ready to ship
100mg USD 750 Ready to ship
200mg USD 1250 Ready to ship
500mg USD 2650 Ready to ship
1g USD 3850 Ready to ship
2g USD 6450 Ready to ship
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Synonym: GW-7647; GW 7647; GW7647.

IUPAC/Chemical Name: 2-((4-(2-(3-cyclohexyl-1-(4-cyclohexylbutyl)ureido)ethyl)phenyl)thio)-2-methylpropanoic acid

InChi Key: PKNYXWMTHFMHKD-UHFFFAOYSA-N

InChi Code: InChI=1S/C29H46N2O3S/c1-29(2,27(32)33)35-26-18-16-24(17-19-26)20-22-31(28(34)30-25-14-7-4-8-15-25)21-10-9-13-23-11-5-3-6-12-23/h16-19,23,25H,3-15,20-22H2,1-2H3,(H,30,34)(H,32,33)

SMILES Code: CC(C)(SC1=CC=C(CCN(C(NC2CCCCC2)=O)CCCCC3CCCCC3)C=C1)C(O)=O

Appearance: White to off-white 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

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:

Biological target: GW7647 is a PPARα agonist, with EC50s of 6 nM, 1.1 μM, and 6.2 μM for human PPARα, PPARγ and PPARδ, respectively.
In vitro activity: mRNA from primary human hepatocytes isolated from four independent donors was collected at five time points (2, 6, 12, 24, and 72 h) from cells treated with five concentrations of GW7647 between 0.001 and 10 μm. Only 192 genes were statistically significantly up- or down-regulated upon treatment of GW7647 at any of the dose or time points, with more than 80% showing up-regulation (Fig. 2B). These up-regulated genes encompassed many lipid metabolism pathway genes that are known targets of PPARα, including ACOX1, CPT1A, and APOA4. The differentially expressed genes we identified correlate strongly with the set of genes regulated by another PPARα-selective agonist, Wy14643 (Figure S1). Reference: Chem Biol Interact. 2014 Feb 25;209:14-24. https://pubmed.ncbi.nlm.nih.gov/24269660/
In vivo activity: This study’s electrophysiological and behavioral evidence demonstrated that PPAR-α activation can acutely inhibit the activity of ASICs in nociceptive DRG neurons. PPAR-α agonist GW7647 decreased the amplitude of proton-activated currents and acidosis-triggered action potentials in rat isolated DRG neurons. Peripheral administration of GW7647 relieved acidosis-evoked nociceptive responses and CFA-induced mechanical hypersensitivity in rats. Reference: Oncotarget. 2017 Nov 3; 8(54): 93051–93062. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5696243/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 16.0 31.80

Preparing Stock Solutions

The following data is based on the product molecular weight 502.76 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. Patil R, Mohanty B, Liu B, Chandrashekaran IR, Headey SJ, Williams ML, Clements CS, Ilyichova O, Doak BC, Genissel P, Weaver RJ, Vuillard L, Halls ML, Porter CJH, Scanlon MJ. A ligand-induced structural change in fatty acid-binding protein 1 is associated with potentiation of peroxisome proliferator-activated receptor α agonists. J Biol Chem. 2019 Mar 8;294(10):3720-3734. doi: 10.1074/jbc.RA118.006848. Epub 2018 Dec 31. PMID: 30598509; PMCID: PMC6416440. 2. McMullen PD, Bhattacharya S, Woods CG, Sun B, Yarborough K, Ross SM, Miller ME, McBride MT, LeCluyse EL, Clewell RA, Andersen ME. A map of the PPARα transcription regulatory network for primary human hepatocytes. Chem Biol Interact. 2014 Feb 25;209:14-24. doi: 10.1016/j.cbi.2013.11.006. Epub 2013 Nov 22. PMID: 24269660. 3. Wu J, Wang JJ, Liu TT, Zhou YM, Qiu CY, Shen DW, Hu WP. PPAR-α acutely inhibits functional activity of ASICs in rat dorsal root ganglion neurons. Oncotarget. 2017 Oct 10;8(54):93051-93062. doi: 10.18632/oncotarget.21805. PMID: 29190977; PMCID: PMC5696243. 4. Tanaka S, Hosogi S, Sawabe Y, Shimamoto C, Matsumura H, Inui T, Marunaka Y, Nakahari T. PPARα induced NOS1 phosphorylation via PI3K/Akt in guinea pig antral mucous cells: NO-enhancement in Ca(2+)-regulated exocytosis. Biomed Res. 2016;37(3):167-78. doi: 10.2220/biomedres.37.167. PMID: 27356604.
In vitro protocol: 1. Patil R, Mohanty B, Liu B, Chandrashekaran IR, Headey SJ, Williams ML, Clements CS, Ilyichova O, Doak BC, Genissel P, Weaver RJ, Vuillard L, Halls ML, Porter CJH, Scanlon MJ. A ligand-induced structural change in fatty acid-binding protein 1 is associated with potentiation of peroxisome proliferator-activated receptor α agonists. J Biol Chem. 2019 Mar 8;294(10):3720-3734. doi: 10.1074/jbc.RA118.006848. Epub 2018 Dec 31. PMID: 30598509; PMCID: PMC6416440. 2. McMullen PD, Bhattacharya S, Woods CG, Sun B, Yarborough K, Ross SM, Miller ME, McBride MT, LeCluyse EL, Clewell RA, Andersen ME. A map of the PPARα transcription regulatory network for primary human hepatocytes. Chem Biol Interact. 2014 Feb 25;209:14-24. doi: 10.1016/j.cbi.2013.11.006. Epub 2013 Nov 22. PMID: 24269660.
In vivo protocol: 1. Wu J, Wang JJ, Liu TT, Zhou YM, Qiu CY, Shen DW, Hu WP. PPAR-α acutely inhibits functional activity of ASICs in rat dorsal root ganglion neurons. Oncotarget. 2017 Oct 10;8(54):93051-93062. doi: 10.18632/oncotarget.21805. PMID: 29190977; PMCID: PMC5696243. 2. Tanaka S, Hosogi S, Sawabe Y, Shimamoto C, Matsumura H, Inui T, Marunaka Y, Nakahari T. PPARα induced NOS1 phosphorylation via PI3K/Akt in guinea pig antral mucous cells: NO-enhancement in Ca(2+)-regulated exocytosis. Biomed Res. 2016;37(3):167-78. doi: 10.2220/biomedres.37.167. PMID: 27356604.

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1: Strömqvist M, Olsson JA, Kärrman A, Brunström B. Transcription of genes involved in fat metabolism in chicken embryos exposed to the peroxisome proliferator-activated receptor alpha (PPARα) agonist GW7647 or to perfluorooctane sulfonate (PFOS) or perfluorooctanoic acid (PFOA). Comp Biochem Physiol C Toxicol Pharmacol. 2012 Jun;156(1):29-36. doi: 10.1016/j.cbpc.2012.03.004. PubMed PMID: 22465071.

2: van der Krieken SE, Popeijus HE, Konings M, Dullens SP, Mensink RP, Plat J. C/EBP-β Is Differentially Affected by PPARα Agonists Fenofibric Acid and GW7647, But Does Not Change Apolipoprotein A-I Production During ER-Stress and Inflammation. J Cell Biochem. 2016 Sep 12. doi: 10.1002/jcb.25731. [Epub ahead of print] PubMed PMID: 27618583.

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4: Ham J, Cho SJ, Ko J, Chin J, Kang H. A facile one-pot preparation of alkyl aminoaryl sulfides for the synthesis of GW7647 as an agonist of peroxisome proliferator-activated receptor alpha. J Org Chem. 2006 Jul 21;71(15):5781-4. PubMed PMID: 16839165.

5: Russo R, LoVerme J, La Rana G, D'Agostino G, Sasso O, Calignano A, Piomelli D. Synergistic antinociception by the cannabinoid receptor agonist anandamide and the PPAR-alpha receptor agonist GW7647. Eur J Pharmacol. 2007 Jul 2;566(1-3):117-9. PubMed PMID: 17434479; PubMed Central PMCID: PMC1997313.

6: Lam VH, Zhang L, Huqi A, Fukushima A, Tanner BA, Onay-Besikci A, Keung W, Kantor PF, Jaswal JS, Rebeyka IM, Lopaschuk GD. Activating PPARα prevents post-ischemic contractile dysfunction in hypertrophied neonatal hearts. Circ Res. 2015 Jun 19;117(1):41-51. doi: 10.1161/CIRCRESAHA.117.306585. PubMed PMID: 25977309.

7: Tanaka S, Sugiyama N, Takahashi Y, Mantoku D, Sawabe Y, Kuwabara H, Nakano T, Shimamoto C, Matsumura H, Marunaka Y, Nakahari T. PPARα autocrine regulation of Ca²⁺-regulated exocytosis in guinea pig antral mucous cells: NO and cGMP accumulation. Am J Physiol Gastrointest Liver Physiol. 2014 Dec 15;307(12):G1169-79. doi: 10.1152/ajpgi.00311.2013. PubMed PMID: 25342048.

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9: Mattsson A, Kärrman A, Pinto R, Brunström B. Metabolic Profiling of Chicken Embryos Exposed to Perfluorooctanoic Acid (PFOA) and Agonists to Peroxisome Proliferator-Activated Receptors. PLoS One. 2015 Dec 1;10(12):e0143780. doi: 10.1371/journal.pone.0143780. PubMed PMID: 26624992; PubMed Central PMCID: PMC4666608.

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11: Yue TL, Bao W, Jucker BM, Gu JL, Romanic AM, Brown PJ, Cui J, Thudium DT, Boyce R, Burns-Kurtis CL, Mirabile RC, Aravindhan K, Ohlstein EH. Activation of peroxisome proliferator-activated receptor-alpha protects the heart from ischemia/reperfusion injury. Circulation. 2003 Nov 11;108(19):2393-9. PubMed PMID: 14557369.

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13: Aleshin S, Grabeklis S, Hanck T, Sergeeva M, Reiser G. Peroxisome proliferator-activated receptor (PPAR)-gamma positively controls and PPARalpha negatively controls cyclooxygenase-2 expression in rat brain astrocytes through a convergence on PPARbeta/delta via mutual control of PPAR expression levels. Mol Pharmacol. 2009 Aug;76(2):414-24. doi: 10.1124/mol.109.056010. PubMed PMID: 19483106.

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16: Muoio DM, Way JM, Tanner CJ, Winegar DA, Kliewer SA, Houmard JA, Kraus WE, Dohm GL. Peroxisome proliferator-activated receptor-alpha regulates fatty acid utilization in primary human skeletal muscle cells. Diabetes. 2002 Apr;51(4):901-9. PubMed PMID: 11916905.

17: van der Meer DL, Degenhardt T, Väisänen S, de Groot PJ, Heinäniemi M, de Vries SC, Müller M, Carlberg C, Kersten S. Profiling of promoter occupancy by PPARalpha in human hepatoma cells via ChIP-chip analysis. Nucleic Acids Res. 2010 May;38(9):2839-50. doi: 10.1093/nar/gkq012. PubMed PMID: 20110263; PubMed Central PMCID: PMC2875002.

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19: Angulo J, Vallejo S, El Assar M, García-Septiem J, Sánchez-Ferrer CF, Rodríguez-Mañas L. Age-related differences in the effects of α and γ peroxisome proliferator-activated receptor subtype agonists on endothelial vasodilation in human microvessels. Exp Gerontol. 2012 Sep;47(9):734-40. doi: 10.1016/j.exger.2012.06.014. PubMed PMID: 22776133.

20: Chen J, Dexheimer TS, Ai Y, Liang Q, Villamil MA, Inglese J, Maloney DJ, Jadhav A, Simeonov A, Zhuang Z. Selective and cell-active inhibitors of the USP1/ UAF1 deubiquitinase complex reverse cisplatin resistance in non-small cell lung cancer cells. Chem Biol. 2011 Nov 23;18(11):1390-400. doi: 10.1016/j.chembiol.2011.08.014. PubMed PMID: 22118673; PubMed Central PMCID: PMC3344384.