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G5045

GW6471

≥98% (HPLC), powder, PPARα antagonist

Synonym(s):

N-((2S)-2-(((1Z)-1-Methyl-3-oxo-3-(4-(trifluoromethyl)phenyl)prop-1-enyl)amino)-3-(4-(2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy)phenyl)propyl)propanamide

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About This Item

Empirical Formula (Hill Notation):
C35H36F3N3O4
CAS Number:
880635-03-0
Molecular Weight:
619.67
UNSPSC Code:
12352200
PubChem Substance ID:
24724489
NACRES:
NA.77
MDL number:
MFCD07784503
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100
Storage condition:
desiccated
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Product Name

GW6471, ≥98% (HPLC)

Quality Level

100

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 5 mg/mL, clear (warmed)

originator

GlaxoSmithKline

storage temp.

2-8°C

SMILES string

CCC(=O)NC[C@H](Cc1ccc(OCCc2nc(oc2C)-c3ccccc3)cc1)N\C(C)=C/C(=O)c4ccc(cc4)C(F)(F)F

InChI

1S/C35H36F3N3O4/c1-4-33(43)39-22-29(40-23(2)20-32(42)26-12-14-28(15-13-26)35(36,37)38)21-25-10-16-30(17-11-25)44-19-18-31-24(3)45-34(41-31)27-8-6-5-7-9-27/h5-17,20,29,40H,4,18-19,21-22H2,1-3H3,(H,39,43)/b23-20-/t29-/m0/s1

InChI key

TYEFSRMOUXWTDN-DYQICHDWSA-N

General description

GW6471 prevents apoptosis and cell cycle arrest at G0/G1 in renal cell carcinoma. It reduces enhanced fatty acid oxidation and oxidative phosphorylation associated with glycolysis inhibition.

Application

GW6471 has been used:
  • to investigate the role of peroxisome proliferator-activated receptors (PPARs) alpha in perfluorooctanoic acid (PFOA) induced developmental cardiotoxicity
  • to abolish the protection of bezafibrate (BZA) against hypertrophy
  • to block the enhanced activity of the hepatitis B virus (HBV) core promoter

Biochem/physiol Actions

GW6471 is a PPARα antagonist, which completely inhibits GW409544-induced activation of PPARα with an IC50 = 0.24 μM. GW6471 induces a PPARα conformation that interacts efficiently with co-repressors.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Nuclear Receptors (PPARs) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by GlaxoSmithKline. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000389461
0000389461
0000230055
0000230055
0000177499

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PPARalpha inhibition modulates multiple reprogrammed metabolic pathways in kidney cancer and attenuates tumor growth
Abu AO, et al.
American Journal of Physiology. Cell Physiology, 308(11), C890-C898 (2015)
Bezafibrate attenuates pressure overload-induced cardiac hypertrophy and fibrosis
Xu SC, et al.
PPAR Research, 2017 (2017)
Chun Wang et al.
Environmental health perspectives, 119(12), 1739-1744 (2011-08-19)
Numerous man-made pollutants activate the aryl hydrocarbon receptor (AhR) and are risk factors for type 2 diabetes. AhR signaling also affects molecular clock genes to influence glucose metabolism. We investigated mechanisms by which AhR activation affects glucose metabolism. Glucose tolerance
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