ChemicalBook > CAS DataBase List > 4-Chloro-N-[2-[[5-(trifluoromethyl)-2-pyridinyl]sulfonyl]ethyl]benzamide

4-Chloro-N-[2-[[5-(trifluoromethyl)-2-pyridinyl]sulfonyl]ethyl]benzamide

Product Name
4-Chloro-N-[2-[[5-(trifluoromethyl)-2-pyridinyl]sulfonyl]ethyl]benzamide
CAS No.
188591-46-0
Chemical Name
4-Chloro-N-[2-[[5-(trifluoromethyl)-2-pyridinyl]sulfonyl]ethyl]benzamide
Synonyms
CS-710;GSK 3787;GSK3787, >=98%;GSK3787 ，S8025;GSK3787/GSK-3787;GSK3787, 10 mM in DMSO;GSK3787;GSK 3787;GSK-3787;PPARβ/δ Antagonist, GSK3787;PPARβ/δ Antagonist, GSK3787;GSK-3787, PPARdelta antagonist
CBNumber
CB02518837
Molecular Formula
C15H12ClF3N2O3S
Formula Weight
392.78
MOL File
188591-46-0.mol
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4-Chloro-N-[2-[[5-(trifluoromethyl)-2-pyridinyl]sulfonyl]ethyl]benzamide Property

Boiling point:
585.1±50.0 °C(Predicted)
Density 
1.448±0.06 g/cm3 (20 ºC 760 Torr)
storage temp. 
2-8°C
solubility 
DMSO: ≥10mg/mL
pka
12.92±0.46(Predicted)
form 
White solid
color 
white to off-white
Stability:
Stable for 1 year for up to year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
InChI
InChI=1S/C15H12ClF3N2O3S/c16-12-4-1-10(2-5-12)14(22)20-7-8-25(23,24)13-6-3-11(9-21-13)15(17,18)19/h1-6,9H,7-8H2,(H,20,22)
InChIKey
JFUIMTGOQCQTPF-UHFFFAOYSA-N
SMILES
C(NCCS(C1=NC=C(C(F)(F)F)C=C1)(=O)=O)(=O)C1=CC=C(Cl)C=C1
CAS DataBase Reference
188591-46-0
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Safety

Hazard Codes 
Xi
Risk Statements 
36
Safety Statements 
26
WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
G7423
Product name
GSK3787
Purity
≥98% (HPLC), white to off-white, powder
Packaging
5mg
Price
$139.65
Updated
2025/07/31
Sigma-Aldrich
Product number
516567
Product name
PPARβ/δ Antagonist, GSK3787
Packaging
10mg
Price
$208
Updated
2025/07/31
Cayman Chemical
Product number
15219
Product name
GSK3787
Purity
≥95%
Packaging
5mg
Price
$47
Updated
2024/03/01
Cayman Chemical
Product number
15219
Product name
GSK3787
Purity
≥95%
Packaging
10mg
Price
$73
Updated
2024/03/01
Sigma-Aldrich
Product number
G7423
Product name
GSK3787
Purity
≥98% (HPLC), white to off-white, powder
Packaging
25mg
Price
$662
Updated
2023/01/07
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4-Chloro-N-[2-[[5-(trifluoromethyl)-2-pyridinyl]sulfonyl]ethyl]benzamide Chemical Properties,Usage,Production

Description

GSK-3787 (188591-46-0) is a selective and irreversible antagonist of the peroxisome proliferator-activated receptor δ (PPARδ) – plC50 = 6.6. It covalently binds to Cys 249 in the PPARd binding site.

Uses

GSK3787 has been used to inhibit the role of peroxisome proliferator-activated receptor-delta (PPARδ), during the pre-implantation period of bovine embryonic development. It has also been used as a PPARδ-specific inhibitor in in vitro maturation (IVM) media to inhibit PPARδ.

Uses

PPARβ/δ is thought to play a role in lipid homeostasis and glucose disposal by regulating genes involved in fatty acid oxidation, reverse cholesterol transport, and carbon substrate utilization in skeletal muscle. It has also been implicated in the progression of certain cancers. GSK3787 is an irreversible antagonist of PPARβ/δ (pIC50 = 6.6) with no measurable affinity for PPARα or PPARγ (pIC50 >5). At 1μM, it inhibits the expression of PPARβ/δ-regulated target genes, pyruvate dehydrogenase kinase 4 and carnitine palmitoyl transferase 1a, which are important for energy homeostasis in human skeletal muscle cells. GSK3787 (at 1 μM) also antagonizes agonist-induced expression of angiopoietin-like protein 4 in mouse fibroblasts, mouse keratinocytes, and human MCF-7, Huh7, and HepG2 cancer cell lines.[Cayman Chemical]

Biochem/physiol Actions

GSK3787 is an orally available selective irreversible Peroxisome Proliferator-Activated Receptor δ (PPARδ) antagonist (pIC50=6.6) with no measurable affinity for hPPARR or hPPARγ (pIC50<5). It acts by covalently modifying Cys249 within the ligand binding pocket, and has been shown to antagonize the induction of PPARδ-regulated target genes in skeletal muscle cells.

in vivo

GSK3787 has pharmacokinetic properties suitable for use as an in vivo PPARδ antagonist tool compound in mice. GSK3787 is administered intravenously (0.5 mg/kg) and orally (10 mg/kg) to male C57BL/6 mice. Mean clearance (CL) and volume of distribution at steady state (Vss) following iv administration are 39±11 (mL/min)/kg and 1.7±0.4 L/kg, respectively. Following oral administration, good exposure (Cmax=881±166 ng/mL, AUCinf=3343±332 h?ng/mL), half-life (2.7±1.1 h), and bioavailability (F=77±17%) are observed[1]. Oral administration of GSK3787 (10 mg/kg) leads to a serum Cmax of 2.2±0.4 μM in C57BL/6 male mice. Oral administration of GW0742 causes an increase in expression of Angptl4 and Adrp mRNA (known PPARβ/δ target genes) in wild-type mouse colon epithelium, and this effect is not found in Pparβ/δ-null mouse colon epithelium. Coadministration of GSK3787 with GW0742 effectively prevents the ligand-induced expression of both Angptl4 and Adrp mRNA in wild-type mouse colon epithelium, and this effect is not found in Pparβ/δ-null mouse colon epithelium. Oral administration of GSK3787 causes a modest increase in promoter occupancy of PPARβ/δ in the PPRE region of both the Angptl4 and Adrp genes, but coadministration of GSK3787 with GW0742 results in markedly less accumulation of PPARβ/δ in the PPRE region of both the Angptl4 and Adrp genes in wild-type mouse colon epithelium[2].

IC 50

PPARδ: 6.6 nM (pIC50)

storage

Store at +4°C

References

[1] BARRY G. SHEARER*. Identification and Characterization of 4-Chloro-N-(2-{[5-trifluoromethyl)-2-pyridyl]sulfonyl}ethyl)benzamide (GSK3787), a Selective and Irreversible Peroxisome Proliferator-Activated Receptor δ (PPARδ) Antagonist[J]. Journal of Medicinal Chemistry, 2010, 53 4: 1857-1861. DOI:10.1021/jm900464j
[2] PRAJAKTA S PALKAR. Cellular and pharmacological selectivity of the peroxisome proliferator-activated receptor-beta/delta antagonist GSK3787.[J]. Molecular Pharmacology, 2010, 78 3: 419-430. DOI:10.1124/mol.110.065508

4-Chloro-N-[2-[[5-(trifluoromethyl)-2-pyridinyl]sulfonyl]ethyl]benzamide Preparation Products And Raw materials

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Preparation Products

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View Lastest Price from 4-Chloro-N-[2-[[5-(trifluoromethyl)-2-pyridinyl]sulfonyl]ethyl]benzamide manufacturers

Henan Aochuang Chemical Co.,Ltd.
Product
4-Chloro-N-[2-[[5-(trifluoromethyl)-2-pyridinyl]sulfonyl]ethyl]benzamide 188591-46-0
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1Ton
Release date
2022-10-13
Career Henan Chemical Co
Product
4-Chloro-N-[2-[[5-(trifluoromethyl)-2-pyridinyl]sulfonyl]ethyl]benzamide 188591-46-0
Price
US $9.80/KG
Min. Order
1KG
Purity
99%
Supply Ability
100kg
Release date
2019-12-21

188591-46-0, 4-Chloro-N-[2-[[5-(trifluoromethyl)-2-pyridinyl]sulfonyl]ethyl]benzamideRelated Search:

KL001 Retinoic acid RET Kinase inhibitor 1 N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-3-methyl-6-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-indole-4-carboxamide GSK484 GSK583 GSK369796 GSK461364 GSK547 GSK-467 GSK481 GSK-3326595 KI16425 WY-14643 T0070907 GW0742 GW9662 Veliparib

  • 4-Chloro-N-[2-[[5-(trifluoromethyl)-2-pyridinyl]sulfonyl]ethyl]benzamide
  • GSK 3787
  • GSK3787/GSK-3787
  • Benzamide, 4-chloro-N-[2-[[5-(trifluoromethyl)-2-pyridinyl]sulfonyl]ethyl]-
  • 4-Chloro-N-[2-[[5-(trifluoromethyl)-2-pyridinyl]sulfonyl]ethyl]-benzamide GSK 3787
  • 4-Chloro-N-(2-{[5-trifluoromethyl)-2-pyridyl]sulfonyl}ethyl)benzamide
  • 4-chloro-N-(2-(5-(trifluoromethyl)pyridin-2-ylsulfonyl)ethyl)benzamide
  • GSK3787;GSK 3787;GSK-3787
  • PPARβ/δ Antagonist, GSK3787
  • GSK3787, >=98%
  • CS-710
  • PPARβ/δ Antagonist, GSK3787 - CAS 188591-46-0 - Calbiochem
  • 4-Chloro-N-[2-[[5-(trifluoromethyl)-2-pyridinyl]sulfonyl]ethyl]benzamide USP/EP/BP
  • GSK3787,airreversibleperoxisomeproliferator-activatedreceptorδ(PPARδ)antagonist
  • GSK-3787, PPARdelta antagonist
  • GSK3787, 10 mM in DMSO
  • PPARβ/δ Antagonist, GSK3787
  • GSK3787 ，S8025
  • 188591-46-0
  • 88591-46-0
  • Inhibitor
  • Inhibitors