SEW2871

Names

[ Name ]:
SEW2871

[Synonym ]:
1,2,4-Oxadiazole, 5-[4-phenyl-5-(trifluoromethyl)-2-thienyl]-3-[3-(trifluoromethyl)phenyl]-
5-[4-Phenyl-5-(trifluoromethyl)-2-thienyl]-3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole
5-[4-phenyl-5-(trifluoromethyl)thiophen-2-yl]-3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole
5-[4-Phenyl-5-(trifluoromethyl)-2-thienyl]-3-[3-(trifluoromethyl)phenyl]- 1,2,4-oxadiazole
5-[4-phenyl-5-(trifluoromethyl)thien-2-yl]-3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole

Biological Activity

[Description]:

SEW2871 is a highly selective, orally active S1P1 agonist with an EC50 of 13.8 nM. SEW2871 activates ERK, Akt, and Rac signaling pathways and induces S1P1 internalization and recycling. SEW2871 reduces lymphocyte numbers in blood and has therapeutic implications in contexts of diabetes, Alzheimer’s disease, liver fibrosis, and inflammatory responses[1][2].

[Target]

EC50: 13.8 nM (S1P1)[2]

[References]

[1]. Park SJ, et al. Sphingosine 1-Phosphate Receptor Modulators and Drug Discovery. Biomol Ther (Seoul). 2017 Jan 1;25(1):80-90.

[2]. Jo E, et al. S1P1-selective in vivo-active agonists from high-throughput screening: off-the-shelf chemical probes of receptor interactions, signaling, and fate. Chem Biol. 2005 Jun;12(6):703-15.

[3]. Dong J, et al. Oral treatment with SEW2871, a sphingosine-1-phosphate type 1 receptor agonist, ameliorates experimental colitis in interleukin-10 gene deficient mice. Clin Exp Immunol. 2014 Jul;177(1):94-101.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
490.3±55.0 °C at 760 mmHg

[ Melting Point ]:
94.5-95.3ºC

[ Molecular Formula ]:
C₂₀H₁₀F₆N₂OS

[ Molecular Weight ]:
440.362

[ Flash Point ]:
250.3±31.5 °C

[ Exact Mass ]:
440.041809

[ PSA ]:
67.16000

[ LogP ]:
8.42

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.535

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300

[ Precautionary Statements ]:
P264-P301 + P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T: Toxic;

[ Risk Phrases ]:
25

[ Safety Phrases ]:
45

[ RIDADR ]:
UN 2811 6.1/PG 3

Articles

Differential activation of receptors and signal pathways upon stimulation by different doses of sphingosine-1-phosphate in endothelial cells.

Exp. Physiol. 100(1) , 95-107, (2015)

What is the central question of this study? Why do different doses of sphingosine-1-phosphate (S1P) induce distinct biological effects in endothelial cells? What is the main finding and its importance...

Pharmacologic targeting of sphingosine-1-phosphate receptor 1 improves the renal microcirculation during sepsis in the mouse.

J. Pharmacol. Exp. Ther. 352(1) , 61-6, (2014)

Microvascular failure is hallmark of sepsis in humans and is recognized as a strong predictor of mortality. In the mouse subjected to cecal ligation and puncture (CLP) to induce a clinically relevant ...

Sphingosine Kinase 2 and Ceramide Transport as Key Targets of the Natural Flavonoid Luteolin to Induce Apoptosis in Colon Cancer Cells.

PLoS ONE 10 , e0143384, (2015)

The plant flavonoid luteolin exhibits different biological effects, including anticancer properties. Little is known on the molecular mechanisms underlying its actions in colorectal cancer (CRC). Here...