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MedKoo Cat#: 522585 | Name: SEW2871
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

SEW2871 is a S1P1 agonist (sphingosine-1-phosphate type 1 receptor agonist). SEW2871 improves cognitive function in Alzheimer's disease model rats. SEW2871 prolongs heterotopic heart allograft survival in mice. SEW2871 reverse the inhibitory effect of S1P on natural killer cell mediated lysis of K562 tumor cells and dendritic cells but not on cytokine release. SEW2871 prolongs heterotopic heart allograft survival in mice.

Chemical Structure

SEW2871
SEW2871
CAS# 256414-75-2

Theoretical Analysis

MedKoo Cat#: 522585

Name: SEW2871

CAS#: 256414-75-2

Chemical Formula: C20H10F6N2OS

Exact Mass: 440.0418

Molecular Weight: 440.36

Elemental Analysis: C, 54.55; H, 2.29; F, 25.89; N, 6.36; O, 3.63; S, 7.28

Price and Availability

Size Price Availability Quantity
10mg USD 210.00 2 Weeks
25mg USD 425.00 2 Weeks
50mg USD 725.00 2 Weeks
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Related CAS #
No Data
Synonym
SEW2871; SEW2871; SEW2871.
IUPAC/Chemical Name
5-(4-phenyl-5-(trifluoromethyl)thiophen-2-yl)-3-(3-(trifluoromethyl)phenyl)-1,2,4-oxadiazole
InChi Key
OYMNPJXKQVTQTR-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H10F6N2OS/c21-19(22,23)13-8-4-7-12(9-13)17-27-18(29-28-17)15-10-14(11-5-2-1-3-6-11)16(30-15)20(24,25)26/h1-10H
SMILES Code
FC(C1=CC(C2=NOC(C3=CC(C4=CC=CC=C4)=C(C(F)(F)F)S3)=N2)=CC=C1)(F)F
Appearance
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, 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
View handling instruction
Biological target:
SEW2871 is an 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.
In vitro activity:
FTY720 and SEW2871 may have potential applications as prophylactic or therapeutic drugs for cancer treatment, based on their ability to counteract the effects of S1P in the context of NK cell interactions with tumor cells and DCs. S1P protected K562 cells and iDCs from NK cell lysis, and this protective effect was reversed by FTY720 and SEW2871, which are antagonists of S1P(1). Reference: Cancer Immunol Immunother. 2010 Apr;59(4):575-86. https://pubmed.ncbi.nlm.nih.gov/19823820/
In vivo activity:
Activating S1PR1 by SEW2871 could improve tight junctions (TJs) via inhibiting ERK1/2/LKB1/AMPK signaling pathway in the ileum of ANIT-treated mice and ANIT-cultured Caco-2 cells. SEW2871 regained ileum TJs by activating S1PR1 in the epithelial cells of ileum mucosa and recovered ileum barrier function. Along with the down-regulated levels of serum LPS, SEW2871 improved liver function and relieved hepatitis via blocking TLR4/MyD88/NF-kB signaling pathway in ANIT-treated mice. Reference: Int Immunopharmacol. 2023 Dec;125(Pt A):111150. https://pubmed.ncbi.nlm.nih.gov/37924700/
Solvent mg/mL mM comments
Solubility
DMSO 25.0 56.77
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 440.36 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. Rolin J, Sand KL, Knudsen E, Maghazachi AA. FTY720 and SEW2871 reverse the inhibitory effect of S1P on natural killer cell mediated lysis of K562 tumor cells and dendritic cells but not on cytokine release. Cancer Immunol Immunother. 2010 Apr;59(4):575-86. doi: 10.1007/s00262-009-0775-7. Epub 2009 Oct 13. PMID: 19823820. 2. Yang T, Li L, Pang J, Heng C, Wei C, Wang X, Xia Z, Huang X, Zhang L, Jiang Z. Modulating intestinal barrier function by sphingosine-1-phosphate receptor 1 specific agonist SEW2871 attenuated ANIT-induced cholestatic hepatitis via the gut-liver axis. Int Immunopharmacol. 2023 Dec;125(Pt A):111150. doi: 10.1016/j.intimp.2023.111150. Epub 2023 Nov 3. PMID: 37924700. 3. Dong J, Wang H, Wu G, Zhao J, Zhang L, Zuo L, Zhu W, Gong J, Li Y, Gu L, Li J. 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. doi: 10.1111/cei.12304. PMID: 24611843; PMCID: PMC4089158.
In vitro protocol:
1. Rolin J, Sand KL, Knudsen E, Maghazachi AA. FTY720 and SEW2871 reverse the inhibitory effect of S1P on natural killer cell mediated lysis of K562 tumor cells and dendritic cells but not on cytokine release. Cancer Immunol Immunother. 2010 Apr;59(4):575-86. doi: 10.1007/s00262-009-0775-7. Epub 2009 Oct 13. PMID: 19823820.
In vivo protocol:
1. Yang T, Li L, Pang J, Heng C, Wei C, Wang X, Xia Z, Huang X, Zhang L, Jiang Z. Modulating intestinal barrier function by sphingosine-1-phosphate receptor 1 specific agonist SEW2871 attenuated ANIT-induced cholestatic hepatitis via the gut-liver axis. Int Immunopharmacol. 2023 Dec;125(Pt A):111150. doi: 10.1016/j.intimp.2023.111150. Epub 2023 Nov 3. PMID: 37924700. 2. Dong J, Wang H, Wu G, Zhao J, Zhang L, Zuo L, Zhu W, Gong J, Li Y, Gu L, Li J. 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. doi: 10.1111/cei.12304. PMID: 24611843; PMCID: PMC4089158.
1: Zou L, Ke L, Wu C, Tong Z, Li W, Li N, Li J. SEW2871 Alleviates the Severity of Caerulein-Induced Acute Pancreatitis in Mice. Biol Pharm Bull. 2015;38(7):1012-9. doi: 10.1248/bpb.b15-00043. Epub 2015 May 2. PubMed PMID: 25948069. 2: Ni Q, Yuan B, Liu T, Lan F, Luo X, Lu X, Huang P, Dai L, Jin X, Yin H. Sphingosine-1-phosphate receptor 1 agonist SEW2871 prolongs heterotopic heart allograft survival in mice. Int Immunopharmacol. 2015 May;26(1):37-42. doi: 10.1016/j.intimp.2015.03.004. Epub 2015 Mar 13. PubMed PMID: 25776899. 3: Dong J, Wang H, Zhao J, Sun J, Zhang T, Zuo L, Zhu W, Gong J, Li Y, Gu L, Li J. SEW2871 protects from experimental colitis through reduced epithelial cell apoptosis and improved barrier function in interleukin-10 gene-deficient mice. Immunol Res. 2015 Mar;61(3):303-11. doi: 10.1007/s12026-015-8625-5. PubMed PMID: 25588868. 4: Dong J, Wang H, Wu G, Zhao J, Zhang L, Zuo L, Zhu W, Gong J, Li Y, Gu L, Li J. 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. doi: 10.1111/cei.12304. PubMed PMID: 24611843; PubMed Central PMCID: PMC4089158. 5: Asle-Rousta M, Oryan S, Ahmadiani A, Rahnema M. Activation of sphingosine 1-phosphate receptor-1 by SEW2871 improves cognitive function in Alzheimer's disease model rats. EXCLI J. 2013 Jun 3;12:449-61. eCollection 2013. PubMed PMID: 26417237; PubMed Central PMCID: PMC4566907. 6: Rolin J, Sand KL, Knudsen E, Maghazachi AA. FTY720 and SEW2871 reverse the inhibitory effect of S1P on natural killer cell mediated lysis of K562 tumor cells and dendritic cells but not on cytokine release. Cancer Immunol Immunother. 2010 Apr;59(4):575-86. doi: 10.1007/s00262-009-0775-7. Epub 2009 Oct 13. PubMed PMID: 19823820. 7: Tsukada YT, Sanna MG, Rosen H, Gottlieb RA. S1P1-selective agonist SEW2871 exacerbates reperfusion arrhythmias. J Cardiovasc Pharmacol. 2007 Dec;50(6):660-9. PubMed PMID: 18091583. 8: Lien YH, Yong KC, Cho C, Igarashi S, Lai LW. S1P(1)-selective agonist, SEW2871, ameliorates ischemic acute renal failure. Kidney Int. 2006 May;69(9):1601-8. PubMed PMID: 16572108.