CS 2100Selective S1P1 agonist CAS# 913827-99-3 |
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Quality Control & MSDS
3D structure
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| Cas No. | 913827-99-3 | SDF | Download SDF |
| PubChem ID | 11977938 | Appearance | Powder |
| Formula | C25H23N3O4S | M.Wt | 461.53 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | Soluble to 5 mM in DMSO with gentle warming | ||
| Chemical Name | 1-[[4-ethyl-5-[5-(4-phenoxyphenyl)-1,2,4-oxadiazol-3-yl]thiophen-2-yl]methyl]azetidine-3-carboxylic acid | ||
| SMILES | CCC1=C(SC(=C1)CN2CC(C2)C(=O)O)C3=NOC(=N3)C4=CC=C(C=C4)OC5=CC=CC=C5 | ||
| Standard InChIKey | DWVJASHDNJMDNH-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C25H23N3O4S/c1-2-16-12-21(15-28-13-18(14-28)25(29)30)33-22(16)23-26-24(32-27-23)17-8-10-20(11-9-17)31-19-6-4-3-5-7-19/h3-12,18H,2,13-15H2,1H3,(H,29,30) | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Sphingosine-1-phosphate receptor 1 (S1P1) agonist (EC50 = 4.0 nM). Exhibits 5000-fold selectivity for human S1P1 over S1P3. Displays efficacy in a rat adjuvant-induced arthritis model. |
CS 2100 Dilution Calculator
CS 2100 Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.1667 mL | 10.8335 mL | 21.6671 mL | 43.3341 mL | 54.1677 mL |
| 5 mM | 0.4333 mL | 2.1667 mL | 4.3334 mL | 8.6668 mL | 10.8335 mL |
| 10 mM | 0.2167 mL | 1.0834 mL | 2.1667 mL | 4.3334 mL | 5.4168 mL |
| 50 mM | 0.0433 mL | 0.2167 mL | 0.4333 mL | 0.8667 mL | 1.0834 mL |
| 100 mM | 0.0217 mL | 0.1083 mL | 0.2167 mL | 0.4333 mL | 0.5417 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Synthesis and evaluation of CS-2100, a potent, orally active and S1P(3)- sparing S1P(1) agonist.[Pubmed:22405291]
Eur J Med Chem. 2012 May;51:92-8.
Modulators of sphingosine phosphate receptor-1 (S1P(1)) have recently been focused as a suppressant of autoimmunity. We have discovered a 4-ethylthiophene-based S1P(1) agonist 1-({4-Ethyl-5-[5-(4-phenoxyphenyl)-1,2,4-oxadiazol-3-yl]-2-thienyl}methyl)azetidi ne-3-carboxylic acid (CS-2100, 8) showing potent S1P(1) agonist activity against S1P(3) and an excellent in vivo potency. We report herein the synthesis of CS-2100 (8) and pharmacological effects such as S1P(1) and S1P(3) agonist activity in vitro, peripheral blood lymphocyte lowering effects and the suppressive effects on adjuvant-induced arthritis and experimental autoimmune encephalomyelitis (EAE) in animal models. The pharmacokinetic data were also reported. CS-2100 (8) had >5000-fold greater agonist activity for human S1P(1) (EC(50); 4.0 nM) relative to S1P(3) (EC(50); >20,000 nM). Following administration of single oral doses of 0.1 and 1 mg/kg of CS-2100 (8) in rats, lymphocyte counts decreased significantly, with a nadir at 8 and/or 12 h post-dose and recovery to vehicle control levels by 24-48 h post-dose. CS-2100 (8) is efficacious in the adjuvant-induced arthritis model in rats (ID(50); 0.44 mg/kg). In the EAE model compared to the vehicle-treated group, significant decreases in the cumulative EAE scores were observed for 0.3 and 1 mg/kg CS-2100 (8) groups in mice. While CS-2100 (8) showed potent efficacy in various animal disease models, it was also revealed that the central 1,2,4-oxadiazole ring of CS-2100 (8) was decomposed by enterobacteria in intestine of rats and monkeys, implicating the latent concern about an external susceptibility in its metabolic process in the upcoming clinical studies.
Discovery of CS-2100, a potent, orally active and S1P3-sparing S1P1 agonist.[Pubmed:22264485]
Bioorg Med Chem Lett. 2012 Feb 15;22(4):1788-92.
S1P(3)-sparing S1P(1) agonists have attracted attention as a suppressant of autoimmunity with reduced side effects. Our synthetic efforts and extensive SAR studies led to the discovery of 10b named CS-2100 with the EC(50) value of 4.0 nM for human S1P(1) and over 5000-fold selectivity against S1P(3). The in vivo immunosuppressive efficacy was evaluated in rats on host versus graft reaction and the ID(50) value was determined at 0.407mg/kg. The docking studies of CS-2100 with the homology model of S1P(1) and S1P(3) showed that the ethyl group on the thiophene ring of CS-2100 was sterically hindered by Phe263 in S1P(3), not in the case of Leu276 in S1P(1). This observation gives an explanation for the excellent S1P(3)-sparing characteristic of CS-2100.
