Etrasimod
Etrasimod ( APD334 ) is a potent, once-daily, oral, highly selective sphingosine 1-phosphate (S1P1) receptor modulator. Etrasimod provides systemic and local effects on specific immune cell types and has the potential to treat multiple immune-mediated inflammatory diseases including ulcerative colitis, Crohn’s disease, and atopic dermatitis.
For research use only. We do not sell to patients.
Chemical Information
| Name | Etrasimod |
|---|---|
| Iupac Chemical Name | (R)-2-(7-((4-cyclopentyl-3-(trifluoromethyl)benzyl)oxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid |
| Synonyms | APD334 ; APD-334 ; APD 334 ; Etrasimod |
| Molecular Formula | C26H26F3NO3 |
| Molecular Weight | 457.49321 |
| Smile | C1(CCCC1)C1=C(C=C(COC2=CC=3C4=C(NC3C=C2)[C@H](CC4)CC(=O)O)C=C1)C(F)(F)F |
| InChiKey | MVGWUTBTXDYMND-QGZVFWFLSA-N |
| InChi | InChI=1S/C26H26F3NO3/c27-26(28,29)22-11-15(5-8-19(22)16-3-1-2-4-16)14-33-18-7-10-23-21(13-18)20-9-6-17(12-24(31)32)25(20)30-23/h5,7-8,10-11,13,16-17,30H,1-4,6,9,12,14H2,(H,31,32)/t17-/m1/s1 |
| CAS Number | 1206123-37-6 |
| Related CAS | 1206123-37-6 |
Ordering Information
| Packaging | Price | Availability | Purity | Shipping Time |
|---|---|---|---|---|
| Bulk | Enquiry | Enquiry | Enquiry |
| Formulation | Off-white solid |
|---|---|
| Purity | 99.73% |
| Storage | 3 years -20ºCpowder |
| Solubility | Soluble in DMSO |
| Handling | Avoid inhalation, contact with eyes and skin. Avoid dust and aerosol formation. Use only in areas with appropriate exhaust ventilation. |
| Shipping Condition | Shipped under ambient temperature as non-hazardous chemical. |
| HS Code |
| Targets | S1P receptor modulator |
|---|---|
| Mechanism | Etrasimod is an oral, selective S1P1, S1P4, and S1P5 receptor modulator. Sphingosine 1-phosphate (S1P) is a membrane-derived lysophospholipid signaling molecule involved in regulation of multiple physiologic and pathophysiologic processes, mediated through the 5 isoforms of the G protein–coupled S1P receptor (S1P1 through S1P5). |
| Cell study | |
| Animal study | Etrasimod (1 mg/kg, i.v.) decreases peripheral lymphocytes in mouse, rat, dog, and monkey (IC50s = 101, 51, 58, and 98 nM, respectively). It delays or prevents the onset and severity of murine experimental autoimmune encephalomyelitis (EAE) when administered at 0.3, 1, or 3 mg/kg. It also leads to lower EAE disease scores relative to vehicle when administered after disease onset and is efficacious in a rat model of collagen-induced arthritis. |
| Clinical study | Phase 3 |
1: Buzard DJ, Kim SH, Lopez L, Kawasaki A, Zhu X, Moody J, Thoresen L, Calderon
I, Ullman B, Han S, Lehmann J, Gharbaoui T, Sengupta D, Calvano L, Montalban AG,
Ma YA, Sage C, Gao Y, Semple G, Edwards J, Barden J, Morgan M, Chen W, Usmani K,
Chen C, Sadeque A, Christopher RJ, Thatte J, Fu L, Solomon M, Mills D, Whelan K,
Al-Shamma H, Gatlin J, Le M, Gaidarov I, Anthony T, Unett DJ, Blackburn A, Rueter
J, Stirn S, Behan DP, Jones RM. Discovery of APD334: Design of a Clinical Stage
Functional Antagonist of the Sphingosine-1-phosphate-1 Receptor. ACS Med Chem
Lett. 2014 Nov 4;5(12):1313-7. doi: 10.1021/ml500389m. eCollection 2014 Dec 11.
PubMed PMID: 25516790; PubMed Central PMCID: PMC4265817.
Chemical Structure
