Etrasimod
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MedKoo CAT#: 407212

CAS#: 1206123-37-6 (free base)

Description: Etrasimod, also known as APD334, is a potent, centrally available, functional antagonists of the S1P1 receptor for use as next generation therapeutics for treating multiple sclerosis (MS) and other autoimmune diseases. APD334 has a favorable PK/PD profile, producing robust lymphocyte lowering at relatively low plasma concentrations in several preclinical species. APD334 was efficacious in a mouse experimental autoimmune encephalomyelitis (EAE) model of MS and a rat collagen induced arthritis (CIA) model and was found to have appreciable central exposure.

Chemical Structure

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Etrasimod
CAS# 1206123-37-6 (free base)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 407212
Name: Etrasimod
CAS#: 1206123-37-6 (free base)
Chemical Formula: C26H26F3NO3
Exact Mass: 457.19
Molecular Weight: 457.493
Elemental Analysis: C, 68.26; H, 5.73; F, 12.46; N, 3.06; O, 10.49

Price and Availability

Size Price Availability Quantity
5mg USD 385 2 weeks
10mg USD 715 2 weeks
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Related CAS #: 1206123-37-6 (free base)   1206123-97-8 (arginine)    

Synonym: APD334; APD-334; APD 334; Etrasimod.

IUPAC/Chemical Name: (R)-2-(7-((4-cyclopentyl-3-(trifluoromethyl)benzyl)oxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid

InChi Key: MVGWUTBTXDYMND-QGZVFWFLSA-N

InChi Code: 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

SMILES Code: O=C(O)C[C@H]1CCC2=C1NC3=C2C=C(OCC4=CC=C(C5CCCC5)C(C(F)(F)F)=C4)C=C3

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:
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Biological target: Etrasimod (APD334) is a potent, selective and orally available antagonist of the sphingosine-1-phosphate-1 (S1P1) receptor with an IC50 value of 1.88 nM in CHO cells.
In vitro activity: TBD
In vivo activity: APD334 was evaluated in a murine experimental autoimmune encephalomyelitis (EAE) model. Prophylactically, APD334 prevented the onset and severity of disease relative to vehicle up to day 25, at which time dosing was discontinued. Treatment began at day 18, by which time all animals had developed severe disease, and APD334 was administered out to day 37. APD334 reversed disease relative to vehicle and was similar to the efficacy observed with fingolimod. Reference: ACS Med Chem Lett. 2014 Nov 4;5(12):1313-7. https://pubmed.ncbi.nlm.nih.gov/25516790/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 29.0 63.39
DMSO:PBS (pH 7.2) (1:1) 0.5 1.09
DMF 30.0 65.57
Ethanol 12.5 27.32

Preparing Stock Solutions

The following data is based on the product molecular weight 457.49 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. 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. PMID: 25516790; PMCID: PMC4265817.
In vitro protocol: TBD
In vivo protocol: 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. PMID: 25516790; PMCID: PMC4265817.

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1: Sandborn WJ, Vermeire S, Peyrin-Biroulet L, Dubinsky MC, Panes J, Yarur A, Ritter T, Baert F, Schreiber S, Sloan S, Cataldi F, Shan K, Rabbat CJ, Chiorean M, Wolf DC, Sands BE, D'Haens G, Danese S, Goetsch M, Feagan BG. Etrasimod as induction and maintenance therapy for ulcerative colitis (ELEVATE): two randomised, double-blind, placebo-controlled, phase 3 studies. Lancet. 2023 Apr 8;401(10383):1159-1171. doi: 10.1016/S0140-6736(23)00061-2. Epub 2023 Mar 2. Erratum in: Lancet. 2023 Mar 25;401(10381):1000. PMID: 36871574.


2: Sandborn WJ, Peyrin-Biroulet L, Zhang J, Chiorean M, Vermeire S, Lee SD, Kühbacher T, Yacyshyn B, Cabell CH, Naik SU, Klassen P, Panés J. Efficacy and Safety of Etrasimod in a Phase 2 Randomized Trial of Patients With Ulcerative Colitis. Gastroenterology. 2020 Feb;158(3):550-561. doi: 10.1053/j.gastro.2019.10.035. Epub 2019 Nov 9. PMID: 31711921.


3: Wils P, Peyrin-Biroulet L. Etrasimod for the treatment of ulcerative colitis. Immunotherapy. 2023 Apr;15(5):311-321. doi: 10.2217/imt-2022-0255. Epub 2023 Feb 15. PMID: 36789612.


4: Vermeire S, Chiorean M, Panés J, Peyrin-Biroulet L, Zhang J, Sands BE, Lazin K, Klassen P, Naik SU, Cabell CH, Sandborn WJ. Long-term Safety and Efficacy of Etrasimod for Ulcerative Colitis: Results from the Open-label Extension of the OASIS Study. J Crohns Colitis. 2021 Jun 22;15(6):950-959. doi: 10.1093/ecco- jcc/jjab016. PMID: 33475734; PMCID: PMC8218705.


5: Ghoneim S. Etrasimod in Ulcerative Colitis. Gastroenterology. 2023 Nov;165(5):1302-1303. doi: 10.1053/j.gastro.2023.05.006. Epub 2023 May 12. PMID: 37178739.


6: Matsuoka K, Hibi T. Etrasimod for ulcerative colitis: evaluating phase III results. Nat Rev Gastroenterol Hepatol. 2023 May 23. doi: 10.1038/s41575-023-00793-0. Epub ahead of print. Erratum in: Nat Rev Gastroenterol Hepatol. 2023 Jul 3;: PMID: 37221319.


7: Hanzel J, Hulshoff MS, Grootjans J, D'Haens G. Emerging therapies for ulcerative colitis. Expert Rev Clin Immunol. 2022 May;18(5):513-524. doi: 10.1080/1744666X.2022.2069562. Epub 2022 May 1. PMID: 35477319.


8: Ramírez-Marín HA, Tosti A. Emerging drugs for the treatment of alopecia areata. Expert Opin Emerg Drugs. 2022 Dec;27(4):379-387. doi: 10.1080/14728214.2022.2149735. Epub 2022 Nov 21. PMID: 36408593.


9: Pérez-Jeldres T, Alvarez-Lobos M, Rivera-Nieves J. Targeting Sphingosine-1-Phosphate Signaling in Immune-Mediated Diseases: Beyond Multiple Sclerosis. Drugs. 2021 Jun;81(9):985-1002. doi: 10.1007/s40265-021-01528-8. Epub 2021 May 13. Erratum in: Drugs. 2021 Aug;81(12):1451. PMID: 33983615; PMCID: PMC8116828.


10: Tamarit-Sebastian S, Ferrer-Soler FM, Lucendo AJ. Current options and investigational drugs for the treatment of eosinophilic esophagitis. Expert Opin Investig Drugs. 2022 Feb;31(2):193-210. doi: 10.1080/13543784.2022.2033207. Epub 2022 Jan 31. PMID: 35072575.


11: Argollo M, Furfaro F, Gilardi D, Roda G, Allocca M, Peyrin-Biroulet L, Danese S. Modulation of sphingosine-1-phosphate in ulcerative colitis. Expert Opin Biol Ther. 2020 Apr;20(4):413-420. doi: 10.1080/14712598.2020.1732919. Epub 2020 Feb 25. PMID: 32093531.


12: Etrasimod 2 mg Once Daily as Treatment for Moderately to Severely Active Ulcerative Colitis: Results From the Phase 3 ELEVATE UC 52 and ELEVATE UC 12 Trials. Gastroenterol Hepatol (N Y). 2022 Jul;18(7 Suppl 2):10. PMID: 36756653; PMCID: PMC9671063.


13: Matsuoka K, Hibi T. Author Correction: Etrasimod for ulcerative colitis: evaluating phase III results. Nat Rev Gastroenterol Hepatol. 2023 Jul 3. doi: 10.1038/s41575-023-00817-9. Epub ahead of print. Erratum for: Nat Rev Gastroenterol Hepatol. 2023 May 23;: PMID: 37400695.


14: Meek PD, Hemstreet B. Emerging therapies for eosinophilic esophagitis. Pharmacotherapy. 2023 Apr;43(4):338-348. doi: 10.1002/phar.2783. Epub 2023 Mar 11. PMID: 36840634.


15: Lee CA, Oh DA, Tang Y, Yi P, Bashir M, English S, Croft M, Blackburn A, Bloom S, Gilder K, Grundy JS. Disposition and Mass Balance of Etrasimod in Healthy Subjects and In Vitro Determination of the Enzymes Responsible for Its Oxidative Metabolism. Clin Pharmacol Drug Dev. 2023 Jun;12(6):553-571. doi: 10.1002/cpdd.1255. Epub 2023 May 3. PMID: 37132407.


16: Chun J, Giovannoni G, Hunter SF. Sphingosine 1-phosphate Receptor Modulator Therapy for Multiple Sclerosis: Differential Downstream Receptor Signalling and Clinical Profile Effects. Drugs. 2021 Feb;81(2):207-231. doi: 10.1007/s40265-020-01431-8. PMID: 33289881; PMCID: PMC7932974.


17: Atreya R, Neurath MF. The sphingosine-1-phosphate receptor agonist etrasimod in ulcerative colitis. Lancet. 2023 Apr 8;401(10383):1132-1133. doi: 10.1016/S0140-6736(23)00228-3. Epub 2023 Mar 2. PMID: 36871570.


18: Pérez-Jeldres T, Tyler CJ, Boyer JD, Karuppuchamy T, Yarur A, Giles DA, Yeasmin S, Lundborg L, Sandborn WJ, Patel DR, Rivera-Nieves J. Targeting Cytokine Signaling and Lymphocyte Traffic via Small Molecules in Inflammatory Bowel Disease: JAK Inhibitors and S1PR Agonists. Front Pharmacol. 2019 Mar 13;10:212. doi: 10.3389/fphar.2019.00212. PMID: 30930775; PMCID: PMC6425155.


19: Silverberg JI, Bissonnette R, Kircik L, Murrell DF, Selfridge A, Liu K, Ahluwalia G, Guttman-Yassky E. Efficacy and safety of etrasimod, a sphingosine 1-phosphate receptor modulator, in adults with moderate-to-severe atopic dermatitis (ADVISE). J Eur Acad Dermatol Venereol. 2023 Jul;37(7):1366-1374. doi: 10.1111/jdv.18914. Epub 2023 Feb 13. PMID: 36695074.


20: Solitano V, Vuyyuru SK, MacDonald JK, Zayadi A, Parker CE, Narula N, Peyrin- Biroulet L, Danese S, Feagan BG, Singh S, Ma C, Jairath V. Efficacy and safety of advanced oral small molecules for inflammatory bowel disease: Systematic review and meta-analysis. J Crohns Colitis. 2023 Jun 15:jjad100. doi: 10.1093/ecco-jcc/jjad100. Epub ahead of print. PMID: 37317532.