etrasimod   Click here for help

GtoPdb Ligand ID: 9331

Synonyms: APD-334 | APD334 | APD334-003 | compound 4 [PMID: 25516790] | Velsipity®
Approved drug Immunopharmacology Ligand
etrasimod is an approved drug (FDA (2023), EMA (2024))
Compound class: Synthetic organic
Comment: Etrasimod (APD334) is a centrally available, selective S1P1 receptor agonist [2]. APD334 is being investigated for clinical efficacy as an immunosuppressant for the treatment of autoimmune diseases.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 62.32
Molecular weight 457.19
XLogP 6.56
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES OC(=O)CC1CCc2c1[nH]c1c2cc(cc1)OCc1ccc(c(c1)C(F)(F)F)C1CCCC1
Isomeric SMILES OC(=O)C[C@H]1CCc2c1[nH]c1c2cc(cc1)OCc1ccc(c(c1)C(F)(F)F)C1CCCC1
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
InChI Key MVGWUTBTXDYMND-QGZVFWFLSA-N
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Summary of Clinical Use Click here for help
Etrasimod (APD334) was advanced to clinical trial in patients with moderately to severely active ulcerative colitis (see NCT02536404). It was approved for this indication by the FDA in October 2023 [4].
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Etrasimod (APD334) behaves as a functional antagonist of S1P1 receptors in that sustained agonist activity results in internalization and proteasomal degradation, and hence reduced expression of lymphocyte S1P1 receptors.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT02536404 Extension Study of APD334-003 in Patients With Moderately to Severely Active Ulcerative Colitis Phase 2 Interventional Arena Pharmaceuticals