etrasimod   Click here for help

GtoPdb Ligand ID: 9331

Synonyms: APD-334 | APD334 | APD334-003 | compound 4 [PMID: 25516790]
Immunopharmacology Ligand
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
Bioactivity Comments
In in vitro β-arrestin recruitment assays APD334 has no measurable activity at S1P2 and S1P3 receptors, and low activity at S1P4 receptors [2]. EC50 for S1P5 receptors is around 4-fold lower than for the primary target S1P1. APD334 has similar ability to induce cAMP accumulation across S1P1 receptors from species including human, rat, mouse, monkey and dog. APD334 produces robust lymphocyte lowering in several preclinical species, and is effective in a mouse experimental autoimmune encephalomyelitis (EAE) model of multiple sclerosis [2].
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
S1P1 receptor Primary target of this compound Hs Agonist Agonist 8.2 – 9.2 pEC50 - 2-3
pEC50 9.2 (EC50 5.7x10-10 M) [3]
pEC50 8.2 (EC50 6.1x10-9 M) [2]
Description: In a β-arrestin recruitment assay.
S1P5 receptor Hs Agonist Agonist 7.6 pEC50 - 2
pEC50 7.6 (EC50 2.44x10-8 M) [2]
Description: In a β-arrestin recruitment assay.
S1P4 receptor Hs Agonist Agonist 6.8 pEC50 - 1-2
pEC50 6.8 (EC50 1.47x10-7 M) [1-2]
Description: In a β-arrestin recruitment assay.