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
Immunopharmacology Disease
Disease X-Refs Comment References
Pyoderma gangrenosum Disease Ontology: DOID:8553
Orphanet: ORPHA48104
Phase 2 clinical candidate for this condition (see NCT03072953).
Inflammatory bowel disease Disease Ontology: DOID:0050589
OMIM: 266600
Phase 2 clinical candidate for IBD patients (including UC and Crohn's disease) with active skin manifestations (see proof of concept study NCT03139032).