ponesimod   Click here for help

GtoPdb Ligand ID: 9320

Synonyms: ACT-128800 | ACT128800 | Compound 8bo [PMID:20446681]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Ponesimod (ACT-128800) is an orally active sphingosine-1-phosphate (S1P) receptor modulator [1] in development as a disease-modifying therapy (DMT) for multiple sclerosis (MS). The compound is reported as a partial S1P4 and S1P5 receptor agonist, with maximum activity 18% and 42% of that induced by the endogenous ligand S1P (at 10μM ACT-128800) [1].
The INN record for ponesimod stipulates the (2R) stereoisomer ((2Z,5Z)-5-{3-chloro-4-[(2R)-2,3-dihydroxypropoxy]phenylmethylidene}-3-(2-methylphenyl)-2-(propylimino)-1,3-thiazolidin-4-one).
Selective SIP1 receptor agonists are being developed and investigated for immunomodulatory/immunosuppresant potential in autoimmune diseases.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 107.66
Molecular weight 460.12
XLogP 3.55
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES CCCN=C1SC(=Cc2ccc(c(c2)Cl)OCC(CO)O)C(=O)N1c1ccccc1C
Isomeric SMILES CCCN=C1S/C(=C\c2ccc(c(c2)Cl)OC[C@@H](CO)O)/C(=O)N1c1ccccc1C
InChI InChI=1S/C23H25ClN2O4S/c1-3-10-25-23-26(19-7-5-4-6-15(19)2)22(29)21(31-23)12-16-8-9-20(18(24)11-16)30-14-17(28)13-27/h4-9,11-12,17,27-28H,3,10,13-14H2,1-2H3/b21-12-,25-23?/t17-/m1/s1
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
9150 ponesimod
Synonyms Click here for help
ACT-128800 | ACT128800 | Compound 8bo [PMID:20446681]
Database Links Click here for help
CAS Registry No. 854107-55-4 (source: WHO INN record)
ChEMBL Ligand CHEMBL1096146
GtoPdb PubChem SID 318164839
PubChem CID 11363176
Search Google for chemical match using the InChIKey LPAUOXUZGSBGDU-ULCCENQXSA-N
Search Google for chemicals with the same backbone LPAUOXUZGSBGDU
Search PubMed clinical trials ponesimod
Search PubMed titles ponesimod
Search PubMed titles/abstracts ponesimod
Search UniChem for chemical match using the InChIKey LPAUOXUZGSBGDU-ULCCENQXSA-N
Search UniChem for chemicals with the same backbone LPAUOXUZGSBGDU