ponesimod

Ligand id: 9320

Name: ponesimod

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 107.66
Molecular weight 460.12
XLogP 4.26
No. Lipinski's rules broken 0

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
IUPAC Name
(5Z)-5-[[3-chloro-4-[(2R)-2,3-dihydroxypropoxy]phenyl]methylidene]-3-(2-methylphenyl)-2-propylimino-1,3-thiazolidin-4-one
International Nonproprietary Names
INN number INN
9150 ponesimod
Synonyms
ACT-128800 | ACT128800 | Compound 8bo [PMID:20446681]
Database Links
CAS Registry No. 854107-55-4 (source: WHO INN record)
ChEMBL Ligand CHEMBL1096146
PubChem CID 11363176
Search Google for chemical match using the InChIKey LPAUOXUZGSBGDU-ULCCENQXSA-N
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Comments
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.