siponimod   

GtoPdb Ligand ID: 9289

Synonyms: BAF-312 | BAF312 | compound 32 [PMID: 24900670] | Mayzent®
siponimod is an approved drug (FDA (2019), EMA (2020))
Compound class: Synthetic organic
Comment: Pharmacologically, siponimod (BAF312) is a selective sphingosine-1-phosphate (S1P) receptor agonist, with some selectivity for the S1P1 and S1P5 receptor isoforms [8]. It is an orally active drug. Siponimod was developed by Novartis for secondary progressive multiple sclerosis (SPMS), originally as a back-up compound for fingolimod. Compared to fingolimod it has more favourable pharmacokinetics.
Novartis announced positive results from their Phase 3 EXPAND study (BAF312 versus placebo) in SPMS (August 2016- link to announcement here).
The SIPR signalling pathway is important in autoimmune biology.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 10
Topological polar surface area 62.13
Molecular weight 516.26
XLogP 8
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CCc1cc(ccc1CN1CC(C1)C(=O)O)C(=NOCc1ccc(c(c1)C(F)(F)F)C1CCCCC1)C
Isomeric SMILES CCc1cc(ccc1CN1CC(C1)C(=O)O)/C(=N/OCc1ccc(c(c1)C(F)(F)F)C1CCCCC1)/C
InChI InChI=1S/C29H35F3N2O3/c1-3-21-14-23(10-11-24(21)15-34-16-25(17-34)28(35)36)19(2)33-37-18-20-9-12-26(22-7-5-4-6-8-22)27(13-20)29(30,31)32/h9-14,22,25H,3-8,15-18H2,1-2H3,(H,35,36)/b33-19+
InChI Key KIHYPELVXPAIDH-HNSNBQBZSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (2019), EMA (2020))
IUPAC Name
1-[[4-[(E)-N-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]-C-methylcarbonimidoyl]-2-ethylphenyl]methyl]azetidine-3-carboxylic acid
International Nonproprietary Names
INN number INN
9491 siponimod
Synonyms
BAF-312 | BAF312 | compound 32 [PMID: 24900670] | Mayzent®
Database Links
CAS Registry No. 1230487-00-9 (source: WHO INN record)
ChEMBL Ligand CHEMBL2336071
DrugCentral Ligand 5326
GtoPdb PubChem SID 318164808
PubChem CID 44599207
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