siponimod   Click here for help

GtoPdb Ligand ID: 9289

Synonyms: BAF-312 | BAF312 | compound 32 [PMID: 24900670] | Mayzent®
Approved drug PDB Ligand Immunopharmacology Ligand
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.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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 Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2019), EMA (2020))
IUPAC Name Click here for help
1-[[4-[(E)-N-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]-C-methylcarbonimidoyl]-2-ethylphenyl]methyl]azetidine-3-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
9491 siponimod
Synonyms Click here for help
BAF-312 | BAF312 | compound 32 [PMID: 24900670] | Mayzent®
Database Links Click here for help
Specialist databases
GPCRdb Ligand siponimod
Reactome Drug Reactome logo R-ALL-9678745
Reactome Reaction Reactome logo R-HSA-9678854
Other databases
CAS Registry No. 1230487-00-9 (source: WHO INN record)
ChEMBL Ligand CHEMBL2336071
DrugCentral Ligand 5326
GtoPdb PubChem SID 318164808
PubChem CID 44599207
RCSB PDB Ligand J8C
Search Google for chemical match using the InChIKey KIHYPELVXPAIDH-HNSNBQBZSA-N
Search Google for chemicals with the same backbone KIHYPELVXPAIDH
Search PubMed clinical trials siponimod
Search PubMed titles siponimod
Search PubMed titles/abstracts siponimod
UniChem Compound Search for chemical match using the InChIKey KIHYPELVXPAIDH-HNSNBQBZSA-N
UniChem Connectivity Search for chemical match using the InChIKey KIHYPELVXPAIDH-HNSNBQBZSA-N