fingolimod   

GtoPdb Ligand ID: 2407

Synonyms: FTY-720 | FTY720 | Gilenya®
fingolimod is an approved drug (FDA (2010), EMA (2011))
Compound class: Synthetic organic
Comment: Fingolimod was the first approved oral therapy for multiple sclerosis.
Fingolimod FTY720) is the prodrug of a S1P receptor agonist [4]. When fingolimod binds to S1P1R the complex is internalised and then degraded, so the drug acts as an indirect functional antagonist by preventing intracellular signalling. It acts as a lymphocyte migration inhibitor, promoting lymphocyte retention in lymphoid tissues, whilst preserving lymphocyte function [7]. Clinical efficacy results from modulation of S1P1 receptors. Adverse effects are thought to be caused by fingolimod's off-target effects on other S1P receptor subtypes.
Selective S1P1R agonists are being developed and investigated for immunomodulatory/immunosuppresant potential.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 3
Rotatable bonds 12
Topological polar surface area 66.48
Molecular weight 307.25
XLogP 4.59
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CCCCCCCCc1ccc(cc1)CCC(CO)(CO)N
Isomeric SMILES CCCCCCCCc1ccc(cc1)CCC(CO)(CO)N
InChI InChI=1S/C19H33NO2/c1-2-3-4-5-6-7-8-17-9-11-18(12-10-17)13-14-19(20,15-21)16-22/h9-12,21-22H,2-8,13-16,20H2,1H3
InChI Key KKGQTZUTZRNORY-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (2010), EMA (2011))
Is prodrug? Yes
Active form fingolimod-phosphate
IUPAC Name
2-amino-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol
International Nonproprietary Names
INN number INN
8341 fingolimod
Synonyms
FTY-720 | FTY720 | Gilenya®
Database Links
BindingDB Ligand 50158336
CAS Registry No. 162359-55-9 (source: Scifinder)
ChEBI CHEBI:63115
ChEMBL Ligand CHEMBL314854
DrugBank Ligand DB08868
DrugCentral Ligand 4167
GtoPdb PubChem SID 135650261
PubChem CID 107970
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Wikipedia Fingolimod

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Tocris
FTY 720
Cat. No. 6176