fingolimod

Ligand id: 2407

Name: fingolimod

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Structure and Physico-chemical Properties

2D Structure
Calculated 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 6.61
No. Lipinski's rules broken 2

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (2010))
Is prodrug? Yes
Active form FTY720-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
PubChem CID 107970
Search Google for chemical match using the InChIKey KKGQTZUTZRNORY-UHFFFAOYSA-N
Search Google for chemicals with the same backbone KKGQTZUTZRNORY
Search PubMed clinical trials fingolimod
Search PubMed titles fingolimod
Search PubMed titles/abstracts fingolimod
Search UniChem for chemical match using the InChIKey KKGQTZUTZRNORY-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone KKGQTZUTZRNORY
Wikipedia Fingolimod
Comments
Fingolimod was the first approved oral therapy for multiple sclerosis.
Fingolimod FTY720) is the prodrug of a SIP receptor agonist [4]. When fingolimod binds to SIP1 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 subtype 1 S1P (S1P1) receptors. Adverse effects are thought to be caused by fingolimod's off-target effects on othe SIP receptor subtypes.
Selective SIP1 receptor agonists are being developed and investigated for immunomodulatory/immunosuppresant potential.