Ligand id: 2407

Name: fingolimod

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Structure and Physico-chemical Properties

2D Structure
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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 4.59
No. Lipinski's rules broken 1

Molecular properties generated using the CDK

Compound class Synthetic organic
Approved drug? Yes (FDA (2010), EMA (2011))
Is prodrug? Yes
Active form fingolimod-phosphate
International Nonproprietary Names
INN number INN
8341 fingolimod
FTY-720 | FTY720 | Gilenya®
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.
Database Links
BindingDB Ligand 50158336
CAS Registry No. 162359-55-9 (source: Scifinder)
ChEMBL Ligand CHEMBL314854
DrugBank Ligand DB08868
GtoPdb PubChem SID 135650261
PubChem CID 107970
Search Google for chemical match using the InChIKey KKGQTZUTZRNORY-UHFFFAOYSA-N
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Search PubMed clinical trials fingolimod
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Search UniChem for chemical match using the InChIKey KKGQTZUTZRNORY-UHFFFAOYSA-N
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Wikipedia Fingolimod