fingolimod   Click here for help

GtoPdb Ligand ID: 2407

Synonyms: FTY-720 | FTY720 | Gilenya®
Approved drug Immunopharmacology Ligand
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.

COVID-19: Fingolimod has been evaluated in a small study of patients with moderate to severe COVID-19 (n=19), with mixed results [10]. Three days of treatment (in addition to standard interventions) did not reduce intubation or mortality rates, compared to placebo controls (n= 21), but it did signficantly reduce the re-admission rate.
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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

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View more information in the IUPHAR Pharmacology Education Project: fingolimod

fingolimod is commercially available from our sponsors

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 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
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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 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 Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2010), EMA (2011))
Is prodrug? Yes
Active form fingolimod-phosphate
IUPAC Name Click here for help
2-amino-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol
International Nonproprietary Names Click here for help
INN number INN
8341 fingolimod
Synonyms Click here for help
FTY-720 | FTY720 | Gilenya®
Database Links Click here for help
Specialist databases
GPCRdb Ligand fingolimod
Reactome Drug Reactome logo R-ALL-9678808
Reactome Reaction Reactome logo R-HSA-9678854
Other databases
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
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
UniChem Compound Search for chemical match using the InChIKey KKGQTZUTZRNORY-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey KKGQTZUTZRNORY-UHFFFAOYSA-N
Wikipedia Fingolimod

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Tocris
FTY 720 (links to external site)
Cat. No. 6176