riluzole   Click here for help

GtoPdb Ligand ID: 2326

Synonyms: Rilutek® | RP-54274 | Tiglutik® (thickened oral suspension)
Approved drug PDB Ligand
riluzole is an approved drug (FDA (1995), EMA (1996))
Compound class: Synthetic organic
Comment: Marketed formulations may contain riluzole hydrochloride (PubChem CID 6419992).
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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

riluzole 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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Click here for structure editor
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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 2
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 76.38
Molecular weight 234.01
XLogP 2.28
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES Nc1nc2c(s1)cc(cc2)OC(F)(F)F
Isomeric SMILES Nc1nc2c(s1)cc(cc2)OC(F)(F)F
InChI InChI=1S/C8H5F3N2OS/c9-8(10,11)14-4-1-2-5-6(3-4)15-7(12)13-5/h1-3H,(H2,12,13)
InChI Key FTALBRSUTCGOEG-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Used in the treatment of amyotrophic lateral sclerosis (ALS, a.k.a. motor neurone disease or MND).
Riluzole, along with amiloride and fluoxetine are repurposing candidates as potential therapeutics for secondary progressive multiple sclerosis (SPMS or late MS), having already been shown to provide neuroprotective benefit [2,6-8]. A Phase 2 clinical trial in secondary progressive MS (NCT01910259, MS-SMART trial) is ongoing (Jan 2018).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The mechanism of action of riluzole is complex, and appears to include inhibition of glutamate release, inactivation of voltage-dependent sodium channels and interference with intracellular events that follow transmitter binding at excitatory amino acid receptors. Due to the complex nature of this drug's MMOA, we do not tag a primary drug target.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT01910259 MS-SMART: Multiple Sclerosis-Secondary Progressive Multi-Arm Randomisation Trial Phase 2 Interventional University College, London
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com
European Medicines Agency (EMA)