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
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 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
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 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
Bioactivity Comments
Riluzole blocks high voltage-activated (HVA) calcium channel currents in rat dorsal root ganglion neurons, in the order of P/Q- > N- >> L-type currents [5]. This mechanism may contribute towards riluzole's neuroprotective action, via the inhibition of excessive excitatory neurotransmitter release (e.g. glutamate) in ischemic conditions, which if left unopposed, leads to neuronal death.
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
K2P4.1 Hs Activator Positive - - 3x10-6 - 1x10-4 3
⤷ Conc range: 3x10-6 - 1x10-4 M [3]
KCa2.3 Rn Activator Agonist - - 3x10-6 - 1x10-5 4
⤷ Conc range: 3x10-6 - 1x10-5 M [4]
TRPC5 Hs Activator Activation 5.0 pEC50 - 9
⤷ pEC50 5.0 (EC50 9.2x10-6 M) [9]
KCa2.3 Hs Activator Agonist 4.9 pEC50 - 10
⤷ pEC50 4.9 (EC50 1.25x10-5 M) [10]
KCa2.2 Rn Activator Agonist 4.9 pEC50 - 10
⤷ pEC50 4.9 (EC50 1.28x10-5 M) [10]
KCa2.1 Hs Activator Agonist 4.7 pEC50 - 10
⤷ pEC50 4.7 (EC50 2.1x10-5 M) [10]
Voltage: -80.0 mV
KCa3.1 Hs Activator - 5.7 pIC50 - 10
⤷ pIC50 5.7 [10]
Kv11.1 Hs Channel blocker Inhibition 4.3 pIC50 - 10
⤷ pIC50 4.3 (IC50 5x10-5 M) [10]
Description: Inhibition of currents via human Kv11.1 (hERG) channels expressed in HEK293 cells in whole-cell patch-clamp experiments.
Kv4.3 Rn Gating inhibitor - 3.9 pIC50 - 1
⤷ pIC50 3.9 [1]
Kv4.2 Rn Channel blocker - 3.9 pIC50 - 10
⤷ pIC50 3.9 (IC50 1.3x10-4 M) [10]
Description: Inhibition of currents via rat Kv4.2 channels expressed in LTK cells in whole-cell patch-clamp experiments.
K2P2.1 Hs Activator - - - -
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K2P4.1 Hs Activator - - - - 3
⤷ studied at 1-100 µM [3]