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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2D Structure
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Physico-chemical Properties
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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
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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)
1. Ahn HS, Kim SE, Jang HJ, Kim MJ, Rhie DJ, Yoon SH, Jo YH, Kim MS, Sung KW, Hahn SJ. (2006)
Interaction of riluzole with the closed inactivated state of Kv4.3 channels.
J Pharmacol Exp Ther, 319 (1): 323-31. [PMID:16815868]
2. Arun T, Tomassini V, Sbardella E, de Ruiter MB, Matthews L, Leite MI, Gelineau-Morel R, Cavey A, Vergo S, Craner M et al.. (2013)
Targeting ASIC1 in primary progressive multiple sclerosis: evidence of neuroprotection with amiloride.
Brain, 136 (Pt 1): 106-15. [PMID:23365093]
3. Duprat F, Lesage F, Patel AJ, Fink M, Romey G, Lazdunski M. (2000)
The neuroprotective agent riluzole activates the two P domain K(+) channels TREK-1 and TRAAK.
Mol Pharmacol, 57 (5): 906-12. [PMID:10779373]
4. Grunnet M, Jespersen T, Angelo K, Frøkjaer-Jensen C, Klaerke DA, Olesen SP, Jensen BS. (2001)
Pharmacological modulation of SK3 channels.
Neuropharmacology, 40 (7): 879-87. [PMID:11378158]
5. Huang CS, Song JH, Nagata K, Yeh JZ, Narahashi T. (1997)
Effects of the neuroprotective agent riluzole on the high voltage-activated calcium channels of rat dorsal root ganglion neurons.
J Pharmacol Exp Ther, 282 (3): 1280-90. [PMID:9316836]
6. Killestein J, Kalkers NF, Polman CH. (2005)
Glutamate inhibition in MS: the neuroprotective properties of riluzole.
J Neurol Sci, 233 (1-2): 113-5. [PMID:15949499]
7. Mostert J, Heersema T, Mahajan M, Van Der Grond J, Van Buchem MA, De Keyser J. (2013)
The effect of fluoxetine on progression in progressive multiple sclerosis: a double-blind, randomized, placebo-controlled trial.
ISRN Neurol, 2013: 370943. [PMID:23984093]
8. Mostert JP, Koch MW, Heerings M, Heersema DJ, De Keyser J. (2008)
Therapeutic potential of fluoxetine in neurological disorders.
CNS Neurosci Ther, 14 (2): 153-64. [PMID:18482027]
9. Richter JM, Schaefer M, Hill K. (2014)
Riluzole activates TRPC5 channels independently of PLC activity.
Br J Pharmacol, 171 (1): 158-70. [PMID:24117252]
10. Sankaranarayanan A, Raman G, Busch C, Schultz T, Zimin PI, Hoyer J, Köhler R, Wulff H. (2009)
Naphtho[1,2-d]thiazol-2-ylamine (SKA-31), a new activator of KCa2 and KCa3.1 potassium channels, potentiates the endothelium-derived hyperpolarizing factor response and lowers blood pressure.
Mol Pharmacol, 75 (2): 281-95. [PMID:18955585]