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R116

Sigma-Aldrich

Riluzole

≥98% (HPLC), solid, glutamate release inhibitor

Synonym(s):

2-Amino-6-(trifluoromethoxy)benzothiazole

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About This Item

Empirical Formula (Hill Notation):
C8H5F3N2OS
CAS Number:
1744-22-5
Molecular Weight:
234.20
MDL number:
MFCD00210213
UNSPSC Code:
12352200
PubChem Substance ID:
24278006
NACRES:
NA.77

product name

Riluzole, solid

form

solid

originator

Sanofi Aventis

SMILES string

Nc1nc2ccc(OC(F)(F)F)cc2s1

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

Gene Information

human ... SCN10A(6336) , SCN11A(11280) , SCN1A(6323) , SCN2A(6326) , SCN3A(6328) , SCN4A(6329) , SCN5A(6331) , SCN7A(6332) , SCN8A(6334) , SCN9A(6335)
rat ... Scnn1g(24768)

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Biochem/physiol Actions

Glutamate release inhibitor; anticonvulsant

Features and Benefits

This compound is featured on the Potassium Channels page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Sanofi Aventis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H300

Hazard Classifications

Acute Tox. 2 Oral

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificates of Analysis (COA)

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Maurizio Anzini et al.
Journal of medicinal chemistry, 53(2), 734-744 (2009-12-03)
A series of amidine, thiourea, and guanidine derivatives of 2-amino-6-(trifluoromethoxy)benzothiazole termed 2, 3, and 4, respectively, and structurally related to riluzole, a neuroprotective drug in many animal models of brain disease, have been synthesized. The biological activity of compounds 2a-e
Ryan S Phillips et al.
eLife, 11 (2022-07-08)
Previously our computational modeling studies (Phillips et al., 2019) proposed that neuronal persistent sodium current (INaP) and calcium-activated non-selective cation current (ICAN) are key biophysical factors that, respectively, generate inspiratory rhythm and burst pattern in the mammalian preBötzinger complex (preBötC)
Michael G Fehlings et al.
Journal of neurosurgery. Spine, 17(1 Suppl), 151-156 (2012-09-19)
In the immediate period after traumatic spinal cord injury (SCI) a variety of secondary injury mechanisms combine to gradually expand the initial lesion size, potentially leading to diminished neurological outcomes at long-term follow-up. Riluzole, a benzothiazole drug, which has neuroprotective
Gwen Schwartz et al.
Progress in brain research, 137, 177-190 (2002-11-21)
Traumatic spinal cord injury is a consequence of a primary mechanical insult and a sequence of progressive secondary pathophysiological events that confound efforts to mitigate neurological deficits. Pharmacotherapy aimed at reducing the secondary injury is limited by a narrow therapeutic
Mark C Bellingham
CNS neuroscience & therapeutics, 17(1), 4-31 (2010-03-20)
Amyotrophic lateral sclerosis (ALS) is a devastating and fatal neurodegenerative disease of adults which preferentially attacks the neuromotor system. Riluzole has been used as the only approved treatment for amyotrophic lateral sclerosis since 1995, but its mechanism(s) of action in
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