Riluzole Chemical Properties

Melting point:

116-118°C

Boiling point:

296.3±50.0 °C(Predicted)

Density 

1.572±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO: ≥25 mg/mL

form 

solid

pka

2.96±0.10(Predicted)

color 

white

Merck 

14,8223

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 2 months.

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)

InChIKey

FTALBRSUTCGOEG-UHFFFAOYSA-N

SMILES

S1C2=CC(OC(F)(F)F)=CC=C2N=C1N

Safety Information

Hazard Codes 

T,Xi

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

DL2830000

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

II

HS Code 

29342000

Toxicity

LD50 in mice (mg/kg): 46 i.p.; 67 orally (Mizoule)

MSDS

• Language:English Provider:6-(Trifluoromethoxy)-1,3-benzothiazol-2-amine
• Language:English Provider:SigmaAldrich

Riluzole Usage And Synthesis

Description

Riluzole belongs to the derivative of benzothiazole with neuroprotective, potential anti-depressant and anxiolytic activities, which is used in the treatment of a certain type of nerve disease called amyotrophic lateral sclerosis (ALS, also known as Lou Gehrig's disease). It is effective to delay the onset of ventilator-dependence or tracheostomy in selected patients, slow down the deterioration of this disease and probably prolong survival by approximately two to three months. Besides, studies have proved that riluzole has anti-depressant activity for refractory depression and serves as an anxiolytic in the treatment of obsessive-compulsive disorder and generalized anxiety disorder.
However, riluzole does not cure the ALS and reverse nerve damage or muscle weakness. It is believed to function as an inhibitor of a natural substance called glutamate. It helps protect the nerves in the brain and spinal cord from too much of glutamate which may contribute to the nerve damage. Riluzole is available in both tablet and liquid form. The liquid formulation may be more suitable for patients with swallowing difficulties.

References

https://en.wikipedia.org/wiki/Riluzole
http://www.medicinenet.com/riluzole_oral_tablets/article.htm
https://pubchem.ncbi.nlm.nih.gov/compound/5070#section=Top

Description

Rilutek was launched in Germany, the UK and US (orphan drug status) for treatment of amyotrophic lateral sclerosis (ALS) and is the first drug approved for this indication. A one step synthesis from 4-(trifluoromethoxy)aniline provides a supply of the compound. The source of its neuroprotective and anticonvulsant activity is not clearly understood. It antagonizes excitatory amino acids and blocks presynaptic release of glutamate, is an antagonist of NMDA-induced acetylcholine release and inhibited glutamate and quisqualate induced increases in cGMP but does not bind to NMDA or Kainic receptors. Rilutek has no affinity for glutamate, GABAbenzodiazepine, glycine and adenosine receptors. It easily crosses the blood brain barrier and depresses glutamatergic neurotransmission, stabilizes voltagedependent Na channels in their inactive form and activates G-protein dependent processes.

Chemical Properties

White Crystalline Solid

Originator

Rhone-Poulenc Rorer (France)

Uses

A neuroprotective agent. Modulates glutamatergic transmission. A glutamate release inhibitor. An anticonvulsant.

Uses

anticonvulsant, glutamate release inhibitor, anti-ALS

Uses

Labeled Riluzole, intended for use as an internal standard for the quantification of Riluzole by GC- or LC-mass spectrometry.

Uses

A neuroprotective agent. A glutamate release inhibitor. An anticonvulsant

Definition

ChEBI: Riluzole is a member of benzothiazoles.

brand name

Rilutek (Sanofi Aventis).

Biological Activity

Novel psychotropic agent with anticonvulsant, hypnotic, anxiolytic, anti-ischemic and anesthetic properties. Riluzole is able to act as a glutamate release inhibitor, blocks voltage-dependent Na + channels and inhibits GABA uptake by striatal synaptosomes.

Biochem/physiol Actions

Glutamate release inhibitor; anticonvulsant

storage

Room temperature

References

[1] BELLINGHAM M C. A Review of the Neural Mechanisms of Action and Clinical Efficiency of Riluzole in Treating Amyotrophic Lateral Sclerosis: What have we Learned in the Last Decade?[J]. CNS Neuroscience & Therapeutics, 2011, 17 1: 4-31. DOI:10.1111/j.1755-5949.2009.00116.x
[2] ANDREA URBANI  Ottorino B. Riluzole inhibits the persistent sodium current in mammalian CNS neurons[J]. European Journal of Neuroscience, 2001, 12 10: 3567-3574. DOI:10.1046/j.1460-9568.2000.00242.x
[3] MARCOS EMÍLIO DOS SANTOS FRIZZO. Riluzole enhances glutamate uptake in rat astrocyte cultures.[J]. Cellular and Molecular Neurobiology, 2004, 24 1: 123-128. DOI:10.1023/b:cemn.0000012717.37839.07
[4] DOBLE A. The pharmacology and mechanism of action of riluzole.[J]. Neurology, 1996, 47 6 Suppl 4: S233-41. DOI:10.1212/wnl.47.6\_suppl\_4.233s
[5] CHRISTOPHER PITTENGER. Riluzole in the treatment of mood and anxiety disorders.[J]. CNS drugs, 2008, 22 9: 761-786. DOI:10.2165/00023210-200822090-00004
[6] JIN NAMKOONG. Metabotropic glutamate receptor 1 and glutamate signaling in human melanoma.[J]. Cancer research, 2007, 67 5: 2298-2305. DOI:10.1158/0008-5472.can-06-3665
[7] CHI ZHANG. Anti-cancer effect of metabotropic glutamate receptor 1 inhibition in human glioma U87 cells: involvement of PI3K/Akt/mTOR pathway.[J]. Cellular Physiology and Biochemistry, 2015: 419-432. DOI:10.1159/000369707
[8] SWETLANA SPERLING. Riluzole: a potential therapeutic intervention in human brain tumor stem-like cells.[J]. Oncotarget, 2017: 96697-96709. DOI:10.18632/oncotarget.18043

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