Synonym
Riluzole, Rilutek, PK 26124, PK26124, PK-26124, RP 54274, RP54274; RP-54274
IUPAC/Chemical Name
6-(trifluoromethoxy)-1,3-benzothiazol-2-amine
InChi Key
FTALBRSUTCGOEG-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
NC1=NC2=CC=C(OC(F)(F)F)C=C2S1
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO and ethanol
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO and ethanol
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Riluzole is a cell-permeable benzothiazole compound than functions as a polyglutamine aggregation inhibitor and stimulates the synthesis of NGF, BDNF, and GDNF in mouse astrocyte cultures. It is reported to offer neuroprotection, slow down disease progression in amyotrophic lateral sclerosis patients, and prolong the lifespan of animal models of Huntington’s disease.
In vitro activity:
This study showed that riluzole has anti-invasive effects on rat Mat-LyLu rat prostate cancer cells. Riluzole under hypoxia can modulate Nav1.7 mRNA and protein expression. Riluzole may ultimately be "repurposed" as an anti-metastatic drug against PCa.
Reference: Basic Clin Pharmacol Toxicol. 2020 Oct;127(4):254-264. https://pubmed.ncbi.nlm.nih.gov/32304618/
In vivo activity:
Riluzole-treated Huntington’s Disease patients displayed significantly less grey matter volume loss and increased metabolic (18)F-fluoro-2-deoxy-D-glucose (FDG) compared to placebo. There was a linear correlation between decreased metabolic FDG uptake and worsening clinical scores, suggesting that Riluzole could be utilized in Huntington’s disease treatment.
Reference: Eur J Nucl Med Mol Imaging. 2009 Jul;36(7):1113-20. https://pubmed.ncbi.nlm.nih.gov/19280185/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
47.0 |
200.68 |
| Ethanol |
47.0 |
200.68 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
234.20
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Rizaner N, Uzun S, Fraser SP, Djamgoz MBA, Altun S. Riluzole: Anti-invasive effects on rat prostate cancer cells under normoxic and hypoxic conditions. Basic Clin Pharmacol Toxicol. 2020 Oct;127(4):254-264. doi: 10.1111/bcpt.13417. Epub 2020 Jun 19. PMID: 32304618.
2. Wu XL, Liu L, Wang QC, Wang HF, Zhao XR, Lin XB, Lv WJ, Niu YB, Lu TL, Mei QB. Antitumor Activity and Mechanism Study of Riluzole and Its Derivatives. Iran J Pharm Res. 2020 Summer;19(3):217-230. doi: 10.22037/ijpr.2020.1101149. PMID: 33680024; PMCID: PMC7757987.
3. Squitieri F, Orobello S, Cannella M, Martino T, Romanelli P, Giovacchini G, Frati L, Mansi L, Ciarmiello A. Riluzole protects Huntington disease patients from brain glucose hypometabolism and grey matter volume loss and increases production of neurotrophins. Eur J Nucl Med Mol Imaging. 2009 Jul;36(7):1113-20. doi: 10.1007/s00259-009-1103-3. Epub 2009 Mar 11. PMID: 19280185.
4. Thakore NJ, Lapin BR, Mitsumoto H, Pooled Resource Open-Access Als Clinical Trials Consortium. Early initiation of riluzole may improve absolute survival in amyotrophic lateral sclerosis. Muscle Nerve. 2022 Dec;66(6):702-708. doi: 10.1002/mus.27724. Epub 2022 Oct 4. PMID: 36117390; PMCID: PMC9828202.
In vitro protocol:
1. Rizaner N, Uzun S, Fraser SP, Djamgoz MBA, Altun S. Riluzole: Anti-invasive effects on rat prostate cancer cells under normoxic and hypoxic conditions. Basic Clin Pharmacol Toxicol. 2020 Oct;127(4):254-264. doi: 10.1111/bcpt.13417. Epub 2020 Jun 19. PMID: 32304618.
2. Wu XL, Liu L, Wang QC, Wang HF, Zhao XR, Lin XB, Lv WJ, Niu YB, Lu TL, Mei QB. Antitumor Activity and Mechanism Study of Riluzole and Its Derivatives. Iran J Pharm Res. 2020 Summer;19(3):217-230. doi: 10.22037/ijpr.2020.1101149. PMID: 33680024; PMCID: PMC7757987.
In vivo protocol:
1. Squitieri F, Orobello S, Cannella M, Martino T, Romanelli P, Giovacchini G, Frati L, Mansi L, Ciarmiello A. Riluzole protects Huntington disease patients from brain glucose hypometabolism and grey matter volume loss and increases production of neurotrophins. Eur J Nucl Med Mol Imaging. 2009 Jul;36(7):1113-20. doi: 10.1007/s00259-009-1103-3. Epub 2009 Mar 11. PMID: 19280185.
2. Thakore NJ, Lapin BR, Mitsumoto H, Pooled Resource Open-Access Als Clinical Trials Consortium. Early initiation of riluzole may improve absolute survival in amyotrophic lateral sclerosis. Muscle Nerve. 2022 Dec;66(6):702-708. doi: 10.1002/mus.27724. Epub 2022 Oct 4. PMID: 36117390; PMCID: PMC9828202.
1: Nagoshi N, Nakashima H, Fehlings MG. Riluzole as a neuroprotective drug for spinal cord injury: from bench to bedside. Molecules. 2015 Apr 29;20(5):7775-89. doi: 10.3390/molecules20057775. Review. PubMed PMID: 25939067.
2: Yu LJ, Wall BA, Chen S. The current management of brain metastasis in melanoma: a focus on riluzole. Expert Rev Neurother. 2015;15(7):779-92. doi: 10.1586/14737175.2015.1055321. Epub 2015 Jun 19. Review. PubMed PMID: 26092602.
3: Wilson JR, Fehlings MG. Riluzole for acute traumatic spinal cord injury: a promising neuroprotective treatment strategy. World Neurosurg. 2014 May-Jun;81(5-6):825-9. doi: 10.1016/j.wneu.2013.01.001. Epub 2013 Jan 4. Review. PubMed PMID: 23295632.
4: Cifra A, Mazzone GL, Nistri A. Riluzole: what it does to spinal and brainstem neurons and how it does it. Neuroscientist. 2013 Apr;19(2):137-44. doi: 10.1177/1073858412444932. Epub 2012 May 16. Review. PubMed PMID: 22596264.
5: Owen RT. Glutamatergic approaches in major depressive disorder: focus on ketamine, memantine and riluzole. Drugs Today (Barc). 2012 Jul;48(7):469-78. doi: 10.1358/dot.2012.48.7.1832873. Review. PubMed PMID: 22844658.
6: Miller RG, Mitchell JD, Moore DH. Riluzole for amyotrophic lateral sclerosis (ALS)/motor neuron disease (MND). Cochrane Database Syst Rev. 2012 Mar 14;3:CD001447. doi: 10.1002/14651858.CD001447.pub3. Review. PubMed PMID: 22419278.
7: Bellingham MC. 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? CNS Neurosci Ther. 2011 Feb;17(1):4-31. doi: 10.1111/j.1755-5949.2009.00116.x. Review. PubMed PMID: 20236142.
8: Grant P, Song JY, Swedo SE. Review of the use of the glutamate antagonist riluzole in psychiatric disorders and a description of recent use in childhood obsessive-compulsive disorder. J Child Adolesc Psychopharmacol. 2010 Aug;20(4):309-15. doi: 10.1089/cap.2010.0009. Review. PubMed PMID: 20807069; PubMed Central PMCID: PMC2958461.
9: Cheah BC, Vucic S, Krishnan AV, Kiernan MC. Riluzole, neuroprotection and amyotrophic lateral sclerosis. Curr Med Chem. 2010;17(18):1942-199. Review. PubMed PMID: 20377511.
10: Zarate CA, Manji HK. Riluzole in psychiatry: a systematic review of the literature. Expert Opin Drug Metab Toxicol. 2008 Sep;4(9):1223-34. doi: 10.1517/17425255.4.9.1223. Review. PubMed PMID: 18721116; PubMed Central PMCID: PMC2587133.
11: Pittenger C, Coric V, Banasr M, Bloch M, Krystal JH, Sanacora G. Riluzole in the treatment of mood and anxiety disorders. CNS Drugs. 2008;22(9):761-86. Review. PubMed PMID: 18698875.
12: Miller RG, Mitchell JD, Lyon M, Moore DH. Riluzole for amyotrophic lateral sclerosis (ALS)/motor neuron disease (MND). Cochrane Database Syst Rev. 2007 Jan 24;(1):CD001447. Review. Update in: Cochrane Database Syst Rev. 2012;3:CD001447. PubMed PMID: 17253460.
13: Bensimon G, Doble A. The tolerability of riluzole in the treatment of patients with amyotrophic lateral sclerosis. Expert Opin Drug Saf. 2004 Nov;3(6):525-34. Review. PubMed PMID: 15500412.
14: Siniscalchi A. [Tolerability of riluzole: a review of the literature]. Clin Ter. 2004 Jan;155(1):25-8. Review. Italian. PubMed PMID: 15147078.
15: Morrison KE. Therapies in amyotrophic lateral sclerosis-beyond riluzole. Curr Opin Pharmacol. 2002 Jun;2(3):302-9. Review. PubMed PMID: 12020475.
16: Gelinas DF. Riluzole. Amyotroph Lateral Scler Other Motor Neuron Disord. 2000 Dec;1 Suppl 4:3-4. Review. PubMed PMID: 11466957.
17: Borrás-Blasco J, Plaza-Macías I, Navarro-Ruiz A, Perís-Martí J, Antón-Cano A. [Riluzole as a treatment for amyotrophic lateral sclerosis]. Rev Neurol. 1998 Dec;27(160):1021-7. Review. Spanish. PubMed PMID: 9951030.
18: Neatherlin JS. Management of amyotrophic lateral sclerosis with riluzole. J Neurosci Nurs. 1998 Aug;30(4):257-60. Review. PubMed PMID: 9791781.
19: Riluzole for amyotrophic lateral sclerosis. Drug Ther Bull. 1997 Feb;35(2):11-2. Review. PubMed PMID: 9282413.
20: Doble A. The pharmacology and mechanism of action of riluzole. Neurology. 1996 Dec;47(6 Suppl 4):S233-41. Review. PubMed PMID: 8959995.
