Riluzole | CAS#1744-22-5

Riluzole
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 318664

CAS#: 1744-22-5

Description: Riluzole is a drug used to treat amyotrophic lateral sclerosis. It delays the onset of ventilator-dependence or tracheostomy in selected patients and may increase survival by approximately two to three months.

Chemical Structure

Riluzole

CAS# 1744-22-5

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318664
Name: Riluzole
CAS#: 1744-22-5
Chemical Formula: C8H5F3N2OS
Exact Mass: 234.01
Molecular Weight: 234.200
Elemental Analysis: C, 41.03; H, 2.15; F, 24.34; N, 11.96; O, 6.83; S, 13.69

Price and Availability

Size	Price	Availability
1g	USD 190	2 Weeks
5g	USD 550	2 Weeks
10g	USD 850	2 Weeks
100g	USD 2950	2 Weeks
1kg	USD 5950	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 850608-87-6 (HCl) 1744-22-5

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

Appearance: Solid powder

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

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Product Data:

Product Data

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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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	47.0	200.68
	Ethanol	47.0	200.68

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.

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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.

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