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Sunday, 29 March 2015

RILUZOLE

Riluzole3DanBS.gif
Riluzole2DACS.svg


Riluzole (Rilutek) is a drug used to treat amyotrophic lateral sclerosis and is marketed by Sanofi-Aventis. It delays the onset ofventilator-dependence or tracheostomy in selected patients and may increase survival by approximately two to three months.[2]

NMR.........http://file.selleckchem.com/downloads/nmr/S161403-Riluzole-NMR-Selleck.pdf






RILUTEK® (riluzole) is a member of the benzothiazole class. Chemically, riluzole is 2-amino-6-(trifluoromethoxy)benzothiazole. Its molecular formula is C8H5F3N2OS and its molecular weight is 234.2. Its structural formula is as follows:
RILUTEK® (riluzole) Structural Formula Illustration
Riluzole is a white to slightly yellow powder that is very soluble in dimethylformamide, dimethylsulfoxide and methanol, freely soluble in dichloromethane, sparingly soluble in 0.1 N HCl and very slightly soluble in water and in 0.1 N NaOH. RILUTEK (riluzole) is available as a capsule-shaped, white, film-coated tablet for oral administration containing 50 mg of riluzole. Each tablet is engraved with “RPR 202” on one side.



Riluzole (hydrochloride) NMR spectra analysis, Chemical CAS NO. 850608-87-6 NMR spectral analysis, Riluzole (hydrochloride) H-NMR spectrum






Riluzole (hydrochloride) NMR spectra analysis, Chemical CAS NO. 850608-87-6 NMR spectral analysis, Riluzole (hydrochloride) C-NMR spectrum

Mechanism

Riluzole preferentially blocks TTX-sensitive sodium channels, which are associated with damaged neurons.[12][13] Riluzole has also been reported to directly inhibit the kainateand NMDA receptors.[14] However, the action of riluzole on glutamate receptors has been controversial, as no binding of the drug to any known sites has been shown for them.[15][16] In addition, as its antiglutamatergic action is still detectable in the presence of sodium channel blockers, it is also uncertain whether or not it acts via this way. Rather, its ability to stimulate glutamate uptake seems to mediate many of its effects.[17][18] In addition to its role in accelerating glutamate clearance from the synapse, Riluzole may also prevent glutamate release from presynaptic terminals.[19] These effects combined could significantly reduce glutamate signaling and cause indirect antagonism without acting at glutamate receptors themselves.

Synthesis








  • Riluzole synthesis: U.S. Patent 4,826,860

    • References[edit]

    1. ^ Jump up to:a b c d e f g h i "PRODUCT INFORMATION RILUTEK® (riluzole) Tablets" (PDF). TGA eBusiness Services. sanofi-aventis australia pty ltd. 6 January 2009. Retrieved 18 February2014.
    2. ^ Jump up to:a b Miller, RG; Mitchell, JD; Moore, DH (14 March 2012). "Riluzole for amyotrophic lateral sclerosis (ALS)/motor neuron disease (MND)." (PDF). The Cochrane Database of Systematic Reviews 3: CD001447. doi:10.1002/14651858.CD001447.pub3.PMID 22419278.
    3. Jump up^ van Kan, HJ; Groeneveld, GJ; Kalmijn, S; Spieksma, M; van den Berg, LH; Guchelaar, HJ (March 2005). "Association between CYP1A2 activity and riluzole clearance in patients with amyotrophic lateral sclerosis." (PDF). British Journal of Clinical Pharmacology 59(3): 310–3. doi:10.1111/j.1365-2125.2004.02233.x. PMC 1884790. PMID 15752377.
    4. Jump up^ 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 August; 20(4): 309–315.
    5. Jump up^ Zarate CA, Jr; Payne, JL; Quiroz, J; Sporn, J; Denicoff, KK; Luckenbaugh, D; Charney, DS; Manji, HK (January 2004). "An open-label trial of riluzole in patients with treatment-resistant major depression.". The American Journal of Psychiatry 161 (1): 171–4.doi:10.1176/appi.ajp.161.1.171. PMID 14702270.
    6. Jump up^ Coric, V; Taskiran, S; Pittenger, C; Wasylink, S; Mathalon, DH; Valentine, G; Saksa, J; Wu, YT; Gueorguieva, R; Sanacora, G; Malison, RT; Krystal, JH (1 September 2005). "Riluzole augmentation in treatment-resistant obsessive-compulsive disorder: an open-label trial.". Biological Psychiatry 58 (5): 424–8. doi:10.1016/j.biopsych.2005.04.043.PMID 15993857.
    7. Jump up^ Mathew, SJ; Amiel, JM; Coplan, JD; Fitterling, HA; Sackeim, HA; Gorman, JM (December 2005). "Open-label trial of riluzole in generalized anxiety disorder.". The American Journal of Psychiatry 162 (12): 2379–81. doi:10.1176/appi.ajp.162.12.2379.PMID 16330605.
    8. Jump up^ "Glutamatergic regulation prevents hippocampal-dependent age-related cognitive decline through dendritic spine clustering". Proceedings of the National Academy of Sciences of the United States of America. Retrieved 18 January 2015.
    9. Jump up^ "Glutamatergic Dysfunction in Cognitive Aging: Riluzole in Mild Alzheimers Disease".rucares.org. Retrieved 12 March 2015.
    10. Jump up^ "Rilutek (riluzole) dosing, indications, interactions, adverse effects, and more".Medscape Reference. WebMD. Retrieved 18 February 2014.
    11. ^ Jump up to:a b c Rossi, S, ed. (2013). Australian Medicines Handbook (2013 ed.). Adelaide: The Australian Medicines Handbook Unit Trust. ISBN 978-0-9805790-9-3. edit
    12. Jump up^ Song, JH; Huang, CS; Nagata, K; Yeh, JZ; Narahashi, T (August 1997). "Differential action of riluzole on tetrodotoxin-sensitive and tetrodotoxin-resistant sodium channels."(PDF). The Journal of Pharmacology and Experimental Therapeutics 282 (2): 707–14.PMID 9262334.
    13. Jump up^ Bellingham, MC (February 2011). "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 Neuroscience & Therapeutics 17 (1): 4–31. doi:10.1111/j.1755-5949.2009.00116.x. PMID 20236142.
    14. Jump up^ Debono MW, Le Guern J, Canton T, Doble A, Pradier L (April 1993). "Inhibition by riluzole of electrophysiological responses mediated by rat kainate and NMDA receptors expressed in Xenopus oocytes". Eur. J. Pharmacol. 235 (2-3): 283–9. doi:10.1016/0014-2999(93)90147-a. PMID 7685290.
    15. Jump up^ Wokke, J (21 September 1996). "Riluzole.". Lancet 348 (9030): 795–9.doi:10.1016/S0140-6736(96)03181-9. PMID 8813989.
    16. Jump up^ Kretschmer BD, Kratzer U, Schmidt WJ (August 1998). "Riluzole, a glutamate release inhibitor, and motor behavior". Naunyn Schmiedebergs Arch. Pharmacol. 358 (2): 181–90.doi:10.1007/pl00005241. PMID 9750003.
    17. Jump up^ Azbill, RD; Mu, X; Springer, JE (July 2000). "Riluzole increases high-affinity glutamate uptake in rat spinal cord synaptosomes". Brain Res. 871 (2): 175–80.doi:10.1016/S0006-8993(00)02430-6. PMID 10899284.
    18. Jump up^ Dunlop, J; Beal McIlvain, H; She, Y; Howland, DS (1 March 2003). "Impaired spinal cord glutamate transport capacity and reduced sensitivity to riluzole in a transgenic superoxide dismutase mutant rat model of amyotrophic lateral sclerosis". J Neurosci. 23 (5): 1688–96. PMID 12629173.
    19. Jump up^ Wang, S.-J (January 2004). "Mechanisms underlying the riluzole inhibition of glutamate release from rat cerebral cortex nerve terminals (synaptosomes)". Neuroscience 125 (1): 191–201. doi:10.1016/j.neuroscience.2004.01.019.


    P.S. : The views expressed are my personal and in no-way suggest the views of the professional body or the company that I represent.
    P.S. : The views expressed are my personal and in no-way suggest the views of the professional body or the company that I represent.
    P.S. : The views expressed are my personal and in no-way suggest the views of the professional body or the company that I represent.



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