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

MedKoo CAT#: 584185

CAS#: 1926203-09-9

Description: Trigriluzole is glutamate release inhibitor, it helps modulate glutamate neurotransmitter and could possibly help with neurodegenerative and neuropsychiatric diseases. The prodrug of riluzole is Trigriluzole.

Chemical Structure

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Trigriluzole
CAS# 1926203-09-9
Instruction

Theoretical Analysis

MedKoo Cat#: 584185
Name: Trigriluzole
CAS#: 1926203-09-9
Chemical Formula: C15H16F3N5O4S
Exact Mass: 419.09
Molecular Weight: 419.379
Elemental Analysis: C, 42.96; H, 3.85; F, 13.59; N, 16.70; O, 15.26; S, 7.64

Price and Availability

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5mg USD 550 2 Weeks
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Synonym: BHV-4157; BHV 4157; BHV4157; troriluzole.

IUPAC/Chemical Name: Glycinamide, glycylglycyl-N2-methyl-N-(6-(trifluoromethoxy)-2-benzothiazolyl)-

InChi Key: UMDHMQFEWPMESQ-UHFFFAOYSA-N

InChi Code: InChI=1S/C15H16F3N5O4S/c1-23(7-13(26)22-12(25)6-20-11(24)5-19)14-21-9-3-2-8(4-10(9)28-14)27-15(16,17)18/h2-4H,5-7,19H2,1H3,(H,20,24)(H,22,25,26)

SMILES Code: O=C(NC(CNC(CN)=O)=O)CN(C)C1=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

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

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

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 419.38 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.

Recalculate based on batch purity %
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:
In vitro protocol:
In vivo protocol:

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1: Romano S, Coarelli G, Marcotulli C, Leonardi L, Piccolo F, Spadaro M, Frontali M, Ferraldeschi M, Vulpiani MC, Ponzelli F, Salvetti M, Orzi F, Petrucci A, Vanacore N, Casali C, Ristori G. Riluzole in patients with hereditary cerebellar ataxia: a randomised, double-blind, placebo-controlled trial. Lancet Neurol. 2015 Oct;14(10):985-91. doi: 10.1016/S1474-4422(15)00201-X. Epub 2015 Aug 25. PubMed PMID: 26321318.

2: 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.

3: Pittenger C, Bloch MH, Wasylink S, Billingslea E, Simpson R, Jakubovski E, Kelmendi B, Sanacora G, Coric V. Riluzole augmentation in treatment-refractory obsessive-compulsive disorder: a pilot randomized placebo-controlled trial. J Clin Psychiatry. 2015 Aug;76(8):1075-84. doi: 10.4088/JCP.14m09123. PubMed PMID: 26214725; PubMed Central PMCID: PMC4560666.

4: Grossman RG, Fehlings MG, Frankowski RF, Burau KD, Chow DS, Tator C, Teng A, Toups EG, Harrop JS, Aarabi B, Shaffrey CI, Johnson MM, Harkema SJ, Boakye M, Guest JD, Wilson JR. A prospective, multicenter, phase I matched-comparison group trial of safety, pharmacokinetics, and preliminary efficacy of riluzole in patients with traumatic spinal cord injury. J Neurotrauma. 2014 Feb 1;31(3):239-55. doi: 10.1089/neu.2013.2969. Epub 2013 Oct 11. PubMed PMID: 23859435; PubMed Central PMCID: PMC3904533.

5: Saleh OA, El-Azzouny AA, Aboul-Enein HY, Badawey AM. Riluzole: validation of stability-indicating HPLC, D1 and DD1 spectrophotometric assays. J Chromatogr Sci. 2014 Jul;52(6):539-46. doi: 10.1093/chromsci/bmt062. Epub 2013 Jun 5. PubMed PMID: 23744878.

6: Hunsberger HC, Weitzner DS, Rudy CC, Hickman JE, Libell EM, Speer RR, Gerhardt GA, Reed MN. Riluzole rescues glutamate alterations, cognitive deficits, and tau pathology associated with P301L tau expression. J Neurochem. 2015 Oct;135(2):381-94. doi: 10.1111/jnc.13230. Epub 2015 Aug 13. PubMed PMID: 26146790; PubMed Central PMCID: PMC4717473.

7: Wu Y, Satkunendrarajah K, Fehlings MG. Riluzole improves outcome following ischemia-reperfusion injury to the spinal cord by preventing delayed paraplegia. Neuroscience. 2014 Apr 18;265:302-12. doi: 10.1016/j.neuroscience.2014.01.059. Epub 2014 Feb 6. PubMed PMID: 24508749.

8: 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.

9: 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.

10: Angstadt JD, Simone AM. Riluzole suppresses postinhibitory rebound in an excitatory motor neuron of the medicinal leech. J Comp Physiol A Neuroethol Sens Neural Behav Physiol. 2014 Aug;200(8):759-75. doi: 10.1007/s00359-014-0919-x. Epub 2014 Jun 3. PubMed PMID: 24890185.

11: Türck P, Frizzo ME. Riluzole stimulates BDNF release from human platelets. Biomed Res Int. 2015;2015:189307. doi: 10.1155/2015/189307. Epub 2015 Jan 6. PubMed PMID: 25629040; PubMed Central PMCID: PMC4300019.

12: Nicholson KJ, Zhang S, Gilliland TM, Winkelstein BA. Riluzole effects on behavioral sensitivity and the development of axonal damage and spinal modifications that occur after painful nerve root compression. J Neurosurg Spine. 2014 Jun;20(6):751-62. doi: 10.3171/2014.2.SPINE13672. Epub 2014 Mar 28. PubMed PMID: 24678596.

13: Grant PJ, Joseph LA, Farmer CA, Luckenbaugh DA, Lougee LC, Zarate CA Jr, Swedo SE. 12-week, placebo-controlled trial of add-on riluzole in the treatment of childhood-onset obsessive-compulsive disorder. Neuropsychopharmacology. 2014 May;39(6):1453-9. doi: 10.1038/npp.2013.343. Epub 2013 Dec 19. PubMed PMID: 24356715; PubMed Central PMCID: PMC3988548.

14: Moon ES, Karadimas SK, Yu WR, Austin JW, Fehlings MG. Riluzole attenuates neuropathic pain and enhances functional recovery in a rodent model of cervical spondylotic myelopathy. Neurobiol Dis. 2014 Feb;62:394-406. doi: 10.1016/j.nbd.2013.10.020. Epub 2013 Oct 29. PubMed PMID: 24184328.

15: Yohay K, Tyler B, Weaver KD, Pardo AC, Gincel D, Blakeley J, Brem H, Rothstein JD. Efficacy of local polymer-based and systemic delivery of the anti-glutamatergic agents riluzole and memantine in rat glioma models. J Neurosurg. 2014 Apr;120(4):854-63. doi: 10.3171/2013.12.JNS13641. Epub 2014 Jan 31. PubMed PMID: 24484234; PubMed Central PMCID: PMC4322948.

16: Whitcomb DJ, Molnár E. Is riluzole a new drug for Alzheimer's disease? J Neurochem. 2015 Oct;135(2):207-9. doi: 10.1111/jnc.13260. Epub 2015 Sep 7. PubMed PMID: 26451974.

17: Yáñez M, Matías-Guiu J, Arranz-Tagarro JA, Galán L, Viña D, Gómez-Pinedo U, Vela A, Guerrero A, Martínez-Vila E, García AG. The neuroprotection exerted by memantine, minocycline and lithium, against neurotoxicity of CSF from patients with amyotrophic lateral sclerosis, is antagonized by riluzole. Neurodegener Dis. 2014;13(2-3):171-9. doi: 10.1159/000357281. Epub 2013 Dec 20. PubMed PMID: 24356417.

18: Farokhnia M, Sabzabadi M, Pourmahmoud H, Khodaie-Ardakani MR, Hosseini SM, Yekehtaz H, Tabrizi M, Rezaei F, Salehi B, Akhondzadeh S. A double-blind, placebo controlled, randomized trial of riluzole as an adjunct to risperidone for treatment of negative symptoms in patients with chronic schizophrenia. Psychopharmacology (Berl). 2014 Feb;231(3):533-42. doi: 10.1007/s00213-013-3261-z. Epub 2013 Sep 8. PubMed PMID: 24013610.

19: Sugiyama A, Saitoh A, Inagaki M, Oka J, Yamada M. Systemic administration of riluzole enhances recognition memory and facilitates extinction of fear memory in rats. Neuropharmacology. 2015 Oct;97:322-8. doi: 10.1016/j.neuropharm.2015.06.007. Epub 2015 Jun 24. PubMed PMID: 26116528.

20: Chew DJ, Carlstedt T, Shortland PJ. The effects of minocycline or riluzole treatment on spinal root avulsion-induced pain in adult rats. J Pain. 2014 Jun;15(6):664-75. doi: 10.1016/j.jpain.2014.03.001. Epub 2014 Mar 22. PubMed PMID: 24667712.