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1744-22-5 molecular structure
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6-(trifluoromethoxy)-1,3-benzothiazol-2-amine

ChemBase ID: 620
Molecular Formular: C8H5F3N2OS
Molecular Mass: 234.1983096
Monoisotopic Mass: 234.00746845
SMILES and InChIs

SMILES:
s1c2c(nc1N)ccc(OC(F)(F)F)c2
Canonical SMILES:
Nc1nc2c(s1)cc(cc2)OC(F)(F)F
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

Cite this record

CBID:620 http://www.chembase.cn/molecule-620.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
6-(trifluoromethoxy)-1,3-benzothiazol-2-amine
IUPAC Traditional name
riluzole
6-(trifluoromethoxy)-1,3-benzothiazol-2-amine
Brand Name
Rilutek
Riluzole HCl
Synonyms
riluzole
Riluzole
2-Amino-6-(trifluoromethoxy)benzothiazole
6-Trifluoromethoxy-benzothiazol-2-ylamine
6-(Trifluoromethoxy)-2-benzothiazolamine
6-(Trifluoromethoxy)-2-aminobenzothiazole
6-(trifluoromethoxy)-1,3-benzothiazol-2-amine
6-(trifluoromethoxy)benzo[d]thiazol-2-amine
2-Amino-6-trifluoro-methoxybenzothiazole
2-Amino-6-(trifluoromethoxy)benzothiazole
Riluzole
PK-26124
RP-54274
Rilutek
Riluzole(Rilutek)
6-(Trifluoromethoxy)-1,3-benzothiazol-2-amine
2-Amino-6-(trifluoromethoxy)-1,3-benzothiazole 97%
CAS Number
1744-22-5
MDL Number
MFCD00210213
PubChem SID
46508094
24278006
160964083
PubChem CID
5070

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 16.440592  H Acceptors
H Donor LogD (pH = 5.5) 3.353241 
LogD (pH = 7.4) 3.3992848  Log P 3.3999074 
Molar Refractivity 44.3727 cm3 Polarizability 18.69663 Å3
Polar Surface Area 48.14 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.83  LOG S -3.77 
Solubility (Water) 3.95e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
DMSO: ≥25 mg/mL expand Show data source
Apperance
white solid expand Show data source
White Solid expand Show data source
Melting Point
108-110°C expand Show data source
114 - 116°C expand Show data source
117°C expand Show data source
119°C expand Show data source
Hydrophobicity(logP)
2.3 expand Show data source
3.235 expand Show data source
Storage Condition
-20°C expand Show data source
Hygroscopic, Refrigerator, Under Inert Atmosphere expand Show data source
Room Temperature (15-30°C) expand Show data source
Storage Warning
TOXIC expand Show data source
Toxic expand Show data source
RTECS
DL2830000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
3 expand Show data source
Risk Statements
25 expand Show data source
Safety Statements
45 expand Show data source
TSCA Listed
false expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H301 expand Show data source
GHS Precautionary statements
P301 + P310 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 2811 6.1/PG 3 expand Show data source
Gene Information
rat ... Scnn1g(24768) expand Show data source
Mechanism of Action
Glutamate transporter activation expand Show data source
High-voltage calcium channel blockade expand Show data source
N-methyl-D-aspartate (NMDA)/glutamate receptor antagonism expand Show data source
Sodium channel blockade expand Show data source
Purity
95% expand Show data source
96% expand Show data source
97% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Application(s)
Anticonvulsant, antiepileptic agent expand Show data source
Used in treatment of amyotrophic lateral sclerosis expand Show data source
Empirical Formula (Hill Notation)
C8H5F3N2OS expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02193713 external link
A glutamate release inhibitor which also blocks voltage-dependent Na+ channels and inhibits GABA uptake.
DrugBank - DB00740 external link
Item Information
Drug Groups approved; investigational
Description A glutamate antagonist (receptors, glutamate) used as an anticonvulsant (anticonvulsants) and to prolong the survival of patients with amyotrophic lateral sclerosis. [PubChem]
Indication For the treatment of amyotrophic lateral sclerosis (ALS, Lou Gehrig's Disease)
Pharmacology Riluzole, a member of the benzothiazole class, is indicated for the treatment of patients with amyotrophic lateral sclerosis (ALS). Riluzole extends survival and/or time to tracheostomy. It is also neuroprotective in various in vivo experimental models of neuronal injury involving excitotoxic mechanisms. The etiology and pathogenesis of amyotrophic lateral sclerosis (ALS) are not known, although a number of hypotheses have been advanced. One hypothesis is that motor neurons, made vulnerable through either genetic predisposition or environmental factors, are injured by glutamate. In some cases of familial ALS the enzyme superoxide dismutase has been found to be defective.
Affected Organisms
Humans and other mammals
Biotransformation Riluzole is extensively metabolized to six major and a number of minor metabolites, which have not all been identified to date. Metabolism is mostly hepatic, consisting of cytochrome P450–dependent hydroxylation and glucuronidation. CYP1A2 is the primary isozyme involved in N-hydroxylation; CYP2D6, CYP2C19, CYP3A4, and CYP2E1 are considered unlikely to contribute significantly to riluzole metabolism in humans.
Absorption Riluzole is well-absorbed (approximately 90%), with average absolute oral bioavailability of about 60% (CV=30%). A high fat meal decreases absorption, reducing AUC by about 20% and peak blood levels by about 45%.
Half Life The mean elimination half-life of riluzole is 12 hours (CV=35%) after repeated doses.
Protein Binding 96% bound to plasma proteins, mainly to albumin and lipoprotein over the clinical concentration range.
References
Song JH, Huang CS, Nagata K, Yeh JZ, Narahashi T: Differential action of riluzole on tetrodotoxin-sensitive and tetrodotoxin-resistant sodium channels. J Pharmacol Exp Ther. 1997 Aug;282(2):707-14. [Pubmed]
Coric V, Taskiran S, Pittenger C, Wasylink S, Mathalon DH, Valentine G, Saksa J, Wu YT, Gueorguieva R, Sanacora G, Malison RT, Krystal JH: Riluzole augmentation in treatment-resistant obsessive-compulsive disorder: an open-label trial. Biol Psychiatry. 2005 Sep 1;58(5):424-8. [Pubmed]
van Kan HJ, Groeneveld GJ, Kalmijn S, Spieksma M, van den Berg LH, Guchelaar HJ: Association between CYP1A2 activity and riluzole clearance in patients with amyotrophic lateral sclerosis. Br J Clin Pharmacol. 2005 Mar;59(3):310-3. [Pubmed]
Zarate CA Jr, Payne JL, Quiroz J, Sporn J, Denicoff KK, Luckenbaugh D, Charney DS, Manji HK: An open-label trial of riluzole in patients with treatment-resistant major depression. Am J Psychiatry. 2004 Jan;161(1):171-4. [Pubmed]
Mathew SJ, Manji HK, Charney DS: Novel drugs and therapeutic targets for severe mood disorders. Neuropsychopharmacology. 2008 Aug;33(9):2080-92. Epub 2008 Jan 2. [Pubmed]
Lamanauskas N, Nistri A: Riluzole blocks persistent Na+ and Ca2+ currents and modulates release of glutamate via presynaptic NMDA receptors on neonatal rat hypoglossal motoneurons in vitro. Eur J Neurosci. 2008 May;27(10):2501-14. Epub 2008 Apr 26. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals - S1614 external link
Research Area: Neurological Disease
Biological Activity:
Riluzole(Rilutek) is a drug used to treat amyotrophic lateral sclerosis. It delays the onset of ventilator-dependence or tracheostomy in selected patients and may increase the survival approximately 3–5 months. [1] Its pharmacological activities in motor neurons include the following: 1) an inhibitory effect on glutamate release 2) inactivation of voltage-dependent sodium channels  3) interference with intracellular events that follow transmitter binding at excitatory amino acid receptors. In animal models, this agent has been shown to exhibit myorelaxant and sedative activities, apparently due to the blockade of glutamatergic neurotransmission. [1]
Sigma Aldrich - R116 external link
Biochem/physiol Actions
Glutamate release inhibitor; anticonvulsant
Sigma Aldrich - R3772 external link
Biochem/physiol Actions
Glutamate release inhibitor
Toronto Research Chemicals - R510000 external link
A neuroprotective agent. Modulates glutamatergic transmission. A glutamate release inhibitor. An anticonvulsant.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Mantz, et al., Eur. J. Pharmacol. , 257 : R7, (1994).
  • • Song JH, Huang CS, Nagata K, Yeh JZ, Narahashi T: Differential action of riluzole on tetrodotoxin-sensitive and tetrodotoxin-resistant sodium channels. J Pharmacol Exp Ther. 1997 Aug;282(2):707-14. Pubmed
  • • Coric V, Taskiran S, Pittenger C, Wasylink S, Mathalon DH, Valentine G, Saksa J, Wu YT, Gueorguieva R, Sanacora G, Malison RT, Krystal JH: Riluzole augmentation in treatment-resistant obsessive-compulsive disorder: an open-label trial. Biol Psychiatry. 2005 Sep 1;58(5):424-8. Pubmed
  • • van Kan HJ, Groeneveld GJ, Kalmijn S, Spieksma M, van den Berg LH, Guchelaar HJ: Association between CYP1A2 activity and riluzole clearance in patients with amyotrophic lateral sclerosis. Br J Clin Pharmacol. 2005 Mar;59(3):310-3. Pubmed
  • • Zarate CA Jr, Payne JL, Quiroz J, Sporn J, Denicoff KK, Luckenbaugh D, Charney DS, Manji HK: An open-label trial of riluzole in patients with treatment-resistant major depression. Am J Psychiatry. 2004 Jan;161(1):171-4. Pubmed
  • • Mathew SJ, Manji HK, Charney DS: Novel drugs and therapeutic targets for severe mood disorders. Neuropsychopharmacology. 2008 Aug;33(9):2080-92. Epub 2008 Jan 2. Pubmed
  • • Lamanauskas N, Nistri A: Riluzole blocks persistent Na+ and Ca2+ currents and modulates release of glutamate via presynaptic NMDA receptors on neonatal rat hypoglossal motoneurons in vitro. Eur J Neurosci. 2008 May;27(10):2501-14. Epub 2008 Apr 26. Pubmed
  • • http://en.wikipedia.org/wiki/Riluzole
  • • Mizoule, J., et al.: Neuropharmacology, 24, 767 (1985)
  • • Wahl, F., et al.: Eur. J. Pharmacol., 230, 209 (1993) Bensimon, G., et al.: N. Engl. J. Med., 330, 585 (1994)
  • • Yagupol'skii, L.M. et al., Zh. Obshch. Khim., 1963, 33, 2301, (synth)
  • • Eur. Pat., 1982, Pharmindustrie, 50 551; CA, 97, 44352, (pharmacol)
  • • Mizoule, J. et al., Neuropharmacology, 1985, 24, 767, (pharmacol)
  • • Tsai, C. et al., Neurol. Neurobiol., 1987, 24, 79, (pharmacol)
  • • Mantz, J. et al., Eur. J. Pharmacol., 1994, 257, R7, (pharmacol)
  • • Bensimon, G. et al., N. Engl. J. Med., 1994, 330, 585, (clin trial)
  • • Rowland, L.P., N. Engl. J. Med., 1994, 330, 636
  • • Mantz, J., CNS Drug Rev., 1996, 2, 40, (rev)
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PATENTS

PATENTS

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