Riluzole

Modify Date: 2024-01-02 10:24:50

Riluzole Structure
Riluzole structure
Common Name Riluzole
CAS Number 1744-22-5 Molecular Weight 234.198
Density 1.6±0.1 g/cm3 Boiling Point 296.3±50.0 °C at 760 mmHg
Molecular Formula C8H5F3N2OS Melting Point 116-118ºC
MSDS Chinese USA Flash Point 133.0±30.1 °C
Symbol GHS06
GHS06
Signal Word Danger

 Use of Riluzole


Riluzole is an anticonvulsant drug and belongs to the family of use-dependent Na+ channel blocker which can also inhibit GABA uptake with an IC50 of 43 μM.

 Names

Name 2-Amino-6-(trifluoromethoxy)benzo[d]thiazole
Synonym More Synonyms

 Riluzole Biological Activity

Description Riluzole is an anticonvulsant drug and belongs to the family of use-dependent Na+ channel blocker which can also inhibit GABA uptake with an IC50 of 43 μM.
Related Catalog
Target

Sodium channel[1] IC50: 43 μM (GABA receptor)[1]

In Vitro Riluzole is an anticonvulsant drug and belongs to the family of use-dependent Na+ channel blocker which can also inhibit GABA uptake with an IC50 of 43 μM. At 20 μM, Riluzole inhibits peak autaptic IPSCs only slightly but prolongs IPSCs reliably. It is also found that Riluzole causes a strong, concentration-dependent, readily reversible enhancement of responses to 2 μM GABA. At higher concentrations of Riluzole, especially 300 μM, GABA currents exhibit apparent desensitization during prolonged co-exposure to 2 μM GABA and Riluzole. The EC50 of Riluzole potentiation of GABA responses is about 60 μM[1].
In Vivo In normal naïve rats, systemic injection of Riluzole (8 mg/kg, i.p.; n=6 rats) decreases the duration of ultrasonic but not audible vocalizations evoked by noxious stimulation of the knee joint compare to vehicle tested in the same rats (P<0.05). Systemic application of Riluzole (8 mg/kg, i.p.; n=19 rats) decreases the vocalizations of arthritic rats compare to predrug and vehicle significantly (P<0.05 to 0.001). Riluzole administered into the CeA significantly decreases the duration of audible and ultrasonic vocalizations evoked by noxious stimulation of the knee compare to predrug values (n=8 rats; P<0.05 to 0.01)[2].
Cell Assay Two-electrode voltage clamp of Xenopus oocytes expressing exogenous GABAA receptors is performed with a CA-1B high performance oocyte clamp. The extracellular recording solution is ND-96 medium. Riluzole is applied from a common tip via a gravity-driven multibarrel drug-delivery system. Data acquisition and analysis are performed with pCLAMP 6 software[1].
Animal Admin Adult male Sprague-Dawley rats (180 to 350 g) are housed in a temperature-controlled room and maintained on a 12-h day/night cycle with unrestricted access to food and water. Pain behaviors are measured before and 5 h after induction of a mono-arthritis in the left knee joint. To test the effects of systemic (intraperitoneal, i.p.) application of Riluzole, pain behaviors are measured 1 h postinjection of Riluzole in normal and arthritic animals. To determine effects of Riluzole into the amygdala, pain behaviors are measured 15 min after starting Riluzole application through a stereotaxically implanted microdialysis probe. To investigate site of action in the amygdala of systemically applied Riluzole, potassium channel blockers are administered into the amygdala 45 min after systemic application of Riluzole and pain behaviors are measured 15 min later, i.e., 1 h postinjection of riluzole (i.p.)[2].
References

[1]. He Y, et al. Neuroprotective agent riluzole potentiates postsynaptic GABA(A) receptor function. Neuropharmacology. 2002 Feb;42(2):199-209.

[2]. Thompson JM, et al. Small-conductance calcium-activated potassium (SK) channels in the amygdala mediate pain-inhibiting effects of clinically available riluzole in a rat model of arthritis pain. Mol Pain. 2015 Aug 28;11:51.

 Chemical & Physical Properties

Density 1.6±0.1 g/cm3
Boiling Point 296.3±50.0 °C at 760 mmHg
Melting Point 116-118ºC
Molecular Formula C8H5F3N2OS
Molecular Weight 234.198
Flash Point 133.0±30.1 °C
Exact Mass 234.007462
PSA 76.38000
LogP 2.84
Vapour Pressure 0.0±0.6 mmHg at 25°C
Index of Refraction 1.615
Storage condition Store at RT
Water Solubility DMSO: ≥25 mg/mL

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DL2830000
CHEMICAL NAME :
Benzothiazole, 2-amino-6-trifluoromethoxy-
CAS REGISTRY NUMBER :
1744-22-5
LAST UPDATED :
199707
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C8-H5-F3-N-O-S
MOLECULAR WEIGHT :
220.20

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
67 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
EPXXDW European Patent Application. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #50551
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
46 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
EPXXDW European Patent Application. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #50551

 Safety Information

Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H301
Precautionary Statements P301 + P310
Personal Protective Equipment Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes T:Toxic;
Risk Phrases R25
Safety Phrases S45
RIDADR UN 2811
WGK Germany 3
RTECS DL2830000
Packaging Group II
HS Code 2934999090

 Synthetic Route

~78%

Riluzole Structure

Riluzole

CAS#:1744-22-5

Literature: Anzini, Maurizio; Chelini, Alessia; Mancini, Alessandra; Cappelli, Andrea; Frosini, Maria; Ricci, Lorenzo; Valoti, Massimo; Magistretti, Jacopo; Castelli, Loretta; Giordani, Antonio; Makovec, Francesco; Vomero, Salvatore Journal of Medicinal Chemistry, 2010 , vol. 53, # 2 p. 734 - 744

~87%

Riluzole Structure

Riluzole

CAS#:1744-22-5

Literature: BRISTOL-MYERS SQUIBB COMPANY; UNIVERSITE DE MONTREAL; LAWRENCE, Michael, R.; MILLER, Michael, M.; SEIFFERT, Dietmar, Alfred; POSY, Shoshana, L.; WONG, Pancras, C.; BANVILLE, Jacques; RUEDIGER, Edward, H.; DEON, Daniel, H.; MARTEL, Alain; TREMBLAY, Francois; GUY, Julia; LAVALLEE, Jean-Francois; GAGNON, Marc Patent: WO2013/163244 A1, 2013 ; Location in patent: Paragraph 00205; 00206 ;

~73%

Riluzole Structure

Riluzole

CAS#:1744-22-5

Literature: Jordan, Alfonzo D.; Luo, Chi; Reitz, Allen B. Journal of Organic Chemistry, 2003 , vol. 68, # 22 p. 8693 - 8696

~%

Riluzole Structure

Riluzole

CAS#:1744-22-5

Literature: US5236940 A1, ;

~%

Riluzole Structure

Riluzole

CAS#:1744-22-5

Literature: US5068238 A1, ;

 Customs

HS Code 2934999090
Summary 2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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 Synonyms

MFCD00210213
2-Benzothiazolamine, 6-(trifluoromethoxy)-
2-Amino-6-(trifluoromethoxy)benzothiazole
6-(Trifluoromethoxy)-1,3-benzothiazol-2-amine
Riluzole
2-Amino-6-trifluoro methoxy benzothiazole
2-Amino-6-trifluoromethoxybenzothiazole
6-(Trifluoromethoxy)-2-benzothiazolamine
Rilutek
6-(Trifluoromethoxy)benzo[d]thiazol-2-amine
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