ContaminantDB: Riluzole

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (6)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:32 UTC

Update Date

2026-05-14 16:47:35 UTC

Accession Number

CHEM002262

Identification

Common Name

Riluzole

Class

Small Molecule

Description

Riluzole is only found in individuals that have used or taken this drug. It is a glutamate antagonist (receptors, glutamate) used as an anticonvulsant (anticonvulsants) and to prolong the survival of patients with amyotrophic lateral sclerosis. [PubChem]The mode of action of riluzole is unknown. Its pharmacological properties include the following, some of which may be related to its effect: 1) an inhibitory effect on glutamate release (activation of glutamate reuptake), 2) inactivation of voltage-dependent sodium channels, and 3) ability to interfere with intracellular events that follow transmitter binding at excitatory amino acid receptors.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Anesthetic
Anticonvulsant
Drug
Ether
Excitatory Amino Acid Antagonist
Metabolite
Neuroprotective Agent
Organic Compound
Organofluoride
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Rilutek	Kegg
Riluzole impax brand	HMDB
2 Amino 6 trifluoromethoxybenzothiazole	HMDB
2-Amino-6-trifluoromethoxybenzothiazole	HMDB
Aventis brand OF riluzole	HMDB
Riluzole aventis brand	HMDB
Impax brand OF riluzole	HMDB
Rhone-poulenc rorer brand OF riluzole	HMDB
Aventis behring brand OF riluzole	HMDB
Rhone poulenc rorer brand OF riluzole	HMDB

Chemical Formula

C₈H₅F₃N₂OS

Average Molecular Mass

234.198 g/mol

Monoisotopic Mass

234.007 g/mol

CAS Registry Number

1744-22-5

IUPAC Name

6-(trifluoromethoxy)-1,3-benzothiazol-2-amine

Traditional Name

riluzole

SMILES

NC1=NC2=C(S1)C=C(OC(F)(F)F)C=C2

InChI Identifier

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)

InChI Key

FTALBRSUTCGOEG-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as benzothiazoles. These are organic compounds containing a benzene fused to a thiazole ring (a five-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiazoles

Sub Class

Not Available

Direct Parent

Benzothiazoles

Alternative Parents

Substituents

1,3-benzothiazole
Benzenoid
1,3-thiazol-2-amine
Azole
Thiazole
Heteroaromatic compound
Trihalomethane
Azacycle
Amine
Organopnictogen compound
Organic oxygen compound
Alkyl halide
Primary amine
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Organic nitrogen compound
Alkyl fluoride
Hydrocarbon derivative
Halomethane
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzothiazoles (CHEBI:8863 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	119°C
Boiling Point	Not Available
Solubility	3.95e-02 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.04 g/L	ALOGPS
logP	2.83	ALOGPS
logP	3.4	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	16.44	ChemAxon
pKa (Strongest Basic)	4.57	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	48.14 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	44.37 m³·mol⁻¹	ChemAxon
Polarizability	18.59 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00li-2940000000-00c484cbc92e6a94bae0	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-2590000000-5a9d0f7cdad7e4f2ec6b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-0390000000-4bd44ae3d25f047943e8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-3940000000-1da38288b84e863a64e5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-000i-0590000000-79d300cfd2b43692d963	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-001i-0190000000-63069bec4e00478eb380	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0190000000-f0b481a2910122ad9bdc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0090000000-d6a855ead1f5f5fe1a37	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0900000000-b797bc65c27579651949	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-4caa5c429c103b56c151	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0090000000-78bd33541d87ef645303	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-0900000000-6f96de4ddfa58b872d2e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-77cd58803ff632c89002	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0090000000-77cd58803ff632c89002	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4r-0490000000-ab117c07a1f16bb2d5f8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-9f868134c3a763fd526e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0090000000-9f868134c3a763fd526e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9320000000-2312256d22d9ca57d014	Spectrum

Toxicity Profile

Route of Exposure

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%.

Mechanism of Toxicity

The mode of action of riluzole is unknown. Its pharmacological properties include the following, some of which may be related to its effect: 1) an inhibitory effect on glutamate release (activation of glutamate reuptake), 2) inactivation of voltage-dependent sodium channels, and 3) ability to interfere with intracellular events that follow transmitter binding at excitatory amino acid receptors.

Metabolism

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. Half Life: The mean elimination half-life of riluzole is 12 hours (CV=35%) after repeated doses.

Toxicity Values

LD50: 85 mg/kg (p.o., mice) (9) LD50: 34.5 mg/kg (i.v, mice) (9) LD50: 45 mg/kg (p.o., rat) (9) LD50: 21 mg/kg (i.v, mice) (9)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the treatment of amyotrophic lateral sclerosis (ALS, Lou Gehrig's Disease)

Minimum Risk Level

Not Available

Health Effects

May cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.

Symptoms

Symptoms include such as nausea and fatigue [Wikipedia].

Treatment

Treatment should be supportive and directed toward alleviating symptoms. Severe methemoglobinemia may be rapidly reversible after treatment with methylene blue. (8)

Concentrations

Not Available

External Links

DrugBank ID

DB00740

HMDB ID

HMDB0014878

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Pratap Padi, Madhusudhan Ganta, Satyanarayana Bollikonda, Sridhar Chaganti, Ramulu Akula, Loka Maheshwari Dommati, “PROCESS FOR PREPARING RILUZOLE.” U.S. Patent US20080108827, issued May 08, 2008.

MSDS

Not Available

General References

1. 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.

2. 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.

3. 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.

4. 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.

5. Mathew SJ, Manji HK, Charney DS: Novel drugs and therapeutic targets for severe mood disorders. Neuropsychopharmacology. 2008 Aug;33(9):2080-92. doi: 10.1038/sj.npp.1301652. Epub 2008 Jan 2.

6. 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. doi: 10.1111/j.1460-9568.2008.06211.x. Epub 2008 Apr 26.

Riluzole (CHEM002262)

Structure for CHEM002262: Riluzole