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Details

Stereochemistry ACHIRAL
Molecular Formula C8H5F3N2OS
Molecular Weight 234.198
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RILUZOLE

SMILES

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

InChI

InChIKey=FTALBRSUTCGOEG-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Description

Riluzole, a member of the benzothiazole class, is indicated for the treatment of patients with amyotrophic lateral sclerosis. 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. Common adverse reactions include headache, abdominal pain, back pain, vomiting, dyspepsia, diarrhea, dizziness. Riluzole-treated patients that take other hepatotoxic drugs may be at increased risk for hepatotoxicity.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Renal tubular impairment during riluzole therapy.
1999 Feb
Acute hepatitis after riluzole administration.
1999 Mar
Riluzole improves functional recovery after ischemia in the rat retina.
1999 Mar
Riluzole for levodopa-induced dyskinesias in advanced Parkinson's disease.
1999 May 22
The neuroprotective agent riluzole activates the two P domain K(+) channels TREK-1 and TRAAK.
2000 May
The role of glutamatergic transmission in the pathogenesis of levodopa-induced dyskinesias. Potential therapeutic approaches.
2001
Multiple system atrophy: pathophysiology and management.
2001
Riluzole for amyotrophic lateral sclerosis (ALS)/motor neuron disease (MND).
2001
Effect of riluzole on the acquisition and expression of amygdala kindling.
2001 Aug
Amyotrophic lateral sclerosis associated with pregnancy.
2001 Dec
The effect of riluzole treatment in rats on the survival of injured adult and grafted embryonic motoneurons.
2001 Jan
Characteristics of hippocampal glycine release in cell-damaging conditions in the adult and developing mouse.
2001 Jul
Riluzole-induced acute pancreatitis.
2001 Jul
[Amyotrophic lateral sclerosis].
2001 Jul 27
Effect of the neuroprotective agent riluzole on intracellular Ca2+ levels in IMR32 neuroblastoma cells.
2001 Jun
Clinical trials in ALS: an overview.
2001 Jun
A double-blind, placebo-controlled randomized clinical trial of alpha-tocopherol (vitamin E) in the treatment of amyotrophic lateral sclerosis. ALS riluzole-tocopherol Study Group.
2001 Mar
Clinical trials: the past, a lesson for the future.
2001 Mar
Riluzole in Huntington's disease (HD): an open label study with one year follow up.
2001 Oct
Neuroprotective agent riluzole dramatically slows inactivation of Kv1.4 potassium channels by a voltage-dependent oxidative mechanism.
2001 Oct
Prognostic value of decremental responses to repetitive nerve stimulation in ALS patients.
2001 Sep 11
Intoxication with riluzole in Huntington's disease.
2001 Sep 25
Riluzole for motor neurone disease. Reply from chairman of appraisal committee at NICE.
2001 Sep 8
A fair innings for NICE?
2002
Cost effectiveness of treatments for amyotrophic lateral sclerosis: a review of the literature.
2002
Workshop on primary progressive multiple sclerosis: meeting summary.
2002 Apr
Modulation of recombinant and native neuronal SK channels by the neuroprotective drug riluzole.
2002 Aug 2
Neuroprotective agent riluzole potentiates postsynaptic GABA(A) receptor function.
2002 Feb
Effect of chronic treatment with riluzole on the nigrostriatal dopaminergic system in weaver mutant mice.
2002 Jul
Lamotrigine derivatives and riluzole inhibit INa,P in cortical neurons.
2002 Jul 2
Early symptom progression rate is related to ALS outcome: a prospective population-based study.
2002 Jul 9
ALS, motor neuron disease, and related disorders: a personal approach to diagnosis and management.
2002 Mar
A double-blind, placebo-controlled and longitudinal study of riluzole in early Parkinson's disease.
2002 Mar
Is glutamate involved in transient lower esophageal sphincter relaxations?
2002 Mar
Kainate-induced currents in rat cortical neurons in culture are modulated by riluzole.
2002 Mar 15
Interaction of high concentrations of riluzole with recombinant skeletal muscle sodium channels and adult-type nicotinic receptor channels.
2002 Oct
Adjunctive modafinil in ALS.
2002 Spring
Patents

Sample Use Guides

In Vivo Use Guide
50 mg twice daily, taken at least 1 hour before or 2 hours after a meal
Route of Administration: Oral
In Vitro Use Guide
In vitro incubation of [14C]riluzole (15 microM) with human hepatic microsomes and NADPH or UDPGA cofactors resulted in formation of N-hydroxyriluzole (K(m) = 30 microM) or an unidentified glucuroconjugate (K(m) = 118 microM). Human microsomal riluzole N-hydroxylation was most strongly inhibited by the CYP1A2 inhibitor alpha-naphthoflavone (IC50 = 0.42 microM). Thus, riluzole is predominantly metabolized by CYP1A2 in human hepatic microsomes to N-hydroxyriluzole.
Name Type Language
RILUZOLE
EMA EPAR   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
RILUZOLE [USP-RS]
Common Name English
RILUZOLE [ORANGE BOOK]
Common Name English
RILUZOLE [INN]
Common Name English
RP 54274
Code English
RILUZOLE [EMA EPAR]
Common Name English
RILUZOLE [USP]
Common Name English
2-BENZOTHIAZOLAMINE, 6-(TRIFLUOROMETHOXY)-
Systematic Name English
RP-54274
Code English
TIGLUTIK
Brand Name English
RILUZOLE [USAN]
Common Name English
RILUZOLE [MI]
Common Name English
RILUZOLE [MART.]
Common Name English
RILUZOLE [JAN]
Common Name English
2-AMINO-6-(TRIFLUOROMETHOXY)BENZOTHIAZOLE
Systematic Name English
RILUZOLE [WHO-DD]
Common Name English
RILUTEK
Brand Name English
BHV-0223
Code English
RILUZOLE [VANDF]
Common Name English
Classification Tree Code System Code
WHO-ATC N07XX02
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
LIVERTOX 849
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
NDF-RT N0000167094
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
FDA ORPHAN DRUG 509415
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
NDF-RT N0000167094
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
FDA ORPHAN DRUG 510015
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
NDF-RT N0000167094
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
EMA ASSESSMENT REPORTS RILUZOLE ZENTIVA (AUTHORIZED: AMYOTROPHIC LATERAL SCLEROSIS)
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
FDA ORPHAN DRUG 72792
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
NDF-RT N0000167094
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
NDF-RT N0000175740
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
FDA ORPHAN DRUG 508715
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
FDA ORPHAN DRUG 100796
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
WHO-VATC QN07XX02
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
EMA ASSESSMENT REPORTS RILUTEK (AUTHORIZED: AMYOTROPHIC LATERAL SCLEROSIS)
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
EU-Orphan Drug EU/3/14/1401
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
FDA ORPHAN DRUG 563216
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
NCI_THESAURUS C264
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
Code System Code Type Description
IUPHAR
2326
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
PRIMARY
MESH
D019782
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
PRIMARY
CAS
1744-22-5
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
PRIMARY
DRUG BANK
DB00740
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
PRIMARY
PUBCHEM
5070
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
PRIMARY
RXCUI
35623
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
PRIMARY RxNorm
INN
5912
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
PRIMARY
EVMPD
SUB10319MIG
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
PRIMARY
WIKIPEDIA
RILUZOLE
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
PRIMARY
EPA CompTox
1744-22-5
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
PRIMARY
MERCK INDEX
M9620
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
PRIMARY Merck Index
ChEMBL
CHEMBL744
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
PRIMARY
NCI_THESAURUS
C47704
Created by admin on Mon Oct 21 20:57:05 UTC 2019 , Edited by admin on Mon Oct 21 20:57:05 UTC 2019
PRIMARY