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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

Molecular Formula C8H5F3N2OS
Molecular Weight 234.198
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
The role of glutamatergic transmission in the pathogenesis of levodopa-induced dyskinesias. Potential therapeutic approaches.
2001
The clinical effectiveness and cost-effectiveness of riluzole for motor neurone disease: a rapid and systematic review.
2001
Amyotrophic lateral sclerosis associated with pregnancy.
2001 Dec
Riluzole reduces hyperactivity of subthalamic neurons induced by unilateral 6-OHDA lesion in the rat brain.
2001 Nov
The Rilutek (riluzole) Global Early Access Programme: an open-label safety evaluation in the treatment of amyotrophic lateral sclerosis.
2001 Sep
Antiepileptic drugs and agents that inhibit voltage-gated sodium channels prevent NMDA antagonist neurotoxicity.
2002
Riluzole for amyotrophic lateral sclerosis (ALS)/motor neuron disease (MND).
2002
A fair innings for NICE?
2002
Cost effectiveness of treatments for amyotrophic lateral sclerosis: a review of the literature.
2002
Riluzole rescues cochlear sensory cells from acoustic trauma in the guinea-pig.
2002
Workshop on primary progressive multiple sclerosis: meeting summary.
2002 Apr
Emerging strategies for drug development in motor neuron disease.
2002 Apr
Sodium channel-blocking agents are not of benefit to rats with kaolin-induced hydrocephalus.
2002 Aug
Riluzole enhances expression of brain-derived neurotrophic factor with consequent proliferation of granule precursor cells in the rat hippocampus.
2002 Aug
Molsidomine potentiates the protective activity of GYKI 52466, a non-NMDA antagonist, MK-801, a non-competitive NMDA antagonist, and riluzole against electroconvulsions in mice.
2002 Aug
Modulation of recombinant and native neuronal SK channels by the neuroprotective drug riluzole.
2002 Aug 2
An ACTH- and ATP-regulated background K+ channel in adrenocortical cells is TREK-1.
2002 Dec 20
Apraxia of eyelid closure in Huntington's disease.
2002 Feb
Pharmacological characterization of a non-inactivating outward current observed in mouse cerebellar Purkinje neurones.
2002 Feb
Contribution of presynaptic Na(+) channel inactivation to paired-pulse synaptic depression in cultured hippocampal neurons.
2002 Feb
Neuroprotective agent riluzole potentiates postsynaptic GABA(A) receptor function.
2002 Feb
Riluzole therapy in cervical dystonia.
2002 Jan
Neuroprotective effect of riluzole in a primate model of Parkinson's disease: behavioral and histological evidence.
2002 Jan
[Tolerance of riluzole in a phase IIIb clinical trial].
2002 Jan-Feb
Riluzole prolongs survival time and alters nuclear inclusion formation in a transgenic mouse model of Huntington's disease.
2002 Jul
Glutamate transporters and retinal excitotoxicity.
2002 Jul
Effect of chronic treatment with riluzole on the nigrostriatal dopaminergic system in weaver mutant mice.
2002 Jul
Effect of Riluzole on serum amino acids in patients with amyotrophic lateral sclerosis.
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
Therapies in amyotrophic lateral sclerosis-beyond riluzole.
2002 Jun
A comparison of the anti-nociceptive effects of voltage-activated Na+ channel blockers in the formalin test.
2002 Jun 12
ALS, motor neuron disease, and related disorders: a personal approach to diagnosis and management.
2002 Mar
Changes in motor unit numbers in patients with ALS: a longitudinal study using the adapted multiple point stimulation method.
2002 Mar
Long-term safety of riluzole in amyotrophic lateral sclerosis.
2002 Mar
Prognostic modelling of therapeutic interventions in amyotrophic lateral sclerosis.
2002 Mar
How useful are retrospective studies in evaluating therapeutic interventions?
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
Riluzole and olanzapine in Huntington's disease.
2002 Mar
Kainate-induced currents in rat cortical neurons in culture are modulated by riluzole.
2002 Mar 15
Interaction between vanilloid and glutamate receptors in the central modulation of nociception.
2002 Mar 29
A study of riluzole in the treatment of advanced stage or elderly patients with amyotrophic lateral sclerosis.
2002 May
Riluzole treatment in advanced ALS.
2002 May
Respiratory rhythm: an emergent network property?
2002 May 30
Voltage-gated sodium ion channels in prostate cancer: expression and activity.
2002 May-Jun
Effect of riluzole on cytosolic Ca2+ increase in human osteosarcoma cells.
2002 Nov
Interaction of high concentrations of riluzole with recombinant skeletal muscle sodium channels and adult-type nicotinic receptor channels.
2002 Oct
Chronic morphine induces downregulation of spinal glutamate transporters: implications in morphine tolerance and abnormal pain sensitivity.
2002 Sep 15
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.
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:57:05 UTC 2019
Edited
by admin
on Mon Oct 21 20:57:05 UTC 2019
Record UNII
7LJ087RS6F
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
ACTIVE MOIETY