Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C15H16F3N5O4S.ClH |
| Molecular Weight | 455.84 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CN(CC(=O)NC1=NC2=C(S1)C=C(OC(F)(F)F)C=C2)C(=O)CNC(=O)CN
InChI
InChIKey=ZRZLEMQBDKNTLJ-UHFFFAOYSA-N
InChI=1S/C15H16F3N5O4S.ClH/c1-23(13(26)6-20-11(24)5-19)7-12(25)22-14-21-9-3-2-8(4-10(9)28-14)27-15(16,17)18;/h2-4H,5-7,19H2,1H3,(H,20,24)(H,21,22,25);1H
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C15H16F3N5O4S |
| Molecular Weight | 419.379 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including:
https://www.drugs.com/mtm/riluzole.html
http://www.rxlist.com/rilutek-drug.htm
https://www.ncbi.nlm.nih.gov/pubmed/8813989
Curator's Comment: description was created based on several sources, including:
https://www.drugs.com/mtm/riluzole.html
http://www.rxlist.com/rilutek-drug.htm
https://www.ncbi.nlm.nih.gov/pubmed/8813989
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.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: Q12791|||Q5SQR9 Gene ID: 3778.0 Gene Symbol: KCNMA1 Target Organism: Homo sapiens (Human) |
|||
Target ID: CHEMBL2231 |
|||
Target ID: CHEMBL3356 |
|||
Target ID: Q14524|||E9PFW7 Gene ID: 6331.0 Gene Symbol: SCN5A Target Organism: Homo sapiens (Human) |
2.3 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | RILUTEK Approved UseRILUTEK is indicated for the treatment of patients with amyotrophic lateral sclerosis (ALS). Riluzole extends survival and/or time to tracheostomy. Launch Date1995 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
359 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/21284699 |
50 mg 1 times / day steady-state, oral dose: 50 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
RILUZOLE plasma | Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2257 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/21284699 |
50 mg 1 times / day steady-state, oral dose: 50 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
RILUZOLE plasma | Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
7.8 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/21284699 |
50 mg 1 times / day steady-state, oral dose: 50 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
RILUZOLE plasma | Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4% |
RILUZOLE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| likely | ||||
| likely | ||||
| likely | ||||
| minor | ||||
| minor | ||||
| minor | ||||
| minor |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| unlikely | ||||
| unlikely | ||||
| unlikely | ||||
| unlikely | ||||
Page: 1.0 |
yes | |||
| yes | ||||
| yes | likely (co-administration study) Comment: Potential inhibitors of CYP1A2 (e.g. caffeine, phenacetin, theophylline, amitriphtyline, and quinolones) could decrease the rate of riluzole elimination, while inducers of CYP1A2 (e.g. cigarette smoke, charcoal-broiled food, rifampicin, and omeprazole) could increase rate of riluzole elimination Page: 8.0 |
|||
| yes | no (pharmacogenomic study) Comment: genetic variations in CYP1A1 and CYP1A2 genes do not seem to influence riluzole levels |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| An ACTH- and ATP-regulated background K+ channel in adrenocortical cells is TREK-1. | 2002-12-20 |
|
| Effect of riluzole on cytosolic Ca2+ increase in human osteosarcoma cells. | 2002-11 |
|
| Interaction of high concentrations of riluzole with recombinant skeletal muscle sodium channels and adult-type nicotinic receptor channels. | 2002-10 |
|
| Chronic morphine induces downregulation of spinal glutamate transporters: implications in morphine tolerance and abnormal pain sensitivity. | 2002-09-15 |
|
| Voltage-gated sodium ion channels in prostate cancer: expression and activity. | 2002-08-10 |
|
| Modulation of recombinant and native neuronal SK channels by the neuroprotective drug riluzole. | 2002-08-02 |
|
| Sodium channel-blocking agents are not of benefit to rats with kaolin-induced hydrocephalus. | 2002-08 |
|
| Riluzole enhances expression of brain-derived neurotrophic factor with consequent proliferation of granule precursor cells in the rat hippocampus. | 2002-08 |
|
| 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. | 2002-08 |
|
| Early symptom progression rate is related to ALS outcome: a prospective population-based study. | 2002-07-09 |
|
| Lamotrigine derivatives and riluzole inhibit INa,P in cortical neurons. | 2002-07-02 |
|
| [Tolerance of riluzole in a phase IIIb clinical trial]. | 2002-07-02 |
|
| Riluzole prolongs survival time and alters nuclear inclusion formation in a transgenic mouse model of Huntington's disease. | 2002-07 |
|
| Glutamate transporters and retinal excitotoxicity. | 2002-07 |
|
| Effect of chronic treatment with riluzole on the nigrostriatal dopaminergic system in weaver mutant mice. | 2002-07 |
|
| Effect of Riluzole on serum amino acids in patients with amyotrophic lateral sclerosis. | 2002-07 |
|
| A comparison of the anti-nociceptive effects of voltage-activated Na+ channel blockers in the formalin test. | 2002-06-12 |
|
| Therapies in amyotrophic lateral sclerosis-beyond riluzole. | 2002-06 |
|
| Respiratory rhythm: an emergent network property? | 2002-05-30 |
|
| A study of riluzole in the treatment of advanced stage or elderly patients with amyotrophic lateral sclerosis. | 2002-05 |
|
| Riluzole treatment in advanced ALS. | 2002-05 |
|
| Workshop on primary progressive multiple sclerosis: meeting summary. | 2002-04 |
|
| Emerging strategies for drug development in motor neuron disease. | 2002-04 |
|
| Interaction between vanilloid and glutamate receptors in the central modulation of nociception. | 2002-03-29 |
|
| Kainate-induced currents in rat cortical neurons in culture are modulated by riluzole. | 2002-03-15 |
|
| ALS, motor neuron disease, and related disorders: a personal approach to diagnosis and management. | 2002-03 |
|
| Changes in motor unit numbers in patients with ALS: a longitudinal study using the adapted multiple point stimulation method. | 2002-03 |
|
| Long-term safety of riluzole in amyotrophic lateral sclerosis. | 2002-03 |
|
| Prognostic modelling of therapeutic interventions in amyotrophic lateral sclerosis. | 2002-03 |
|
| How useful are retrospective studies in evaluating therapeutic interventions? | 2002-03 |
|
| A double-blind, placebo-controlled and longitudinal study of riluzole in early Parkinson's disease. | 2002-03 |
|
| Is glutamate involved in transient lower esophageal sphincter relaxations? | 2002-03 |
|
| Riluzole and olanzapine in Huntington's disease. | 2002-03 |
|
| Apraxia of eyelid closure in Huntington's disease. | 2002-02 |
|
| Pharmacological characterization of a non-inactivating outward current observed in mouse cerebellar Purkinje neurones. | 2002-02 |
|
| Contribution of presynaptic Na(+) channel inactivation to paired-pulse synaptic depression in cultured hippocampal neurons. | 2002-02 |
|
| Neuroprotective agent riluzole potentiates postsynaptic GABA(A) receptor function. | 2002-02 |
|
| Riluzole therapy in cervical dystonia. | 2002-01 |
|
| Neuroprotective effect of riluzole in a primate model of Parkinson's disease: behavioral and histological evidence. | 2002-01 |
|
| 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 |
|
| Adjunctive modafinil in ALS. | 2002 |
|
| Amyotrophic lateral sclerosis associated with pregnancy. | 2001-12 |
|
| Riluzole reduces hyperactivity of subthalamic neurons induced by unilateral 6-OHDA lesion in the rat brain. | 2001-11 |
|
| The Rilutek (riluzole) Global Early Access Programme: an open-label safety evaluation in the treatment of amyotrophic lateral sclerosis. | 2001-09 |
|
| 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 |
Sample Use Guides
50 mg twice daily, taken at least 1 hour before or 2
hours after a meal
Route of Administration:
Oral
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
Edited
Tue Apr 01 20:06:02 GMT 2025
by
admin
on
Tue Apr 01 20:06:02 GMT 2025
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| Record UNII |
BQ5F77DZS3
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| Record Status |
Validated (UNII)
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| Record Version |
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-
Download
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Official Name | English | ||
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Preferred Name | English | ||
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Common Name | English | ||
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Systematic Name | English | ||
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Code | English |
| Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
520016
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1926204-76-3
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DE-175
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133082858
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BQ5F77DZS3
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C174644
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300000011157
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