TRORILUZOLE HYDROCHLORIDE

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

Structure Search

SMILES

Cl.CN(CC(=O)NC1=NC2=CC=C(OC(F)(F)F)C=C2S1)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

HIDE SMILES / InChI

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020599s017lbl.pdf
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Calcium-activated potassium channel subunit alpha-1 25 Target ID: Q12791\|\|\|Q5SQR9 Gene ID: 3778.0 Gene Symbol: KCNMA1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/18068197	Activator 1430
Cytochrome P450 1A1 31 Target ID: CHEMBL2231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17852022	Substrate 661
Cytochrome P450 1A2 72 Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17852022 \| https://www.ncbi.nlm.nih.gov/pubmed/15752377	Substrate 661
Sodium channel protein type 5 subunit alpha 9 Target ID: Q14524\|\|\|E9PFW7 Gene ID: 6331.0 Gene Symbol: SCN5A Target Organism: Homo sapiens (Human) Sources: http://www.drugbank.ca/drugs/DB00740 \| https://www.ncbi.nlm.nih.gov/pubmed/20590601 \| https://www.ncbi.nlm.nih.gov/pubmed/18068197	Blocker 537	2.3 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Amyotrophic lateral sclerosis 41 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020599s017lbl.pdf	Primary		Approved 8429	RILUTEK Approved Use RILUTEK is indicated for the treatment of patients with amyotrophic lateral sclerosis (ALS). Riluzole extends survival and/or time to tracheostomy. Launch Date 1995

C_max

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

T_1/2

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

F_unbound

Value	Dose	Co-administered	Analyte	Population
4% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020599s017lbl.pdf			RILUZOLE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
100 mg 2 times / day multiple, oral Highest studied dose Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8676624 Page: p.1429	unhealthy, ADULT n = 244 Health Status: unhealthy Condition: amyotrophic lateral sclerosis Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 244 Sources: https://pubmed.ncbi.nlm.nih.gov/8676624 Page: p.1429	Disc. AE: Lung function decreased... Other AEs: AST increased, Vomiting... AEs leading to discontinuation/dose reduction: Lung function decreased (4%) Other AEs: AST increased (11.9%) Vomiting (1%) Abdominal pain (3%) Dizziness (1%) Asthenia (4%) Malaise (2%) Nausea (5%) Sources: https://pubmed.ncbi.nlm.nih.gov/8676624 Page: p.1429

AEs

AE	Significance	Dose	Population
Dizziness	1%	100 mg 2 times / day multiple, oral Highest studied dose Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8676624 Page: p.1429	unhealthy, ADULT n = 244 Health Status: unhealthy Condition: amyotrophic lateral sclerosis Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 244 Sources: https://pubmed.ncbi.nlm.nih.gov/8676624 Page: p.1429
Vomiting	1%	100 mg 2 times / day multiple, oral Highest studied dose Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8676624 Page: p.1429	unhealthy, ADULT n = 244 Health Status: unhealthy Condition: amyotrophic lateral sclerosis Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 244 Sources: https://pubmed.ncbi.nlm.nih.gov/8676624 Page: p.1429
AST increased	11.9%	100 mg 2 times / day multiple, oral Highest studied dose Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8676624 Page: p.1429	unhealthy, ADULT n = 244 Health Status: unhealthy Condition: amyotrophic lateral sclerosis Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 244 Sources: https://pubmed.ncbi.nlm.nih.gov/8676624 Page: p.1429
Malaise	2%	100 mg 2 times / day multiple, oral Highest studied dose Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8676624 Page: p.1429	unhealthy, ADULT n = 244 Health Status: unhealthy Condition: amyotrophic lateral sclerosis Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 244 Sources: https://pubmed.ncbi.nlm.nih.gov/8676624 Page: p.1429
Abdominal pain	3%	100 mg 2 times / day multiple, oral Highest studied dose Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8676624 Page: p.1429	unhealthy, ADULT n = 244 Health Status: unhealthy Condition: amyotrophic lateral sclerosis Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 244 Sources: https://pubmed.ncbi.nlm.nih.gov/8676624 Page: p.1429
Asthenia	4%	100 mg 2 times / day multiple, oral Highest studied dose Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8676624 Page: p.1429	unhealthy, ADULT n = 244 Health Status: unhealthy Condition: amyotrophic lateral sclerosis Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 244 Sources: https://pubmed.ncbi.nlm.nih.gov/8676624 Page: p.1429
Lung function decreased	4% Disc. AE	100 mg 2 times / day multiple, oral Highest studied dose Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8676624 Page: p.1429	unhealthy, ADULT n = 244 Health Status: unhealthy Condition: amyotrophic lateral sclerosis Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 244 Sources: https://pubmed.ncbi.nlm.nih.gov/8676624 Page: p.1429
Nausea	5%	100 mg 2 times / day multiple, oral Highest studied dose Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8676624 Page: p.1429	unhealthy, ADULT n = 244 Health Status: unhealthy Condition: amyotrophic lateral sclerosis Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 244 Sources: https://pubmed.ncbi.nlm.nih.gov/8676624 Page: p.1429

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737 inhibitor 1587	inhibitor 1767	substrate 1217 inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
Nav1.5 97 Cav1.2 45 CYP1A2 1524 CYP2A6 707 CYP2D1 6 CYP2C19 1478	CYP1A1 349 CYP1A2 1054 CYP2C19 991 CYP2E1 667 P-gp 1537 BCRP 561

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/020599Orig1s000rev.pdf#page=344 Page: 344.0	likely
CYP2A6 739	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/020599Orig1s000rev.pdf#page=344 Page: 344.0	likely
CYP2D1 8	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/020599Orig1s000rev.pdf#page=344 Page: 344.0	likely
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/020599Orig1s000rev.pdf#page=344 Page: 344.0	minor
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/020599Orig1s000rev.pdf#page=344 Page: 344.0	minor
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/020599Orig1s000rev.pdf#page=344 Page: 344.0	minor
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/020599Orig1s000rev.pdf#page=344 Page: 344.0	minor

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP2C19 991	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/020599Orig1s000rev.pdf#page=8 Page: 8.0	unlikely
CYP2D6 1217	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/020599Orig1s000rev.pdf#page=8 Page: 8.0	unlikely
CYP2E1 667	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/020599Orig1s000rev.pdf#page=8 Page: 8.0	unlikely
CYP3A4 1737	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/020599Orig1s000rev.pdf#page=8 Page: 8.0	unlikely
BCRP 561	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/19146924/ Page: 1.0	yes
P-gp 1537	substrate 3367 Sources: https://www.sciencedirect.com/science/article/abs/pii/S092809871830191X Page: 3.0	yes
CYP1A2 1054	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/020599Orig1s000rev.pdf#page=8 Page: 8.0	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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/020599Orig1s000rev.pdf#page=8 Page: 8.0
CYP1A1 349	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/17852022/#:~:text=Riluzole%20is%20the%20only%20FDA,the%20extra-hepatic%20cytochrome%20CYP1A1.&text=The%20mean%20peak%20riluzole%20level,54.3%2B%2F-37.5%20ng%2Fml.	yes	no (pharmacogenomic study) Comment: genetic variations in CYP1A1 and CYP1A2 genes do not seem to influence riluzole levels Sources: https://pubmed.ncbi.nlm.nih.gov/17852022/#:~:text=Riluzole%20is%20the%20only%20FDA,the%20extra-hepatic%20cytochrome%20CYP1A1.&text=The%20mean%20peak%20riluzole%20level,54.3%2B%2F-37.5%20ng%2Fml.

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
Cav1.2 49	inhibitor 1626 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2635097/
Nav1.5 100	inhibitor 1626 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2635097/
hERG 1647	inhibitor 1626 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2635097/

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY429479	https://www.001chemical.com/chem/1744-22-5
3B Scientific (Wuhan) Corp	3B3-064767	http://www.3bsc.com/index/pro_info.php?id=103958
AA Blocks	AA007UEE	http://www.aablocks.com/goods/Goods/detail?id=AA007UEE
AEchem Scientific Corp., USA	AE061167	https://www.aechemsc.com/info_products/AE061167.php
AK Scientific, Inc. (AKSCI)	H090	http://www.aksci.com/item_detail.php?cat=H090
AK Scientific, Inc. (AKSCI)	J10184	http://www.aksci.com/item_detail.php?cat=J10184
AK Scientific, Inc. (AKSCI)	J10441	http://www.aksci.com/item_detail.php?cat=J10441
Aaron Chemicals	AR007V66	http://www.aaronchem.com/1744-22-5
AbMole Bioscience	M1968	http://www.abmole.com/products/riluzole.html
Acadechem	ACDS-033221	http://www.acadechemical.com/product/107920
Achemica	ACMC-209e89	http://www.achemica.com/prodinfo/?id=124074
Achemo Scientific Limited	AC-12673	http://www.achemo.com/product_view.asp?ID=2563
Achemtek	0104-047110	http://www.achemtek.com/1744-22-5
Acros Organics	AC459360050	https://www.fishersci.com/shop/products/riluzole-98-acros-organics-1/AC459360050
Acros Organics	AC459360010	https://www.fishersci.com/shop/products/riluzole-98-acros-organics-2/AC459360010
Acros Organics	AC459360100	https://www.fishersci.com/shop/products/riluzole-98-acros-organics/AC459360100
Active Biopharma	ABP000632	http://www.activebiopharma.com/1744-22-5
Adooq BioScience	A10795	https://www.adooq.com/riluzole-rilutek.html
Alfa Aesar	H61328	https://www.alfa.com/en/catalog/H61328/
Alfa Chemistry	AP1744225-A	https://reagents.alfa-chemistry.com/product/riluzole-cas-1744-22-5-6499.html
Alfa Chemistry	AP1744225-B	https://reagents.alfa-chemistry.com/product/riluzole-cas-1744-22-5-cas-1744-22-5-6500.html
Alichem	59004961	http://www.alichem.com/en/products/1744-22-5.html
Alinda	ALBB-006046	http://alinda.ru/finechem_en_.html?i=ALBB-006046
Alsachim	1422	http://www.alsachim.com/product-C3236-glo.bal-view.html
Ambeed	A221527	https://www.ambeed.com/products/1744-22-5.html
Ambinter	Amb1046443	http://www.ambinter.com/reference/1046443
Angene	AGN-PC-0JK747	http://www.angenechemical.com/productshow/AGN-PC-0JK747.html
Anward	ANW-22711	http://www.anward.com/pro_result/5333
ApexBio Technology	A8513	http://www.apexbt.com/riluzole.html
Ark Pharm	AK-59567	http://www.arkpharminc.com/products/1744-22-5.html
AstaTech, Inc.	46085	http://www.astatechinc.com/CPSResult.php?CRNO=1426
Aurora Fine Chemicals LLC	A00.246.676	http://online.aurorafinechemicals.com/info?ID=A00.246.676
Aurora Fine Chemicals LLC	K00.691.742	http://online.aurorafinechemicals.com/info?ID=K00.691.742
Aurum Pharmatech LLC	A-5766	http://www.Aurumpharmatech.com/Product/ProductDetails/A_5766
AvaChem Scientific	6737	https://www.avachem.com/productSearch.asp?6737
Avantor Inc	TCA2423-25G	https://us.vwr.com/store/product/16809061/2-amino-6-trifluoromethoxy-benzothiazole-98-0-by-hplc-titration-analysis
Avantor Inc	TCA2423-5G	https://us.vwr.com/store/product/16809061/2-amino-6-trifluoromethoxy-benzothiazole-98-0-by-hplc-titration-analysis
Avantor Inc	BT214735-25G	https://us.vwr.com/store/product/16901932/2-amino-6-trifluoromethoxy-benzothiazole-98
Avantor Inc	BT214735-5G	https://us.vwr.com/store/product/16901932/2-amino-6-trifluoromethoxy-benzothiazole-98
BLD Pharm	BD18886	http://www.bldpharm.com/products/1744-22-5.html
BOC Sciences	1215552-03-6	https://www.bocsci.com/riluzole-13c-15n2-cas-1215552-03-6-item-479096.html
BioChemPartner	BCP02142	http://www.biochempartner.com/1744-22-5-BCP02142
BioCrick	BCC3849	http://www.biocrick.com/Riluzole-BCC3849.html
Boerchem	BC219019	http://www.boerchem.com/?product_36879.html
CSNpharm	CSN12584	https://www.csnpharm.com/products/riluzole.html
Capot Chemical	14501	http://www.capotchem.com/en/14501.htm
Capot Chemical	PubChem14501	http://www.capotchem.com/en/14501.htm
Chem Scene	CS-2156	http://www.chemscene.com/1744-22-5.html
ChemMol	30108902	http://www.chemmol.com/chemmol/30108902.html
ChemMol	44005820	http://www.chemmol.com/chemmol/44005820.html
ChemMol	49401142	http://www.chemmol.com/chemmol/49401142.html
ChemMol	81402522	http://www.chemmol.com/chemmol/81402522.html
Chemenu	CM110360	http://www.chemenu.com/products/CM110360
Chemspace	CSSB00000233500	https://chem-space.com/CSSB00000233500
Clearsynth	CS-EB-02294	https://www.clearsynth.com/en/CSEB02294.html
Clearsynth	CS-O-06928	https://www.clearsynth.com/en/CSO06928.html
Clearsynth	CS-O-11735	https://www.clearsynth.com/en/CSO11735.html
DC Chemicals	DC8985	http://www.dcchemicals.com/product_show-Riluzole.html
Debye Scientific	DB-030335	http://www.debyesci.com/DB-030335.html
EMD Biosciences	557324	http://www.emdbiosciences.com/products/EMD_BIO-557324
EMD Millipore	557324	http://www.emdbiosciences.com/products/EMD_BIO-557324
Enamine	Z166605314	https://www.enaminestore.com/catalog/Z166605314
Finetech	FT-0611194	http://www.finetechnology-ind.com/prod/detail/pub/1744-22-5.html
Glentham Life Sciences	GP5490	http://www.glentham.com/products/product/GP5490/
Hairui	HR137750	http://www.hairuichem.com/en/product/1744-22-5.html
Hefei Hirisun Pharmatech Co., Ltd	HR080410	http://www.hirisunpharm.com/1744-22-5.html
Hello Bio	HB6093	https://www.hellobio.com/riluzole.html
LGC Standards	LGCFOR1382.00	https://www.lgcstandards.com/US/en/p/LGCFOR1382.00
LGC Standards	MM1382.00	https://www.lgcstandards.com/US/en/p/MM1382.00
Lab Network	LN00110713	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00110713
Matrix Scientific	1333	https://www.matrixscientific.com/001333.html
MedChem Express	HY-B0211	https://www.medchemexpress.com/riluzole.html
Molcore	MC429479	https://www.molcore.com/product/1744-22-5
OChem	8856	http://www.ocheminc.com/index.php?act=psearch&pid=744R225
Oakwood	4026	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=1839&ExtHyperLink=1
Renno Tech	RP28111	http://www.rennotech.com/product_show.asp?id=33728
Selleck Chemicals	S1614	http://www.selleckchem.com/products/Riluzole(Rilutek).html
Shanghai Send Pharmaceutical Technology Co., Ltd	send41629	http://shsendpharm.com/
Sigma-Aldrich	R116_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/r116?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1604337_USP	https://www.sigmaaldrich.com/catalog/product/usp/1604337?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S017564	http://www.sinfoobiotech.com/product/1020962
Smolecule	S541428	http://www.smolecule.com/products/s541428
TCI (Tokyo Chemical Industry)	A2423	http://www.tcichemicals.com/eshop/en/us/commodity/A2423/index.html
THE BioTek	bt-280693	https://www.thebiotek.com/product/inhibitors/bt-280693
VladaChem	VL144143	https://www.vladachem.com/product.php?products=1744-22-5
VladaChem	VL280931-25G	https://www.vladachem.com/product.php?products=1744-22-5
Yuhao Chemical	RT4705	http://www.chemyuhao.com/1744-22-5.html
abcr GmbH	AB104584	http://www.abcr.com/shop/en/AB104584
eNovation Chemicals	D371376	http://www.enovationchem.com/productDetails.asp?productID=D371376
eNovation Chemicals	D404602	https://www.enovationchem.com/ProductDetails.asp?ProductID=D404602
eNovation Chemicals	D958015	https://www.enovationchem.com/ProductDetails.asp?ProductID=D958015
iChemical	EBD12611	http://www.ichemical.com/products/1744-22-5.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-9362288181	https://mcule.com/MCULE-9362288181/

PubMed

Title	Date	PubMed
The role of glutamatergic transmission in the pathogenesis of levodopa-induced dyskinesias. Potential therapeutic approaches.	2001	12001656
The clinical effectiveness and cost-effectiveness of riluzole for motor neurone disease: a rapid and systematic review.	2001	11809124
Amyotrophic lateral sclerosis associated with pregnancy.	2001 Dec	11799421
Riluzole reduces hyperactivity of subthalamic neurons induced by unilateral 6-OHDA lesion in the rat brain.	2001 Nov	11748743
The Rilutek (riluzole) Global Early Access Programme: an open-label safety evaluation in the treatment of amyotrophic lateral sclerosis.	2001 Sep	11771772
Antiepileptic drugs and agents that inhibit voltage-gated sodium channels prevent NMDA antagonist neurotoxicity.	2002	12192617
Riluzole for amyotrophic lateral sclerosis (ALS)/motor neuron disease (MND).	2002	12076411
A fair innings for NICE?	2002	12052097
Cost effectiveness of treatments for amyotrophic lateral sclerosis: a review of the literature.	2002	12052096
Riluzole rescues cochlear sensory cells from acoustic trauma in the guinea-pig.	2002	12031350
Workshop on primary progressive multiple sclerosis: meeting summary.	2002 Apr	11990876
Emerging strategies for drug development in motor neuron disease.	2002 Apr	11922857
Sodium channel-blocking agents are not of benefit to rats with kaolin-induced hydrocephalus.	2002 Aug	12182785
Riluzole enhances expression of brain-derived neurotrophic factor with consequent proliferation of granule precursor cells in the rat hippocampus.	2002 Aug	12154010
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	12126871
Modulation of recombinant and native neuronal SK channels by the neuroprotective drug riluzole.	2002 Aug 2	12163105
An ACTH- and ATP-regulated background K+ channel in adrenocortical cells is TREK-1.	2002 Dec 20	12368289
Apraxia of eyelid closure in Huntington's disease.	2002 Feb	12075860
Pharmacological characterization of a non-inactivating outward current observed in mouse cerebellar Purkinje neurones.	2002 Feb	11834618
Contribution of presynaptic Na(+) channel inactivation to paired-pulse synaptic depression in cultured hippocampal neurons.	2002 Feb	11826057
Neuroprotective agent riluzole potentiates postsynaptic GABA(A) receptor function.	2002 Feb	11804616
Riluzole therapy in cervical dystonia.	2002 Jan	11835465
Neuroprotective effect of riluzole in a primate model of Parkinson's disease: behavioral and histological evidence.	2002 Jan	11835434
[Tolerance of riluzole in a phase IIIb clinical trial].	2002 Jan-Feb	12090150
Riluzole prolongs survival time and alters nuclear inclusion formation in a transgenic mouse model of Huntington's disease.	2002 Jul	12210870
Glutamate transporters and retinal excitotoxicity.	2002 Jul	12112376
Effect of chronic treatment with riluzole on the nigrostriatal dopaminergic system in weaver mutant mice.	2002 Jul	12093102
Effect of Riluzole on serum amino acids in patients with amyotrophic lateral sclerosis.	2002 Jul	12067327
Lamotrigine derivatives and riluzole inhibit INa,P in cortical neurons.	2002 Jul 2	12151762
Early symptom progression rate is related to ALS outcome: a prospective population-based study.	2002 Jul 9	12105314
Therapies in amyotrophic lateral sclerosis-beyond riluzole.	2002 Jun	12020475
A comparison of the anti-nociceptive effects of voltage-activated Na+ channel blockers in the formalin test.	2002 Jun 12	12079688
ALS, motor neuron disease, and related disorders: a personal approach to diagnosis and management.	2002 Mar	12170396
Changes in motor unit numbers in patients with ALS: a longitudinal study using the adapted multiple point stimulation method.	2002 Mar	12061946
Long-term safety of riluzole in amyotrophic lateral sclerosis.	2002 Mar	12061945
Prognostic modelling of therapeutic interventions in amyotrophic lateral sclerosis.	2002 Mar	12061944
How useful are retrospective studies in evaluating therapeutic interventions?	2002 Mar	12061942
A double-blind, placebo-controlled and longitudinal study of riluzole in early Parkinson's disease.	2002 Mar	12039422
Is glutamate involved in transient lower esophageal sphincter relaxations?	2002 Mar	11913413
Riluzole and olanzapine in Huntington's disease.	2002 Mar	11882065
Kainate-induced currents in rat cortical neurons in culture are modulated by riluzole.	2002 Mar 15	11835519
Interaction between vanilloid and glutamate receptors in the central modulation of nociception.	2002 Mar 29	11937094
A study of riluzole in the treatment of advanced stage or elderly patients with amyotrophic lateral sclerosis.	2002 May	12021952
Riluzole treatment in advanced ALS.	2002 May	12021937
Respiratory rhythm: an emergent network property?	2002 May 30	12062027
Voltage-gated sodium ion channels in prostate cancer: expression and activity.	2002 May-Jun	12168861
Effect of riluzole on cytosolic Ca2+ increase in human osteosarcoma cells.	2002 Nov	12372901
Interaction of high concentrations of riluzole with recombinant skeletal muscle sodium channels and adult-type nicotinic receptor channels.	2002 Oct	12362421
Chronic morphine induces downregulation of spinal glutamate transporters: implications in morphine tolerance and abnormal pain sensitivity.	2002 Sep 15	12223586
Adjunctive modafinil in ALS.	2002 Spring	11983803

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

TRORILUZOLE HYDROCHLORIDE

Official Name

English

TRORILUZOLE HYDROCHLORIDE [USAN]

Common Name

English

Glycylglycyl-N2-methyl-N-[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]glycinamide monohydrochloride

Systematic Name

English

BHV-4157

Code

English

GLYCINAMIDE, GLYCYLGLYCYL-N2-METHYL-N-(6-(TRIFLUOROMETHOXY)-2-BENZOTHIAZOLYL)-, HYDROCHLORIDE (1:1)

Systematic Name

English

BHV-4157 HYDROCHLORIDE

Code

English

Classification Tree Code System Code

FDA ORPHAN DRUG

520016