Details of the Drug

General Information of Drug (ID: DMECBWN)

Drug Name

Riluzole

Synonyms

Rilutek; Riluzol; Riluzolum; Riluzole HCl; RP 54274; ALBB-006046; BF-37; PK-26124; R-116; RP-54274; Rilutek (TN); Riluzol [INN-Spanish]; Riluzole [USAN:INN]; Riluzolum [INN-Latin]; ZERO/001785; Amino-2 trifluoromethoxy-6 benzothiazole; Amino-2 trifluoromethoxy-6 benzothiazole [French]; Riluzole (JAN/USAN/INN); PK-26124, RP-54274, Rilutek, Riluzole; 2-Amino-6-(trifluoromethoxy)-benzothiazole; 2-Amino-6-(trifluoromethoxy)benzothiazole; 2-Amino-6-trifluoro-methoxybenzothiazole; 2-amino-6-(trifluoromethoxy)-1,3-benzothiazole; 2-amino-6-(trifluoromethoxy)benzo[d]thiazole; 2-amino-6-(trifluoromethoxyl)benzothiazole; 2-amino-6-trifluoromethoxybenzothiazole; 6-(trifluoromethoxy)-1,3-benzothiazol-2-amine; 6-(trifluoromethoxy)benzo[d]thiazol-2-amine; 6-Trifluoromethoxy-benzothiazol-2-ylamine; 6-trifluoromethoxybenzothiazole-2-yl-amine

Indication

Disease Entry	ICD 11	Status	REF
Amyotrophic lateral sclerosis	8B60.0	Approved	[1]

Therapeutic Class

Anticonvulsants

Affected Organisms

Humans and other mammals

ATC Code

N07XX02: Riluzole

N07XX: Other nervous system drugs

N07X: OTHER NERVOUS SYSTEM DRUGS

N07: OTHER NERVOUS SYSTEM DRUGS

N: NERVOUS SYSTEM

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

234.2

Logarithm of the Partition Coefficient (xlogp)

3.6

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [2]
Bioavailability: 64% of drug becomes completely available to its intended biological destination(s) [3]
Clearance: The drug present in the plasma can be removed from the body at the rate of 11.3 mL/min/kg [4]
Elimination: 2% of drug is excreted from urine in the unchanged form [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 12 hours [4]
Metabolism: The drug is metabolized via the hepatic []
Unbound Fraction: The unbound fraction of drug in plasma is 0.04% [4]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 3.5 L/kg [4]

Chemical Identifiers

Formula: C8H5F3N2OS
IUPAC Name: 6-(trifluoromethoxy)-1,3-benzothiazol-2-amine
Canonical SMILES: C1=CC2=C(C=C1OC(F)(F)F)SC(=N2)N
InChI: 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)
InChIKey: FTALBRSUTCGOEG-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 5070
ChEBI ID: CHEMBL744
CAS Number: 1744-22-5
UNII: 7LJ087RS6F
DrugBank ID: DB00740
TTD ID: D0H0KB
VARIDT ID: DR00205
INTEDE ID: DR1425
ACDINA ID: D00595

Drug-Molecule Activity Atlas (DMA)^NEW

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Drug ADMET Endpoint Profile (DAE)^NEW

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Combinatorial Drugs (CBD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Voltage-gated sodium channel alpha Nav1.9 (SCN11A)	TTN9VTF	SCNBA_HUMAN	Blocker	[5]

Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Breast cancer resistance protein (ABCG2)	DTI7UX6	ABCG2_HUMAN	Substrate	[6]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 1A1 (CYP1A1)	DE6OQ3W	CP1A1_HUMAN	Substrate	[7]
UDP-glucuronosyltransferase 1A1 (UGT1A1)	DEYGVN4	UD11_HUMAN	Substrate	[8]
Cytochrome P450 1A2 (CYP1A2)_{Main DME}	DEJGDUW	CP1A2_HUMAN	Substrate	[9]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Cyclic AMP-dependent transcription factor ATF-6 alpha (ATF6)	OTAFHAVI	ATF6A_HUMAN	Gene/Protein Processing	[10]
Kallikrein-2 (KLK2)	OT9RE37R	KLK2_HUMAN	Gene/Protein Processing	[10]
Nuclear receptor subfamily 1 group I member 2 (NR1I2)	OTC5U0N5	NR1I2_HUMAN	Gene/Protein Processing	[11]
Utrophin	OT7TZ637	UTRN_HUMAN	Gene/Protein Processing	[12]
X-box-binding protein 1	OTJYCREE	XBP1_HUMAN	Gene/Protein Processing	[10]

Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Riluzole (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Remdesivir	DMBFZ6L	Moderate	Increased risk of hepatotoxicity by the combination of Riluzole and Remdesivir.	1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019]	[13]
Bedaquiline	DM3906J	Moderate	Increased risk of hepatotoxicity by the combination of Riluzole and Bedaquiline.	Antimicrobial drug resistance [MG50-MG52]	[14]
Aminophylline	DML2NIB	Minor	Decreased metabolism of Riluzole caused by Aminophylline mediated inhibition of CYP450 enzyme.	Asthma [CA23]	[15]
Obeticholic acid	DM3Q1SM	Moderate	Decreased metabolism of Riluzole caused by Obeticholic acid mediated inhibition of CYP450 enzyme.	Autoimmune liver disease [DB96]	[16]
Ofloxacin	DM0VQN3	Minor	Decreased metabolism of Riluzole caused by Ofloxacin mediated inhibition of CYP450 enzyme.	Bacterial infection [1A00-1C4Z]	[15]
Norfloxacin	DMIZ6W2	Minor	Decreased metabolism of Riluzole caused by Norfloxacin mediated inhibition of CYP450 enzyme.	Bacterial infection [1A00-1C4Z]	[15]
Pexidartinib	DMS2J0Z	Major	Increased risk of hepatotoxicity by the combination of Riluzole and Pexidartinib.	Bone/articular cartilage neoplasm [2F7B]	[17]
Osilodrostat	DMIJC9X	Moderate	Decreased metabolism of Riluzole caused by Osilodrostat mediated inhibition of CYP450 enzyme.	Cushing syndrome [5A70]	[18]
Cannabidiol	DM0659E	Moderate	Increased risk of hepatotoxicity by the combination of Riluzole and Cannabidiol.	Epileptic encephalopathy [8A62]	[19]
Brentuximab vedotin	DMWLC57	Moderate	Increased risk of hepatotoxicity by the combination of Riluzole and Brentuximab vedotin.	Hodgkin lymphoma [2B30]	[20]
Mipomersen	DMGSRN1	Major	Increased risk of hepatotoxicity by the combination of Riluzole and Mipomersen.	Hyper-lipoproteinaemia [5C80]	[21]
Teriflunomide	DMQ2FKJ	Major	Increased risk of hepatotoxicity by the combination of Riluzole and Teriflunomide.	Hyper-lipoproteinaemia [5C80]	[22]
BMS-201038	DMQTAGO	Major	Increased risk of hepatotoxicity by the combination of Riluzole and BMS-201038.	Hyper-lipoproteinaemia [5C80]	[23]
Givosiran	DM5PFIJ	Moderate	Decreased metabolism of Riluzole caused by Givosiran mediated inhibition of CYP450 enzyme.	Inborn porphyrin/heme metabolism error [5C58]	[24]
Osimertinib	DMRJLAT	Moderate	Increased metabolism of Riluzole caused by Osimertinib mediated induction of CYP450 enzyme.	Lung cancer [2C25]	[25]
Capmatinib	DMYCXKL	Moderate	Decreased metabolism of Riluzole caused by Capmatinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[26]
Calaspargase pegol	DMQZBXI	Moderate	Increased risk of hepatotoxicity by the combination of Riluzole and Calaspargase pegol.	Malignant haematopoietic neoplasm [2B33]	[27]
Idelalisib	DM602WT	Moderate	Increased risk of hepatotoxicity by the combination of Riluzole and Idelalisib.	Mature B-cell leukaemia [2A82]	[28]
Vemurafenib	DM62UG5	Moderate	Decreased metabolism of Riluzole caused by Vemurafenib mediated inhibition of CYP450 enzyme.	Melanoma [2C30]	[29]
Exjade	DMHPRWG	Moderate	Decreased metabolism of Riluzole caused by Exjade mediated inhibition of CYP450 enzyme.	Mineral absorption/transport disorder [5C64]	[30]
Olaparib	DM8QB1D	Moderate	Increased metabolism of Riluzole caused by Olaparib mediated induction of CYP450 enzyme.	Ovarian cancer [2C73]	[13]
Rucaparib	DM9PVX8	Moderate	Decreased metabolism of Riluzole caused by Rucaparib mediated inhibition of CYP450 enzyme.	Ovarian cancer [2C73]	[31]
Abametapir	DM2RX0I	Moderate	Decreased metabolism of Riluzole caused by Abametapir mediated inhibition of CYP450 enzyme.	Pediculosis [1G00]	[32]
Leflunomide	DMR8ONJ	Major	Increased risk of hepatotoxicity by the combination of Riluzole and Leflunomide.	Rheumatoid arthritis [FA20]	[22]
Trabectedin	DMG3Y89	Moderate	Increased risk of hepatotoxicity by the combination of Riluzole and Trabectedin.	Solid tumour/cancer [2A00-2F9Z]	[19]


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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Brushite	E00392	104805	Diluent
Carmellose sodium	E00625	Not Available	Disintegrant
Magnesium stearate	E00208	11177	lubricant
Polyethylene glycol 400	E00653	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyethylene glycol 6000	E00655	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Triacetin	E00080	5541	Humectant; Plasticizing agent; Solvent
Vinylpyrrolidone	E00668	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent


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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Riluzole 50 mg tablet	50 mg	Oral Tablet	Oral

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References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2326).
2	BDDCS applied to over 900 drugs
3	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
4	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5	Secondary injury mechanisms of spinal cord trauma: a novel therapeutic approach for the management of secondary pathophysiology with the sodium channel blocker riluzole. Prog Brain Res. 2002;137:177-90.
6	Interactions between riluzole and ABCG2/BCRP transporter. Neurosci Lett. 2009 Mar 6;452(1):12-6.
7	Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
8	Involvement of human CYP1A isoenzymes in the metabolism and drug interactions of riluzole in vitro. J Pharmacol Exp Ther. 1997 Sep;282(3):1465-72.
9	Association between CYP1A2 activity and riluzole clearance in patients with amyotrophic lateral sclerosis. Br J Clin Pharmacol. 2005 Mar;59(3):310-3.
10	Riluzole induces AR degradation via endoplasmic reticulum stress pathway in androgen-dependent and castration-resistant prostate cancer cells. Prostate. 2019 Feb;79(2):140-150. doi: 10.1002/pros.23719. Epub 2018 Oct 2.
11	Screening of a chemical library reveals novel PXR-activating pharmacologic compounds. Toxicol Lett. 2015 Jan 5;232(1):193-202. doi: 10.1016/j.toxlet.2014.10.009. Epub 2014 Oct 16.
12	Drug discovery for Duchenne muscular dystrophy via utrophin promoter activation screening. PLoS One. 2011;6(10):e26169. doi: 10.1371/journal.pone.0026169. Epub 2011 Oct 20.
13	Cerner Multum, Inc. "Australian Product Information.".
14	Product Information. Sirturo (bedaquiline). Janssen Pharmaceuticals, Titusville, NJ.
15	Product Information. Rilutek (riluzole). Rhone-Poulenc Rorer, Collegeville, PA.
16	Product Information. Ocaliva (obeticholic acid). Intercept Pharmaceuticals, Inc., New York, NY.
17	Product Information. Turalio (pexidartinib). Daiichi Sankyo, Inc., Parsippany, NJ.
18	Product Information. Isturisa (osilodrostat). Recordati Rare Diseases Inc, Lebanon, NJ.
19	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
20	Product Information. Adcetris (brentuximab vedotin). Seattle Genetics Inc, Bothell, WA.
21	Product Information. Kynamro (mipomersen). Genzyme Corporation, Cambridge, MA.
22	Canadian Pharmacists Association.
23	Product Information. Juxtapid (lomitapide). Aegerion Pharmaceuticals Inc, Cambridge, MA.
24	Product Information. Givlaari (givosiran). Alnylam Pharmaceuticals, Cambridge, MA.
25	Product Information. Tagrisso (osimertinib). Astra-Zeneca Pharmaceuticals, Wilmington, DE.
26	Product Information. Tabrecta (capmatinib). Novartis Pharmaceuticals, East Hanover, NJ.
27	Al-Nawakil C, Willems L, Mauprivez C, et.al "Successful treatment of l-asparaginase-induced severe acute hepatotoxicity using mitochondrial cofactors." Leuk Lymphoma 55 (2014): 1670-4. [PMID: 24090500]
28	Product Information. Zydelig (idelalisib). Gilead Sciences, Foster City, CA.
29	Product Information. Zelboraf (vemurafenib). Genentech, South San Francisco, CA.
30	Product Information. Exjade (deferasirox). Novartis Pharmaceuticals, East Hanover, NJ.
31	EMA. European Medicines Agency. European Union "EMA - List of medicines under additional monitoring.".
32	Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.