Riluzole

An orally administered neuroprotective drug used for the treatment of amyotrophic lateral sclerosis (ALS). Riluzole modulates glutamatergic neurotransmission, partly by inhibiting voltage-gated sodium channels and reducing presynaptic glutamate release, thereby limiting neuronal excitability. Its precise therapeutic mechanism in ALS remains incompletely understood. Riluzole provides a modest survival benefit but does not reverse established motor neuron damage. Important adverse effects include elevated liver enzymes, hepatotoxicity, nausea, and fatigue

CAS Number: 1744-22-5

Molecular Mass: 234.2 g/mol

Formula: C₈H₅F₃N₂OS

Smiles: Nc1nc2ccc(OC(F)(F)F)cc2s1

Synonymes:

Riluzole, riluzole, 1744-22-5, Rilutek, 2-Amino-6-(trifluoromethoxy)benzothiazole, 6-(trifluoromethoxy)-1,3-benzothiazol-2-amine, RP-54274, Riluzol, Riluzolum, 2-amino-6-trifluoromethoxybenzothiazole, 2-Benzothiazolamine, 6-(trifluoromethoxy)-, RP 54274, Tiglutik, NSC-753433, NSC-759823, EXSERVAN, 7LJ087RS6F, BHV-0223, BENZOTHIAZOLE, 2-AMINO-6-TRIFLUOROMETHOXY-, PK26124, PK 26124, RP54274, Teglutik, 2 Amino 6 trifluoromethoxybenzothiazole, TIGLUTIK KIT, RefChem:58435, N07XX02, 605-724-6, 6-(trifluoromethoxy)benzo[d]thiazol-2-amine, PK-26124, C8H5F3N2OS, 6-(trifluoromethoxy)-2-benzothiazolamine, 2-Benzothiazolamine,6-(trifluoromethoxy)-, 2-amino-6-(trifluoromethoxy)benzo[d]thiazole, Amino-2 trifluoromethoxy-6 benzothiazole, MLS000069369, 6-Trifluoromethoxy-benzothiazol-2-ylamine, DTXSID3045192, 2-Amino-6-(trifluoromethoxy)-benzothiazole, CHEMBL744, SMR000058231, MFCD00210213, NCGC00015882-09, 6-(trifluoromethoxy)benzothiazole-2-ylamine, Riluzol [INN-Spanish], Riluzolum [INN-Latin], 6-trifluoromethoxy-1,3-benzothiazol-2-ylamine, F3282-0020, DTXCID1025192, Rilutek (TN), CAS-1744-22-5, Amino-2 trifluoromethoxy-6 benzothiazole [French], UNII-7LJ087RS6F, Riluzole, solid, Riluzole?, Riluzole [USAN:USP:INN:BAN], BF-37, 2-amino-6-(trifluoromethoxy)-1,3-benzothiazole, ALBB-006046, Riluzole (Rilutek), Prestwick-03A08, Riluzole (Standard), Tocris-0768, Opera_ID_548, RILUZOLE [USAN], Lopac-R-116, RILUZOLE [INN], RILUZOLE [JAN], RILUZOLE [MI], Prestwick0_000167, Prestwick1_000167, Prestwick2_000167, Prestwick3_000167, Spectrum2_000550, RILUZOLE [MART.], Biomol-NT_000245, RILUZOLE [USP-RS], RILUZOLE [WHO-DD], cid_5070, Riluzole (JAN/USP/INN), RILUZOLE [EMA EPAR], Lopac0_001064, SCHEMBL78905, BSPBio_000033, Riluzole - Bio-X trade mark, BIDD:GT0055, SPBio_000599, SPBio_001954, RILUZOLE [ORANGE BOOK], BPBio1_000037, BPBio1_000837, CHEBI:8863, GTPL2326, orb1310698, RILUZOLE [USP IMPURITY], RILUZOLE [USP MONOGRAPH], SCHEMBL29359189, BDBM30705, HY-B0211R, Bio1_000416, Bio1_000905, Bio1_001394, GLXC-07553, HMS1773G08, HMS2089O19, HMS2094G07, HMS2233E14, HMS3263E10, HMS3371A09, HMS3657E13, HMS5079I20, HMS5171H17, Pharmakon1600-01505348, SMSSF-0055855, HY-B0211, QYB55203, Tiglutik (thickened oral suspension), Tox21_110252, Tox21_501064, AC-730, BBL013272, CCG-39528, EBC-11108, HB6093, MSK160656, NSC753433, NSC759823, s1614, SBB012436, STK503686, AKOS000265071, Tox21_110252_1, DB00740, FR27733, KS-5231, LP01064, NSC 753433, NSC 759823, SDCCGSBI-0051034.P003, 2-amino-6-trifluoromethoxy-benzothiazole, 6-(trifluoromethoxy)benzothiazol-2-amine, 6-trifluoromethoxy-2-amino-benzothiazole, NCGC00015882-01, NCGC00015882-02, NCGC00015882-03, NCGC00015882-04, NCGC00015882-05, NCGC00015882-06, NCGC00015882-07, NCGC00015882-08, NCGC00015882-10, NCGC00015882-11, NCGC00015882-12, NCGC00015882-13, NCGC00015882-15, NCGC00015882-28, NCGC00023141-02, NCGC00023141-04, NCGC00023141-05, NCGC00023141-06, NCGC00261749-01, 6-(trifluoromethoxy)-2-aminobenzothiazole, 6-trifluoromethoxybenzo[d]thiazol-2-amine, BR164340, ST038494, ST068834, SBI-0051034.P002, 2-Amino-6-(Trifluoromethoxy) Benzothiazole, DB-030335, A2423, EU-0101064, NS00005892, R1174, SW196805-4, EN300-23782, C07937, D00775, VU0239571-11, F004026, Q415744, SR-01000002997-3, BRD-K21283037-001-02-5, BRD-K21283037-001-20-7, BRD-K21283037-001-21-5, BRD-K21283037-003-03-9, BRD-K21283037-003-06-2, BRD-K21283037-003-11-2, Z164707762, Riluzole, 6-(Trifluoromethoxy)-1,3-benzothiazol-2-amine, Riluzole, United States Pharmacopeia (USP) Reference Standard, 6-Trifluoromethoxy-2-aminobenzothiazole, 6-(Trifluoromethoxy)-1,3-benzothiazol-2-amine

Bioactivity: Neuroprotective agent; modulator of glutamatergic neurotransmission; inhibitor of voltage-gated sodium channels and glutamate release

Solubility in Different Solvents

Solvent	Temperature [K]	Crystal form	Solubility [mg/mL]	Reference
1-Butanol	278.15	-	587.4	[144]
1-Butanol	283.15	-	632.4	[144]
1-Butanol	288.15	-	672.7	[144]
1-Butanol	293.15	-	724.1	[144]
1-Butanol	298.15	-	785.1	[144]
1-Butanol	303.15	-	862.8	[144]
1-Butanol	308.15	-	925.4	[144]
1-Butanol	313.15	-	1014.1	[144]
1-Butanol	318.15	-	1137.9	[144]
1-Butanol	323.15	-	1261.7	[144]
1-Pentanol	278.15	-	537.2	[144]
1-Pentanol	283.15	-	564.8	[144]
1-Pentanol	288.15	-	599.0	[144]
1-Pentanol	293.15	-	649.2	[144]
1-Pentanol	298.15	-	713.5	[144]
1-Pentanol	303.15	-	770.3	[144]
1-Pentanol	308.15	-	834.1	[144]
1-Pentanol	313.15	-	922.6	[144]
1-Pentanol	318.15	-	1020.3	[144]
1-Pentanol	323.15	-	1092.2	[144]
1-Propanol	278.15	-	694.5	[144]
1-Propanol	278.15	-	694.7	[145]
1-Propanol	283.15	-	738.1	[144]
1-Propanol	283.15	-	738.3	[145]
1-Propanol	288.15	-	796.5	[144]
1-Propanol	288.15	-	796.6	[145]
1-Propanol	293.15	-	858.9	[144]
1-Propanol	293.15	-	858.7	[145]
1-Propanol	298.15	-	932.8	[144]
1-Propanol	298.15	-	932.9	[145]
1-Propanol	303.15	-	1026.8	[144]
1-Propanol	303.15	-	1027.0	[145]
1-Propanol	308.15	-	1124.7	[144]
1-Propanol	308.15	-	1124.7	[145]
1-Propanol	313.15	-	1234.9	[144]
1-Propanol	313.15	-	1234.6	[145]
1-Propanol	318.15	-	1381.4	[144]
1-Propanol	318.15	-	1381.7	[145]
1-Propanol	323.15	-	1513.5	[144]
1-Propanol	323.15	-	1513.8	[145]
2-Methoxyethanol	278.15	-	1871.3	[144]
2-Methoxyethanol	283.15	-	1980.5	[144]
2-Methoxyethanol	288.15	-	2033.7	[144]
2-Methoxyethanol	293.15	-	2137.8	[144]
2-Methoxyethanol	298.15	-	2211.5	[144]
2-Methoxyethanol	303.15	-	2275.8	[144]
2-Methoxyethanol	308.15	-	2383.9	[144]
2-Methoxyethanol	313.15	-	2471.1	[144]
2-Methoxyethanol	318.15	-	2564.4	[144]
2-Methoxyethanol	323.15	-	2644.0	[144]
Acetone	278.15	-	1918.1	[144]
Acetone	278.15	-	1917.9	[145]
Acetone	283.15	-	1976.7	[144]
Acetone	283.15	-	1977.1	[145]
Acetone	288.15	-	2028.6	[144]
Acetone	288.15	-	2029.0	[145]
Acetone	293.15	-	2128.6	[144]
Acetone	293.15	-	2128.4	[145]
Acetone	298.15	-	2239.4	[144]
Acetone	298.15	-	2239.5	[145]
Acetone	303.15	-	2319.5	[144]
Acetone	303.15	-	2319.9	[145]
Acetone	308.15	-	2424.0	[144]
Acetone	308.15	-	2423.7	[145]
Acetone	313.15	-	2526.4	[144]
Acetone	313.15	-	2526.0	[145]
Acetone	318.15	-	2659.1	[144]
Acetone	318.15	-	2658.8	[145]
Acetone	323.15	-	2782.4	[144]
Acetone	323.15	-	2782.5	[145]
Acetonitrile	278.15	-	845.3	[144]
Acetonitrile	283.15	-	964.7	[144]
Acetonitrile	288.15	-	1100.3	[144]
Acetonitrile	293.15	-	1230.3	[144]
Acetonitrile	298.15	-	1436.2	[144]
Acetonitrile	303.15	-	1601.5	[144]
Acetonitrile	308.15	-	1893.8	[144]
Acetonitrile	313.15	-	2191.2	[144]
Acetonitrile	318.15	-	2473.4	[144]
Acetonitrile	323.15	-	2696.8	[144]
Amyl Acetate	278.15	-	859.6	[144]
Amyl Acetate	283.15	-	884.1	[144]
Amyl Acetate	288.15	-	915.8	[144]
Amyl Acetate	293.15	-	942.1	[144]
Amyl Acetate	298.15	-	981.8	[144]
Amyl Acetate	303.15	-	1019.6	[144]
Amyl Acetate	308.15	-	1066.4	[144]
Amyl Acetate	313.15	-	1136.6	[144]
Amyl Acetate	318.15	-	1195.2	[144]
Amyl Acetate	323.15	-	1294.0	[144]
Dimethylacetamide	278.15	-	247.1	[144]
Dimethylacetamide	283.15	-	273.9	[144]
Dimethylacetamide	288.15	-	300.0	[144]
Dimethylacetamide	293.15	-	332.5	[144]
Dimethylacetamide	298.15	-	373.3	[144]
Dimethylacetamide	303.15	-	415.6	[144]
Dimethylacetamide	308.15	-	459.6	[144]
Dimethylacetamide	313.15	-	506.4	[144]
Dimethylacetamide	318.15	-	570.7	[144]
Dimethylacetamide	323.15	-	625.9	[144]
Ethanol	278.15	-	892.0	[144]
Ethanol	278.15	-	892.0	[145]
Ethanol	283.15	-	940.7	[144]
Ethanol	283.15	-	940.6	[145]
Ethanol	288.15	-	994.3	[144]
Ethanol	288.15	-	994.4	[145]
Ethanol	293.15	-	1077.9	[144]
Ethanol	293.15	-	1077.9	[145]
Ethanol	298.15	-	1142.4	[144]
Ethanol	298.15	-	1142.7	[145]
Ethanol	303.15	-	1228.3	[144]
Ethanol	303.15	-	1228.3	[145]
Ethanol	308.15	-	1347.3	[144]
Ethanol	308.15	-	1347.4	[145]
Ethanol	313.15	-	1471.0	[144]
Ethanol	313.15	-	1471.1	[145]
Ethanol	318.15	-	1625.2	[144]
Ethanol	318.15	-	1625.0	[145]
Ethanol	323.15	-	1725.7	[144]
Ethanol	323.15	-	1726.1	[145]
Glycol monopropyl ether	278.15	-	1693.8	[144]
Glycol monopropyl ether	283.15	-	1769.8	[144]
Glycol monopropyl ether	288.15	-	1821.8	[144]
Glycol monopropyl ether	293.15	-	1928.6	[144]
Glycol monopropyl ether	298.15	-	2006.4	[144]
Glycol monopropyl ether	303.15	-	2065.9	[144]
Glycol monopropyl ether	308.15	-	2133.1	[144]
Glycol monopropyl ether	313.15	-	2190.8	[144]
Glycol monopropyl ether	318.15	-	2256.9	[144]
Glycol monopropyl ether	323.15	-	2322.0	[144]
Propyl acetate	278.15	-	1112.9	[144]
Propyl acetate	283.15	-	1158.6	[144]
Propyl acetate	288.15	-	1192.9	[144]
Propyl acetate	293.15	-	1231.0	[144]
Propyl acetate	298.15	-	1289.8	[144]
Propyl acetate	303.15	-	1332.2	[144]
Propyl acetate	308.15	-	1410.1	[144]
Propyl acetate	313.15	-	1488.5	[144]
Propyl acetate	318.15	-	1586.9	[144]
Propyl acetate	323.15	-	1691.4	[144]
isopropyl acetate	278.15	-	1011.9	[144]
isopropyl acetate	283.15	-	1051.5	[144]
isopropyl acetate	288.15	-	1090.9	[144]
isopropyl acetate	293.15	-	1134.6	[144]
isopropyl acetate	298.15	-	1196.5	[144]
isopropyl acetate	303.15	-	1238.1	[144]
isopropyl acetate	308.15	-	1280.2	[144]
isopropyl acetate	313.15	-	1355.6	[144]
isopropyl acetate	318.15	-	1453.2	[144]
isopropyl acetate	323.15	-	1519.8	[144]

Molecule 3D descriptors

Descriptor	Value
PMI1	266.9651
PMI2	2151.5233
PMI3	2325.6497
NPR1	0.1148
NPR2	0.9251
RadiusOfGyration	3.1825
InertialShapeFactor	0.0035
Eccentricity	0.9934
Asphericity	0.6949
SpherocityIndex	0.0361
PBF	0.1654