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    Chemistry

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    Also known as: 1744-22-5, Rilutek, 2-amino-6-(trifluoromethoxy)benzothiazole, 6-(trifluoromethoxy)benzo[d]thiazol-2-amine, 6-(trifluoromethoxy)-1,3-benzothiazol-2-amine, Rp-54274
    Molecular Formula
    C8H5F3N2OS
    Molecular Weight
    234.20  g/mol
    InChI Key
    FTALBRSUTCGOEG-UHFFFAOYSA-N
    FDA UNII
    7LJ087RS6F
    Riluzole
    A glutamate antagonist (RECEPTORS, GLUTAMATE) used as an anticonvulsant (ANTICONVULSANTS) and to prolong the survival of patients with AMYOTROPHIC LATERAL SCLEROSIS.
    Riluzole is a Benzothiazole.
    1 2D Structure

    Riluzole

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    6-(trifluoromethoxy)-1,3-benzothiazol-2-amine
    2.1.2 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)
    2.1.3 InChI Key
    FTALBRSUTCGOEG-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1=CC2=C(C=C1OC(F)(F)F)SC(=N2)N
    2.2 Other Identifiers
    2.2.1 UNII
    7LJ087RS6F
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2 Amino 6 Trifluoromethoxybenzothiazole

    2. 2-amino-6-trifluoromethoxybenzothiazole

    3. Pk 26124

    4. Pk-26124

    5. Pk26124

    6. Rilutek

    7. Rp 54274

    8. Rp-54274

    9. Rp54274

    2.3.2 Depositor-Supplied Synonyms

    1. 1744-22-5

    2. Rilutek

    3. 2-amino-6-(trifluoromethoxy)benzothiazole

    4. 6-(trifluoromethoxy)benzo[d]thiazol-2-amine

    5. 6-(trifluoromethoxy)-1,3-benzothiazol-2-amine

    6. Rp-54274

    7. 2-amino-6-trifluoromethoxybenzothiazole

    8. 2-amino-6-(trifluoromethoxy)benzo[d]thiazole

    9. 2-benzothiazolamine, 6-(trifluoromethoxy)-

    10. Pk-26124

    11. Rp 54274

    12. Tiglutik

    13. 2-amino-6-(trifluoromethoxy)-benzothiazole

    14. Riluzole (rilutek)

    15. Amino-2 Trifluoromethoxy-6 Benzothiazole

    16. Mls000069369

    17. 6-trifluoromethoxy-benzothiazol-2-ylamine

    18. 2-benzothiazolamine,6-(trifluoromethoxy)-

    19. Chembl744

    20. Nsc-753433

    21. Nsc-759823

    22. Smr000058231

    23. 7lj087rs6f

    24. Chebi:8863

    25. Riluzol

    26. 2-amino-6-(trifluoromethoxy)-1,3-benzothiazole

    27. Benzothiazole, 2-amino-6-trifluoromethoxy-

    28. Bhv-0223

    29. Ncgc00015882-09

    30. Riluzolum

    31. Riluzol [inn-spanish]

    32. Riluzolum [inn-latin]

    33. Dsstox_cid_25192

    34. Dsstox_rid_80739

    35. Dsstox_gsid_45192

    36. C8h5f3n2os

    37. Rilutek (tn)

    38. Cas-1744-22-5

    39. Amino-2 Trifluoromethoxy-6 Benzothiazole [french]

    40. Unii-7lj087rs6f

    41. 2-amino-6-(trifluoromethoxyl)benzothiazole

    42. Riluzole, Solid

    43. Riluzole [usan:usp:inn:ban]

    44. Riluzole- Bio-x

    45. Bf-37

    46. Albb-006046

    47. Mfcd00210213

    48. Prestwick-03a08

    49. Exservan

    50. Pk26124

    51. 6-(trifluoromethoxy)-2-benzothiazolamine

    52. Tocris-0768

    53. Pk 26124

    54. 6-trifluoromethoxybenzothiazole-2-yl-amine

    55. Opera_id_548

    56. Riluzole [usan]

    57. Lopac-r-116

    58. Riluzole [inn]

    59. Riluzole [jan]

    60. Riluzole [mi]

    61. Riluzole-13c-15n2

    62. Prestwick0_000167

    63. Prestwick1_000167

    64. Prestwick2_000167

    65. Prestwick3_000167

    66. Spectrum2_000550

    67. Riluzole [mart.]

    68. Biomol-nt_000245

    69. Riluzole [usp-rs]

    70. Riluzole [who-dd]

    71. Cid_5070

    72. Riluzole (jan/usp/inn)

    73. Riluzole [ema Epar]

    74. Lopac0_001064

    75. Schembl78905

    76. Bspbio_000033

    77. Bidd:gt0055

    78. Spbio_000599

    79. Spbio_001954

    80. Riluzole [orange Book]

    81. Bpbio1_000037

    82. Bpbio1_000837

    83. Gtpl2326

    84. Zinc6481

    85. Riluzole [usp Impurity]

    86. Dtxsid3045192

    87. Riluzole [usp Monograph]

    88. Bdbm30705

    89. Bio1_000416

    90. Bio1_000905

    91. Bio1_001394

    92. Hms1773g08

    93. Hms2089o19

    94. Hms2094g07

    95. Hms2233e14

    96. Hms3263e10

    97. Hms3371a09

    98. Hms3657e13

    99. Pharmakon1600-01505348

    100. Amy14166

    101. Bcp02142

    102. Hy-b0211

    103. Riluzole - Cas 1744-22-5

    104. Tiglutik (thickened Oral Suspension)

    105. Tox21_110252

    106. Tox21_501064

    107. Ac-730

    108. Bbl013272

    109. Ccg-39528

    110. Nsc753433

    111. Nsc759823

    112. S1614

    113. Stk503686

    114. Akos000265071

    115. Tox21_110252_1

    116. Db00740

    117. Ks-5231

    118. Lp01064

    119. Nsc 753433

    120. Nsc 759823

    121. Sdccgsbi-0051034.p003

    122. 2-amino-6-trifluoromethoxy-benzothiazole

    123. 6-trifluoromethoxy-2-amino-benzothiazole

    124. Ncgc00015882-01

    125. Ncgc00015882-02

    126. Ncgc00015882-03

    127. Ncgc00015882-04

    128. Ncgc00015882-05

    129. Ncgc00015882-06

    130. Ncgc00015882-07

    131. Ncgc00015882-08

    132. Ncgc00015882-10

    133. Ncgc00015882-11

    134. Ncgc00015882-12

    135. Ncgc00015882-13

    136. Ncgc00015882-15

    137. Ncgc00015882-28

    138. Ncgc00023141-02

    139. Ncgc00023141-04

    140. Ncgc00023141-05

    141. Ncgc00023141-06

    142. Ncgc00261749-01

    143. 6-(trifluoromethoxy)-2-aminobenzothiazole

    144. 6-trifluoromethoxybenzo[d]thiazol-2-amine

    145. Br164340

    146. Sbi-0051034.p002

    147. 2-amino-6-(trifluoromethoxy) Benzothiazole

    148. Db-030335

    149. Eu-0101064

    150. Ft-0611194

    151. R1174

    152. Sw196805-4

    153. En300-23782

    154. 6-trifluoromethoxy-1,3-benzothiazol-2-ylamine

    155. C07937

    156. D00775

    157. Vu0239571-11

    158. 744r225

    159. Q415744

    160. Sr-01000002997-3

    161. Brd-k21283037-001-02-5

    162. Brd-k21283037-003-03-9

    163. Brd-k21283037-003-06-2

    164. F3282-0020

    165. Z166605314

    166. Riluzole, United States Pharmacopeia (usp) Reference Standard

    167. 2-amino-6-(trifluoromethoxy)-1,3-benzothiazole;2-amino-6-(trifluoromethoxy)benzothiazole

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 234.20 g/mol
    Molecular Formula C8H5F3N2OS
    XLogP33.6
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count1
    Exact Mass234.00746845 g/mol
    Monoisotopic Mass234.00746845 g/mol
    Topological Polar Surface Area76.4 Ų
    Heavy Atom Count15
    Formal Charge0
    Complexity238
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameRilutek
    PubMed HealthRiluzole (By mouth)
    Drug ClassesCentral Nervous System Agent
    Drug LabelRILUTEK (riluzole) is a member of the benzothiazole class. Chemically, riluzole is 2-amino-6-(trifluoromethoxy)benzothiazole. Its molecular formula is C8H5F3N2OS and its molecular weight is 234.2. Its structural formula is as follows:Riluzole is a...
    Active IngredientRiluzole
    Dosage FormTablet
    RouteOral
    Strength50mg
    Market StatusPrescription
    CompanyCovis Pharma Sarl

    2 of 4  
    Drug NameRiluzole
    PubMed HealthRiluzole (By mouth)
    Drug ClassesCentral Nervous System Agent
    Drug LabelRILUTEK (riluzole) is a member of the benzothiazole class. Chemically, riluzole is 2-amino-6-(trifluoromethoxy)benzothiazole. Its molecular formula is C8H5F3N2OS and its molecular weight is 234.2. Its structural formula is as follows:Riluzole is a...
    Active IngredientRiluzole
    Dosage FormTablet
    RouteOral
    Strength50mg
    Market StatusPrescription
    CompanyMylan Pharms; Apotex; Sun Pharm Inds; Glenmark Generics; Impax Labs

    3 of 4  
    Drug NameRilutek
    PubMed HealthRiluzole (By mouth)
    Drug ClassesCentral Nervous System Agent
    Drug LabelRILUTEK (riluzole) is a member of the benzothiazole class. Chemically, riluzole is 2-amino-6-(trifluoromethoxy)benzothiazole. Its molecular formula is C8H5F3N2OS and its molecular weight is 234.2. Its structural formula is as follows:Riluzole is a...
    Active IngredientRiluzole
    Dosage FormTablet
    RouteOral
    Strength50mg
    Market StatusPrescription
    CompanyCovis Pharma Sarl

    4 of 4  
    Drug NameRiluzole
    PubMed HealthRiluzole (By mouth)
    Drug ClassesCentral Nervous System Agent
    Drug LabelRILUTEK (riluzole) is a member of the benzothiazole class. Chemically, riluzole is 2-amino-6-(trifluoromethoxy)benzothiazole. Its molecular formula is C8H5F3N2OS and its molecular weight is 234.2. Its structural formula is as follows:Riluzole is a...
    Active IngredientRiluzole
    Dosage FormTablet
    RouteOral
    Strength50mg
    Market StatusPrescription
    CompanyMylan Pharms; Apotex; Sun Pharm Inds; Glenmark Generics; Impax Labs

    4.2 Drug Indication

    For the treatment of amyotrophic lateral sclerosis (ALS, Lou Gehrig's Disease)

    FDA Label

    Investigated for use/treatment in atopic dermatitis.

    Rilutek is indicated to extend life or the time to mechanical ventilation for patients with amyotrophic lateral sclerosis (ALS).

    Clinical trials have demonstrated that Rilutek extends survival for patients with ALS.

    Survival was defined as patients who were alive, not intubated for mechanical ventilation and tracheotomy-free.

    There is no evidence that Rilutek exerts a therapeutic effect on motor function, lung function, fasciculations, muscle strength and motor symptoms.

    Rilutek has not been shown to be effective in the late stages of ALS.

    Safety and efficacy of Rilutek has only been studied in ALS. Therefore, Rilutek should not be used in patients with any other form of motor-neurone disease.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Riluzole, a member of the benzothiazole class, is indicated for the treatment of patients with amyotrophic lateral sclerosis (ALS). Riluzole extends survival and/or time to tracheostomy. It is also neuroprotective in various in vivo experimental models of neuronal injury involving excitotoxic mechanisms. The etiology and pathogenesis of amyotrophic lateral sclerosis (ALS) are not known, although a number of hypotheses have been advanced. One hypothesis is that motor neurons, made vulnerable through either genetic predisposition or environmental factors, are injured by glutamate. In some cases of familial ALS the enzyme superoxide dismutase has been found to be defective.

    BF-37 interferes directly with cellular processes of the immune system of the skin, thereby diminishing the inflammation that underlies the reddening and itching.

    5.2 MeSH Pharmacological Classification

    Anticonvulsants

    Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.)

    Excitatory Amino Acid Antagonists

    Drugs that bind to but do not activate excitatory amino acid receptors, thereby blocking the actions of agonists. (See all compounds classified as Excitatory Amino Acid Antagonists.)

    Neuroprotective Agents

    Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids. (See all compounds classified as Neuroprotective Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    RILUZOLE
    5.3.2 FDA UNII
    7LJ087RS6F
    5.3.3 Pharmacological Classes
    Benzothiazoles [CS]; Benzothiazole [EPC]
    5.4 ATC Code

    N07XX02

    N07XX02

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    N - Nervous system

    N07 - Other nervous system drugs

    N07X - Other nervous system drugs

    N07XX - Other nervous system drugs

    N07XX02 - Riluzole

    5.5 Absorption, Distribution and Excretion

    Absorption

    Riluzole is well-absorbed (approximately 90%), with average absolute oral bioavailability of about 60% (CV=30%). A high fat meal decreases absorption, reducing AUC by about 20% and peak blood levels by about 45%.

    5.6 Metabolism/Metabolites

    Riluzole is extensively metabolized to six major and a number of minor metabolites, which have not all been identified to date. Metabolism is mostly hepatic, consisting of cytochrome P450–dependent hydroxylation and glucuronidation. CYP1A2 is the primary isozyme involved in N-hydroxylation; CYP2D6, CYP2C19, CYP3A4, and CYP2E1 are considered unlikely to contribute significantly to riluzole metabolism in humans.

    Riluzole has known human metabolites that include 4-hydroxy-riluzole, 5-hydroxy-riluzole, 7-hydroxy-riluzole, and N-Hydroxyriluzole.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.7 Biological Half-Life

    The mean elimination half-life of riluzole is 12 hours (CV=35%) after repeated doses.

    5.8 Mechanism of Action

    The mode of action of riluzole is unknown. 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.

    BF-37 inhibits the proliferation of T-cells. An increased proliferation of these immune cells is believed to cause atopic dermatitis. Biofrontera assumes that BF-37 interferes directly with cellular processes of the immune systems of the skin, thereby diminishing the inflammation that underlines the reddening and itching.

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    20-Jan-2021
    15-Jul-2024
    KGS
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    DOSAGE - TABLET;ORAL - 50MG

    USFDA APPLICATION NUMBER - 20599

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    DOSAGE - FILM;ORAL - 50MG

    USFDA APPLICATION NUMBER - 212640

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