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3 Canada
5 Australia
1 South Africa
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TABLET;ORAL - 50MG, FILM;ORAL - 50MG

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3 US Patents, 4 Health Canada Patents

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1 USP , 2 Others

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Farmak Riluzole

Synopsis

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Canada

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Listed Dossiers

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DRUG PRODUCT COMPOSITIONS

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EDQM

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US Medicaid (USD)

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243EXCIPIENTS BY APPLICATIONS

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

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 Formula	C₈H₅F₃N₂OS
Molecular Weight	234.20 g/mol
XLogP3	3.6
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	1
Exact Mass	234.00746845 g/mol
Monoisotopic Mass	234.00746845 g/mol
Topological Polar Surface Area	76.4 Å²
Heavy Atom Count	15
Formal Charge	0
Complexity	238
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Rilutek
PubMed Health	Riluzole (By mouth)
Drug Classes	Central Nervous System Agent
Drug Label	RILUTEK (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 Ingredient	Riluzole
Dosage Form	Tablet
Route	Oral
Strength	50mg
Market Status	Prescription
Company	Covis Pharma Sarl

2 of 4
Drug Name	Riluzole
PubMed Health	Riluzole (By mouth)
Drug Classes	Central Nervous System Agent
Drug Label	RILUTEK (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 Ingredient	Riluzole
Dosage Form	Tablet
Route	Oral
Strength	50mg
Market Status	Prescription
Company	Mylan Pharms; Apotex; Sun Pharm Inds; Glenmark Generics; Impax Labs

3 of 4
Drug Name	Rilutek
PubMed Health	Riluzole (By mouth)
Drug Classes	Central Nervous System Agent
Drug Label	RILUTEK (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 Ingredient	Riluzole
Dosage Form	Tablet
Route	Oral
Strength	50mg
Market Status	Prescription
Company	Covis Pharma Sarl

4 of 4
Drug Name	Riluzole
PubMed Health	Riluzole (By mouth)
Drug Classes	Central Nervous System Agent
Drug Label	RILUTEK (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 Ingredient	Riluzole
Dosage Form	Tablet
Route	Oral
Strength	50mg
Market Status	Prescription
Company	Mylan 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

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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