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Chemistry

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Also known as: 59804-37-4, Mobiflex, Tilcotil, Tenoxicamum, Liman, Tenoxicamum [inn-latin]

Molecular Formula

C₁₃H₁₁N₃O₄S₂

Molecular Weight

337.4 g/mol

InChI Key

LZNWYQJJBLGYLT-UHFFFAOYSA-N

FDA UNII

Z1R9N0A399

Tenoxicam, an antiinflammatory agent with analgesic and antipyretic properties, is used to treat osteoarthritis and control acute pain.

1 2D Structure

Tenoxicam

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-hydroxy-2-methyl-1,1-dioxo-N-pyridin-2-ylthieno[2,3-e]thiazine-3-carboxamide

2.1.2 InChI

InChI=1S/C13H11N3O4S2/c1-16-10(13(18)15-9-4-2-3-6-14-9)11(17)12-8(5-7-21-12)22(16,19)20/h2-7,17H,1H3,(H,14,15,18)

2.1.3 InChI Key

LZNWYQJJBLGYLT-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN1C(=C(C2=C(S1(=O)=O)C=CS2)O)C(=O)NC3=CC=CC=N3

2.2 Other Identifiers

2.2.1 UNII

Z1R9N0A399

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-hydroxy-2-methyl-n-2-pyridyl-2h-thieno(2,3-e)-1,2-thiazine-3-carboxamide 1,1-dioxide

2. Apo-tenoxicam

3. Artriunic

4. Mobiflex

5. Novo-tenoxicam

6. Reutenox

7. Ro 12-0068

8. Ro-12-0068

9. Tilcotil

2.3.2 Depositor-Supplied Synonyms

1. 59804-37-4

2. Mobiflex

3. Tilcotil

4. Tenoxicamum

5. Liman

6. Tenoxicamum [inn-latin]

7. Ro 12-0068

8. Ro-12-0068

9. Ro 12-0068/000

10. 4-hydroxy-2-methyl-n-(pyridin-2-yl)-2h-thieno[2,3-e][1,2]thiazine-3-carboxamide 1,1-dioxide

11. Nsc-758397

12. Mls000069830

13. Chebi:32192

14. Z1r9n0a399

15. 4-hydroxy-2-methyl-n-2-pyridinyl-2h-thieno(2,3-e)-1,2-thiazine-3-carboxamide 1,1-dioxide

16. Ncgc00016889-01

17. Alganex

18. Smr000058865

19. Ro-120068000

20. Cas-59804-37-4

21. 2h-thieno(2,3-e)-1,2-thiazine-3-carboxamide, 4-hydroxy-2-methyl-n-2-pyridinyl-, 1,1-dioxide

22. 2h-thieno[2,3-e]-1,2-thiazine-3-carboxamide,4-hydroxy-2-methyl-n-2-pyridinyl-, 1,1-dioxide

23. 4-hydroxy-2-methyl-1,1-dioxo-n-pyridin-2-ylthieno[2,3-e]thiazine-3-carboxamide

24. Dsstox_cid_25486

25. Dsstox_rid_80909

26. Dsstox_gsid_45486

27. 4-hydroxy-2-methyl-n-2-pyridinyl-2h-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide

28. Octiveran

29. Rexalgan

30. 4-hydroxy-2-methyl-n-pyridin-2-yl-2h-thieno-[2,3-e][1,2]thiazine-3-carboxamide 1,1-dioxide

31. 4-hydroxy-2-methyl-n-pyridin-2-yl-2h-thieno[2,3-e][1,2]thiazine-3-carboxamide 1,1-dioxide

32. Tilcotil (tn)

33. Ccris 5264

34. Sr-01000721894

35. Brn 0572193

36. Tenoxicam (jan/usan/inn)

37. Unii-z1r9n0a399

38. 4-hydroxy-2-methyl-n-2-pyridyl-2h-thieno(2,3-e)-1,2-thiazine-3-carboxamide 1,1-dioxide

39. Tenoxicam [usan:inn:ban:jan]

40. Tenoxicam, Nsaid

41. 2h-thieno[2,3-e]-1,2-thiazine-3-carboxamide, 4-hydroxy-2-methyl-n-2-pyridinyl-, 1,1-dioxide

42. Mobiflex, Tenoxicam

43. Prestwick_849

44. Tenoxicam(mobiflex)

45. Mfcd00083502

46. Ro-120068

47. Spectrum_001430

48. Tenoxicam [inn]

49. Tenoxicam [jan]

50. Tenoxicam [mi]

51. Tenoxicam [usan]

52. Opera_id_1757

53. Prestwick0_000527

54. Prestwick1_000527

55. Prestwick2_000527

56. Prestwick3_000527

57. Spectrum2_001080

58. Spectrum3_001563

59. Spectrum4_000731

60. Spectrum5_001615

61. Tenoxicam [mart.]

62. Tenoxicam [who-dd]

63. (3z)-3-[hydroxy-(pyridin-2-ylamino)methylidene]-2-methyl-1,1-dioxothieno[2,3-e]thiazin-4-one

64. Schembl25343

65. Schembl25344

66. Bspbio_000513

67. Bspbio_003066

68. Kbiogr_001022

69. Kbioss_001910

70. Mls001074071

71. Mls006011432

72. Bidd:gt0650

73. Divk1c_000252

74. Spectrum1503142

75. Spbio_001100

76. Spbio_002434

77. Bpbio1_000565

78. Chembl302795

79. Chembl3188633

80. Dtxsid8045486

81. Schembl13448847

82. Tenoxicam [ep Monograph]

83. Bcbcmap01_000251

84. Bdbm92332

85. Hms500m14

86. Kbio1_000252

87. Kbio2_001910

88. Kbio2_004478

89. Kbio2_007046

90. Kbio3_002566

91. Ninds_000252

92. Hms1569j15

93. Hms1923i15

94. Hms2090p19

95. Hms2092l20

96. Hms2096j15

97. Hms2232k23

98. Hms3370l01

99. Hms3656o10

100. Hms3713j15

101. Hms3884n04

102. Pharmakon1600-01503142

103. Bcp03624

104. Hy-b0440

105. Tox21_110666

106. Bbl028173

107. Ccg-40126

108. Nsc758397

109. S2512

110. Stk637103

111. Zinc12503102

112. Zinc40884328

113. Akos000282084

114. Akos026750148

115. Tenoxicam Degradation Impurity Standard

116. Tox21_110666_1

117. Zinc100006429

118. Ac-4526

119. Db00469

120. Ks-1313

121. Nsc 758397

122. Idi1_000252

123. Smp1_000040

124. Ncgc00016889-02

125. Ncgc00016889-03

126. Ncgc00016889-05

127. Ncgc00016889-06

128. Ncgc00095260-01

129. Ncgc00095260-02

130. Bt166206

131. Bcp0726000170

132. Sbi-0051780.p002

133. Ft-0659572

134. Sw219788-1

135. T2750

136. C75797

137. D01767

138. Q45050

139. Ab00052322-11

140. Ab00052322_12

141. Ab00052322_13

142. 804t374

143. A832479

144. Ro-12-0068/000

145. Sr-01000721894-2

146. Sr-01000721894-4

147. Q63395752

148. Tenoxicam, British Pharmacopoeia (bp) Reference Standard

149. Tenoxicam, European Pharmacopoeia (ep) Reference Standard

150. 4-hydroxy-2-methyl-n-(2-pyridyl)-2h-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide

151. N-(2-pyridyl)-4-hydroxy-2-methyl-2h-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide

152. (3e)-3-[hydroxy(pyridin-2-ylamino)methylene]-2-methyl-2,3-dihydro4h-thieno[2,3-e] [1,2]thiazin-4-one-1,1-dioxide

153. (3z)-2-methyl-1,1-bis(oxidanylidene)-3-[oxidanyl-(pyridin-2-ylamino)methylidene]thieno[2,3-e][1,2]thiazin-4-one

154. (3z)-3-[hydroxy-(2-pyridinylamino)methylidene]-2-methyl-1,1-dioxo-4-thieno[2,3-e]thiazinone

155. 4-hydroxy-2-methyl-n-(pyridin-2-yl)-2h-thieno[2,3-e][1,2]thiazine-3-carboxamide1,1-dioxide

156. 4-hydroxy-2-methyl-n-pyridin-2-yl-2h-thieno[2,3-e][1,2]thiazine-3-carboxamide 1,1-dioxide (tenoxicam)

2.4 Create Date

2011-12-26

3 Chemical and Physical Properties

Molecular Formula	C₁₃H₁₁N₃O₄S₂
Molecular Weight	337.4 g/mol
XLogP3	1.1
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	2
Exact Mass	337.01909819 g/mol
Monoisotopic Mass	337.01909819 g/mol
Topological Polar Surface Area	136 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	599
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 Indication

For the treatment of rheumatoid arthritis, osteoarthritis, backache, and pain.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Tenoxicam, an antiinflammatory agent with analgesic and antipyretic properties, is used to treat osteoarthritis and control acute pain.

5.2 MeSH Pharmacological Classification

Anti-Inflammatory Agents, Non-Steroidal

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

Cyclooxygenase Inhibitors

Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes. (See all compounds classified as Cyclooxygenase Inhibitors.)

5.3 ATC Code

M01AC02

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

M - Musculo-skeletal system

M01 - Antiinflammatory and antirheumatic products

M01A - Antiinflammatory and antirheumatic products, non-steroids

M01AC - Oxicams

M01AC02 - Tenoxicam

5.4 Absorption, Distribution and Excretion

Absorption

Oral absorption of tenoxicam is rapid and complete (absolute bioavailability 100%).

5.5 Metabolism/Metabolites

Tenoxicam is metabolized in the liver to several pharmacologically inactive metabolites (mainly 5'-hydroxy-tenoxicam).

Tenoxicam has known human metabolites that include 5'-Hydroxytenoxicam.

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

5.6 Biological Half-Life

72 hours (range 59 to 74 hours)

5.7 Mechanism of Action

The antiinflammatory effects of tenoxicam may result from the inhibition of the enzyme cycooxygenase and the subsequent peripheral inhibition of prostaglandin synthesis. As prostaglandins sensitize pain receptors, their inhibition accounts for the peripheral analgesic effects of tenoxicam. Antipyresis may occur by central action on the hypothalamus, resulting in peripheral dilation, increased cutaneous blood flow, and subsequent heat loss.

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