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Alter Brand Of Nimesulide

Alter Brand of Nimesulide

Synopsis, Chemistry

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Also known as: 51803-78-2, N-(4-nitro-2-phenoxyphenyl)methanesulfonamide, Mesulid, Aulin, Flogovital, Sulidene

Molecular Formula

C₁₃H₁₂N₂O₅S

Molecular Weight

308.31 g/mol

InChI Key

HYWYRSMBCFDLJT-UHFFFAOYSA-N

FDA UNII

V4TKW1454M

Nimesulide is a nonsteroidal arylsulfonamide with anti-inflammatory properties. Nimesulide inhibits the cyclooxygenase-mediated conversion of arachidonic acid to pro-inflammatory prostaglandins. Modestly selective for COX-2, this agent binds to the enzyme, thereby inactivating it. Nimesulide may inhibit some carcinogenic COX-2-related carcinogenic effects on xenobiotic metabolism, apoptosis, immune surveillance and angiogenesis (overexpressed COX-2 in tumor epithelial cells enhances production of vascular growth factors and the formation of capillary-like networks). (NCI04)

1 2D Structure

Alter Brand of Nimesulide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-(4-nitro-2-phenoxyphenyl)methanesulfonamide

2.1.2 InChI

InChI=1S/C13H12N2O5S/c1-21(18,19)14-12-8-7-10(15(16)17)9-13(12)20-11-5-3-2-4-6-11/h2-9,14H,1H3

2.1.3 InChI Key

HYWYRSMBCFDLJT-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CS(=O)(=O)NC1=C(C=C(C=C1)[N+](=O)[O-])OC2=CC=CC=C2

2.2 Other Identifiers

2.2.1 UNII

V4TKW1454M

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-nitro-2-phenoxymethanesulfonanilide

2. Antifloxil

3. Aulin

4. Eskaflam

5. Guaxan

6. Lizepat

7. Mesulid

8. Nexen

9. Nimesil

10. R 805

11. R-805

12. Redaflam

2.3.2 Depositor-Supplied Synonyms

1. 51803-78-2

2. N-(4-nitro-2-phenoxyphenyl)methanesulfonamide

3. Mesulid

4. Aulin

5. Flogovital

6. Sulidene

7. Nimed

8. 4-nitro-2-phenoxymethanesulfonanilide

9. R-805

10. Methanesulfonamide, N-(4-nitro-2-phenoxyphenyl)-

11. R 805

12. Nisulid

13. 4'-nitro-2'-phenoxymethanesulfonanilide

14. 4-nitro-2-phenoxy-methanesulfonanilide

15. Nsc-758412

16. Chembl56367

17. Mls000069680

18. V4tkw1454m

19. Methanesulfonanilide, 4'-nitro-2'-phenoxy-

20. Chebi:44445

21. Ncgc00015725-02

22. R805

23. Smr000058484

24. Cas-51803-78-2

25. Dsstox_cid_17250

26. Dsstox_rid_79316

27. Dsstox_gsid_37250

28. Antifloxil

29. Nimesulida

30. Nimesulidum

31. Guaxan

32. Nimesulidum [inn-latin]

33. Nimesulida [inn-spanish]

34. Nim

35. Nimesulide [inn:ban]

36. Sr-01000000218

37. Einecs 257-431-4

38. 4'-nitro-2'-phenoxymethansulfonanilid

39. Brn 2421175

40. Unii-v4tkw1454m

41. Aldoron

42. Nimedex

43. Orthobid

44. Ccris 8225

45. Nise Gel

46. Nimesulide,(s)

47. Prestwick_618

48. Mfcd00079470

49. Spectrum_001577

50. Nimesulide [mi]

51. Nimesulide (jan/inn)

52. Nimesulide [inn]

53. Nimesulide [jan]

54. Opera_id_1247

55. Prestwick0_000194

56. Prestwick1_000194

57. Prestwick2_000194

58. Prestwick3_000194

59. Spectrum2_001541

60. Spectrum3_001576

61. Spectrum4_000178

62. Spectrum5_000964

63. Lopac-n-1016

64. N-(4-nitro-2-phenoxy-phenyl)methanesulfonamide

65. Nimesulide [mart.]

66. Nimesulide [who-dd]

67. Lopac0_000855

68. Schembl24882

69. Bspbio_000147

70. Bspbio_001103

71. Bspbio_003112

72. Kbiogr_000443

73. Kbiogr_000695

74. Kbioss_000443

75. Kbioss_002057

76. Mls001148268

77. Divk1c_000693

78. Spectrum1503231

79. Spbio_001382

80. Spbio_002068

81. N-(4-nitro-2-phenoxyphenyl)

82. Bpbio1_000163

83. Gtpl7401

84. Nim-03

85. Dtxsid3037250

86. Nimesulide [ep Impurity]

87. Bcbcmap01_000034

88. Hms502c15

89. Kbio1_000693

90. Kbio2_000443

91. Kbio2_002057

92. Kbio2_003011

93. Kbio2_004625

94. Kbio2_005579

95. Kbio2_007193

96. Kbio3_000825

97. Kbio3_000826

98. Kbio3_002612

99. Nimesulide [ep Monograph]

100. Nimesulide For Peak Identification

101. Ninds_000693

102. Bio2_000382

103. Bio2_000862

104. Hms1362g05

105. Hms1568h09

106. Hms1792g05

107. Hms1922k17

108. Hms1990g05

109. Hms2089b14

110. Hms2095h09

111. Hms2234k19

112. Hms3262l11

113. Hms3269g17

114. Hms3371j19

115. Hms3403g05

116. Hms3414p09

117. Hms3649a04

118. Hms3655d13

119. Hms3678p07

120. Hms3712h09

121. Hms3884c22

122. Pharmakon1600-01503231

123. Bcp10076

124. Hy-b0363

125. Zinc4617749

126. Tox21_110207

127. Tox21_301850

128. Tox21_500855

129. Bdbm50056999

130. Ccg-39319

131. Ei-287

132. Nsc758412

133. S2040

134. Stl018679

135. Akos015897356

136. Tox21_110207_1

137. Ac-4524

138. Db04743

139. Ks-1277

140. Lp00855

141. Nsc 758412

142. Sdccgsbi-0050831.p004

143. Idi1_000693

144. Idi1_002137

145. Ncgc00015725-01

146. Ncgc00015725-03

147. Ncgc00015725-04

148. Ncgc00015725-05

149. Ncgc00015725-06

150. Ncgc00015725-07

151. Ncgc00015725-08

152. Ncgc00015725-09

153. Ncgc00015725-10

154. Ncgc00015725-11

155. Ncgc00015725-12

156. Ncgc00015725-13

157. Ncgc00015725-15

158. Ncgc00015725-16

159. Ncgc00015725-29

160. Ncgc00021842-03

161. Ncgc00021842-04

162. Ncgc00021842-05

163. Ncgc00021842-06

164. Ncgc00021842-07

165. Ncgc00021842-08

166. Ncgc00255661-01

167. Ncgc00261540-01

168. Bn166246

169. Nimesulide 100 Microg/ml In Acetonitrile

170. Sbi-0050831.p003

171. Db-052029

172. Ab00052332

173. Eu-0100855

174. Ft-0630650

175. N0984

176. Sw196785-3

177. D01049

178. D70376

179. N 1016

180. Q20994

181. Ab00052332-16

182. Ab00052332_17

183. Ab00052332_18

184. N-[4-nitro-2-(phenoxy)phenyl]methanesulfonamide

185. 803n782

186. A828786

187. Sr-01000000218-2

188. Sr-01000000218-6

189. Sr-01000000218-7

190. W-105866

191. Brd-k76775527-001-06-2

192. Brd-k76775527-001-18-7

193. Sr-01000000218-11

194. Nimesulide, European Pharmacopoeia (ep) Reference Standard

195. Nimesulide, Pharmaceutical Secondary Standard; Certified Reference Material

196. Nimesulide For Peak Identification, European Pharmacopoeia (ep) Reference Standard

197. 1364966-82-4

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₃H₁₂N₂O₅S
Molecular Weight	308.31 g/mol
XLogP3	2.6
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	4
Exact Mass	308.04669266 g/mol
Monoisotopic Mass	308.04669266 g/mol
Topological Polar Surface Area	110 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	450
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 acute pain, the symptomatic treatment of osteoarthritis and primary dysmenorrhoea in adolescents and adults above 12 years old.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Food, gender and advanced age have negligible effects on nimesulide pharmacokinetics.

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

M - Musculo-skeletal system

M01 - Antiinflammatory and antirheumatic products

M01A - Antiinflammatory and antirheumatic products, non-steroids

M01AX - Other antiinflammatory and antirheumatic agents, non-steroids

M01AX17 - Nimesulide

M - Musculo-skeletal system

M02 - Topical products for joint and muscular pain

M02A - Topical products for joint and muscular pain

M02AA - Antiinflammatory preparations, non-steroids for topical use

M02AA26 - Nimesulide

5.4 Absorption, Distribution and Excretion

Absorption

Rapidly absorbed following oral administration.

Route of Elimination

Renal (50%), fecal (29%)

5.5 Metabolism/Metabolites

Hepatic. Extensive biotransformation, mainly to 4-hydroxynimesulide (which also appears to be biologically active).

5.6 Biological Half-Life

1.84.7 hours

5.7 Mechanism of Action

The therapeutic effects of Nimesulide are the result of its complete mode of action which targets a number of key mediators of the inflammatory process such as: COX-2 mediated prostaglandins, free radicals, proteolytic enzymes and histamine.