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Chemistry

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Also known as: 4394-00-7, Landruma, Nifluril, Forenol, Nifluminic acid, Niflugel

Molecular Formula

C₁₃H₉F₃N₂O₂

Molecular Weight

282.22 g/mol

InChI Key

JZFPYUNJRRFVQU-UHFFFAOYSA-N

FDA UNII

4U5MP5IUD8

An analgesic and anti-inflammatory agent used in the treatment of rheumatoid arthritis.

1 2D Structure

Niflumic Acid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[3-(trifluoromethyl)anilino]pyridine-3-carboxylic acid

2.1.2 InChI

InChI=1S/C13H9F3N2O2/c14-13(15,16)8-3-1-4-9(7-8)18-11-10(12(19)20)5-2-6-17-11/h1-7H,(H,17,18)(H,19,20)

2.1.3 InChI Key

JZFPYUNJRRFVQU-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC(=CC(=C1)NC2=C(C=CC=N2)C(=O)O)C(F)(F)F

2.2 Other Identifiers

2.2.1 UNII

4U5MP5IUD8

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Acid, Niflumic

2. Donalgin

3. Flunir

4. Niflactol

5. Niflugel

6. Nifluril

2.3.2 Depositor-Supplied Synonyms

1. 4394-00-7

2. Landruma

3. Nifluril

4. Forenol

5. Nifluminic Acid

6. Niflugel

7. Acido Niflumico

8. Acide Niflumique

9. Up 83

10. 2-{[3-(trifluoromethyl)phenyl]amino}pyridine-3-carboxylic Acid

11. Acide Niflumique [inn-french]

12. Acido Niflumico [inn-spanish]

13. Acidum Niflumicum [inn-latin]

14. 2-[3-(trifluoromethyl)anilino]pyridine-3-carboxylic Acid

15. 2-(3-(trifluoromethyl)anilino)nicotinic Acid

16. 2-(3-(trifluoromethyl)-phenyl)aminonicotinic Acid

17. 2-(3-trifluoromethylanilino)nicotinic Acid

18. 2-((3-(trifluoromethyl)phenyl)amino)nicotinic Acid

19. 2-[3-(trifluoromethyl)anilino]nicotinic Acid

20. 3-pyridinecarboxylic Acid, 2-[[3-(trifluoromethyl)phenyl]amino]-

21. Lopac-n-0630

22. 2-{[3-(trifluoromethyl)phenyl]amino}nicotinic Acid

23. 2-(3-(trifluoromethyl)phenylamino)nicotinic Acid

24. Niflumic Acid (inn)

25. Nsc-758196

26. 2-[(3-trifluoromethyl)phenyl]amino-3-pyridine-carboxylic Acid

27. 4u5mp5iud8

28. Mls000069713

29. Nfl

30. Chebi:34888

31. 3-pyridinecarboxylic Acid, 2-((3-(trifluoromethyl)phenyl)amino)-

32. Up-83

33. Ncgc00015724-10

34. Niflumate

35. Smr000058199

36. Cas-4394-00-7

37. Dsstox_cid_3368

38. 2-(3-[trifluoromethyl]anilino)nicotinic Acid

39. Acidum Niflumicum

40. Dsstox_rid_76996

41. Niflumic Acid [inn]

42. Dsstox_gsid_23368

43. Acide Niflumique [french]

44. Acido Niflumico [italian]

45. Niflamol

46. Niflugel (tn)

47. Sc 1332

48. Ccris 5740

49. Sr-01000000231

50. 2-(alpha,alpha,alpha-trifluoro-m-toluidino)nicotinic Acid

51. Einecs 224-516-2

52. 2-(3-trifluoromethyl-phenylamino)-nicotinic Acid

53. Unii-4u5mp5iud8

54. Brn 0489360

55. 2-[[3-(trifluoromethyl)phenyl]amino]pyridine-3-carboxylic Acid

56. Niflumic-acid

57. Ni-flumic Acid

58. Niflumic Acid [inn:ban:dcf]

59. Actol, Analgesic

60. Aza-2 Dimethyl-2',3' (tetrazolyl-5)-6 Diphenylamino [french]

61. Prestwick_890

62. Mfcd00010569

63. Aza-2 Dimethyl-2',3' (tetrazolyl-5)-6 Diphenylamino

64. Spectrum_001353

65. 1td7

66. Opera_id_1746

67. Prestwick0_000255

68. Prestwick1_000255

69. Prestwick2_000255

70. Prestwick3_000255

71. Spectrum2_000794

72. Spectrum3_001485

73. Spectrum4_000043

74. Spectrum5_001216

75. Niflumic Acid (hit 16)

76. N 0630

77. Niflumic Acid [mi]

78. 2-[(3-trifluoromethylphenyl)amino]nicotinic Acid

79. Cbiol_001828

80. Lopac0_000845

81. Schembl24706

82. Bspbio_000070

83. Bspbio_001393

84. Bspbio_003069

85. Kbiogr_000113

86. Kbiogr_000505

87. Kbioss_000113

88. Kbioss_001833

89. 5-22-13-00598 (beilstein Handbook Reference)

90. Mls001076327

91. Chembl63323

92. Divk1c_000277

93. Spectrum1502015

94. Spbio_000928

95. Spbio_002289

96. Niflumic Acid [mart.]

97. Bpbio1_000078

98. Gtpl2439

99. Niflumic Acid [who-dd]

100. Dtxsid1023368

101. Bdbm85507

102. Hms500n19

103. Kbio1_000277

104. Kbio2_000113

105. Kbio2_001833

106. Kbio2_002681

107. Kbio2_004401

108. Kbio2_005249

109. Kbio2_006969

110. Kbio3_000225

111. Kbio3_000226

112. Kbio3_002569

113. Ninds_000277

114. 2-[(3-trifluoromethyl)phenyl]amino]-3-pyridinecarboxylic Acid

115. Bio1_000114

116. Bio1_000603

117. Bio1_001092

118. Bio2_000113

119. Bio2_000593

120. Hms1361f15

121. Hms1568d12

122. Hms1791f15

123. Hms1921d12

124. Hms1989f15

125. Hms2090d19

126. Hms2095d12

127. Hms2234f11

128. Hms3262j11

129. Hms3374h01

130. Hms3402f15

131. Hms3649a08

132. Hms3656p14

133. Hms3712d12

134. Hms3885i03

135. Nicotinic Acid, 2-(alpha,alpha,alpha-trifluoro-m-toluidino)-

136. Pharmakon1600-01502015

137. Zinc125031

138. Hy-b0493

139. Niflumic Acid [ep Impurity]

140. Nsc_4488

141. Tox21_110206

142. Tox21_500845

143. Bbl003619

144. Ccg-40157

145. Dl-457

146. Nicotinic Acid, 2-(.alpha.,.alpha.,.alpha.-trifluoro-m-toluidino)-

147. Niflumic Acid [ep Monograph]

148. Nsc758196

149. S3018

150. Stk803109

151. Akos000519590

152. Tox21_110206_1

153. Ac-2652

154. Db04552

155. Gs-3202

156. Lp00845

157. Nsc 758196

158. Sdccgsbi-0050821.p004

159. Idi1_000277

160. Idi1_033863

161. Ncgc00015724-01

162. Ncgc00015724-02

163. Ncgc00015724-03

164. Ncgc00015724-04

165. Ncgc00015724-05

166. Ncgc00015724-06

167. Ncgc00015724-07

168. Ncgc00015724-08

169. Ncgc00015724-09

170. Ncgc00015724-11

171. Ncgc00015724-12

172. Ncgc00015724-13

173. Ncgc00015724-14

174. Ncgc00015724-17

175. Ncgc00015724-29

176. Ncgc00023636-03

177. Ncgc00023636-04

178. Ncgc00023636-05

179. Ncgc00023636-06

180. Ncgc00023636-07

181. Ncgc00023636-08

182. Ncgc00023636-09

183. Ncgc00261530-01

184. Cas_4394-00-7

185. Sbi-0050821.p003

186. 2(3'-trifluormethylanilino)-nicotinic Acid

187. Ab00052255

188. Am20070143

189. Eu-0100845

190. Ft-0603659

191. Niflumic Acid 100 Microg/ml In Acetonitrile

192. Sw197011-3

193. T2353

194. A23222

195. D08275

196. H10042

197. S00109

198. Ab00052255-17

199. Ab00052255_18

200. Ab00052255_19

201. 2-((3-(trifluoromethyl)phenyl)amino)nicotinicacid

202. 394n007

203. Q304285

204. Sr-01000000231-2

205. Sr-01000000231-5

206. Sr-01000000231-6

207. W-106215

208. Brd-k98763141-001-04-3

209. Brd-k98763141-001-06-8

210. Brd-k98763141-001-17-5

211. Sr-01000000231-11

212. 2-[3-(trifluoromethyl)anilino]-3-pyridinecarboxylic Acid

213. Niflumic Acid, European Pharmacopoeia (ep) Reference Standard

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₃H₉F₃N₂O₂
Molecular Weight	282.22 g/mol
XLogP3	3.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	3
Exact Mass	282.06161202 g/mol
Monoisotopic Mass	282.06161202 g/mol
Topological Polar Surface Area	62.2 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	349
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

Used in the treatment of rheumatoid arthritis.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Niflumic acid, a nonsteroidal anti-inflammatory fenamate, is a Ca²⁺-activated Cl^- channel blocker.

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

M02AA17

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

M01AX - Other antiinflammatory and antirheumatic agents, non-steroids

M01AX02 - Niflumic acid

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

M02AA17 - Niflumic acid

5.4 Absorption, Distribution and Excretion

Absorption