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ASolution Tolfenamic Acid

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Chemistry

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Also known as: 13710-19-5, Clotam, 2-[(3-chloro-2-methylphenyl)amino]benzoic acid, Tolfedine, N-(3-chloro-2-methylphenyl)anthranilic acid, Gea 6414

Molecular Formula

C₁₄H₁₂ClNO₂

Molecular Weight

261.70 g/mol

InChI Key

YEZNLOUZAIOMLT-UHFFFAOYSA-N

FDA UNII

3G943U18KM

Tolfenamic Acid is an orally available, benzoic acid derivative and a non-steroidal anti-inflammatory drug (NSAID) with anti-inflammatory, antipyretic, analgesic and potential anti-neoplastic activities. Tolfenamic acid inhibits the activity of the enzymes cyclooxygenase (COX) I and II, resulting in a decreased formation of precursors of prostaglandins and thromboxanes. The decrease in prostaglandin synthesis results in the therapeutic effects of this agent. Tolfenamic acid also inhibits thromboxane A2 synthesis, by thromboxane synthase, which decreases platelet aggregation. In addition, this agent exerts anti-tumor effects through COX-dependent and independent pathways. Specifically, this agent induces the production of reactive oxygen species, causes DNA damage, increases nuclear factor-kappa B (NF-kB) activation and the expression of activating transcription factor 3 (ATF3) and NSAID-activated gene-1 (NAG1), and inhibits the expression of specificity proteins (Sp), which reduces the expression of Sp-dependent anti-apoptotic and growth-promoting proteins. Altogether, this enhances tumor cell apoptosis, and reduces tumor cell growth and angiogenesis.

1 2D Structure

Tolfenamic Acid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-(3-chloro-2-methylanilino)benzoic acid

2.1.2 InChI

InChI=1S/C14H12ClNO2/c1-9-11(15)6-4-8-12(9)16-13-7-3-2-5-10(13)14(17)18/h2-8,16H,1H3,(H,17,18)

2.1.3 InChI Key

YEZNLOUZAIOMLT-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=C(C=CC=C1Cl)NC2=CC=CC=C2C(=O)O

2.2 Other Identifiers

2.2.1 UNII

3G943U18KM

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Bifenac

2. Clotam

3. Gea 6414

4. N-(3-chloro-2-methylphenyl)anthranilic Acid

5. N-(3-chloro-o-tolyl)anthranilic Acid

6. Rociclyn

2.3.2 Depositor-Supplied Synonyms

1. 13710-19-5

2. Clotam

3. 2-[(3-chloro-2-methylphenyl)amino]benzoic Acid

4. Tolfedine

5. N-(3-chloro-2-methylphenyl)anthranilic Acid

6. Gea 6414

7. Acido Tolfenamico

8. 2-((3-chloro-2-methylphenyl)amino)benzoic Acid

9. Acide Tolfenamique

10. Acidum Tolfenamicum

11. 2-(3-chloro-2-methylanilino)benzoic Acid

12. Benzoic Acid, 2-[(3-chloro-2-methylphenyl)amino]-

13. N-(2-methyl-3-chlorophenyl)anthranilic Acid

14. N-(3-chloro-o-tolyl)-anthranilic Acid

15. Nsc-757873

16. Anthranilic Acid, N-(3-chloro-o-tolyl)-

17. Chebi:32243

18. N-(3-chloro-o-tolyl)anthranilic

19. 3g943u18km

20. Mfcd00133865

21. Ncgc00016705-05

22. Bifenac

23. N-(3-chloro-ortho-tolyl) Anthranilic Acid

24. Cas-13710-19-5

25. Dsstox_cid_25409

26. Dsstox_rid_80860

27. Dsstox_gsid_45409

28. Benzoic Acid, 2-((3-chloro-2-methylphenyl)amino)-

29. Tolfine

30. 2-([3-chloro-2-methylphenyl]amino)benzoic Acid

31. Sr-01000000102

32. N-(3-chloro-o-tolyl)anthranilic Acid

33. Tolfenamic

34. Tolfenamic-acid

35. Unii-3g943u18km

36. Acide Tolfenamique [inn-french]

37. Acido Tolfenamico [inn-spanish]

38. Acidum Tolfenamicum [inn-latin]

39. Tolfenamic Acid [inn:ban:jan]

40. Prestwick_579

41. Einecs 237-264-3

42. Clotam (tn)

43. Tolfenamicacid

44. Brn 0657821

45. Spectrum_001263

46. Tolfenamic Acid, Nsaid

47. Prestwick0_000205

48. Prestwick1_000205

49. Prestwick2_000205

50. Prestwick3_000205

51. Spectrum2_001446

52. Spectrum3_001762

53. Spectrum4_000238

54. Spectrum5_001143

55. Oprea1_692996

56. Schembl25190

57. Tolfenamic Acid (jan/inn)

58. Bspbio_000189

59. Bspbio_003223

60. Kbiogr_000935

61. Kbioss_001743

62. Tolfenamic Acid [mi]

63. Flufenamic Acid Analogue, 32

64. Mls000028531

65. Bidd:gt0343

66. Spectrum1501198

67. Tolfenamic Acid [inn]

68. Tolfenamic Acid [jan]

69. Spbio_001311

70. Spbio_002110

71. Bpbio1_000209

72. Chembl121626

73. Cid_610479

74. Gtpl8769

75. Zinc2188

76. Dtxsid1045409

77. Tolfenamic Acid [mart.]

78. Bdbm35905

79. Kbio2_001743

80. Kbio2_004311

81. Kbio2_006879

82. Kbio3_002723

83. Yeznlouzaiomlt-uhfffaoysa-

84. Tolfenamic Acid [who-dd]

85. Hms1568j11

86. Hms1921p13

87. Hms2090d04

88. Hms2095j11

89. Hms2230j13

90. Hms3370a02

91. Hms3651e06

92. Hms3712j11

93. Hms3884m16

94. Pharmakon1600-01501198

95. Hy-b0335

96. Tox21_110570

97. Ccg-39189

98. Nsc757873

99. S1959

100. Tolfenamic Acid [ep Impurity]

101. Akos012836098

102. Tolfenamic Acid [ep Monograph]

103. Tox21_110570_1

104. 2-(3-chloro-o-toluidino)benzoic Acid

105. Db09216

106. Nsc 757873

107. 2(3-chloro-2-methylanilino)benzoic Acid

108. Ncgc00016705-01

109. Ncgc00016705-02

110. Ncgc00016705-03

111. Ncgc00016705-04

112. Ncgc00016705-06

113. Ncgc00016705-07

114. Ncgc00016705-10

115. Ncgc00022587-03

116. Ncgc00022587-04

117. Ncgc00022587-05

118. As-13748

119. Da-11289

120. N-(3-chloro-ortho-tolyl)anthranilic Acid

121. Smr000058289

122. Sy052546

123. Sbi-0051687.p002

124. 2-(3-chloro-2-methylanilino)benzoic Acid #

125. Ab00052244

126. Ft-0652603

127. Sw196753-3

128. Unm000001237003

129. 2-(3-chloro-2-methylphenylamino)benzoic Acid

130. 2-((3-chloro-2-methylphenyl)amino)benzoicacid

131. D01183

132. D78227

133. Q59412

134. Tolfenamic Acid 100 Microg/ml In Acetonitrile

135. Ab00052244-15

136. Ab00052244_16

137. Ab00052244_17

138. Tolfenamic Acid 1000 Microg/ml In Acetonitrile

139. A807198

140. Benzoic Acid, 2-(3-chloro-2-methylphenylamino)-

141. 2-[(3-chloranyl-2-methyl-phenyl)amino]benzoic Acid

142. J-006962

143. Sr-01000000102-2

144. Sr-01000000102-3

145. Tolfenamic Acid, Vetranal(tm), Analytical Standard

146. Brd-k50133271-001-05-4

147. Brd-k50133271-001-10-4

148. Tolfenamic Acid, European Pharmacopoeia (ep) Reference Standard

149. Tolfenamic Acid, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₁₄H₁₂ClNO₂
Molecular Weight	261.70 g/mol
XLogP3	5.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Exact Mass	261.0556563 g/mol
Monoisotopic Mass	261.0556563 g/mol
Topological Polar Surface Area	49.3 Å²
Heavy Atom Count	18
Formal Charge	0
Complexity	298
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

In the information for tolfenamic acid, it is stated that this drug, being an NSAID, is effective in treating the pain associated with the acute attack of migraines in adults.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Studies have shown that tolfenamic acid presents a non-dose dependent partial inhibition of irritant-induced temperature rise as well as a dose-dependent inhibition of skin edema. By studying its NSAID properties more closely, it was noted a dose-related inhibition of serum thromboxane which indicated the inhibition of COX-1. In the same line, there was noted a inhibition of prostaglandin E2 synthesis which marks a related COX-2 inhibition. The maximal inhibition of thromboxane was greater than 80% as well as is proven to be a potent prostaglandin E inhibitor.

5.2 MeSH Pharmacological Classification

Analgesics

Compounds capable of relieving pain without the loss of CONSCIOUSNESS. (See all compounds classified as Analgesics.)

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.)

Calcium Channel Blockers

A class of drugs that act by selective inhibition of calcium influx through cellular membranes. (See all compounds classified as Calcium Channel Blockers.)

Serotonin Antagonists

Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or SEROTONIN RECEPTOR AGONISTS. (See all compounds classified as Serotonin Antagonists.)

Prostaglandin Antagonists

Compounds that inhibit the action of prostaglandins. (See all compounds classified as Prostaglandin Antagonists.)

5.3 ATC Code

M - Musculo-skeletal system

M01 - Antiinflammatory and antirheumatic products

M01A - Antiinflammatory and antirheumatic products, non-steroids

M01AG - Fenamates

M01AG02 - Tolfenamic acid

5.4 Absorption, Distribution and Excretion

Absorption

Tolfenamic acid pharmacokinetic is marked by a short tmax of 0.94-2.04 h. It also presented a linear pharmacokinetic profile with an AUC from 13-50 mcg/ml.h if administered in a dose of 2-8 mg/kg respectively. The oral absorption is delayed and it gives a mean lag-time to absorption of 32 min. The peak plasma concentration of 11.1 mcg/ml. The bioavailability of tolfenamic acid is around 75%.

Route of Elimination

Tolfenamic acid is cleared relatively fast and it undergoes by hepatic metabolism where the produced metabolites are renally cleared as glucuronic acid conjugates. Most of the elimination occurs by extrarenal mechanisms in which the unchanged drug together with its glucuronide in urine accounts for only 8.8% of the administered dose.

Volume of Distribution

The volume of distribution is of 1.79-3.2 L/kg. When tested intravenously, the reported steady-state volume of distribution was 0.33 L/kg.

Clearance

The estimated clearance rate of tolfenamic acid is 0.142-0.175 L.h/kg. When tested intravenously, the reported clearance rate was 72.4 ml.h/kg.

5.5 Metabolism/Metabolites

The first pass metabolism accounts for 20% of the administered dose of tolfenamic acid. Urine metabolite studies have demonstrated the identification of five metabolites from which three of them are monohydroxylated, one is monohydroxylated and hydroxylated and one last metabolite that presented and oxidized methyl group to form a carboxyl group. Two of these hydroxylated metabolites are N-(2-hydroxymethyl-3-chlorophenyl)-anthranilic acid and N-(2-hydroxymethyl-3-chloro-4-hydroxyphenyl)-anthranilic acid.

5.6 Biological Half-Life

The estimated half-life of tolfenamic acid is 8.01-13.50 hours. When tested intravenously, the reported half-life was 6.1h.

5.7 Mechanism of Action

Tolfenamic acid inhibits the biosynthesis of prostaglandins, and it also presents inhibitory actions on the prostaglandin receptors. As commonly thought, the mechanism of action of tolfenamic acid is based on the major mechanism of NSAIDs which consists of the inhibition of COX-1 and COX-2 pathways to inhibit prostaglandin secretion and action and thus, to exert its anti-inflammatory and pain-blocking action. Nonetheless, some report currently indicates that tolfenamic acid inhibits leukotriene B4 chemotaxis of human polymorphonuclear leukocytes leading to an inhibition of even 25% of the chemotactic response. This activity is a not ligand specific additional anti-inflammatory mechanism of tolfenamic acid.

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