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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
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 Weight 261.70 g/mol
Molecular Formula C14H12ClNO2
XLogP35.2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Exact Mass261.0556563 g/mol
Monoisotopic Mass261.0556563 g/mol
Topological Polar Surface Area49.3 Ų
Heavy Atom Count18
Formal Charge0
Complexity298
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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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OF KOREA","quantity":"50.00","actualQuantity":"50","unit":"KGS","unitRateFc":"85","totalValueFC":"3618.4","currency":"USD","unitRateINR":6106.9802,"date":"22-Nov-2024","totalValueINR":"305349.01","totalValueInUsd":"3618.4","indian_port":"Bombay Air","hs_no":"29224990","bill_no":"5813062","productDescription":"API","marketType":"REGULATED MARKET","country":"REPUBLIC OF KOREA","selfForZScoreResived":"Pharma Grade","supplierPort":"Bombay Air","supplierAddress":"101,1ST FLR,GANESH BHUVAN CO-OP.HSG, MARG,MULUND(E) MUMBAI, MAHARASHTRA","customerAddress":""},{"dataSource":"API Export","activeIngredients":"","year":"2024","qtr":"Q4","strtotime":1732473000,"product":"PHARMACEUTICAL RAW MATERIAL TOLFENAMIC ACID BP (HARMLESS DRUG)","address":"21-BRAHMANIYA PARA","city":"RAJKOT\/GUJARAT","supplier":"NIRA LIFE SCIENCES ","supplierCountry":"INDIA","foreign_port":"DHAKA","customer":"STANDARD CHARTERED BANK","customerCountry":"BANGLADESH","quantity":"2000.00","actualQuantity":"2000","unit":"KGS","unitRateFc":"42","totalValueFC":"77865.9","currency":"USD","unitRateINR":3285.48,"date":"25-Nov-2024","totalValueINR":"6570960","totalValueInUsd":"77865.9","indian_port":"Ahmedabad Air","hs_no":"29224990","bill_no":"5891678","productDescription":"API","marketType":"LESS REGULATED MARKET","country":"BANGLADESH","selfForZScoreResived":"Pharma Grade","supplierPort":"Ahmedabad Air","supplierAddress":"21-BRAHMANIYA PARA, RAJKOT\/GUJARAT","customerAddress":""}]
27-Jan-2021
25-Nov-2024
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ABOUT THIS PAGE

Tolfenamic Acid Manufacturers

A Tolfenamic Acid manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Tolfenamic Acid, including repackagers and relabelers. The FDA regulates Tolfenamic Acid manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Tolfenamic Acid API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Tolfenamic Acid manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Tolfenamic Acid Suppliers

A Tolfenamic Acid supplier is an individual or a company that provides Tolfenamic Acid active pharmaceutical ingredient (API) or Tolfenamic Acid finished formulations upon request. The Tolfenamic Acid suppliers may include Tolfenamic Acid API manufacturers, exporters, distributors and traders.

click here to find a list of Tolfenamic Acid suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Tolfenamic Acid USDMF

A Tolfenamic Acid DMF (Drug Master File) is a document detailing the whole manufacturing process of Tolfenamic Acid active pharmaceutical ingredient (API) in detail. Different forms of Tolfenamic Acid DMFs exist exist since differing nations have different regulations, such as Tolfenamic Acid USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Tolfenamic Acid DMF submitted to regulatory agencies in the US is known as a USDMF. Tolfenamic Acid USDMF includes data on Tolfenamic Acid's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Tolfenamic Acid USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Tolfenamic Acid suppliers with USDMF on PharmaCompass.

Tolfenamic Acid CEP

A Tolfenamic Acid CEP of the European Pharmacopoeia monograph is often referred to as a Tolfenamic Acid Certificate of Suitability (COS). The purpose of a Tolfenamic Acid CEP is to show that the European Pharmacopoeia monograph adequately controls the purity of Tolfenamic Acid EP produced by a given manufacturer. Suppliers of raw materials can prove the suitability of Tolfenamic Acid to their clients by showing that a Tolfenamic Acid CEP has been issued for it. The manufacturer submits a Tolfenamic Acid CEP (COS) as part of the market authorization procedure, and it takes on the role of a Tolfenamic Acid CEP holder for the record. Additionally, the data presented in the Tolfenamic Acid CEP (COS) is managed confidentially and offers a centralized system acknowledged by numerous nations, exactly like the Tolfenamic Acid DMF.

A Tolfenamic Acid CEP (COS) is recognised by all 36 nations that make up the European Pharmacopoeia Convention. Tolfenamic Acid CEPs may be accepted in nations that are not members of the Ph. Eur. at the discretion of the authorities there.

click here to find a list of Tolfenamic Acid suppliers with CEP (COS) on PharmaCompass.

Tolfenamic Acid WC

A Tolfenamic Acid written confirmation (Tolfenamic Acid WC) is an official document issued by a regulatory agency to a Tolfenamic Acid manufacturer, verifying that the manufacturing facility of a Tolfenamic Acid active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Tolfenamic Acid APIs or Tolfenamic Acid finished pharmaceutical products to another nation, regulatory agencies frequently require a Tolfenamic Acid WC (written confirmation) as part of the regulatory process.

click here to find a list of Tolfenamic Acid suppliers with Written Confirmation (WC) on PharmaCompass.

Tolfenamic Acid GMP

Tolfenamic Acid Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Tolfenamic Acid GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Tolfenamic Acid GMP manufacturer or Tolfenamic Acid GMP API supplier for your needs.

Tolfenamic Acid CoA

A Tolfenamic Acid CoA (Certificate of Analysis) is a formal document that attests to Tolfenamic Acid's compliance with Tolfenamic Acid specifications and serves as a tool for batch-level quality control.

Tolfenamic Acid CoA mostly includes findings from lab analyses of a specific batch. For each Tolfenamic Acid CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Tolfenamic Acid may be tested according to a variety of international standards, such as European Pharmacopoeia (Tolfenamic Acid EP), Tolfenamic Acid JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Tolfenamic Acid USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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