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Prestwick3_000054
Also known as: 61-68-7, Ponstel, 2-[(2,3-dimethylphenyl)amino]benzoic acid, Mephenamic acid, Mephenaminic acid, Ponstan
Molecular Formula
C15H15NO2
Molecular Weight
241.28  g/mol
InChI Key
HYYBABOKPJLUIN-UHFFFAOYSA-N
FDA UNII
367589PJ2C

A non-steroidal anti-inflammatory agent with analgesic, anti-inflammatory, and antipyretic properties. It is an inhibitor of cyclooxygenase.
Mefenamic acid is a Nonsteroidal Anti-inflammatory Drug. The mechanism of action of mefenamic acid is as a Cyclooxygenase Inhibitor.
1 2D Structure

Prestwick3_000054

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(2,3-dimethylanilino)benzoic acid
2.1.2 InChI
InChI=1S/C15H15NO2/c1-10-6-5-9-13(11(10)2)16-14-8-4-3-7-12(14)15(17)18/h3-9,16H,1-2H3,(H,17,18)
2.1.3 InChI Key
HYYBABOKPJLUIN-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=C(C(=CC=C1)NC2=CC=CC=C2C(=O)O)C
2.2 Other Identifiers
2.2.1 UNII
367589PJ2C
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Acid, Mefenamic

2. Apo Mefenamic

3. Apo-mefenamic

4. Contraflam

5. Coslan

6. Dysman

7. Mefac

8. Mefacit

9. Mefenaminic Acid

10. Mefic

11. Nu Mefenamic

12. Nu-mefenamic

13. Parkemed

14. Pinalgesic

15. Pms Mefenamic Acid

16. Pms-mefenamic Acid

17. Ponalar

18. Ponalgic

19. Ponmel

20. Ponstan

21. Ponstan Forte

22. Ponstel

23. Ponsyl

24. Pontal

2.3.2 Depositor-Supplied Synonyms

1. 61-68-7

2. Ponstel

3. 2-[(2,3-dimethylphenyl)amino]benzoic Acid

4. Mephenamic Acid

5. Mephenaminic Acid

6. Ponstan

7. 2-((2,3-dimethylphenyl)amino)benzoic Acid

8. Parkemed

9. Coslan

10. Mefacit

11. Ponalar

12. Methenamic Acid

13. Mefenaminsaeure

14. Bonabol

15. Lysalgo

16. Tanston

17. Vialidon

18. Bafameritin-m

19. Tamany Bonsan

20. Ponstan Forte

21. Acide Mefenamique

22. Namphen

23. Pontal

24. Mefanamic Acid

25. Bafhameritin-m

26. Cn-35355

27. N-2,3-xylylanthranilic Acid

28. 2-(2,3-dimethylanilino)benzoic Acid

29. Mefenamate

30. Mefenacid

31. Ponstil

32. Ponstyl

33. Mefenaminic Acid

34. Hl 1

35. Inf-3355

36. Inf 3355

37. Acido Mefenamico

38. Ci-473

39. N-(2,3-xylyl)anthranilic Acid

40. Acidum Mefenamicum

41. N-(2,3-xylyl)-2-aminobenzoic Acid

42. N-(2,3-dimethylphenyl)anthranilic Acid

43. Agn-1255

44. Cl 473

45. Gardan

46. Benzoic Acid, 2-[(2,3-dimethylphenyl)amino]-

47. 2-(2,3-dimethylphenylamino)benzoic Acid

48. Anthranilic Acid, N-2,3-xylyl-

49. Cn 35355

50. Nsc 94437

51. Benzoic Acid, 2-((2,3-dimethylphenyl)amino)-

52. Ci 473

53. Nsc-94437

54. 2-diphenylaminecarboxylic Acid, 2',3'-dimethyl-

55. Chembl686

56. Mls000069709

57. Chebi:6717

58. Benzoic Acid, 2-(2,3-dimethylphenyl)amino-

59. M01ag01

60. Nsc94437

61. 367589pj2c

62. J2.344b

63. Cas-61-68-7

64. Ncgc00016278-07

65. Smr000058188

66. Dsstox_cid_3243

67. Mefenaminsaeure [german]

68. Dsstox_rid_76938

69. Dsstox_gsid_23243

70. Ac. Mefenamico [italian]

71. In-m

72. Acide Mefenamique [french]

73. Acide Mefenamique [inn-french]

74. Acido Mefenamico [inn-spanish]

75. Acidum Mefenamicum [inn-latin]

76. 2-(2,3-xylidino)benzoic Acid

77. Hsdb 3115

78. Sr-01000000216

79. Einecs 200-513-1

80. Mfcd00051721

81. Brn 2216243

82. Mefenamic-acid

83. Unii-367589pj2c

84. Prestwick_506

85. Anthranilic Acid, N-(2,3-xylyl)-

86. Mefenamic Acid,(s)

87. Spectrum_000174

88. Cpd000058188

89. Opera_id_542

90. Mefenamic Acid [usan:usp:inn:ban:jan]

91. Prestwick0_000054

92. Prestwick1_000054

93. Prestwick2_000054

94. Prestwick3_000054

95. Spectrum2_001941

96. Spectrum3_001082

97. Spectrum4_001235

98. Spectrum5_001341

99. M1782

100. Anthranilic Acid,3-xylyl-

101. Cid_4044

102. Schembl3544

103. Mefenamic Acid [mi]

104. Oprea1_193889

105. Bspbio_000207

106. Bspbio_002724

107. Kbiogr_001730

108. Kbioss_000654

109. Mefenamic Acid [inn]

110. Mefenamic Acid [jan]

111. Mls001074162

112. Divk1c_000298

113. Mefenamic Acid [hsdb]

114. Mefenamic Acid [usan]

115. Spectrum1501103

116. Spbio_002001

117. Spbio_002128

118. Mefenamic Acid [vandf]

119. Bpbio1_000229

120. F0850-6853

121. Gtpl2593

122. Sgcut00005

123. Wln: Qvr Bmr B1 C1

124. Mefenamic Acid [mart.]

125. Dtxsid5023243

126. Mefenamic Acid [usp-rs]

127. Mefenamic Acid [who-dd]

128. Hms500o20

129. Kbio1_000298

130. Kbio2_000654

131. Kbio2_003222

132. Kbio2_005790

133. Kbio3_001944

134. Zinc20241

135. Brd8217

136. Ninds_000298

137. Hms1568k09

138. Hms1921d13

139. Hms2090b07

140. Hms2092b17

141. Hms2095k09

142. Hms2232p18

143. Hms3259m19

144. Hms3370k18

145. Hms3652a10

146. Hms3712k09

147. Hms3885o22

148. Pharmakon1600-01501103

149. Mefenamic Acid (jp17/usp/inn)

150. Mefenamic Acid, Analytical Standard

151. Albb-025759

152. Bcp08499

153. Brd-8217

154. Hy-b0574

155. To_000071

156. Tox21_110344

157. Tox21_301983

158. Bbl003564

159. Bdbm50134036

160. Ccg-39434

161. Mefenamic Acid [orange Book]

162. Nsc757834

163. S4078

164. Stk666691

165. Mefenamic Acid [ep Monograph]

166. Akos001025551

167. Akos002388313

168. Benzoic Acid,3-dimethylphenyl)amino]-

169. Mefenamic Acid [usp Monograph]

170. Tox21_110344_1

171. Db00784

172. Nc00517

173. Nsc-757834

174. Idi1_000298

175. Smp2_000141

176. 2-(2,3-dimethylanilino)benzoic Acid #

177. 2-(2,3-dimethylphenyl)aminobenzoic Acid

178. Ncgc00016278-01

179. Ncgc00016278-02

180. Ncgc00016278-03

181. Ncgc00016278-04

182. Ncgc00016278-05

183. Ncgc00016278-06

184. Ncgc00016278-10

185. Ncgc00022393-03

186. Ncgc00022393-04

187. Ncgc00022393-05

188. Ncgc00255401-01

189. Ac-11160

190. As-12677

191. Sbi-0051636.p002

192. 2-(2,3-dimethyl-phenylamino)-benzoic Acid

193. 2-[(2,3-dimethylphenyl) Amino]benzoic Acid

194. 2-diphenylaminecarboxylic Acid,3'-dimethyl-

195. Ab00052200

196. Am20060688

197. Ft-0628184

198. Sw196700-3

199. Unm000001233403

200. 1-methyl-3-benzylimidazolium Tetrafluoroborate

201. C02168

202. D00151

203. Ab00052200-17

204. Ab00052200_18

205. Ab00052200_19

206. A833367

207. Q284321

208. 2-(2,3-dimethylanilino)benzoic Acid;mefenamic Acid

209. Sr-01000000216-2

210. Sr-01000000216-4

211. W-105113

212. Brd-k92778217-001-06-1

213. Z56755828

214. 2-(2,3-dimethyl-phenylamino)-benzoic Acid(mefenamic Acid)

215. Mefenamic Acid, European Pharmacopoeia (ep) Reference Standard

216. Mefenamic Acid, United States Pharmacopeia (usp) Reference Standard

217. 4-methyl-n-(3-{3-[(4-methylpiperidin-1-yl)carbonyl]imidazo[2,1-b][1,3]thiazol-6-yl}phenyl)benzenesulfonamide

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 241.28 g/mol
Molecular Formula C15H15NO2
XLogP35.1
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Exact Mass241.110278721 g/mol
Monoisotopic Mass241.110278721 g/mol
Topological Polar Surface Area49.3 Ų
Heavy Atom Count18
Formal Charge0
Complexity292
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 Information
1 of 4  
Drug NameMefenamic acid
PubMed HealthMefenamic Acid (By mouth)
Drug ClassesAnalgesic, Antimigraine, Central Nervous System Agent
Drug LabelMefenamic acid is a member of the fenamate group of nonsteroidal anti-inflammatory drugs (NSAIDs). Each Size 1 Yellow-Yellow capsule, with PAD imprinted on the cap & 195 imprinted on the body, contains 250 mg of mefenamic acid for o...
Active IngredientMefenamic acid
Dosage FormCapsule
RouteOral
Strength250mg
Market StatusPrescription
CompanyVintage Pharms; Breckenridge Pharm; Lupin; Micro Labs

2 of 4  
Drug NamePonstel
PubMed HealthMefenamic Acid (By mouth)
Drug ClassesAnalgesic, Antimigraine, Central Nervous System Agent
Drug LabelPONSTEL (mefenamic acid) is a member of the fenamate group of nonsteroidal anti-inflammatory drugs (NSAIDs). Each blue-banded, ivory capsule contains 250 mg of mefenamic acid for oral administration. Mefenamic acid is a white to greyish-white, odor...
Active IngredientMefenamic acid
Dosage FormCapsule
RouteOral
Strength250mg
Market StatusPrescription
CompanyShionogi

3 of 4  
Drug NameMefenamic acid
PubMed HealthMefenamic Acid (By mouth)
Drug ClassesAnalgesic, Antimigraine, Central Nervous System Agent
Drug LabelMefenamic acid is a member of the fenamate group of nonsteroidal anti-inflammatory drugs (NSAIDs). Each Size 1 Yellow-Yellow capsule, with PAD imprinted on the cap & 195 imprinted on the body, contains 250 mg of mefenamic acid for o...
Active IngredientMefenamic acid
Dosage FormCapsule
RouteOral
Strength250mg
Market StatusPrescription
CompanyVintage Pharms; Breckenridge Pharm; Lupin; Micro Labs

4 of 4  
Drug NamePonstel
PubMed HealthMefenamic Acid (By mouth)
Drug ClassesAnalgesic, Antimigraine, Central Nervous System Agent
Drug LabelPONSTEL (mefenamic acid) is a member of the fenamate group of nonsteroidal anti-inflammatory drugs (NSAIDs). Each blue-banded, ivory capsule contains 250 mg of mefenamic acid for oral administration. Mefenamic acid is a white to greyish-white, odor...
Active IngredientMefenamic acid
Dosage FormCapsule
RouteOral
Strength250mg
Market StatusPrescription
CompanyShionogi

4.2 Therapeutic Uses

Anti-Inflammatory Agents, Non-Steroidal; Cyclooxygenase Inhibitors

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


MEFENAMIC ACID (PONSTEL) ... PROVIDES ANALGESIA IN MAN SIMILAR TO THAT PRODUCED BY ASPIRIN.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 343


...INDICATED FOR RELIEF OF PAIN RESULTING FROM DENTAL EXTRACTIONS.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1050


DRUG PREFERABLY SHOULD BE TAKEN WITH FOOD.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 349


MEFENAMIC ACID SHOWED FAVORABLE RESULTS RELATIVE TO SOME ANALGESICS.

ANDERSON ET AL; TRIAL OF PROSTAGLANDIN SYNTHETASE INHIBITORS IN PRIMARY DYSMENORRHEA; LANCET 1(FEB 18) 345-348 (1978)


4.3 Drug Warning

SINCE IT IS NOT SUPERIOR TO ESTABLISHED ANALGESICS & CAN CAUSE SERIOUS TOXICITY, USE OF MEFENAMIC ACID IS NOT RECOMMENDED. IF IT IS USED, ADMIN SHOULD NOT BE EXTENDED BEYOND 7 DAYS. IF DIARRHEA OCCURS, DRUG MUST BE DISCONTINUED & NOT USED AGAIN. IT SHOULD NOT BE USED IN CHILDREN OR IN WOMEN OF CHILDBEARING AGE.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 343


IT IS CONTRAINDICATED IN PT WITH ULCERATION OF UPPER OR LOWER INTESTINAL TRACT...& PT KNOWN TO BE HYPERSENSITIVE TO DRUG. ...CONSIDER ITS USE ONLY IN CASES WHICH EITHER CAN NOT TOLERATE OR DO NOT RESPOND TO LESS TOXIC AGENTS.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1050


MEFENAMIC ACID IS CONTRAINDICATED IN PT...WITH IMPAIRED RENAL FUNCTION, & SHOULD BE USED WITH CAUTION IN ASTHMATICS BECAUSE IT MAY EXACERBATE CONDITION.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 349


Maternal Medication usually Compatible with Breast-Feeding: Mefenamic acid: Reported Sign or Symptom in Infant or Effect on Lactation: None. /from Table 6/

Report of the American Academy of Pediatrics Committee on Drugs in Pediatrics 93 (1): 141 (1994)


4.4 Drug Indication

For the treatment of rheumatoid arthritis, osteoarthritis, dysmenorrhea, and mild to moderate pain, inflammation, and fever.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Mefenamic acid, an anthranilic acid derivative, is a member of the fenamate group of nonsteroidal anti-inflammatory drugs (NSAIDs). It exhibits anti-inflammatory, analgesic, and antipyretic activities. Similar to other NSAIDs, mefenamic acid inhibits prostaglandin synthetase.


5.2 MeSH Pharmacological Classification

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.)


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.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
MEFENAMIC ACID
5.3.2 FDA UNII
367589PJ2C
5.3.3 Pharmacological Classes
Cyclooxygenase Inhibitors [MoA]; Nonsteroidal Anti-inflammatory Drug [EPC]; Anti-Inflammatory Agents, Non-Steroidal [CS]
5.4 ATC Code

M - Musculo-skeletal system

M01 - Antiinflammatory and antirheumatic products

M01A - Antiinflammatory and antirheumatic products, non-steroids

M01AG - Fenamates

M01AG01 - Mefenamic acid


5.5 Absorption, Distribution and Excretion

Absorption

Mefenamic acid is rapidly absorbed after oral administration.


Route of Elimination

The fecal route of elimination accounts for up to 20% of the dose, mainly in the form of unconjugated 3-carboxymefenamic acid.3 The elimination half-life of mefenamic acid is approximately two hours. Mefenamic acid, its metabolites and conjugates are primarily excreted by the kidneys. Both renal and hepatic excretion are significant pathways of elimination.


Volume of Distribution

1.06 L/kg [Normal Healthy Adults (18-45 yr)]


Clearance

Oral cl=21.23 L/hr [Healthy adults (18-45 yrs)]


CROSSES PLACENTAL BARRIER IN MONKEYS...EXCRETED IN URINE, BILE &/OR FECES...

American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1967


ABSORBED SLOWLY FROM GI TRACT...HIGH PERCENTAGE...BOUND TO PLASMA PROTEINS. PEAK PLASMA LEVELS APPEAR IN 2 TO 4 HR...ANALGESIA MAY PERSIST FOR UP TO 6 HR...ABOUT 50%...IS EXCRETED IN URINE WITHIN 24 HR /HUMAN, ORAL/

American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1967


5.6 Metabolism/Metabolites

Mefenamic acid undergoes metabolism by CYP2C9 to 3-hydroxymethyl mefenamic acid, and further oxidation to a 3-carboxymefenamic acid may occur. The activity of these metabolites has not been studied. Mefenamic acid is also glucuronidated directly.


MEFENAMIC ACID...IS TRANSFORMED TO HYDROXYMETHYL DERIVATIVE & TO ACID BY MAJOR, IF NOT ONLY, METABOLIC PATHWAY IN DOG, MONKEY, & HUMAN.

Testa, B. and P. Jenner. Drug Metabolism: Chemical & Biochemical Aspects. New York: Marcel Dekker, Inc., 1976., p. 12


Mefenamic acid has known human metabolites that include 3-hydroxymethyl mefenamic aci.

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


5.7 Biological Half-Life

2 hours


...ABOUT 50%...IS EXCRETED IN URINE WITHIN 24 HR /HUMAN, ORAL/

American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1967


5.8 Mechanism of Action

Mefenamic acid binds the prostaglandin synthetase receptors COX-1 and COX-2, inhibiting the action of prostaglandin synthetase. As these receptors have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity, the symptoms of pain are temporarily reduced.


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