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Also known as: 22071-15-4, 2-(3-benzoylphenyl)propanoic acid, Orudis, 2-(3-benzoylphenyl)propionic acid, Actron, Capisten
Molecular Formula
C16H14O3
Molecular Weight
254.28  g/mol
InChI Key
DKYWVDODHFEZIM-UHFFFAOYSA-N
FDA UNII
90Y4QC304K

Ketoprofen
An IBUPROFEN-type anti-inflammatory analgesic and antipyretic. It is used in the treatment of rheumatoid arthritis and osteoarthritis.
Ketoprofen is a Nonsteroidal Anti-inflammatory Drug. The mechanism of action of ketoprofen is as a Cyclooxygenase Inhibitor.
1 2D Structure

Ketoprofen

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(3-benzoylphenyl)propanoic acid
2.1.2 InChI
InChI=1S/C16H14O3/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12/h2-11H,1H3,(H,18,19)
2.1.3 InChI Key
DKYWVDODHFEZIM-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(C1=CC(=CC=C1)C(=O)C2=CC=CC=C2)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
90Y4QC304K
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 19,583 Rp

2. 2-(3-benzoylphenyl)propionic Acid

3. Alrheumat

4. Alrheumum

5. Benzoylhydratropic Acid

6. Orudis

7. Profenid

8. Rp 19583

9. Rp, 19,583

10. Rp-19583

11. Rp19583

2.3.2 Depositor-Supplied Synonyms

1. 22071-15-4

2. 2-(3-benzoylphenyl)propanoic Acid

3. Orudis

4. 2-(3-benzoylphenyl)propionic Acid

5. Actron

6. Capisten

7. Oruvail

8. M-benzoylhydratropic Acid

9. Alrheumat

10. Ketoprofene

11. Profenid

12. Aneol

13. 3-benzoylhydratropic Acid

14. Alrheumun

15. Epatec

16. Iso-k

17. Orudis (tn)

18. Rp-19583

19. Ketoprofeno

20. Ketoprophene

21. 2-[3-(phenylcarbonyl)phenyl]propanoic Acid

22. Ketorin

23. Sector

24. (rs)-ketoprofen

25. 2-(m-benzoylphenyl)propionic Acid

26. Actron Ketoprofen

27. Racemic Ketoprofen

28. Benzeneacetic Acid, 3-benzoyl-.alpha.-methyl-

29. 3-benzoyl-alpha-methylbenzeneacetic Acid

30. Ru 4733

31. Ketoprofen (actron)

32. Chebi:6128

33. Chembl571

34. Nsc-758144

35. Propionic Acid, 2-(3-benzoylphenyl)-

36. (s)-ketoprofen;dexketoprofen

37. 19583 Rp

38. Hydratropic Acid, M-benzoyl-

39. L'acide (benzoyl-3-phenyl)-2-propionique

40. Mls000079024

41. Idea-033

42. R.p. 19,583

43. 90y4qc304k

44. Orudis Kt

45. 1189508-77-7

46. 19583rp

47. Ru-4733

48. Kefenid

49. Ketopron

50. Menamin

51. Meprofen

52. Orugesic

53. Oscorel

54. Smr000040181

55. Fastum

56. Ketoprofen 100 Microg/ml In Acetonitrile

57. Lertus

58. Toprec

59. Toprek

60. Dexal

61. Dsstox_cid_771

62. R.p. 19583

63. Racemic-ketoprofen

64. Dsstox_rid_75783

65. Dsstox_gsid_20771

66. Ketoprofenum

67. Rp 19583

68. Ketoprofene [inn-french]

69. Ketoprofenum [inn-latin]

70. Ketoprofeno [inn-spanish]

71. Ketoprofen (+-)

72. (+-)-m-benzoylhydratropic Acid

73. Benzeneacetic Acid, 3-benzoyl-alpha-methyl-

74. Sr-01000075949

75. Rac Ketoprofen

76. Ccris 4508

77. (+-)-3-benzoyl-alpha-methylbenzeneacetic Acid

78. (+/-)-m-benzoylhydratropic Acid

79. (+) Ketoprofen

80. Ncgc00016757-01

81. Ketoprofen ,(s)

82. Acide (benzoyl-3-phenyl)-2-propionique [french]

83. Prestwick_617

84. Einecs 244-759-8

85. 2-[3-(benzoyl)phenyl]propanoic Acid

86. Cas-22071-15-4

87. Mfcd00055790

88. Nexcede

89. Ketoprofen-13c-d3

90. 2-(3-benzoylphenyl)-propionic Acid

91. Hydratropic Acid, M-benzoyl-, (+-)-

92. Acide (benzoyl-3-phenyl)-2-propionique

93. Spectrum_001309

94. Ketoprofen [mi]

95. Opera_id_509

96. Ketoprofen [inn]

97. Ketoprofen [jan]

98. Prestwick0_000219

99. Prestwick1_000219

100. Prestwick2_000219

101. Prestwick3_000219

102. Spectrum2_000956

103. Spectrum3_001479

104. Spectrum4_000028

105. Spectrum5_001254

106. Ketoprofen [usan]

107. M-benzoyl-hydratropic Acid

108. Ketoprofen [vandf]

109. Epitope Id:131783

110. K 1751

111. Ketoprofen [mart.]

112. Schembl2896

113. Ketoprofen [who-dd]

114. (+/-)-ketoprofen

115. Lopac0_000686

116. Oprea1_117113

117. Bspbio_000237

118. Bspbio_003037

119. Kbiogr_000435

120. Kbioss_001789

121. 22161-86-0

122. Mls000028446

123. Mls001201752

124. Mls001306444

125. Mls002548889

126. Mls006011967

127. Bidd:gt0443

128. Divk1c_000598

129. Spectrum1501215

130. Unii-90y4qc304k

131. Spbio_000952

132. Spbio_002158

133. Benzeneacetic Acid, 3-benzoyl-alpha-methyl-, (+-)-

134. Bpbio1_000261

135. Gtpl4795

136. Ketoprofen (jp17/usp/inn)

137. Ketoprofen [green Book]

138. Ketoprofen, >=98% (tlc)

139. Dtxsid6020771

140. Ketoprofen [ep Impurity]

141. Ketoprofen [orange Book]

142. Dkywvdodhfezim-uhfffaoysa-

143. Hms501n20

144. Kbio1_000598

145. Kbio2_001789

146. Kbio2_004357

147. Kbio2_006925

148. Kbio3_002537

149. 2-(3-benzoylphenyl)propanoicacid

150. Ketoprofen [ep Monograph]

151. Ketoprofen [usp Impurity]

152. Ninds_000598

153. Hms1568l19

154. Hms1921b12

155. Hms2089b16

156. Hms2092l19

157. Hms2095l19

158. Hms2234h16

159. Hms3259i05

160. Hms3262i13

161. Hms3372m08

162. Hms3373g09

163. Hms3649n10

164. Hms3655c15

165. Hms3712l19

166. Hms3884k04

167. Ketoprofen [usp Monograph]

168. Pharmakon1600-01501215

169. Bcp23428

170. Hy-b0227

171. 2-(3'-benzoylphenyl)propionic Acid

172. 2-(3-benzoylphenyl) Propionic Acid

173. Alpha(3-benzoylphenyl)propionic Acid

174. Tox21_110594

175. Tox21_200847

176. Tox21_500686

177. (.+/-.)-m-benzoylhydratropic Acid

178. 2-(3-benzoylphenyl) Propionoic Acid

179. Alpha-(m-benzoylphenyl)propionic Acid

180. Bdbm50022271

181. Ccg-39685

182. Nsc758144

183. S1645

184. Stl450995

185. (r)-(-)-ketoprofen-[13c,d3]

186. 2-(3-benzoylphenyl)propanoic Acid #

187. Alpha-(3-benzoylphenyl)propionic Acid

188. Akos007930512

189. Alpha-(m-benzoylphenyl) Propionic Acid

190. Ketoprofen 100 Microg/ml In Methanol

191. Tox21_110594_1

192. Ac-1486

193. Bcp9000810

194. Db01009

195. Ketoprofen [usan:usp:inn:ban:jan]

196. Ks-5031

197. Lp00686

198. Nc00459

199. Nsc 758144

200. Sdccgsbi-0050664.p004

201. Idi1_000598

202. (rs)-2-(3-benzoylphenyl)propanoic Acid

203. Ncgc00015578-02

204. Ncgc00015578-03

205. Ncgc00015578-04

206. Ncgc00015578-05

207. Ncgc00015578-07

208. Ncgc00015578-08

209. Ncgc00015578-10

210. Ncgc00015578-12

211. Ncgc00015578-23

212. Ncgc00094043-01

213. Ncgc00094043-02

214. Ncgc00094043-03

215. Ncgc00094043-04

216. Ncgc00258401-01

217. Ncgc00261371-01

218. Bk166172

219. ((c)i)-ketoprofen-d4(propionic-d4 Acid)

220. 3-benzoyl-.alpha.-methylbenzeneacetic Acid

221. Bcp0726000302

222. Sbi-0050664.p003

223. (+/-)-2-(3-benzoylphenyl)propionic Acid

224. L''acide (benzoyl-3-phenyl)-2-propionique

225. Unm-0000306100

226. Ab00052249

227. Am20060549

228. Eu-0100686

229. Ft-0602834

230. Ft-0670646

231. Ft-0670647

232. K0038

233. Ketoprofen, Meets Usp Testing Specifications

234. Orudis, Profenid, Dexal, Keduril, Ketofen,

235. Sw196784-3

236. Bim-0050664.0001

237. C01716

238. D00132

239. D78110

240. Ketoprofen, Vetranal(tm), Analytical Standard

241. Ab00052249-17

242. Ab00052249-19

243. Ab00052249-20

244. Ab00052249_21

245. Ab00052249_22

246. 071k154

247. A815896

248. Q409192

249. Q-201268

250. Sr-01000075949-1

251. Sr-01000075949-6

252. Sr-01000075949-9

253. (.+/-.)-3-benzoyl-.alpha.-methylbenzeneacetic Acid

254. Brd-a97739905-001-05-9

255. Brd-a97739905-001-15-8

256. Sr-01000075949-18

257. F2173-0960

258. Z1695709452

259. (+/-)-3-benzoyl-.alpha.-methylbenzeneacetic Acid

260. Ketoprofen, British Pharmacopoeia (bp) Reference Standard

261. Ketoprofen, European Pharmacopoeia (ep) Reference Standard

262. Ketoprofen, United States Pharmacopeia (usp) Reference Standard

263. N-fmoc-3-amino-4-(4-tert-butoxy-phenyl)-butyricacid

264. Ketoprofen, Pharmaceutical Secondary Standard; Certified Reference Material

265. 154907-35-4

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 254.28 g/mol
Molecular Formula C16H14O3
XLogP33.1
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count4
Exact Mass254.094294304 g/mol
Monoisotopic Mass254.094294304 g/mol
Topological Polar Surface Area54.4 Ų
Heavy Atom Count19
Formal Charge0
Complexity331
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameKetoprofen
PubMed HealthKetoprofen (By mouth)
Drug ClassesAnalgesic, Antimigraine, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
Drug LabelKetoprofen is a non-steroidal anti-inflammatory drug. The chemical name for ketoprofen is 2-(3-benzoylphenyl)-propionic acid with the following structural formula:C16H14O3M.W. 254.29It has a pKa of 5.94 in methanol: water (3:1) an...
Active IngredientKetoprofen
Dosage FormCapsule; Capsule, extended release
RouteOral
Strength200mg; 25mg; 150mg; 75mg; 100mg; 50mg
Market StatusPrescription
CompanyActavis Labs Fl; Teva; Dorado Pharma; Mylan

2 of 2  
Drug NameKetoprofen
PubMed HealthKetoprofen (By mouth)
Drug ClassesAnalgesic, Antimigraine, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
Drug LabelKetoprofen is a non-steroidal anti-inflammatory drug. The chemical name for ketoprofen is 2-(3-benzoylphenyl)-propionic acid with the following structural formula:C16H14O3M.W. 254.29It has a pKa of 5.94 in methanol: water (3:1) an...
Active IngredientKetoprofen
Dosage FormCapsule; Capsule, extended release
RouteOral
Strength200mg; 25mg; 150mg; 75mg; 100mg; 50mg
Market StatusPrescription
CompanyActavis Labs Fl; Teva; Dorado Pharma; Mylan

4.2 Drug Indication

For symptomatic treatment of acute and chronic rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, primary dysmenorrhea and mild to moderate pain associated with musculotendinous trauma (sprains and strains), postoperative (including dental surgery) or postpartum pain.


FDA Label


Treatment of musculoskeletal and connective tissue pain


5 Pharmacology and Biochemistry
5.1 Pharmacology

Ketoprofen is a nonsteroidal anti-inflammatory agent (NSAIA) with analgesic and antipyretic properties. Ketoprofen has pharmacologic actions similar to those of other prototypical NSAIDs, which inhibit prostaglandin synthesis. Ketoprofen is used to treat rheumatoid arthritis, osteoarthritis, dysmenorrhea, and alleviate moderate pain.


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
KETOPROFEN
5.3.2 FDA UNII
90Y4QC304K
5.3.3 Pharmacological Classes
Cyclooxygenase Inhibitors [MoA]; Nonsteroidal Anti-inflammatory Drug [EPC]; Anti-Inflammatory Agents, Non-Steroidal [CS]
5.4 ATC Code

M02AA10

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

M01AE - Propionic acid derivatives

M01AE03 - Ketoprofen


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

M02AA10 - Ketoprofen


5.5 Absorption, Distribution and Excretion

Absorption

Ketoprofen is rapidly and well-absorbed orally, with peak plasma levels occurring within 0.5 to 2 hours.


Route of Elimination

In a 24 hour period, approximately 80% of an administered dose of ketoprofen is excreted in the urine, primarily as the glucuronide metabolite.


Clearance

Oral-dose cl=6.9 +/- 0.8 L/h [Ketoprofen Immediate-release capsules (4 50 mg)]

Oral-dose cl=6.8 +/- 1.8 L/h [Ketoprofen Extended-release capsules (1 200 mg)]

0.08 L/kg/h

0.7 L/kg/h [alcoholic cirrhosis patients]


5.6 Metabolism/Metabolites

Rapidly and extensively metabolized in the liver, primarily via conjugation to glucuronic acid. No active metabolites have been identified.


Ketoprofen has known human metabolites that include Ketoprofen glucuronide.

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


5.7 Biological Half-Life

Conventional capsules: 1.1-4 hours

Extended release capsules: 5.4 hours due to delayed absorption (intrinsic clearance is same as conventional capsules)


5.8 Mechanism of Action

The anti-inflammatory effects of ketoprofen are believed to be due to inhibition cylooxygenase-2 (COX-2), an enzyme involved in prostaglandin synthesis via the arachidonic acid pathway. This results in decreased levels of prostaglandins that mediate pain, fever and inflammation. Ketoprofen is a non-specific cyclooxygenase inhibitor and inhibition of COX-1 is thought to confer some of its side effects, such as GI upset and ulceration. Ketoprofen is thought to have anti-bradykinin activity, as well as lysosomal membrane-stabilizing action. Antipyretic effects may be due to action on the hypothalamus, resulting in an increased peripheral blood flow, vasodilation, and subsequent heat dissipation.


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04-Jan-2021
29-Aug-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

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