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Ibuprofen
Also known as: 15687-27-1, 2-(4-isobutylphenyl)propanoic acid, Motrin, Brufen, Advil, Nuprin
Molecular Formula
C13H18O2
Molecular Weight
206.28  g/mol
InChI Key
HEFNNWSXXWATRW-UHFFFAOYSA-N
FDA UNII
WK2XYI10QM

A non-steroidal anti-inflammatory agent with analgesic, antipyretic, and anti-inflammatory properties
Ibuprofen is a Nonsteroidal Anti-inflammatory Drug. The mechanism of action of ibuprofen is as a Cyclooxygenase Inhibitor.
1 2D Structure

Ibuprofen

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[4-(2-methylpropyl)phenyl]propanoic acid
2.1.2 InChI
InChI=1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)
2.1.3 InChI Key
HEFNNWSXXWATRW-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(C)CC1=CC=C(C=C1)C(C)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
WK2XYI10QM
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Advil

2. Alpha-methyl-4-(2-methylpropyl)benzeneacetic Acid

3. Benzeneacetic Acid, Alpha-methyl-4-(2-methylpropyl)- Trimethylsilyl Ester

4. Brufen

5. Ibumetin

6. Ibuprofen Zinc

7. Ibuprofen, (+-)-isomer

8. Ibuprofen, (r)-isomer

9. Ibuprofen, (s)-isomer

10. Ibuprofen, Aluminum Salt

11. Ibuprofen, Calcium Salt

12. Ibuprofen, Copper (2+) Salt

13. Ibuprofen, Magnesium Salt

14. Ibuprofen, Potassium Salt

15. Ibuprofen, Sodium Salt

16. Ibuprofen, Zinc Salt

17. Ibuprofen-zinc

18. Motrin

19. Nuprin

20. Rufen

21. Salprofen

22. Trauma Dolgit Gel

23. Trauma-dolgit Gel

2.3.2 Depositor-Supplied Synonyms

1. 15687-27-1

2. 2-(4-isobutylphenyl)propanoic Acid

3. Motrin

4. Brufen

5. Advil

6. Nuprin

7. Nurofen

8. Medipren

9. Dolgit

10. Liptan

11. 2-[4-(2-methylpropyl)phenyl]propanoic Acid

12. Anflagen

13. Buburone

14. Butylenin

15. Ibumetin

16. Ibuprocin

17. Ebufac

18. Lamidon

19. Rufen

20. Mynosedin

21. Apsifen

22. Epobron

23. Haltran

24. Roidenin

25. Trendar

26. Adran

27. Andran

28. Bluton

29. Nobfen

30. Nobgen

31. Pediaprofen

32. Ibuprohm

33. Nobfelon

34. Brufort

35. Burana

36. Inabrin

37. Pantrop

38. Rebugen

39. Suspren

40. Tabalon

41. (rs)-ibuprofen

42. Anco

43. Urem

44. Ibu-slo

45. Brufanic

46. Napacetin

47. Ibufen

48. Ibuprin

49. Profen

50. Ibren

51. Midol

52. 4-isobutylhydratropic Acid

53. Cap-profen

54. Tab-profen

55. Ibu-tab

56. P-isobutylhydratropic Acid

57. Proartinal

58. Dibufen

59. Optifen

60. Ostofen

61. Panafen

62. Proflex

63. Quadrax

64. Uprofen

65. Carol

66. Dolgin

67. Cobo

68. (+-)-ibuprofen

69. (+/-)-ibuprofen

70. Artril 300

71. 4-isobutyl-alpha-methylphenylacetic Acid

72. Midol 200

73. Duralbuprofen

74. Butacortelone

75. Amibufen

76. Caldolor

77. Dolgirid

78. Ibuprofeno

79. Ibuprofenum

80. Lebrufen

81. Seclodin

82. Amelior

83. Femadon

84. Ibutid

85. Inoven

86. Alpha-(4-isobutylphenyl)propionic Acid

87. Brufen Retard

88. Ibu-attritin

89. Dolo-dolgit

90. Aches-n-pain

91. Ip-82

92. (+-)-p-isobutylhydratropic Acid

93. Pedea

94. Rd 13621

95. Hydratropic Acid, P-isobutyl-

96. Ib-100

97. (4-isobutylphenyl)-alpha-methylacetic Acid

98. 58560-75-1

99. U-18,573

100. P-isobutyl-2-phenylpropionic Acid

101. (+-)-2-(p-isobutylphenyl)propionic Acid

102. Alpha-(p-isobutylphenyl)propionic Acid

103. 2-(4-isobutylphenyl)propionic Acid

104. Alpha-p-isobutylphenylpropionic Acid

105. (+-)-alpha-methyl-4-(2-methylpropyl)benzeneacetic Acid

106. Benzeneacetic Acid, .alpha.-methyl-4-(2-methylpropyl)-

107. Chebi:5855

108. Alpha-methyl-4-(2-methylpropyl)benzeneacetic Acid

109. Benzeneacetic Acid, Alpha-methyl-4-(2-methylpropyl)-

110. M01ae01

111. (+/-)-p-isobutylhydratropic Acid

112. 2-(p-isobutylphenyl)propionic Acid

113. Novoprofen

114. Amersol

115. Dolocyl

116. Lidifen

117. Mfcd00010393

118. Paxofen

119. Rafen

120. Wk2xyi10qm

121. Ibu

122. Chembl521

123. Ifen

124. U-18573

125. 2-(4-isobutyl-phenyl)-propionic Acid

126. Nsc-256857

127. Alpha-methyl-4-(isobutyl)phenylacetic Acid

128. Mls000069733

129. Balkaprofen

130. Betaprofen

131. Daiprophen

132. Jenaprofen

133. Antagil

134. Antalfene

135. Antarene

136. Antiflam

137. Artofen

138. Bruflam

139. Bufigen

140. Bukrefen

141. Buracaps

142. Citalgan

143. Combiflam

144. Dansida

145. Dentigoa

146. Dignoflex

147. Dolmaral

148. Dolofen

149. Dolofin

150. Dolofort

151. Dologel

152. Dolomax

153. Doloren

154. Doltibil

155. Dorival

156. Duobrus

157. Dysdolen

158. Easifon

159. Esprenit

160. Exneural

161. Femafen

162. Femapirin

163. Femidol

164. Fenspan

165. Fibraflex

166. Gelufene

167. Gynofug

168. Ibubest

169. Ibubeta

170. Ibucasen

171. Ibudolor

172. Ibuflamar

173. Ibugesic

174. Ibuhexal

175. Ibulagic

176. Ibuleve

177. Ibulgan

178. Ibumerck

179. Ibupirac

180. Junifen

181. Kratalgin

182. Librofem

183. Malafene

184. Manypren

185. Mensoton

186. Neobrufen

187. Nerofen

188. Noalgil

189. Nobafon

190. Noritis

191. Novadol

192. Novogent

193. Nuprilan

194. Opturem

195. Oralfene

196. Ostarin

197. Paduden

198. Perofen

199. R.d. 13621

200. Ranofen

201. Relcofen

202. Rhinadvil

203. Sadefen

204. Salivia

205. Sednafen

206. Seklodin

207. Seskafen

208. Siyafen

209. Solpaflex

210. Sugafen

211. Suprafen

212. Syntofene

213. Tatanal

214. Unipron

215. Alaxan

216. Anafen

217. Artril

218. Brofen

219. Bufeno

220. Bupron

221. Dolibu

222. Dolven

223. Duafen

224. Emflam

225. Eputex

226. Faspic

227. Fenbid

228. Fendol

229. Grefen

230. Ibudol

231. Ibufug

232. Ibugel

233. Ibugen

234. Ibular

235. Ibulav

236. Ibumed

237. Ibusal

238. Inflam

239. Isodol

240. Lopane

241. Melfen

242. Moment

243. Narfen

244. Ozonol

245. Provon

246. Stelar

247. Tempil

248. Bloom

249. Cesra

250. Cunil

251. Dalsy

252. Ergix

253. Gofen

254. Ipren

255. Irfen

256. Kesan

257. Rofen

258. Rufin

259. Rupan

260. Tofen

261. Tonal

262. Upfen

263. Zafen

264. Zofen

265. Drin

266. Ibol

267. Pediatric Advil

268. Apo-ibuprofen

269. Neo-helvagit

270. Deep Relief

271. Ibu-slow

272. Novo-profen

273. Neo-mindol

274. Dolofen-f

275. Donjust B

276. Nagifen-d

277. Dura-ibu

278. Children's Advil

279. Motrin Ib

280. Togal N

281. Children's Motrin

282. Nsc256857

283. Ibu-tab 200

284. .alpha.-(p-isobutylphenyl)propionic Acid

285. Children's Ibuprofen

286. Ncgc00015529-09

287. Dularbuprofen

288. .alpha.-(4-isobutylphenyl)propionic Acid

289. Acide (isobutyl-4 Phenyl)-2 Propionique

290. Ibuprofene

291. Ibuprophen

292. Smr000058184

293. Tabalon 400

294. Junior Strength Advil

295. (+/-)-2-(p-isobutylphenyl)propionic Acid

296. 4-isobutyl-.alpha.-methylphenylacetic Acid

297. Brufen 400

298. Emflam-200

299. Kontagripp Mono

300. Dolo Puren

301. Dsstox_cid_732

302. Junior Strength Motrin

303. Novo Dioxadol

304. Schmerz-dolgit

305. Act-3

306. Ak+c2278tren

307. Hemagene Tailleur

308. Advil Liqui-gels

309. Adex 200

310. Junior Strength Ibuprofen

311. Dsstox_rid_75759

312. Dsstox_gsid_20732

313. Advil, Children's

314. Am-fam 400

315. Codral Period Pain

316. Children's Elixsure

317. (+-)-ibuprophen

318. .alpha.-methyl-4-(2-methylpropyl)benzeneacetic Acid

319. Midol Ib Cramp Relief

320. Alivium

321. Genpril

322. Advil Migraine

323. Bayer Select Pain Relief

324. Ibuprofene [inn-french]

325. Ibuprofenum [inn-latin]

326. Perrigo Ibuprofen

327. Racemic Ibuprofen

328. Ibuprofeno [inn-spanish]

329. Motrin Migraine Pain

330. Motrin Ib Gelcaps

331. Ucb 79171

332. Alpha-(4-isobutylphenyl)propionate

333. Cas-15687-27-1

334. Motrin (tn)

335. Ccris 3223

336. Advil (tn)

337. Children's Advil-flavored

338. Hsdb 3099

339. Children's Elixsure Ib

340. Sr-01000000214

341. Einecs 239-784-6

342. Unii-wk2xyi10qm

343. Advil Migraine Liqui-gels

344. U 18573

345. Nsc 256857

346. Brn 2049713

347. Ibupril

348. Ibuprox

349. Aktren

350. Ibux

351. Rac Ibuprofen

352. (+/-)-2-(4-isobutylphenyl)propanoic Acid

353. Cdt-ibuprofen

354. Mfcd00069289

355. Nurofen Meltlets

356. (y)-ibuprofen

357. Ibuprofen,(s)

358. Midol Liquid Gels

359. (+) Ibuprofen

360. Ibuprofen (advil)

361. Acide (isobutyl-4-phenyl)-2 Propionique [french]

362. (?)-ibuprofen

363. Ibuprofen [usan]

364. (s)-ibuprofen-d3

365. P-isobutylhydratropate

366. Ibuprofen [usan:usp:inn:ban:jan]

367. Combunox (salt/mix)

368. (a+/-)-ibuprofen

369. Spectrum_000849

370. Acide (isobutyl-4-phenyl)-2 Propionique

371. Ibuprofen [inn]

372. Ibuprofen [jan]

373. Opera_id_554

374. Ibuprofen [mi]

375. Ibuprofen [hsdb]

376. Ibuprofen [inci]

377. Spectrum2_000129

378. Spectrum3_000465

379. Spectrum4_000015

380. Spectrum5_000862

381. Ibuprofen [vandf]

382. Wln: Qvy&r Diy

383. Cbmicro_005634

384. Epitope Id:139973

385. Ibuprofen [mart.]

386. P-isobutyl-hydratropic Acid

387. Ec 239-784-6

388. I 4883

389. Cambridge Id 5152402

390. Ibuprofen [usp-rs]

391. Ibuprofen [who-dd]

392. Ibuprofen [who-ip]

393. Schembl3001

394. Lopac0_000691

395. Bspbio_002170

396. Ibuprofen - Adooq Bioscience

397. Ibuprofen [ema Epar]

398. Ibuprofen-[u-ring-13c6]

399. Kbiogr_000389

400. Kbioss_001329

401. Mls001146965

402. P-isobutyl-2-phenylpropionate

403. Bidd:gt0050

404. Divk1c_000887

405. Spectrum1500347

406. Ibuprofen, >=98% (gc)

407. Spbio_000178

408. Ibuprofen (jp17/usp/inn)

409. Alpha-p-isobutylphenylpropionate

410. Gtpl2713

411. Motrin Ib Gelcaps (salt/mix)

412. Ibuprofen [orange Book]

413. 2-p-isobutylphenylpropionic Acid

414. Dtxsid5020732

415. Ibuprofen [ep Monograph]

416. Ibuprofen [usp Impurity]

417. Hefnnwsxxwatrw-uhfffaoysa-

418. Hms502m09

419. Kbio1_000887

420. Kbio2_001329

421. Kbio2_003897

422. Kbio2_006465

423. Kbio3_001390

424. Advil Cold & Sinus (salt/mix)

425. Ibuprofen [usp Monograph]

426. Ibuprofen 1.0 Mg/ml In Methanol

427. Ninds_000887

428. Sine-aid Ib Caplets (salt/mix)

429. Benzeneacetic Acid, Alpha-methyl-4-(2-methylpropyl), (+-)-

430. Hms1920f15

431. Hms2089p05

432. Hms2091n03

433. Hms2230n04

434. Hms3259g05

435. Hms3262k03

436. Hms3372m09

437. Hms3649m11

438. Hms3651a15

439. Hms3884i04

440. Pharmakon1600-01500347

441. Combunox Component Ibuprofen

442. Ibuprofenum [who-ip Latin]

443. Act03248

444. Albb-025647

445. Bcp10423

446. Bcp20325

447. Bcp25225

448. Reprexain Component Ibuprofen

449. Zag-1701

450. ( Inverted Question Mark)-ibuprofen

451. (.+-.)-p-isobutylhydratropic Acid

452. Children's Elixsure Ib (salt/mix)

453. Tox21_110170

454. Tox21_201384

455. Tox21_302829

456. Tox21_500691

457. 1189866-35-0 (unlabeled)

458. 2-(4'-isobutylphenyl)propionic Acid

459. 2-(4-isobutylphenyl) Propanoic Acid

460. 2-(4-isobutylphenyl) Propionic Acid

461. 2-(4-isobutylphenyl)-propionic Acid

462. Bbl010660

463. Bdbm50009859

464. Ccg-38947

465. Nsc757073

466. S1638

467. Stk177358

468. Vicoprofen Component Ibuprofen

469. (.+/-.)-p-isobutylhydratropic Acid

470. 2-(4-isobutylphenyl)-propionoic Acid

471. Ibuprofen 100 Microg/ml In Methanol

472. 2-(4'-isobutylphenyl)-propionic Acid

473. Akos003237488

474. Akos016340658

475. Ibuprofen Component Of Combunox

476. Propanoic Acid, 2-(4-isobutylphenyl)

477. Tox21_110170_1

478. ( Inverted Exclamation Marka)-ibuprofe

479. Cs-1931

480. Db01050

481. Ibuprofen Component Of Reprexain

482. Ks-5029

483. Lp00691

484. Nc00458

485. Nsc-757073

486. Sb19113

487. Sdccgsbi-0050669.p005

488. Sine-aid Ib Component Ibuprofen

489. St-1482

490. ( Inverted Exclamation Marka)-ibuprofen

491. Alpha-(4-isobutylphenyl)-propionic Acid

492. Alpha-(p-isobutylphenyl)-propionic Acid

493. Ibuprofen Component Of Vicoprofen

494. Idi1_000887

495. 2-(4-isobutylphenyl)propionic Acid-d3;

496. Ncgc00015529-04

497. Ncgc00015529-05

498. Ncgc00015529-06

499. Ncgc00015529-07

500. Ncgc00015529-08

501. Ncgc00015529-10

502. Ncgc00015529-12

503. Ncgc00015529-13

504. Ncgc00015529-14

505. Ncgc00015529-15

506. Ncgc00015529-18

507. Ncgc00015529-32

508. Ncgc00089819-02

509. Ncgc00089819-03

510. Ncgc00089819-04

511. Ncgc00089819-05

512. Ncgc00089819-06

513. Ncgc00089819-07

514. Ncgc00256416-01

515. Ncgc00258935-01

516. Ncgc00261376-01

517. Ac-11312

518. Bi166241

519. Hy-78131

520. Ibuprofen Component Of Sine-aid Ib

521. Nci60_002065

522. Sy046826

523. Ibuprofen, Vetec(tm) Reagent Grade, 97%

524. Sbi-0050669.p004

525. .alpha.-2-(p-isobutylphenyl)propionic Acid

526. Db-043333

527. Db-071312

528. Ibuprofen, Meets Usp Testing Specifications

529. (.+-.)-2-(p-isobutylphenyl)propionic Acid

530. 4-isobutylphenyl)-.alpha.-methylacetic Acid

531. Am20060782

532. Bb 0258487

533. Eu-0100691

534. Ft-0601629

535. Ft-0642971

536. Ft-0655194

537. Ft-0670257

538. Ft-0670258

539. I0415

540. Sw203738-2

541. (.+/-.)-2-(p-isobutylphenyl)propionic Acid

542. Advil Allergy Sinus Component Ibuprofen

543. Ibuprofen, Vetranal(tm), Analytical Standard

544. (r/s)-alpha-methyl-4-isobutylphenylacetic Acid

545. C01588

546. D00126

547. Ab00052020-16

548. Ab00052020-17

549. Ab00052020_18

550. Ab00052020_19

551. Children's Advil Cold Component Ibuprofen

552. 687i271

553. A831926

554. Advil Congestion Relief Component Ibuprofen

555. Children's Motrin Cold Component Ibuprofen

556. Ibuprofen Component Of Advil Allergy Sinus

557. Q186969

558. Ibuprofen Component Of Children's Advil Cold

559. Ibuprofen Component Of Children's Motrin Cold

560. J-009349

561. Sr-01000000214-2

562. Sr-01000000214-4

563. Brd-a17655518-001-02-0

564. Brd-a17655518-001-12-9

565. Ibuprofen Component Of Advil Congestion Relief

566. Sr-01000000214-13

567. F2173-0233

568. Ibuprofen, British Pharmacopoeia (bp) Reference Standard

569. Z1695709473

570. (+/-)-alpha-methyl-4-(2-methylpropyl)benzeneacetic Acid

571. Ibuprofen, European Pharmacopoeia (ep) Reference Standard

572. Ibuprofen, United States Pharmacopeia (usp) Reference Standard

573. Benzeneacetic Acid, .alpha.-methyl-4-(2-methylpropyl), (.+/-.)-

574. Benzeneacetic Acid, .alpha.-methyl-4-(2-methylpropyl), (+/-)-

575. Dexibuprofen;(s)-ibuprofen; L 669455; L-669,455, Mk 233; Mk-233

576. Ibuprofen, Pharmaceutical Secondary Standard; Certified Reference Material

577. Ibuprofen For Peak Identification, European Pharmacopoeia (ep) Reference Standard

578. 2-(4-isobutylphenyl)-propionic Acid ; Alpha-methyl-4-(2-methylpropyl)benzeneacetic Acid ; P-isobutylhydratropic Acid

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 206.28 g/mol
Molecular Formula C13H18O2
XLogP33.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count4
Exact Mass206.130679813 g/mol
Monoisotopic Mass206.130679813 g/mol
Topological Polar Surface Area37.3 Ų
Heavy Atom Count15
Formal Charge0
Complexity203
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 44  
Drug NameIbuprofen
Active IngredientIbuprofen
Dosage FormTablet; Capsule; Suspension; Suspension/drops; Tablet, chewable
RouteOral
Strength200mg; eq 200mg free acid and potassium salt; 100mg/5ml; 600mg; 800mg; 400mg; 300mg; 100mg; 40mg/ml; 50mg
Market StatusOver the Counter; Prescription
CompanyVintage Pharms; Amneal Pharms; Marksans Pharma; Merro Pharm; Dr Reddys La; Pld Acquisitions; Lnk; Banner Pharmacaps; Mcneil; Ohm; Par Pharm; Granules India; Perrigo R And D; Svads Holdings Sa; Amneal Pharms Ny; Shasun Usa; Actavis Mid Atlantic; Perrigo; C

2 of 44  
Drug NameIbuprohm
Active IngredientIbuprofen
Dosage FormTablet
RouteOral
Strength200mg
Market StatusOver the Counter
CompanyOhm Labs

3 of 44  
Drug NameIbu-tab
Drug LabelIBU tablets contain the active ingredient ibuprofen, which is (-2 - (p - isobutylphenyl) propionic acid. Ibuprofen is a white powde rwith a melting point of 74-77C and is very slightly soluble in water(
Active IngredientIbuprofen
Dosage FormTablet
RouteOral
Strength600mg; 400mg
Market StatusPrescription
CompanyAlra

4 of 44  
Drug NameIbu-tab 200
Active IngredientIbuprofen
Dosage FormTablet
RouteOral
Strength200mg
Market StatusOver the Counter
CompanyAlra

5 of 44  
Drug NameJunior strength advil
Active IngredientIbuprofen
Dosage FormTablet; Tablet, chewable
RouteOral
Strength100mg
Market StatusOver the Counter
CompanyPfizer

6 of 44  
Drug NameJunior strength ibuprofen
Active IngredientIbuprofen
Dosage FormTablet
RouteOral
Strength100mg
Market StatusOver the Counter
CompanyPerrigo

7 of 44  
Drug NameJunior strength motrin
Active IngredientIbuprofen
Dosage FormTablet; Tablet, chewable
RouteOral
Strength100mg
Market StatusOver the Counter
CompanyMcneil Cons

8 of 44  
Drug NameMotrin ib
Active IngredientIbuprofen
Dosage FormTablet
RouteOral
Strength200mg
Market StatusOver the Counter
CompanyMcneil

9 of 44  
Drug NameMotrin migraine pain
Active IngredientIbuprofen
Dosage FormTablet
RouteOral
Strength200mg
Market StatusOver the Counter
CompanyMcneil

10 of 44  
Drug NameNeoprofen
Active IngredientIbuprofen lysine
Dosage FormInjectable
RouteIntravenous
Strengtheq 20mg base/2ml (eq 10mg base/ml)
Market StatusPrescription
CompanyRecordati Rare

11 of 44  
Drug NamePediatric advil
Active IngredientIbuprofen
Dosage FormSuspension/drops
RouteOral
Strength100mg/2.5ml
Market StatusOver the Counter
CompanyPfizer

12 of 44  
Drug NameProfen
Active IngredientIbuprofen
Dosage FormTablet
RouteOral
Strength200mg
Market StatusOver the Counter
CompanyContract Pharmacal

13 of 44  
Drug NameTab-profen
Active IngredientIbuprofen
Dosage FormTablet
RouteOral
Strength200mg
Market StatusOver the Counter
CompanyPerrigo

14 of 44  
Drug NameAdvil
PubMed HealthIbuprofen
Drug ClassesAnalgesic, Antimigraine, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
Active IngredientIbuprofen sodium; Ibuprofen
Dosage FormTablet
RouteOral
Strength200mg; eq 200mg base
Market StatusOver the Counter
CompanyPfizer Cons Hlthcare; Pfizer

15 of 44  
Drug NameAdvil liqui-gels
PubMed HealthIbuprofen
Drug ClassesAnalgesic, Antimigraine, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
Drug LabelCaldolor contains the active ingredient ibuprofen, which is ()-2-(p-isobutylphenyl) propionic acid. Ibuprofen is a white powder with a melting point of 74-77C. It has a molecular weight of 206.28. It is very slightly soluble in water (
Active IngredientIbuprofen
Dosage FormCapsule
RouteOral
Strengtheq 200mg free acid and potassium salt
Market StatusOver the Counter
CompanyPfizer

16 of 44  
Drug NameAdvil migraine liqui-gels
PubMed HealthIbuprofen
Drug ClassesAnalgesic, Antimigraine, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
Active IngredientIbuprofen
Dosage FormCapsule
RouteOral
Strengtheq 200mg free acid and potassium salt
Market StatusOver the Counter
CompanyPfizer

17 of 44  
Drug NameCaldolor
PubMed HealthIbuprofen (By mouth)
Drug ClassesAnalgesic, Antimigraine, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
Active IngredientIbuprofen
Dosage FormSolution
RouteIntravenous
Strength800mg/8ml (100mg/ml)
Market StatusPrescription
CompanyCumberland Pharms

18 of 44  
Drug NameChildren's advil
Drug LabelIBU tablets contain the active ingredient ibuprofen, which is (-2 - (p - isobutylphenyl) propionic acid. Ibuprofen is a white powde rwith a melting point of 74-77C and is very slightly soluble in water(
Active IngredientIbuprofen
Dosage FormTablet, chewable; Suspension
RouteOral
Strength50mg; 100mg/5ml
Market StatusOver the Counter
CompanyPfizer

19 of 44  
Drug NameChildren's advil-flavored
Active IngredientIbuprofen
Dosage FormSuspension
RouteOral
Strength100mg/5ml
Market StatusOver the Counter
CompanyPfizer

20 of 44  
Drug NameChildren's elixsure
Active IngredientIbuprofen
Dosage FormSuspension
RouteOral
Strength100mg/5ml
Market StatusOver the Counter
CompanyMoberg Pharma North

21 of 44  
Drug NameChildren's ibuprofen
Active IngredientIbuprofen
Dosage FormSuspension
RouteOral
Strength100mg/5ml
Market StatusOver the Counter
CompanyPerrigo

22 of 44  
Drug NameChildren's motrin
Active IngredientIbuprofen
Dosage FormSuspension/drops; Tablet, chewable; Suspension
RouteOral
Strength40mg/ml; 50mg; 100mg/5ml
Market StatusOver the Counter
CompanyMcneil Cons; Mcneil

23 of 44  
Drug NameIbuprofen
Active IngredientIbuprofen
Dosage FormTablet; Capsule; Suspension; Suspension/drops; Tablet, chewable
RouteOral
Strength200mg; eq 200mg free acid and potassium salt; 100mg/5ml; 600mg; 800mg; 400mg; 300mg; 100mg; 40mg/ml; 50mg
Market StatusOver the Counter; Prescription
CompanyVintage Pharms; Amneal Pharms; Marksans Pharma; Merro Pharm; Dr Reddys La; Pld Acquisitions; Lnk; Banner Pharmacaps; Mcneil; Ohm; Par Pharm; Granules India; Perrigo R And D; Svads Holdings Sa; Amneal Pharms Ny; Shasun Usa; Actavis Mid Atlantic; Perrigo; C

24 of 44  
Drug NameIbuprohm
Active IngredientIbuprofen
Dosage FormTablet
RouteOral
Strength200mg
Market StatusOver the Counter
CompanyOhm Labs

25 of 44  
Drug NameIbu-tab
Drug LabelIBU tablets contain the active ingredient ibuprofen, which is (-2 - (p - isobutylphenyl) propionic acid. Ibuprofen is a white powde rwith a melting point of 74-77C and is very slightly soluble in water(
Active IngredientIbuprofen
Dosage FormTablet
RouteOral
Strength600mg; 400mg
Market StatusPrescription
CompanyAlra

26 of 44  
Drug NameIbu-tab 200
Active IngredientIbuprofen
Dosage FormTablet
RouteOral
Strength200mg
Market StatusOver the Counter
CompanyAlra

27 of 44  
Drug NameJunior strength advil
Active IngredientIbuprofen
Dosage FormTablet; Tablet, chewable
RouteOral
Strength100mg
Market StatusOver the Counter
CompanyPfizer

28 of 44  
Drug NameJunior strength ibuprofen
Active IngredientIbuprofen
Dosage FormTablet
RouteOral
Strength100mg
Market StatusOver the Counter
CompanyPerrigo

29 of 44  
Drug NameJunior strength motrin
Active IngredientIbuprofen
Dosage FormTablet; Tablet, chewable
RouteOral
Strength100mg
Market StatusOver the Counter
CompanyMcneil Cons

30 of 44  
Drug NameMotrin ib
Active IngredientIbuprofen
Dosage FormTablet
RouteOral
Strength200mg
Market StatusOver the Counter
CompanyMcneil

31 of 44  
Drug NameMotrin migraine pain
Active IngredientIbuprofen
Dosage FormTablet
RouteOral
Strength200mg
Market StatusOver the Counter
CompanyMcneil

32 of 44  
Drug NameNeoprofen
Active IngredientIbuprofen lysine
Dosage FormInjectable
RouteIntravenous
Strengtheq 20mg base/2ml (eq 10mg base/ml)
Market StatusPrescription
CompanyRecordati Rare

33 of 44  
Drug NamePediatric advil
Active IngredientIbuprofen
Dosage FormSuspension/drops
RouteOral
Strength100mg/2.5ml
Market StatusOver the Counter
CompanyPfizer

34 of 44  
Drug NameProfen
Active IngredientIbuprofen
Dosage FormTablet
RouteOral
Strength200mg
Market StatusOver the Counter
CompanyContract Pharmacal

35 of 44  
Drug NameTab-profen
Active IngredientIbuprofen
Dosage FormTablet
RouteOral
Strength200mg
Market StatusOver the Counter
CompanyPerrigo

36 of 44  
Drug NameAdvil
PubMed HealthIbuprofen
Drug ClassesAnalgesic, Antimigraine, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
Active IngredientIbuprofen sodium; Ibuprofen
Dosage FormTablet
RouteOral
Strength200mg; eq 200mg base
Market StatusOver the Counter
CompanyPfizer Cons Hlthcare; Pfizer

37 of 44  
Drug NameAdvil liqui-gels
PubMed HealthIbuprofen
Drug ClassesAnalgesic, Antimigraine, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
Drug LabelCaldolor contains the active ingredient ibuprofen, which is ()-2-(p-isobutylphenyl) propionic acid. Ibuprofen is a white powder with a melting point of 74-77C. It has a molecular weight of 206.28. It is very slightly soluble in water (
Active IngredientIbuprofen
Dosage FormCapsule
RouteOral
Strengtheq 200mg free acid and potassium salt
Market StatusOver the Counter
CompanyPfizer

38 of 44  
Drug NameAdvil migraine liqui-gels
PubMed HealthIbuprofen
Drug ClassesAnalgesic, Antimigraine, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
Active IngredientIbuprofen
Dosage FormCapsule
RouteOral
Strengtheq 200mg free acid and potassium salt
Market StatusOver the Counter
CompanyPfizer

39 of 44  
Drug NameCaldolor
PubMed HealthIbuprofen (By mouth)
Drug ClassesAnalgesic, Antimigraine, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
Active IngredientIbuprofen
Dosage FormSolution
RouteIntravenous
Strength800mg/8ml (100mg/ml)
Market StatusPrescription
CompanyCumberland Pharms

40 of 44  
Drug NameChildren's advil
Drug LabelIBU tablets contain the active ingredient ibuprofen, which is (-2 - (p - isobutylphenyl) propionic acid. Ibuprofen is a white powde rwith a melting point of 74-77C and is very slightly soluble in water(
Active IngredientIbuprofen
Dosage FormTablet, chewable; Suspension
RouteOral
Strength50mg; 100mg/5ml
Market StatusOver the Counter
CompanyPfizer

41 of 44  
Drug NameChildren's advil-flavored
Active IngredientIbuprofen
Dosage FormSuspension
RouteOral
Strength100mg/5ml
Market StatusOver the Counter
CompanyPfizer

42 of 44  
Drug NameChildren's elixsure
Active IngredientIbuprofen
Dosage FormSuspension
RouteOral
Strength100mg/5ml
Market StatusOver the Counter
CompanyMoberg Pharma North

43 of 44  
Drug NameChildren's ibuprofen
Active IngredientIbuprofen
Dosage FormSuspension
RouteOral
Strength100mg/5ml
Market StatusOver the Counter
CompanyPerrigo

44 of 44  
Drug NameChildren's motrin
Active IngredientIbuprofen
Dosage FormSuspension/drops; Tablet, chewable; Suspension
RouteOral
Strength40mg/ml; 50mg; 100mg/5ml
Market StatusOver the Counter
CompanyMcneil Cons; Mcneil

4.2 Therapeutic Uses

Analgesics, Non-Narcotic; Anti-Inflammatory Agents, Non-Steroidal; Cyclooxygenase Inhibitors

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


Ibuprofen ... /is/ indicated for reduction of fever. /Included in US product labeling/

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 22nd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2002. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 415


Ibuprofen ... /is/ used for relief of the pain and inflammation of acute gouty arthritis and acute calcium pyrophosphate deposition disease (pseudogout; chondrocalcinosis articularis; synovitis, crystal-induced). Only immediate-release dosage forms are recommended for relief of acute attacks because of their more rapid onset of action relative to delayed-release or extended-release dosage forms. /NOT included in US product labeling/

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 22nd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2002. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 414


Ibuprofen ... /is/ indicated for relief of mild to moderate pain, especially when anti-inflammatory actions may also be desired, e.g., following dental, obstetric, or orthopedic surgery, and for relief of musculoskeletal pain due to soft tissue athletic injuries (strains or sprains). Only immediate-release dosage forms are recommended for relief of acute pain because of their more rapid onset of actin relative to delayed-release or extended-release dosage forms. /Included in US product labeling/

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 22nd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2002. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 414


For more Therapeutic Uses (Complete) data for IBUPROFEN (28 total), please visit the HSDB record page.


4.3 Drug Warning

Ibuprofen should be used with caution in patients with peptic ulcer disease, GI perforation or bleeding, bleeding abnormalities (especially in patients who may be adversely affected by prolongation of bleeding time), impaired renal function, hypertension, or compromised cardiac function.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 1971


CAUTION IN THE USE OF IBUPROFEN IN SYSTEMIC LUPUS ERYTHEMATOSUS IS ADVISED, PARTICULARLY IF THERE IS HISTORY OF SALICYLATE INTOLERANCE.

PMID:439358 FINCH WR, STROTTMAN MP; JAMA 241 (JUN 15): 2616 (1979)


Ibuprofen is not recommended for use by pregnant women, or by those who are breast-feeding their infants.

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 712


IBUPROFEN ELEVATES BILIRUBIN, ALKALINE PHOSPHATASE, ASPARTATE AMINOTRANSFERASE (SGOT), AND ALANINE AMINOTRANSFERASE (SGPT) ABOVE THE NORMAL RANGE, AND CAUSES ISOLATED CASES OF JAUNDICE. /FROM TABLE/

Hansten, P.D. Drug Interactions. 4th ed. Philadelphia: Lea and Febiger, 1979., p. 504


For more Drug Warnings (Complete) data for IBUPROFEN (14 total), please visit the HSDB record page.


4.4 Drug Indication

Ibuprofen is the most commonly used and prescribed NSAID. It is very common over the counter medication widely used as an analgesic, anti-inflammatory and antipyretic. The use of ibuprofen and its enantiomer [DB09213] in a racemic mix is common for the management of mild to moderate pain related to dysmenorrhea, headache, migraine, postoperative dental pain, spondylitis, osteoarthritis, rheumatoid arthritis, and soft tissue disorder. Due to its activity against prostaglandin and thromboxane synthesis, ibuprofen has been attributed to alteration of platelet function and prolongation of gestation and labor. As ibuprofen is a widely used medication, the main therapeutic indications are: * Patent Ductus Arteriosus - it is a neonatal condition wherein the ductus arteriosus (blood vessel that connects the main pulmonary artery to the proximal descending aorta) fails to close after birth causing severe risk of heart failure. The prostaglandin inhibition of ibuprofen has been studied for the treatment of this condition as it is known that prostaglandin E2 is responsible for keeping the ductus arteriosus open. * Rheumatoid- and osteo-arthritis - ibuprofen is very commonly used in the symptomatic treatment of inflammatory, musculoskeletal and rheumatic disorders. * Cystic fibrosis - the use of high dosages of ibuprofen has been proven to decrease inflammation and decreasing polymorphonuclear cell influx in the lungs. * Orthostatic hypotension - ibuprofen can induce sodium retention and antagonize the effect of diuretics which has been reported to be beneficial for patients with severe orthostatic hypotension. * Dental pain - ibuprofen is used to manage acute and chronic orofacial pain. * Minor pain - ibuprofen is widely used to reduce minor aches and pains as well as to reduce fever and manage dysmenorrhea. It is very commonly used for the relief of acute indications such as fever and tension headaches. * Investigational uses - efforts have been put into developing ibuprofen for the prophylaxis of Alzheimer's disease, Parkinson disease, and breast cancer.


FDA Label


Treatment of a haemodynamically significant patent ductus arteriosus in preterm newborn infants less than 34 weeks of gestational age.


Treatment of pain


Treatment of febrile disorders, Treatment of pain


Treatment of febrile disorders, Treatment of pain


5 Pharmacology and Biochemistry
5.1 Pharmacology

Ibuprofen has multiple actions in different inflammatory pathways involved in acute and chronic inflammation. The main effects reported in ibuprofen are related to the control of pain, fever and acute inflammation by the inhibition of the synthesis of prostanoids by COX-1 and COX-2. Pain relief is attributed to peripheral affected regions and central nervous system effects in the pain transmission mediated by the dorsal horn and higher spinothalamic tract. Some reports have tried to link the pain regulation with a possible enhancement on the synthesis of endogenous cannabinoids and action on the NMDA receptors. The effect on pain has been shown to be related to the cortically evoked potentials. The antipyretic effect is reported to be linked to the effect on the prostanoid synthesis due to the fact that the prostanoids are the main signaling mediator of pyresis in the hypothalamic-preoptic region. The use of ibuprofen in dental procedures is attributed to the local inhibition of prostanoid production as well as to anti-oedemic activity and an increase of plasma beta-endorphins. Some reports have suggested a rapid local reduction of the expression of COX-2 in dental pulp derived by the administration of ibuprofen. The administration of ibuprofen in patients with rheumatic diseases has shown to control joint symptoms. Ibuprofen is largely used in OTC products such as an agent for the management of dysmenorrhea which has been proven to reduce the amount of menstrual prostanoids and to produce a reduction in the uterine hypercontractility. As well, it has been reported to reduce significantly the fever and the pain caused by migraines. This effect is thought to be related to the effect on platelet activation and thromboxane A2 production which produces local vascular effects in the affected regions. This effect is viable as ibuprofen can enter in the central nervous system. In the investigational uses of ibuprofen, it has been reported to reduce neurodegeneration when given in low doses over a long time. On the other hand, its use in Parkinson disease is related to the importance of inflammation and oxidative stress in the pathology of this condition. The use of ibuprofen for breast cancer is related to a study that shows a decrease of 50% in the rate of breast cancer.


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.)


Analgesics, Non-Narcotic

A subclass of analgesic agents that typically do not bind to OPIOID RECEPTORS and are not addictive. Many non-narcotic analgesics are offered as NONPRESCRIPTION DRUGS. (See all compounds classified as Analgesics, Non-Narcotic.)


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
IBUPROFEN
5.3.2 FDA UNII
WK2XYI10QM
5.3.3 Pharmacological Classes
Cyclooxygenase Inhibitors [MoA]; Nonsteroidal Anti-inflammatory Drug [EPC]; Anti-Inflammatory Agents, Non-Steroidal [CS]
5.4 ATC Code

C01EB16


M01AE01

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


C - Cardiovascular system

C01 - Cardiac therapy

C01E - Other cardiac preparations

C01EB - Other cardiac preparations

C01EB16 - Ibuprofen


G - Genito urinary system and sex hormones

G02 - Other gynecologicals

G02C - Other gynecologicals

G02CC - Antiinflammatory products for vaginal administration

G02CC01 - Ibuprofen


M - Musculo-skeletal system

M01 - Antiinflammatory and antirheumatic products

M01A - Antiinflammatory and antirheumatic products, non-steroids

M01AE - Propionic acid derivatives

M01AE01 - Ibuprofen


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

M02AA13 - Ibuprofen


R - Respiratory system

R02 - Throat preparations

R02A - Throat preparations

R02AX - Other throat preparations

R02AX02 - Ibuprofen


5.5 Absorption, Distribution and Excretion

Absorption

It is very well absorbed orally and the peak serum concentration can be attained in 1 to 2 hours after extravascular administration. When ibuprofen is administered immediately after a meal there is a slight reduction in the absorption rate but there is no change in the extent of the absorption. When orally administered, the absorption of ibuprofen in adults is very rapidly done in the upper GI tract. The average Cmax, Tmax and AUC ranges around 20 mcg/ml, 2 h and 70 mcg.h/ml. These parameters can vary depending on the enantiomer form, route, and dose of administration.


Route of Elimination

Ibuprofen is rapidly metabolized and eliminated in the urine thus, this via accounts for more than 90% of the administered dose. It is completely eliminated in 24 hours after the last dose and almost all the administered dose goes through metabolism, representing about 99% of the eliminated dose. The biliary excretion of unchanged drug and active phase II metabolites represents 1% of the administered dose. In summary, ibuprofen is excreted as metabolites or their conjugates. The elimination of ibuprofen is not impaired by old age or the presence of renal impairment.


Volume of Distribution

The apparent volume of distribution of ibuprofen is of 0.1 L/kg.


Clearance

The clearance rate ranges between 3-13 L/h depending on the route of administration, enantiomer type and dosage.


Ibuprofen is rapidly absorbed after oral admin, & peak concns in plasma are observed after 15-30 min. The half-life in plasma is about 2 hr. Ibuprofen is extensively (99%) bound to plasma proteins, but the drug occupies only a fraction of the total drug-binding sites at usual concns. Ibuprofen passes slowly into the synovial spaces & may remain there in higher concn as the concns in plasma decline. In experimental animals, ibuprofen & its metabolites pass easily across the placenta. The excretion of ibuprofen is rapid & complete. More than 90% of an ingested dose is excreted in the urine as metabolites or their conjugates.

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 712


ENTERO-HEPATIC CIRCULATION OF (14)C-IBUPROFEN & ITS METABOLITES MAY HAVE OCCURRED IN DOGS RECEIVING REPEATED ORAL DOSES ... SINCE LEVELS IN BILE ... WERE 40-FOLD THOSE IN PLASMA.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 47


AFTER ORAL DOSES OF 400 MG IBUPROFEN, SERIAL BLOOD SAMPLES WERE TAKEN (5 MALE VOLUNTEERS, 4 ARTHRITIC PATIENT). EVIDENCE SHOWED 2 COMPARTMENT MODEL: NO EVIDENCE SHOWN OF DRUG ACCUM IN PERIPHERAL COMPARTMENT.

COLLIER PS ET AL; BR J CLIN PHARMACOL 5(JUNE) 528 (1978)


The enantiomeric composition of ibuprofen in plasma was investigated following oral administration of 200 mg of the racemic drug in a conventional tablet or 300 mg in a novel controlled release pellet formulation to 4 healthy volunteers, aged 24 to 37 yr, in a randomized, crossover study. The plasma concentration time profiles suggest that drug release from the controlled release preparation was suitably modified and that the fluctuation between the peaks and troughs observed following a conventional tablet formulation were reduced. The plasma concentrations of (+)-ibuprofen (S-ibuprofen) were greater than those of (-)-ibuprofen (R-ibuprofen) following either formulation, and the enantiomeric plasma ratio (S/R) was reduced, both in magnitude and variability, following the controlled release preparation. The proportion of the total area under the plasma concentration time curves, due to (S)-ibuprofen, were slightly reduced following the controlled release formulation compared to the tablet formulation. The importance of a consideration of stereochemistry in bioequivalence studies of chiral drugs is discussed.

Avgerinos A et al; Int J Pharm 68 (Feb 1): 97-103 (1991)


For more Absorption, Distribution and Excretion (Complete) data for IBUPROFEN (11 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Ibuprofen is rapidly metabolized and biotransformed in the liver to the formation of major metabolites which are the hydroxylated and carboxylated derivatives. As soon as it is absorbed, the R-enantiomer undergoes extensive enantiomeric conversion (53-65%) to the more active S-enantiomer _in vivo_ by the activity of alpha-methylacyl-CoA racemase. Ibuprofen metabolism can be divided in phase I which is represented by the hydroxylation of the isobutyl chains for the formation of 2 or 3-hydroxy derivatives followed by oxidation to 2-carboxy-ibuprofen and p-carboxy-2-propionate. These oxidative reactions are performed by the activity of the cytochrome P450 isoforms CYP 2C9, CYP 2C19 and CYP 2C8. Therefore, these enzymes participate in the oxidation of the alkyl side chain to hydroxyl and carboxyl derivatives. From this enzymes, the major catalyst in the formation of oxidative metabolites is the isoform CYP 2C9. The metabolic phase I is followed by a phase II in which the oxidative metabolites may be conjugated to glucuronide prior to excretion. This activity forms phenolic and acyl glucuronides.


TWO MAJOR METABOLIC PATHWAYS IN MAN & IN ANIMALS PROCEED BY OXIDATIVE ATTACK OF ISOBUTYL SIDE CHAIN; THEY ARE HYDROXYLATION OF THE TERTIARY CARBON TO YIELD A STABLE TERTIARY ALCOHOL, & OXIDATION OF 1 OF THE 2 GEMINAL METHYL GROUPS TO YIELD THE ACID.

Testa, B. and P. Jenner. Drug Metabolism: Chemical & Biochemical Aspects. New York: Marcel Dekker, Inc., 1976., p. 22


IBUPROFEN GIVES 2-(4-(2-CARBOXYPROPYL)PHENYL)PROPIONIC ACID & 2-(4-(2-HYDROXY-2-METHYLPROPYL)PHENYL)PROPIONIC ACID IN MAN. /FROM TABLE/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. I-14


The pharmacokinetics of oral ibuprofen following a dose of 0.8 g given 3 times a day for 14 days were studied in 7 functionally anephric patients (aged 34-66 yr) undergoing hemodialysis. No accumulation of ibuprofen plasma concns & an absence of intact ibuprofen in dialysate indicated clearance through metabolic pathways. The metabolites did accumulate significantly with mean plasma levels of 249 mcg/ml for the carboxy derivatives & 57 mcg/ml for the hydroxy derivatives of ibuprofen. However, both were detected in the dialysate. Dialysis clearance calculated by arterial & venous difference was found to agree with actual recovery in dialysate for both metabolites. Side effects were not observed in any subject.

PMID:3958223 Antal EJ et al; J Clin Pharmacol 26 (Mar): 184-90 (1986)


5.7 Biological Half-Life

The serum half-life of ibuprofen is 1.2-2 hours. In patients with a compromised liver function, the half-life can be prolonged to 3.1-3.4 hours.


... After oral admin ... the half-life in plasma is about 2 hr.

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 712


5.8 Mechanism of Action

The exact mechanism of action of ibuprofen is unknown. However, ibuprofen is considered an NSAID and thus it is a non-selective inhibitor of cyclooxygenase, which is an enzyme involved in prostaglandin (mediators of pain and fever) and thromboxane (stimulators of blood clotting) synthesis via the arachidonic acid pathway. Ibuprofen is a non-selective COX inhibitor and hence, it inhibits the activity of both COX-1 and COX-2. The inhibition of COX-2 activity decreases the synthesis of prostaglandins involved in mediating inflammation, pain, fever, and swelling while the inhibition of COX-1 is thought to cause some of the side effects of ibuprofen including GI ulceration.


IBUPROFEN AT 25 MG/KG IV INCREASED THE PRIMARY AND TOTAL HEMOSTATIC PLUG FORMATION TIME IN RABBIT EAR CHAMBERS WITH LASER-INDUCED INJURY. THE SAME DOSE INCREASED THE NUMBER OF CUMULATIVE EMBOLI OVER A 10 MINUTE PERIOD AFTER A LASER INJURY TO ARTERIOLES. IN DOGS, DOSES OF 10, 25, AND 50 MG/KG DID NOT ENHANCE THE RELEASE OF (125)I-LABELED FIBRIN DEGRADATION PRODUCTS FROM THE THROMBI AFTER INCUBATION IN PLASMIN, BUT THE LARGEST DOSE SIGNIFICANTLY DECREASED THE THROMBUS WEIGHT 90 AND 180 MINUTES AFTER DRUG ADMINISTRATION. THUS, IBUPROFEN HAD AN INHIBITORY EFFECT ON PLATELET FUNCTION IN VIVO AND IN LARGE DOSES DIMINISHED THE THROMBUS WEIGHT.

ESQUIVEL CO ET AL; THROMB HAEMOSTASIS 48 (1): 87 (1982)


L-Arginine (L-arg) exhibits multiple biological properties and plays an important role in the regulation of different functions in pathological conditions. Many of these effects could be achieved on this amino acid serving as a substrate for the enzyme nitric oxide synthase (NOS). At the gastrointestinal level, recent reports revealed its protective activities involving a hyperemic response increasing the gastric blood flow. The aim of this study was to characterize the relationship between NOS activity/expression and prostaglandin changes (PGs) in rats gastric mucosa, with L-arg associated resistance to the nonsteroidal anti-inflammatory drug (NSAID) ibuprofen (IBP). The protective effect of oral L-arg (100 mg/kg body wt), administerred together with IBP (100 mg/kg body wt, per os), was evident enough 90 min after drug administration, although a significant protection persisted for more than 6 hr. Pretreatment with N(G)-nitro-L-arginine (L-NNA) (40 mg/kg body wt, intraperitoneally), a competitive inhibitor of constitutive NOS, partly altered the protection afforded by the amino acid. In contrast, no changes could be observed after inducible NOS inhibition [aminoguanidine (AG) 50 mg/Kg body wt, intraperitoneally). L-arg, plus IBP, produced a significant increase of the cyclic GMP (cGMP) response in tissue samples from rat stomach, 90 min and 6 h after drug administration. iNOS activity and mRNA expression were higher in IBP-treated rats, and no differences were observed in inducible responses in the L-arg plus IBP group. No variations in the cNOS activity and expression were found among the different groups of animals assayed. The measurement of mucosal PGE2 content confirmed that biosynthesis of the eicosanoid is maintained by L-arg for over 90 min after IBP, while a total inhibition was observed 6 hr later. The mechanisms of the L-arg protective effect on the damaged induced by IBP could be explained by the different period after drug administration. The early phase is mediated by cyclooxygenase/prostaglandins pathway (COX/PGs) although NO liberated by cNOS and the guanylate cyclase/cGMP pathway could be also relevant. The later phase implicates inhibition of the iNOS/NO response.

PMID:11837731 Jimenez D et al; Dig Dis Sci 47 (1): 44-53 (2002)


We previously showed the non-steroidal anti-inflammatory drug (NSAID) ibuprofen suppresses inflammation and amyloid in the APPsw (Tg2576) Tg2576 transgenic mouse. The mechanism for these effects and the impact on behavior are unknown. We now show ibuprofen's effects were not mediated by alterations in amyloid precursor protein (APP) expression or oxidative damage (carbonyls). Six months ibuprofen treatment in Tg+ females caused a decrease in open field behavior (p < 0.05), restoring values similar to Tg- mice. Reduced caspase activation per plaque provided further evidence for a neuroprotective action of ibuprofen.The impact of a shorter 3 month duration ibuprofen trial, beginning at a later age (from 14 to 17 months), was also investigated. Repeated measures ANOVA of Abeta levels (soluble and insoluble) demonstrated a significant ibuprofen treatment effect (p < 0.05). Post-hoc analysis showed that ibuprofen-dependent reductions of both soluble Abeta and Abeta42 were most marked in entorhinal cortex (p < 0.05). Although interleukin-1beta and insoluble Abeta were more effectively reduced with longer treatment, the magnitude of the effect on soluble Abeta was not dependent on treatment duration.

PMID:11755007 Lim GP et al; Neurobiol Aging 22 (6): 983-91 (2001)


Trying to decrease the production of Amyloid beta (Abeta) has been envisaged as a promising approach to prevent neurodegeneration in Alzheimer's disease (AD). A chronic inflammatory reaction with activated microglia cells and astrocytes is a constant feature of AD. The participation of the immune system in the disease process is further documented in several retrospective clinical studies showing an inverse relationship between the prevalence of AD and nonsteroidal anti-inflammatory drug (NSAID) therapy. Previously, we demonstrated that the combination of the proinflammatory cytokines TNFalpha with IFNgamma induces the production of Abeta-42 and Abeta-40 in human neuronal cells. In the present study, the neuronal cell line Sk-n-sh was incubated for 12 h with the cyclooxygenase inhibitor ibuprofen and subsequently stimulated with the cytokines TNFalpha and IFNgamma. Ibuprofen treatment decreased the secretion of total Abeta in the conditioned media of cytokine stimulated cells by 50% and prevented the accumulation of Abeta-42 and Abeta-40 in detergent soluble cell extracts. Viability of neuronal cells measured by detection of apoptosis was neither influenced by ibuprofen nor by cytokine treatment. The reduction in the production of Abeta by ibuprofen was presumably due to a decreased production of betaAPP, which in contrast to the control proteins M2 pyruvate kinase, beta-tubulin and the cytokine inducible ICAM-1 was detected at low concentration in ibuprofen treated cells. The data demonstrate a possible mechanism how ibuprofen may decrease the risk and delay the onset of AD.

PMID:11741404 Blasko I et al; Neurobiol Dis 8 (6): 1094-101 (2001)


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