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Chemical Compound Review

Atriscal     (2S)-2-[4-(2-methylpropyl) phenyl]propanoic...

Synonyms: Seractil, Dolomin, DexOptifen, DEXIBUPROFEN, Dexibuprofene, ...
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Disease relevance of ibuprofen


High impact information on ibuprofen

  • There were no significant differences between oral and intravenous doses for the area under the curve values, terminal rate constants, clearances, metabolite formation clearances, and serum protein binding for (R)- and (S)-ibuprofen [6].
  • Although 12.5-100 mg/kg doses of DM alone produced no reliable effects, treatments with ibuprofen (IB, 50 and 100 mg/kg but not 12.5 or 25 mg/kg) produced mild analgesia in arthritic rats as determined using the Randall-Sellito test [7].
  • METHODS AND MATERIALS: Nonselective COX inhibitor, ibuprofen (IB), and selective COX-2 inhibitor, SC-236, were used to determine the cytotoxicity and radiosensitization at varying pH of culture media [8].
  • The most important finding was that Vv(alt mito/myocyte) was 0.09 +/- 0.16 and 0.02 +/- 0.04 in the hearts receiving PMN+PMA alone and when scavengers were added, respectively, whilst no changes in mitochondrial ultrastructure was observed after addition of IBU, BW 755C or DCM [9].
  • Using a crossover study design, the renal clearance of sulfate was assessed in conscious female Lewis rats during control periods and following the infusion of two structurally dissimilar nonsteroidal anti-inflammatory drugs, ibuprofen (IBU) and indomethacin (INDO) [10].

Chemical compound and disease context of ibuprofen

  • The aim of this double-blind randomized trial was to compare the isolated active enantiomer dexibuprofen (S(+)-ibuprofen) with the double dose of racemic ibuprofen and to show a dose-response relationship of dexibuprofen in painful osteoarthritis of the hip [3].
  • Treatment of all five strains of Salmonella with APAP, ASA or IB under all four metabolic conditions did not induce any appreciable increases in revertant colony counts, as compared to the negative controls [11].
  • At maximum erythema (8-12 h after UVB), the following approximate reductions in SBF (compared to control responses) were noted: 42-58% for combination therapies, 33-40% for IB or IN alone, and 17% for BD alone [12].

Biological context of ibuprofen

  • The role of prostaglandins in the effects of IBU and INDO on sulfate homeostasis was investigated by examining the influence of concomitant intraarterial PGE2 administration (infusion of 0.1 micrograms/min) on nonsteroidal anti-inflammatory drug-induced alterations in sulfate renal clearance [10].
  • 4. Interindividual variation in the pharmacokinetics of (S)-ibuprofen following administration of the racemate was similar to that following the administration of the single isomer suggesting that chiral inversion is not a major factor contributing to variability in the disposition of this drug [13].
  • Water activity affects the esterification rates of (R)- and (S)-ibuprofen differently, leading to higher enantioselectivity at lower water activities [14].
  • Ibuprofen (Ibu; 1,200 mg/day, to reduce PG-induced vasodilation) and placebo were administered orally for 2 days before two separate testing sessions in a double-blind manner [15].
  • Resting heart rate was reduced in Ibu (52 +/- 3 beats/min) compared with placebo (57 +/- 3 beats/min) (P < 0.05) without change to MPP [15].

Anatomical context of ibuprofen

  • Furthermore, it was shown that perturbation of IB absorption from the gastrointestinal tract may serve as an important discriminative measure for identification of the inversion site [16].
  • In the male trial, CFA injection (P<.01) caused TMJ swelling and chromodacryorrhea (CFA-CON); IBU eliminated these changes in the CFA+IBU group [17].
  • CIbT or CIT alone reduced the number of spontaneous lung metastases and restored anti-YAC-1 killer function of splenocytes with NK-like phenotype (AGM-1+, Thy-1-, Lyt-2-); some anti-C3L5 killer function was also generated in the high dose Ibu group and the killer cell showed AGM-1+, Thy-1+ and Lyt-2+ phenotype [5].
  • TA-60 did not inhibit the activity of the PG degradating enzyme, 15-hydroxy PG dehydrogenase (15-OH-PG-DH) of the gastric mucosa like the other non-steroidal anti-inflammatory drugs (NSAIDs): IP, PBZ and IM [18].

Associations of ibuprofen with other chemical compounds


Gene context of ibuprofen

  • Ibuprofen (IBU) and bovine serum albumin (BSA) were selected as model drugs and loaded onto the unmodified and functionalized SBA-15 [24].
  • 3. No difference was found (P > 0.05) between treatments in the percentage of the dose recovered in the urine as (R)- or (S)-ibuprofen plus metabolites (S-IBU: 80.2 +/- 8.47 vs RAC: 74.1 +/- 14.0%) [13].
  • Ninety-eight (41%) physicians prescribed long-term use of oral steroids for 413 (5%) patients, 103 (42%) prescribed inhaled steroids for 1,032 (12%) patients, and 108 (45%) prescribed high-dose IBU for 723 (8%) patients to control CF [25].
  • A reversed-phase liquid chromatographic method was developed for 2-(4-isobutylphenyl)propionic acid (IBPP) in bulk drug and compressed tablets containing 100-600 mg of drug per tablet [26].
  • Solid lipid nanoparticles (SLN) containing or not (S)-(+)-2-(4-isobutylphenyl)propionic acid (ibuprofen) were prepared with Preciol ATO 5 as lipid phase by the hot homogenization technique and characterized through particle size analyses and zeta potential measurements [27].

Analytical, diagnostic and therapeutic context of ibuprofen


  1. Stereoselective disposition of ibuprofen in patients with renal dysfunction. Chen, C.Y., Chen, C.S. J. Pharmacol. Exp. Ther. (1994) [Pubmed]
  2. Reevaluation of some double-blind, randomized studies of dexibuprofen (Seractil): a state-of-the-art overview. Studies in patients with lumbar vertebral column syndrome, rheumatoid arthritis, distortion of the ankle joint, gonarthrosis, ankylosing spondylitis, and activated coxarthrosis. Rahlfs, V.W., Stat, C. Journal of clinical pharmacology. (1996) [Pubmed]
  3. Evaluation of the efficacy and dose-response relationship of dexibuprofen (S(+)-ibuprofen) in patients with osteoarthritis of the hip and comparison with racemic ibuprofen using the WOMAC osteoarthritis index. Singer, F., Mayrhofer, F., Klein, G., Hawel, R., Kollenz, C.J. International journal of clinical pharmacology and therapeutics. (2000) [Pubmed]
  4. The effect of a dexibuprofen mouth rinse on experimental gingivitis in humans. Rosin, M., Kähler, S.T., Hessler, M., Schwahn, C.h., Kuhr, A., Kocher, T. Journal of clinical periodontology. (2005) [Pubmed]
  5. Immunotherapy of mammary adenocarcinoma metastases in C3H/HeN mice with chronic administration of cyclo-oxygenase inhibitors alone or in combination with IL-2. Khoo, N.K., Chan, F.P., Saarloos, M.N., Lala, P.K. Clin. Exp. Metastasis (1992) [Pubmed]
  6. Lack of presystemic inversion of (R)- to (S)-ibuprofen in humans. Hall, S.D., Rudy, A.C., Knight, P.M., Brater, D.C. Clin. Pharmacol. Ther. (1993) [Pubmed]
  7. Effects of the combined oral administration of NSAIDs and dextromethorphan on behavioral symptoms indicative of arthritic pain in rats. Price, D.D., Mao, J., Lu, J., Caruso, F.S., Frenk, H., Mayer, D.J. Pain (1996) [Pubmed]
  8. Pronounced radiosensitization of cultured human cancer cells by COX inhibitor under acidic microenvironment. Shah, T., Ryu, S., Lee, H.J., Brown, S., Kim, J.H. Int. J. Radiat. Oncol. Biol. Phys. (2002) [Pubmed]
  9. Cardiac injury by activated leukocytes: effect of cyclooxygenase and lipoxygenase inhibition evaluated by electron microscopical morphometry. Semb, A.G., Ytrehus, K., Vaage, J., Myklebust, R. J. Mol. Cell. Cardiol. (1996) [Pubmed]
  10. Influence of NSAID-induced inhibition of renal prostaglandin synthesis on inorganic sulfate clearance in rats. Morris, M.E., Benincosa, L.J. Proc. Soc. Exp. Biol. Med. (1992) [Pubmed]
  11. Mutagenicity testing of selected analgesics in Ames Salmonella strains. Oldham, J.W., Preston, R.F., Paulson, J.D. Journal of applied toxicology : JAT. (1986) [Pubmed]
  12. Synergistic effects of oral nonsteroidal drugs and topical corticosteroids in the therapy of sunburn in humans. Hughes, G.S., Francom, S.F., Means, L.K., Bohan, D.F., Caruana, C., Holland, M. Dermatology (Basel) (1992) [Pubmed]
  13. Variability in the stereoselective disposition of ibuprofen in patients with rheumatoid arthritis. Geisslinger, G., Stock, K.P., Loew, D., Bach, G.L., Brune, K. British journal of clinical pharmacology. (1993) [Pubmed]
  14. Influence of water activity on the enantioselective esterification of (R,S)-ibuprofen by Candida antarctica lipase B in solventless media. Pepin, P., Lortie, R. Biotechnol. Bioeng. (1999) [Pubmed]
  15. Failure of prostaglandins to modulate the time course of blood flow during dynamic forearm exercise in humans. Shoemaker, J.K., Naylor, H.L., Pozeg, Z.I., Hughson, R.L. J. Appl. Physiol. (1996) [Pubmed]
  16. Pharmacokinetic analysis of the enantiomeric inversion of chiral nonsteroidal antiinflammatory drugs. Mehvar, R., Jamali, F. Pharm. Res. (1988) [Pubmed]
  17. Meal pattern changes associated with temporomandibular joint inflammation/pain in rats; analgesic effects. Kerins, C.A., Carlson, D.S., McIntosh, J.E., Bellinger, L.L. Pharmacol. Biochem. Behav. (2003) [Pubmed]
  18. Inhibition of prostaglandin biosynthesis by a new anti-inflammatory drug, TA-60. Muramatsu, M., Tanaka, M., Fujita, A., Otomo, S., Aihara, H., Amano, T. J. Pharmacobio-dyn. (1985) [Pubmed]
  19. Metabolism of human articular chondrocytes cultured in alginate beads. Longterm effects of interleukin 1beta and nonsteroidal antiinflammatory drugs. Sanchez, C., Mateus, M.M., Defresne, M.P., Crielaard, J.M., Reginster, J.Y., Henrotin, Y.E. J. Rheumatol. (2002) [Pubmed]
  20. Comparison of the bioavailability of dexibuprofen administered alone or as part of racemic ibuprofen. Gabard, B., Nirnberger, G., Schiel, H., Mascher, H., Kikuta, C., Mayer, J.M. Eur. J. Clin. Pharmacol. (1995) [Pubmed]
  21. Binding studies of taxanes to human serum albumin by bioaffinity chromatography and circular dichroism. Bertucci, C., Cimitan, S., Riva, A., Morazzoni, P. Journal of pharmaceutical and biomedical analysis. (2006) [Pubmed]
  22. Modification of pepsinogen I levels and their correlation with gastrointestinal injury after administration of dexibuprofen, ibuprofen or diclofenac: a randomized, open-label, controlled clinical trial. Gómez, B.J., Caunedo, A., Redondo, L., Esteban, J., Sáenz-Dana, M., Blasco, M., Hergueta, P., Rodríguez-Téllez, M., Romero, R., Pellicer, F.J., Herrerías, J.M. International journal of clinical pharmacology and therapeutics. (2006) [Pubmed]
  23. Analysis of competitive binding of ligands to human serum albumin using NMR relaxation measurements. Cui, Y.F., Bai, G.Y., Li, C.G., Ye, C.H., Liu, M.L. Journal of pharmaceutical and biomedical analysis. (2004) [Pubmed]
  24. Functionalized SBA-15 materials as carriers for controlled drug delivery: influence of surface properties on matrix-drug interactions. Song, S.W., Hidajat, K., Kawi, S. Langmuir : the ACS journal of surfaces and colloids. (2005) [Pubmed]
  25. The use of anti-inflammatory medications in cystic fibrosis: trends and physician attitudes. Oermann, C.M., Sockrider, M.M., Konstan, M.W. Chest (1999) [Pubmed]
  26. Determination of 2-(4-isobutylphenyl)propionic acid in bulk drug and compressed tablets by reversed-phase high-performance liquid chromatography. Asmus, P.A. J. Chromatogr. (1985) [Pubmed]
  27. Solid lipid nanoparticles incorporated in dextran hydrogels: A new drug delivery system for oral formulations. Casadei, M.A., Cerreto, F., Cesa, S., Giannuzzo, M., Feeney, M., Marianecci, C., Paolicelli, P. International journal of pharmaceutics. (2006) [Pubmed]
  28. Uniform-sized molecularly imprinted polymer for (S)-ibuprofen retention properties in aqueous mobile phases. Haginaka, J., Sanbe, H., Takehira, H. Journal of chromatography. A. (1999) [Pubmed]
  29. The enantioselective immunoaffinity extraction of an optically active ibuprofen-modified peptide fragment. Ikegawa, S., Isriyanthi, N.M., Nagata, M., Yahata, K., Ito, H., Mano, N., Goto, J. Anal. Biochem. (2001) [Pubmed]
  30. d-Ibuprofen in ocular inflammation induced by paracentesis of the rabbit eye. Tjebbes, G.W., van Delft, J.L., Barthen, E.R., van Haeringen, N.J. Prostaglandins (1990) [Pubmed]
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