The world's first wiki where authorship really matters (Nature Genetics, 2008). Due credit and reputation for authors. Imagine a global collaborative knowledge base for original thoughts. Search thousands of articles and collaborate with scientists around the globe.

wikigene or wiki gene protein drug chemical gene disease author authorship tracking collaborative publishing evolutionary knowledge reputation system wiki2.0 global collaboration genes proteins drugs chemicals diseases compound
Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

Keral     (2S)-2-[3-(phenylcarbonyl) phenyl]propanoic...

Synonyms: DEXKETOPROFEN, AC1LDIBR, CHEMBL75435, SureCN66987, AG-E-62116, ...
Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of ZINC00005560


High impact information on ZINC00005560


Biological context of ZINC00005560

  • Changes in urodynamic parameters induced by LPS were prevented by doses of either dexketoprofen (1 mg kg(-1), i.v.) or NS-398 (2 mg kg(-1), i.v.) which were ineffective in control animals [9].
  • 6. In sucrose gap experiments, (S)-ketoprofen (10-100 microM) produced a time-dependent shortening of spontaneous action potentials of the guinea-pig renal pelvis and reduced the amplitude and duration of the accompanying phasic contractions [10].
  • 5. There was no difference between AUC for (R)- and (S)-ketoprofen for either unbound or total drug [11].
  • IC50 values obtained for dexketoprofen, (-)-R-ketoprofen, and rac-ketoprofen were 3.5 microM, 45.3 microM, and 5.8 microM, respectively [12].
  • A new (S)-ketoprofen specific esterase (EST-Y29) was identified from a metagenome library from environmental samples, which showed homologies with class C-beta lactamase, penicillin binding protein, and other lipases/esterases [13].

Anatomical context of ZINC00005560

  • 4. In the guinea-pig isolated ureter, phasic contractions were induced by EFS (5 ms pulse width, 60 V): (S)-ketoprofen (100-500 microM) had no effect on the EFS-evoked contractions [10].
  • The absorption ratios of (R)- and (S)-ketoprofen for the absorption process from the gastrointestinal tract into the systemic circulation were 87.0% and 83.8%, respectively [14].
  • In liver homogenates or subcellular fractions, the enantiomer (S)-ketoprofen (S-KP) was recovered unchanged, whereas (R)-ketoprofen (R-KP) was partially converted into its Coenzyme A (CoA) thioester and inverted to S-KP [15].
  • Thus, the safety indexes (UD50/ED50) of the stomach (or small intestine) for M-5011, IND, KP, DIF, TIA and ZLT were 140.05 (73.16), 42.67 (22.76), 71.57 (38.39), 6.16 (3.29), 13.15 (9.74) and 6.60 (3.26), respectively [16].
  • These results correlated with those obtained in the study of racemic ketoprofen and its enantiomers on cyclooxygenase activity of rat brain microsomes, where dexketoprofen also inhibited enzymatic activity stereoselectively [12].

Associations of ZINC00005560 with other chemical compounds

  • When contraction of the ureter was evoked by 80 mM KCl, indomethacin produced about 30 and 80% inhibition at 100 and 300 microM, respectively, while (S)-ketoprofen (300 microM) was ineffective [10].
  • Significant levels of prostaglandin F2 alpha (PGF2 alpha) were synthesized in rat brain fragments after 10 min of incubation at 37 degrees C. Dexketoprofen was found to be a potent inhibitor of this PGF2 alpha production in rat brain (IC50 = 6.2 nM), and it completely suppressed PGF2 alpha production at 1 microM concentration [12].
  • By using such an immobilized enzyme as biocatalyst, the process for preparing enantiopure (S)-ketoprofen becomes simpler and more practical as compared with the previously reported procedures and the product was obtained with >94% ee at 22.3% conversion in the presence of an optimal concentration (0.5 mg/ml) of Tween-80 at pH 3 [17].
  • Kinetic studies on the intramolecular acyl migration of beta-1-O-acyl glucuronides: application to the glucuronides of (R)- and (S)-ketoprofen, (R)- and (S)-hydroxy-ketoprofen metabolites, and tolmetin by 1H-NMR spectroscopy [18].
  • Odds ratios for a decrease in pain score of at least 1 from baseline (on the 11 point scale) when given dexketoprofen rather than diclofenac at 15, 30, 45, and 60 minutes were; 2.66 (1.19 to 5.98), 3.52 (1.60 to 7.73), 4.48 (1.72 to 11.65), and 5.54 (1.90 to 16.15) [19].

Gene context of ZINC00005560


Analytical, diagnostic and therapeutic context of ZINC00005560


  1. Comparison of the efficacy and tolerability of dexketoprofen and ketoprofen in the treatment of primary dysmenorrhea. Ezcurdia, M., Cortejoso, F.J., Lanzón, R., Ugalde, F.J., Herruzo, A., Artigas, R., Fernández, F., Torres, F., Mauleón, D. Journal of clinical pharmacology. (1998) [Pubmed]
  2. (S)-ketoprofen accumulation in premature neonates with renal failure who were exposed to the racemate during pregnancy. Bannwarth, B., Lagrange, F., Péhourcq, F., Llanas, B., Demarquez, J.L. British journal of clinical pharmacology. (1999) [Pubmed]
  3. Photoallergic contact dermatitis from dexketoprofen: study of 6 cases. Goday-Bujan, J.J., Rodríguez-Lozano, J., Martínez-González, M.C., Fonseca, E. Contact Derm. (2006) [Pubmed]
  4. Enantiospecific inhibition of ligature-induced periodontitis in beagles with topical (S)-ketoprofen. Paquette, D.W., Fiorellini, J.P., Martuscelli, G., Oringer, R.J., Howell, T.H., McCullough, J.R., Reasner, D.S., Williams, R.C. Journal of clinical periodontology. (1997) [Pubmed]
  5. Stereoselective esterase activity of human serum albumin toward ketoprofen glucuronide. Dubois-Presle, N., Lapicque, F., Maurice, M.H., Fournel-Gigleux, S., Magdalou, J., Abiteboul, M., Siest, G., Netter, P. Mol. Pharmacol. (1995) [Pubmed]
  6. Clinical pharmacokinetics of dexketoprofen. Barbanoj, M.J., Antonijoan, R.M., Gich, I. Clinical pharmacokinetics. (2001) [Pubmed]
  7. Preclinical and clinical development of dexketoprofen. Mauleón, D., Artigas, R., García, M.L., Carganico, G. Drugs (1996) [Pubmed]
  8. Dexketoprofen-induced antinociception in animal models of acute pain: Synergy with morphine and paracetamol. Miranda, H.F., Puig, M.M., Dursteler, C., Prieto, J.C., Pinardi, G. Neuropharmacology (2007) [Pubmed]
  9. Pharmacological evaluation of the role of cyclooxygenase isoenzymes on the micturition reflex following experimental cystitis in rats. Lecci, A., Birder, L.A., Meini, S., Catalioto, R.M., Tramontana, M., Giuliani, S., Criscuoli, M., Maggi, C.A. Br. J. Pharmacol. (2000) [Pubmed]
  10. Modulation by stereoselective inhibition of cyclo-oxygenase of electromechanical coupling in the guinea-pig isolated renal pelvis. Santicioli, P., Carganico, G., Meini, S., Giuliani, S., Giachetti, A., Maggi, C.A. Br. J. Pharmacol. (1995) [Pubmed]
  11. The influence of renal function on the enantioselective pharmacokinetics and pharmacodynamics of ketoprofen in patients with rheumatoid arthritis. Hayball, P.J., Nation, R.L., Bochner, F., Sansom, L.N., Ahern, M.J., Smith, M.D. British journal of clinical pharmacology. (1993) [Pubmed]
  12. Stereoselective inhibition of rat brain cyclooxygenase by dexketoprofen. Carabaza, A., Cabré, F., García, A.M., Rotllan, E., García, M.L., Mauleón, D. Chirality. (1997) [Pubmed]
  13. Identification and characterization of a novel (S)-ketoprofen-specific esterase. Yoon, S., Kim, S., Ryu, Y., Kim, T.D. Int. J. Biol. Macromol. (2007) [Pubmed]
  14. Moment analysis of stereoselective enterohepatic circulation and unidirectional chiral inversion of ketoprofen enantiomers in rat. Yasui, H., Yamaoka, K., Nakagawa, T. Journal of pharmaceutical sciences. (1996) [Pubmed]
  15. Stereoselective metabolic pathways of ketoprofen in the rat: incorporation into triacylglycerols and enantiomeric inversion. Carabaza, A., Suesa, N., Tost, D., Pascual, J., Gomez, M., Gutierrez, M., Ortega, E., Montserrat, X., Garcia, A.M., Mis, R., Cabre, F., Mauleon, D., Carganico, G. Chirality. (1996) [Pubmed]
  16. Antinociceptive activity of a novel non-steroidal anti-inflammatory drug (M-5011) with low ulcerogenic effects in mice. Murakami, N., Takase, H., Tomita, T., Iwata, K., Naruse, T. Jpn. J. Pharmacol. (1996) [Pubmed]
  17. Integration of purification with immobilization of Candida rugosa lipase for kinetic resolution of racemic ketoprofen. Liu, Y.Y., Xu, J.H., Wu, H.Y., Shen, D. J. Biotechnol. (2004) [Pubmed]
  18. Kinetic studies on the intramolecular acyl migration of beta-1-O-acyl glucuronides: application to the glucuronides of (R)- and (S)-ketoprofen, (R)- and (S)-hydroxy-ketoprofen metabolites, and tolmetin by 1H-NMR spectroscopy. Skordi, E., Wilson, I.D., Lindon, J.C., Nicholson, J.K. Xenobiotica (2005) [Pubmed]
  19. Randomised controlled trial of the onset of analgesic efficacy of dexketoprofen and diclofenac in lower limb injury. Leman, P., Kapadia, Y., Herington, J. Emergency medicine journal : EMJ. (2003) [Pubmed]
  20. Analgesic, antiinflammatory, and antipyretic effects of S(+)-ketoprofen in vivo. Cabré, F., Fernández, M.F., Calvo, L., Ferrer, X., García, M.L., Mauleón, D. Journal of clinical pharmacology. (1998) [Pubmed]
  21. Kinetic resolution of ketoprofen ester catalyzed by lipase from a mutant of CBS 5791. Liu, J., Zhang, Y., Qiu, L., Yang, F., Ye, L., Xia, Y. J. Ind. Microbiol. Biotechnol. (2004) [Pubmed]
  22. Differential effects of spinal (R)-ketoprofen and (S)-ketoprofen against signs of neuropathic pain and tonic nociception: evidence for a novel mechanism of action of (R)-ketoprofen against tactile allodynia. Ossipov, M.H., Jerussi, T.P., Ren, K., Sun, H., Porreca, F. Pain (2000) [Pubmed]
  23. The effect of food and an antacid on the bioavailability of dexketoprofen trometamol. McEwen, J., De Luca, M., Casini, A., Gich, I., Barbanoj, M.J., Tost, D., Artigas, R., Mauleón, D. Journal of clinical pharmacology. (1998) [Pubmed]
  24. Determination of (R)- and (S)-ketoprofen in human plasma by liquid chromatography/tandem mass spectrometry following automated solid-phase extraction in the 96-well format. Eichhold, T.H., Bailey, R.E., Tanguay, S.L., Hoke, S.H. Journal of mass spectrometry : JMS. (2000) [Pubmed]
  25. Effect of perioperative administration of dexketoprofen on opioid requirements and inflammatory response following elective hip arthroplasty. Iohom, G., Walsh, M., Higgins, G., Shorten, G. British journal of anaesthesia. (2002) [Pubmed]
WikiGenes - Universities