Advanced search
Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 34, 2004 - Issue 11-12
Submit an article Journal homepage
327
Views
25
CrossRef citations to date
0
Altmetric
Research Article

Characterization and quantification of metabolites of racemic ketoprofen excreted in urine following oral administration to man by 1H-NMR spectroscopy, directly coupled HPLC-MS and HPLC-NMR, and circular dichroism

E. Skordi Biological Chemistry, Sir Alexander Fleming Building, Imperial College London, South Kensington, London SW7 2AZ, UKCorrespondence[email protected]
,
I. D. Wilson Department of Drug Metabolism and Pharmacokinetics, AstraZeneca, Mereside, Alderley Park, Macclesfield SK10 4TG, UK
,
J. C. Lindon Biological Chemistry, Sir Alexander Fleming Building, Imperial College London, South Kensington, London SW7 2AZ, UK
&
J. K. Nicholson Biological Chemistry, Sir Alexander Fleming Building, Imperial College London, South Kensington, London SW7 2AZ, UK
Pages 1075-1089 | Received 15 Mar 2004, Published online: 22 Sep 2008

Reference

  • AKIRA, K., TAIRA, T., HASEGAWA, H., SAKUMA, C. and SHINOHARA, Y., 1998, Studies on the stereoselective internal acyl migration of ketoprofen glucuronides using 13C labeling and nuclear magnetic resonance spectroscopy. Drug Metabolism and Disposition, 26, 457–464.
  • ALKATHEERI, N. A., WASFI, I. A., KVANAGH, P. and LAMBERT, M., 1999a, Identification and confirmation of 3-hydroxy metabolite of ketoprofen in camels by gas chromatography-mass spectrometry and nuclear magnetic resonance spectroscopy. Journal of Chromatography B, 732, 299–306.
  • ALKATHEERI, N. A., WASFI, I. A. and LAMBERT, M., 1999b, Pharmacokinetics and metabolism of ketoprofen after intravenous and intramuscular administration in camels. Journal of Veterinary and Pharmacology Therapeutics, 22, 127–135.
  • FOSTER, R. T., JAMALI, F. and RUSSELL, A. S., 1989, Ketoprofen enantiomers in synovial fluid. journal of Pharmaceutical Science, 78, 881–882.
  • JAMALI, F. and BROCKS, D. R., 1990, Clinical pharmacokinetics of ketoprofen and its enantiomers. Clinical Pharmacokinetics, 19, 197–217.
  • JAMALI, F., LOVLIN, R. and ABER G., 1997, Bi-directional chiral inversion of ketoprofen in CD-1 mice. Chirality, 9, 29–31.
  • JAMALI, F., RUSSELL, A. S., FOSTER, R. T. and LEMKO, C., 1990, Ketoprofen pharmacokinetics in humans: Evidence of enantiomeric inversion and lack of interaction. Journal of Pharmaceutical Science, 79, 460–461.
  • JULOU, L., GUYONNET, J. C., DUCROT, R. and PASQUET, J., 1976, Some pharmacological and toxicological studies on ketoprofen. Rheumatology and Rehabilitation, Suppl., 5–10.
  • KUROSAWA, M., YAMASHITA, S., TSUJI, T. and OHTAKE, I., 1994, The metabolic fate of ketoprofen in the horse after oral and intramuscular administration. In Proceedings of the 10th International Conference of Racing Analysts and Veterinarians, Stockholm, Sweden.
  • LINDON, J. C., NICHOLSON, J. K., SIDELMANN, U. G. and WILSON, I. D., 1997, Directly coupled HPLC-NMR and its application to drug metabolism. Drug Metabolism Reviews, 29, 705–746.
  • MULLER, N., PAYAN, E., LAPIQUE, F., BANNWARTH, B. and NETTER, P., 1990, Pharmacological aspects of chiral nonsteroidal anti-inflammatory drugs. Fundamentals of Clinical Pharmacology, 4, 617–634.
  • NICHOLSON, J. K., FOXALL, P. J. D., SPRAUL, M., FARRANT, R. D. and LINDON, J. C., 1995,750 MHz 1H and 1H-13C NMR spectroscopy of human blood plasma. Analytical Chemistry, 67, 793–811.
  • POPULAIRE, P., TERLAIN, B., PASCAL, S., DECOUVELAERE, B., RENARD, A. and THOMAS, J.-P., 1973, Biological behaviour: serum levels, excretion and biotransformation of 2-(3-benzoylpheny1)-propanoic acid or ketoprofen in animals and man. Annals of Pharmacy France, 31, 735–749.
  • RUDY, A. C., Liu, Y., BRATER, D. C. and HALL, S. D., 1998, Stereoselective pharmacokinetics and inversion of (R)-ketoprofen in healthy volunteers. Journal of Clinical Pharmacology, 38, 3S–10S.
  • RYAN, M., TODI, F. and MENDONCA, M., 1994, The fate of ketoprofen in the horse after administration of ketofen. Proceedings of the 10th International Conference of Racing Analysts and Veterinarians, Stockholm, Sweden.
  • SHOCKCOR, J. P., UNGER, S. E., SAVINA, P., NICHOLSON, J. K. and LINDON, J. C., 2000, Application of directly coupled LC-NMR-MS to the structural elucudation of metabolites of the HIV-1 reverse-transcriptase inhibitor BW935U83. Journal of Chromatography B, 748, 269–279.
  • SIDELMANN, U. G., BJØRNSDOTTIR, I., SHOCKCOR, J. P., HANSEN, S. H., LINDON, J. C. and NICHOLSON, J. K., 2001, Directly coupled HPLC-NMR and HPLC-MS approaches for the rapid characterisation of drug metabolites in urine: application to the human metabolism of naproxen. Journal of Pharmaceutical and Biomedical Analysis, 24, 569–579.
  • SPAHN-LANGGUTH, H. and BENET, L. Z., 1992, Acyl glucuronides revisited: is the glucuronidation process a toxification as well as a detoxification mechanism? Drug Metabolism Reviews, 24, 5–48.
  • TRAFICANTE, D. D. and NEMETH, G. A., 1987, A new improved apodization function for resolution enhancement in NMR spectroscopy. Journal of Magnetic Resonance, 71, 237–245.
  • UPTON, R. A., BUSKIN, J. N., WILLIAMS, R. L., HOLFORD, N. H. G. and RIEGELMAN, S., 1980, Negligible excretion of unchanged ketoprofen, naproxen and probenecid in urine. Journal of Pharmaceutical Science, 69, 1254–1257.
  • VOLLAND, C., SUN, H. and BENET, L. Z., 1990, Stereoselective analysis of fenoprofen and its metabolites. Journal of Chromatography, 534, 127–138.
  • WILSON, I. D. and NICHOLSON, J. K., 1987, Solid-phase extraction chromatography and nuclear magnetic resonance spectrometry for the identification and isolation of drug metabolites in urine. Analytical Chemistry, 59, 2830–2832.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.