Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 33, 2003 - Issue 10
108
Views
21
CrossRef citations to date
0
Altmetric
Research Article

Disposition of flurbiprofen in man: influence of stereochemistry and age

, , &
Pages 1043-1057 | Received 20 Feb 2003, Published online: 22 Sep 2008

References

  • ADVENIER, C., Roux, A., GOBERT, C., MASSINS, P., VAROQUAUX, 0. and FLOUVAT, B., 1983, Pharmacokinetics of ketoprofen in the elderly. British Journal of Clinical Pharmacology, 16, 65–70.
  • BLOUIN, R., CHAUDHARY, I., NISHIHARA, K. and Cox, S., 1993, The effects of liver and renal disease on stereoselective serum binding of flurbiprofen. British Journal of Clinical Pharmacology, 35, 62–64.
  • BRUNE, K., BECK, W. S., GEISSLINGER, G., MENZEL-SOGLOWEK, S., PESKAR, B. M. and PESKAR, B. A., 1991, Aspirin-like drugs block pain independently of prostaglandin synthesis inhibition. Experientia, 47, 257–261.
  • BURITOVA, J. and BESSON, J.-M., 1998, Peripheral and/or central effects of racemic-, S(+)- and R( — )-flurbiprofen on inflammatory nociceptive processes: a c-FOS protein study in the rat spinal cord. British Journal of Pharmacology, 125, 87–101.
  • CARABAZA, A., CABRE, F., ROTLLAN, E., GómEz, M., GUTIERREZ, M., GARCIA, L. and MAULEON, D., 1996, Stereoselective inhibition of inducible cyclooxygenase by chiral nonsteroidal antiinflam-matory drugs. Journal of Clinical Pharmacology, 36, 505–512.
  • CEFALI, E. A., POYNOR, W. J., SICA, D. and Cox, S., 1991, Pharmacokinetic comparison of flurbiprofen in end-stage renal disease subjects and subjects with normal renal function. Journal of Clinical Pharmacology, 31, 808–814.
  • CUNNINGHAM, G., DODD, T. R. P., GRANT, D. J., McMurtuo, M. E. J. and RICHARDS, R. M. E., 1997, Drug related problems in elderly patients admitted to Tayside hospitals, methods for prevention and subsequent reassessment. Age and Ageing, 26, 375–382.
  • DENNIS, M. J., FRENCH, P. C., CROME, P., BABIKE, M., SHILLINGFORD, J. and HOPKINS, R., 1985, Pharmacokinetic profile of controlled release ketoprofen in elderly patients. British Journal of Clinical Pharmacology, 20, 567–573.
  • DODHIA, V., PATEL, N., HUTT, A. J. and FORBES, B., 2002, Stereoselective and metabolite-mediated antiproliferative effects of non-steroidal anti-inflammatory drugs. Journal of Pharmacy and Pharmacology, 54 (Suppl.), S–100.
  • FRYE, R. F., TRACY, T. S., HUTZLER, J. M., KORZEKWA, K. R., CANNON, Y., PAULI, M., HUANG, S.-M. and BRANCH, R. A., 2000, Flurbiprofen as a selective in vivo probe of CYP2C9 activity. Pharmaceutical Research, 67, 109.
  • GEISSLINGER, G. and SCHAIBLE, H.-G., 1996, New insight into the site and mode of antinociceptive action of flurbiprofen enantiomers. Journal of Clinical Pharmacology, 36, 513–520.
  • GEISSLINGER, G., LöTscH, J., MENZEL, S., KOBAL, G. and BRUNE, K., 1994, Stereoselective disposition of flurbiprofen in healthy subjects following administration of the single enantiomers. British Journal of Clinical Pharmacology, 37, 392–394.
  • GEISSLINGER, G., MUTH-SELBACH, U., COSTE, 0., VETTER, G., SCHRQDTER, A., SCHAIBLE, H.-G., BRUNE, K. and TEGEDER, I., 2000, Inhibition of noxious stimulus-induced spinal prostaglandin E2 release by flurbiprofen enantiomers: a microdialysis study. Journal of Neurochemistry, 74, 2094–2100.
  • HAMDOUNE, M., MOUNIE, J., MAGDALOU, J., MASMOUDI, T., GOUDONNET, H. and ESCOUSSE, A., 1995, Characterization of the in vitro glucuronidation of flurbiprofen enantiomers. Drug Metabolism and Disposition, 23, 343–348.
  • HAMDY, R. C., BIRD, A., LE GALLEZ, P., HILL, J. and HIND, I. D., 1990, A multiple dose pharmacokinetic and tolerance study of once daily dose 200 mg sustained-release flurbiprofen capsules in young and very elderly patients. European Journal of Clinical Pharmacology, 39, 267–270.
  • HAMDY, R. C., NASAR, A., JAMES, M., HIND, I. D. and MARCHANT, B., 1980, Pharmacokinetics of flurbiprofen in elderly subjects. British Journal of Clinical Practise, 9 (Suppl.), 6–9.
  • HAMMAN, M. A., THOMPSON, G. A. and HALL, S. D., 1997, Regioselective and stereoselective metabolism of ibuprofen by human cytochrome P450 2C. Biochemical Pharmacology, 54, 33–41.
  • HAMMERLEIN, A., DERENDORF, H. and LOWENTHAL, D. T., 1998, Pharmacokinetic and pharmacody-namic changes in the elderly — clinical implications. Clinical Pharmacokinetics, 35, 49–64.
  • HUTZLER, J. M., FRYE, R. F. and TRACY, T. S., 2000, Sensitive and specific high-performance liquid chromatographic assay for 4'-hydroxyflurbiprofen and flurbiprofen in human urine and plasma. Journal of Chromatography B, 749, 119–125.
  • IN'T VELD, B. A., RUITENBERG, A., HOFMAN, A., LAANNER, L. J., VAN DUIJI, C. M., STIJNEN, T., BRETELER, M. M. B. and STRICKER, B. H. C., 2001, Nonsteroidal antiinfiammatory drugs and the risk of Alzheimer's disease. New England Journal of Medicine, 345, 1515–1521.
  • JAMALI, F., BERRY, B. W., TEHRANI, M. R. and RUSSELL, A. S., 1988, Stereoselective pharmacokinetics of flurbiprofen in humans and rats. Journal of Pharmaceutical Sciences, 77, 666–669.
  • JAMALI, F., COLLINS, D. S., BERRY, B. W., MOLDER, S., CHEUNG, R., MuCoLL, K. and CHEUNG, H., 1991, Comparative bioavailability of two flurbiprofen products: stereospecific versus conventional approach. Biopharmaceutics and Drug Disposition, 12, 435–455.
  • JERUSSI, T. P., CAUBET, J.-F., MCCRAY, J. E. and HANDLEY, D. A., 1998, Clinical endoscopic evaluation of the gastroduodenal tolerance to (R)-ketoprofen, (R)-flurbiprofen, racemic ketoprofen and paracetamol: a randomized, single-blind, placebo-controlled trial. Journal of Clinical Pharmacology, 38, 19S–24S.
  • KEAN, W. F., ANTAL, E. J., GRACE, E. M., CAUVIER, H., RISCHKE, J. and BUCHANAN, W. W., 1992, The pharmacokinetics of flurbiprofen in younger and elderly patients with rheumatoid arthritis. Journal of Clinical Pharmacology, 32, 41–48.
  • KEEGAN, P. and LOUGHMAN, B. E., 2001, Early clinical trials of chemopreventive and biologic agents: designs, populations and end points. Urology, 57 (Suppl 4A), 216–219.
  • KNADLER, M. P. and HALL, S. D., 1990, Stereoselective arylpropionyl-CoA thioester formation in vitro. Chirality, 2, 67–73.
  • KNADLER, M. P. and HALL, S. D., 1991, Stereoselective hydrolysis of flurbiprofen conjugates. Drug Metabolism and Disposition, 19, 280–282.
  • KNADLER, M. P., BRATER, D. C. and HALL, S. D., 1989, Plasma protein binding of flurbiprofen: enantioselectivity and influence of pathophysiological status. Journal of Pharmacology and Experimental Therapeutics, 249, 378–385.
  • KNADLER, M. P., BRATER, D. C. and HALL, S. D., 1992a, Stereoselective disposition of flurbiprofen in normal volunteers. British Journal of Clinical Pharmacology, 33, 369–375.
  • KNADLER, M. P., BRATER, D. C. and HALL, S. D., 1992b, Stereoselective disposition of flurbiprofen in uraemic patients. British Journal of Clinical Pharmacology, 33, 377–383.
  • KNIFinvicxi, R. D., WILLIAMS, K. M. and DAY, R. 0., 1989, Chiral inversion of 2-arylpropionic acid non-steroidal anti-inflammatory drugs I. In vitro studies of ibuprofen and flurbiprofen. Biochemical Pharmacology, 38, 4389–4395.
  • MAHMUD, T., SOMASUNDARAM, S., SIGTHORSSON, G., SIMPSON, R. J., RAFI, S., FOSTER, R., TAVARES, I. A., ROSETH, A., HUTT, A. J., JACOB, M., PACY, J., SCOTT, D. L., WRIGGLESWORTH, J. M. and BJARNSON, I., 1998, Enantiomers of flurbiprofen can distinguish key pathophysiological steps of NSAID enteropathy in the rat. Gut, 43, 775–782.
  • MCCRACKEN, J. D., WECHTER, W. J., LIM, Y., CHASE, R. L., KANTOCI, D., MURRAY, E. D., QUIGGLE, D. D. and MINEYAMA, Y., 1996, Antiproliferative effects of the enantiomers of flurbiprofen. Journal of Clinical Pharmacology, 36, 540–545.
  • MENZEL-SOGLOWEK, S., GEISSLINGER, G., BECK, W. S. and BRUNE, K., 1992, Variability of inversion of (R)-flurbiprofen in different species. Journal of Pharmaceutical Sciences, 81, 888–891.
  • MOONEY, H., ROBERTS, R. and COOKSLEY, W., 1985, Alterations in the liver with ageing. Gastroenterology, 14, 757–771.
  • MORIHARA, T., CFR3, T., UBEDA, 0., BEECH, W. and COLE, G. M., 2002, Selective inhibition of A1342 production by NSAID R-enantiomers. Journal of Neurochemistry, 83, 1009–1012.
  • OELKERS, R., NEUPERT, W., WILLIAMS, K. M., BRUNE, K. and GEISSLINGER, G., 1997, Disposition and effects of flurbiprofen enantiomers in human serum and blister fluid. British Journal of Clinical Pharmacology, 43, 145–153.
  • PAGE, J. and HENRY, D., 2000, Consumption of NSAIDs and the development of congestive heart failure in elderly patients. An under recognized public health problem. Archives of Internal Medicine, 160, 777–784.
  • PATEL, B. K., VALENTOVA, J. and HUTT, A. J., 2002, Chromatographic separation and enantiomeric resolution of flurbiprofen and its major metabolites. Chromatographia, 55, 135–142.
  • PATEL, B. K., VALENTOVA, J. and HUTT, A. J., 2003, Stereospecific analysis of flurbiprofen and its major metabolites in plasma and urine by chiral-phase liquid chromatography. Chromatographia, 57, 7–18.
  • PORUBEK, D. J., SANINS, S. M., STEPHENS, J. R., GRILLO, M. P., KAISER, D. G., HALSTEAD, G. W., ADAMS, W. J. and BAILLIE, T. A., 1991, Metabolic chiral inversion of flurbiprofen-CoA in vitro. Biochemical Pharmacology, 42, R1—R4.
  • RISDALL, P. C., ADAMS, S. S., CRAMPTON, E. L. and MARCHANT, B., 1978, The disposition and metabolism of flurbiprofen in several species including man. Xenobiotica, 8, 691–704.
  • ROWLAND, M. and TOZER, T. N., 1995, Metabolite kinetics. In Clinical Pharmacokinetics (Philadelphia: Lea & Febiger), pp. 367–394.
  • RUDY, A. C., KNIGHT, P. M., BRATER, D. C. and HALL, S. D., 1995, Enantioselective disposition of ibuprofen in elderly persons with or without renal impairment. Journal of Pharmacology and Experimental Therapeutics, 273, 88–93.
  • SCHMUCKER, D. L., WOODHOUSE, K. W., WANG, R. K., WYNNE, H., JAMES, 0. F., McMANus, M. and KREMERS, P., 1990, Effects of age and gender on in vitro properties of human liver microsomal monooxygenases. Clinical Pharmacology and Therapeutics, 48, 365–374.
  • SMALL, R. E., Cox, S. R. and ADAMS, W. R., 1990, Influence of H2 receptor antagonists on the disposition of the enantiomers of flurbiprofen. Journal of Clinical Pharmacology, 30, 660–664.
  • SOTANIEMI, E. A., ARRANTO, A. J., PELKONEN, 0. and PASANEN, M., 1997, Age and cytochrome P450-linked drug metabolism in humans. An analysis of 226 subjects with equal histopathologic conditions. Clinical Pharmacology and Therapeutics, 61, 331–339.
  • SURI, A., GRUNDY, B. L. and DERENDORF, H., 1997, Pharmacokinetics and pharmacodynamics of the enantiomers of ibuprofen and flurbiprofen after oral administration. International Journal of Clinical Pharmacology and Therapeutics, 35, 1–8.
  • SZPUNAR, G. J., ALBERT, K. S., BOLE, G. G., DREYFUS, J. N., LOCKWOOD, G. F. and WAGNER, J. F., 1987, Pharmacokinetics of flurbiprofen in man. I. Area/dose relationships. Biopharmaceutics and Drug Disposition, 8, 273–283.
  • TAN, S. C., PATEL, B. K., JACKSON, S. H. D., SWIFT, C. G. and HUTT, A. J., 2003, Influence of age on the enantiomeric disposition of ibuprofen in healthy volunteers. British Journal of Clinical Pharmacology, 55, 579–587.
  • TEGEDER, I., NIEDERBERGER, E., ISRAR, E., GeHRING, H., BRUNE, K., EUCHENHOFER, C., GRöscx, S. and GEISSLINGER, G., 2001a, Inhibition of NF-KB and AP-1 activation by R- and S-flurbiprofen. FASEB Journal, 15, 2–4.
  • TEGEDER, I., PFEILSCHIFTER, J. and GEISSLINGER, G., 2001b, Cyclooxygenase-independent actions of cyclooxygenase inhibitors. FASEB Journal, 15, 2057–2072.
  • TRACY, T. S., MARRA, C., WRIGHTON, S. A., GONZALEZ, F. J. and KORZEKWA, K. R., 1996, Studies of flurbiprofen 4'-hydroxylation — additional evidence suggesting the sole involvement of cytochrome P450 2C9. Biochemical Pharmacology, 52, 1305–1309.
  • TRACY, T. S., ROSENBLUTH, B. W., WRIGHTON, S. A., GONZALEZ, F. J. and KORZEKWA, K. R., 1995, Role of cytochrome P450 2C9 and an allelic variant in the 4'-hydroxylation of (R)- and (S)-flurbiprofen. Biochemical Pharmacology, 49, 1269–1275.
  • TRAMER, M. R., MOORE, R. A., REYNOLDS, D. J. M. and McQuAY, H. J., 2000, Quantitative estimation of rare adverse events which follow a biological progression: a new model applied to chronic NSAID use. Pain, 85, 169–182.
  • WALLACE, S. M. and VERBEECK, R. K., 1987, Plasma protein binding of drugs in the elderly. Clinical Pharmacokinetics, 12, 41–72.
  • WECHTER, W. J., BIGORNIA, A. E., MURRAY, E. D., LEVINE, B. H. and YOUNG, J. W., 1993, Rac-Flurbiprofen is more ulcerogenic than its (S)-enantiomer. Chirality, 5, 492–494.
  • WECHTER, W. J., LEIPOLD, D. D., MURRAY, E. D., QUIGGLE, D. D., MCCRACKEN, J. D., BARRIOS, R. S. and GREENBERG, N. M., 2000b, E-7869 (R-Flurbiprofen) inhibits progression of prostate cancer in the TRAMP mouse. Cancer Research, 60, 2203–2208.
  • WECHTER, W. J., MURRAY, E. D., KANTOCI, D., QUIGGLE, D. D., LEIPOLD, D. D., GIBSON, K. M. and MCCRACKEN, J. D., 2000a, Treatment and survival study in the C57BL/6J-APCmini+ (MIN) mouse with R-flurbiprofen. Life Sciences, 66, 745–753.
  • WEGGEN, S., ERIKSEN, J. L., DAS, P., SAGI, S. A., WANG, R., PIETRZIK, C. U., FINDLAY, K. A., SMITH, T. E., MURPHY, M. P., BUTLER, T., KANG, D. E., MARQUEZ-STERLING, N., GOLDE, T. E. and Koo, E. H., 2001, A subset of NSAIDs lower amyloidogenic A1342 independently of cyclooxygenase activity. Nature, 414, 212–216.
  • WOLFE, M. M., LICHTENSTEIN, D. R. and SINGH, G., 1999, Gastrointestinal toxicity of NSAIDs. New England Journal of Medicine, 340, 1888–1899.
  • WOODHOUSE, K. W. and WYNNE, H., 1987, The pharmacokinetics of non-steroidal anti-inflammatory drugs in the elderly. Clinical Pharmacokinetics, 12, 111–122.
  • YOUNG, M. A., AARONS, L. and TOON, S., 1991, The pharmacokinetics of the enantiomers of flurbiprofen in patients with rheumatoid arthritis. British Journal of Clinical Pharmacology, 31, 102–104.

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:

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:

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.