Pharmacokinetics and metabolism of orally administered firocoxib, a novel second generation coxib, in horses

Journal of Veterinary Pharmacology and Therapeutics

Volumn 30, Issue 3, 2007, Pages 208-217

  Kvaternick, V ^a   Pollmeier, M ^a   Fischer, J ^a   Hanson, P D ^a  

^a BOEHRINGER INGELHEIM PHARMA GMBH AND CO KG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOOXYGENASE 2 INHIBITOR; DESCYCLOPROPYLMETHYLFIROCOXIB; DRUG METABOLITE; FIROCOXIB; GLUCURONIDE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; AREA UNDER THE CURVE; ARTICLE; BIOTRANSFORMATION; CONTROLLED STUDY; DEALKYLATION; DISTRIBUTION VOLUME; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG CLEARANCE; DRUG DISTRIBUTION; DRUG ELIMINATION; DRUG HALF LIFE; DRUG METABOLISM; FEMALE; GLUCURONIDATION; HORSE; MALE; METABOLITE; NONHUMAN; PRIORITY JOURNAL; SINGLE DRUG DOSE; URINARY EXCRETION;

4-BUTYROLACTONE; ADMINISTRATION, ORAL; ANIMALS; AREA UNDER CURVE; CROSS-OVER STUDIES; CYCLOOXYGENASE 2 INHIBITORS; FEMALE; HORSES; INJECTIONS, INTRAVENOUS; MALE; SULFONES;

ANIMALIA; EQUIDAE;

EID: 34247606782     PISSN: 01407783     EISSN: 13652885     Source Type: Journal    
DOI: 10.1111/j.1365-2885.2007.00840.x     Document Type: Article

References (38)

1. Beretta, C., Garavaglia, G. Cavelli, M. (2005) COX-1 and COX-2 inhibition in horse by phenylbutazone, flunixin, carprofen and meloxicam: an in-vitro analysis. Pharmacological Research, 52, 302 306.
2. Bingham, C.O. III. (2002) Development and clinical applications of COX-2 selective inhibitors for the treatment of osteoarthritis and rheumatoid arthritis. Cleveland Clinic Journal of Medicine, 69 (Suppl. 1 5 12.
3. Bombardier, C., Laine, L., Reicin, A., Shapiro, D., Burgos-Vargas, R., Davis, B., Day, R., Ferraz, M., Hawkey, C.J., Hochberg, M.C., Kvein, T.K. Schnitzer, T.J. (2000) Comparison of upper gastrointestinal toxicity of rofecoxib and naproxen in patients with rheumatoid arthritis. New England Journal of Medicine, 343, 1520 1528.
4. Brideau, C., Van Staden, C. Chan, C.C. (2001) In vitro effects of cyclooxygenase inhibitors in whole blood of horses, dogs, and cats. American Journal of Veterinary Research, 62, 1755 1760.
5. Brzozowska, I., Targosz, A., Sliwowski, Z., Kwiecien, S., Drozdowicz, D., Pajdo, R., Konturek, P.C., Brzozowski, T., Pawlik, M., Konturek, S.J., Pawlik, W.W. Hahn, E.G. (2004) Healing of chronic gastric ulcers in diabetic rats treated with native aspirin, nitric oxide (NO)-derivative of aspirin and cyclooxygenase (COX)-2 inhibitor. Journal of Physiology and Pharmacology, 55, 773 790.
6. Brzozowski, T., Konturek, P.C., Konturek, S.J., Sliwowski, Z., Pajdo, R., Drozdowicz, D., Ptak, A. Hahn, E.G. (2001) Classic NSAID and selective cyclooxygenase (COX)-1 and COX-2 inhibitors in healing of chronic gastric ulcers. Microscopy Research and Technique, 53, 343 353.
7. Buttar, N.S. Wang, K.K. (2000) The 'Aspirin' of the new millennium: cyclooxygenase-2 inhibitors. Mayo Clinic Proceedings, 75, 1027 1038.
8. Chan, C.C., Boyce, S., Brideau, C., Charleson, S., Cromlish, W., Ethier, D., Evans, J., Ford-Hutchinson, A.W., Forrest, M.J., Gauthier, J.Y., Gordon, R., Gresser, M., Guay, J., Kargman, S., Kennedy, B., Leblanc, Y., Leger, S., Mancini, J., O'Neill, G.P., Ouellet, M., Patrick, D., Percival, M.D., Perrier, H., Prasit, P., Rodger, I., Tagari, P., Therien, M., Vickers, P., Cisco, D., Wang, Z., Webb, J., Wong, E., Xu, L-J., Young, R.N., Zamboni, R. Riendeau, D. (1999) Rofecoxib [Vioxx, MK-0966; 4-(4′-methylsulfonylphenyl)-3-phenyl-2- (5H)-furanone]: a potent and orally active cyclooxygenase-2 inhibitor. Pharmacological and biochemical profiles. Journal of Pharmacology and Experimental Therapeutics, 290, 551 560.
9. Ermondi, G., Caron, G., Lawrence, R. Longo, D. (2004) Docking studies on NSAID/COX-2 isozyme complexes using contact statistic analysis. Journal of Computer Aided Molecular Design, 18, 683 696.
10. Fitzpatrick, F.A. (2004) Cyclooxygenase enzymes: regulation and function. Current Pharmaceutical Design, 10, 577 588.
11. Forsyth, S.F., Guilford, W.G. Lawoko, C.R.O. (1996) Endoscopic evaluation of the gastroduodenal mucosa following non-steroidal anti-inflammatory drug administration in the dog. New Zealand Veterinary Journal, 44, 179 181.
12. Futaki, N., Yoshikawa, K., Hamasaka, Y., Arai, I., Higuchi, S., Iizuka, H. Otomo, S. (1993) NS-398, a novel non-steroidal anti-inflammatory drug with potent analgesic and antipyretic effects, which causes minimal stomach lesions. General Pharmacology, 24, 105 110.
13. Garavito, R.M. Mulichak, A.M. (2003) The structure of mammalian cyclooxygenase. Annual Review of Biophysical and Biomolecular Structures, 32, 183 206.
14. Gierse, J.K., McDonald, J.J., Hauser, S.D., Rangwala, S.H., Koboldt, C.M. Seibert, K. (1996) A single amino acid difference between cyclooxygenase-1 (COX-1) and -2 (COX-2) reverses the selectivity of cox-2 inhibitors. Journal of Biological Chemistry, 271, 15810 15814.
15. Gilroy, D.W., Lawrence, T., Perretti, M. Rossi, A.G. (2004) Inflammatory resolution: new opportunities for drug discovery. Nature Reviews Drug Discovery, 3, 401 416.
16. Goodrich, L.R. Nixon, A.J. (2006) Medical treatment of osteoarthritis in horse - A review. The Veterinary Journal, 171, 51 69.
17. Hawkey, C.J. (2002) Cyclooxygenase inhibition: between the devil and the deep blue sea. Gut, 50 (Suppl. 3 25 30.
18. Kahn, C. (ed. 2005) The Merck Veterinary Manual, 9th edn. Merck & Co., Inc., Whitehouse Station, NJ.
19. Lees, P., Aliabadi, F.S. Landoni, M.F. (2002) Pharmacodynamics and enantioselective pharmacokinetics of racemic carprofen in the horse. Journal of Veterinary Pharmacology and Therapeutics, 25, 433 448.
20. Masferrer, J.L., Zweifel, B.S., Manning, P.T., Hauser, S.D., Leahy, K.M., Isakson, W. Seibert, K. (1994) Selective inhibition of inducible cyclooxygenase 2 in vivo is antiinflammatory and nonulcerogenic. Proceedings from the National Academy of Sciences, 91, 3228 3232.
21. McCann, M.E., Andersen, D.R., Zhang, D., Brideau, C., Black, W.C., Hanson, P.D. Hickey, G.J. (2004) In vitro effects and in vivo efficacy of a novel cyclooxygenase-2 inhibitor in dogs with experimentally induced synovitis. American Journal of Veterinary Research, 65, 503 512.
22. McCann, M.E., Andersen, D.R., Brideau, C., Black, W.C., Zhang, D-H. Hickey, G.J. (2006) In vitro activity and in vivo efficacy of a novel COX-2 inhibitor in the horse. Journal of Veterinary Internal Medicine (in press).
23. Mehanna, A.S. (2003) NSAIDs: chemistry and pharmacological actions. American Journal of Pharmaceutical Education, 67, 1 8.
24. Nicoll-Griffith, D.A., Yergey, J.A., Trimble, L.A., Silva, J.M., Li, C., Chauret, N., Gauthier, J.Y., Grimm, E., Leger, S., Roy, P., Therien, M., Wang, Z., Prasit, P., Zamboni, R., Young, R.N., Brideau, C., Chan, C.C., Mancini, J. Riendeau, D. (2000) Synthesis, characterization, and activity of metabolites derived from the cyclooxygenae-2 inhibitor rofecoxib (MK-0966, VioxxTM). Bioorganic & Medicinal Chemistry Letters, 10, 2683 2686.
25. Patrignani, P., Tacconelli, S., Sciulli, M.G. Capone, M.L. (2005) New insights into COX-2 biology and inhibition. Brain Research Reviews, 48, 352 359.
26. Reimer, M.E., Johnston, S.A., Leib, M.S., Duncan, R.B., Reimer, D.C., Marini, M. Gimbert, K. (1999) The gastroduodenal effects of buffered aspirin, carprofen, and etodolac in healthy dogs. Journal of Veterinary Internal Medicine, 13, 472 477.
27. Ricketts, A.P., Lundy, K.M. Seibel, S.B. (1998) Evaluation of selective inhibition of canine cyclooxygenase 1 and 2 by carprofen and other nonsteroidal anti-inflammatory drugs. American Journal of Veterinary Research, 59, 1441 1446.
28. Rowlinson, S.W., Crews, B.C., Goodwin, D.C., Schneider, C., Gierse, J.K. Marnett, L.J. (2000) Spatial requirements for 15-(R)-Hydroxy-5Z,8Z,11Z,13E- eicosatetraenoic acid synthesis within the cyclooxygenase active site of murine COX-2. Journal of Biological Chemistry, 275, 6586 6591.
29. van Ryn, J., Trummlitz, G. Pairet, M. (2000) COX-2 selectivity and inflammatory processes. Current Medicinal Chemistry, 7, 1145 1161.
30. Scheiman, J.M. (1996) NSAIDS, gastrointestinal injury, and cytoprotection. Gastroenterology Clinics of North America, 25, 279 298.
31. Schnitzer, T.J. Hochberg, M.C. (2002) COX-2-selective inhibitors in the treatment of arthritis. Cleveland Clinic Journal of Medicine, 69 (Suppl. 1 20 30.
32. Schnitzer, T.J., Burmester, G.R., Mysler, E., Hochberg, M.C., Doherty, M., Ehrsam, E., Gitton, X., Krammer, G., Mellein, B., Matchaba, P., Gimona, A. Hawkey, C.J. (2004) Comparison of lumiracoxib with naproxen and ibuprofen in the Therapeutic Arthritis Research and Gastrointestinal Event Trial (TARGET), reduction in ulcer complications: randomised controlled trial. Lancet, 364, 665 674.
33. Silverstein, F.E., Faich, G., Goldstein, J.L., Simon, L.S., Pincus, T., Whelton, A., Makuch, R., Eisen, G., Agrawal, N.M., Stenson, W.F., Burr, A.M., Zhao, W.W., Kent, J.D., Lefkowith, J.B., Verburg, K.M. Geis, G.S. (2000) Gastrointestinal toxicity with celecoxib vs nonsteroidal anti-inflammatory drugs for osteoarthritis and rheumatoid arthritis: the CLASS Study: a randomized controlled trial. Celecoxib Long-term Arthritis Safety Study. Journal of the American Medical Association, 284, 1247 1255.
34. Simmons, D.L., Botting, R.M. Hla, T. (2004) Cyclooxygenase isozymes: the biology of prostaglandin synthesis and inhibition. Pharmacological Reviews, 56, 387 437.
35. Steele, V.E., Hawke, E.T., Viner, J.L. Lubet, R.A. (2003) Mechanisms and applications of non-steroidal anti-inflammatory drugs in the chemoprevention of cancer. Mutation Research, 523-524, 137 144.
36. Stichtenoth, D.O. Frolich, J.C. (2003) The second generation of COX-2 inhibitors: what advantages do the newest offer Drugs, 63, 33 45.
37. Wilson, J.E., Chandrasekharan, N.V., Westover, K.D., Eager, K.B. Simmons, D.L. (2004) Determination of expression of cyclooxygenase-1 and -2 isozymes in canine tissues and their differential sensitivity to nonsteroidal anti-inflammatory drugs. American Journal of Veterinary Research, 65, 810 818.
38. Zhang, F., Engebretson, S.P., Morton, R.S., Cavanaugh, P.F., Subbaramaiah, K. Dannenberg, A.J. (2003) The overexpression of cyclo-oxygenase-2 in chronic periodontitis. Journal of the American Dental Association, 134, 861 867.