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Chemical Compound Review

Etropain     5-chloro-2-(6-methylpyridin- 3-yl)-3-(4...

Synonyms: Torcoxia, Arcoxia, Kingcox, Nucoxia, Etoricoxib, ...
 
 
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Disease relevance of Etoricoxib

 

High impact information on Etoricoxib

  • This 2-part, double-blind, placebo-controlled study was conducted to determine the safety and efficacy of etoricoxib, a COX-2 selective inhibitor, for the treatment of hemophilic arthropathy [6].
  • Evaluation of the efficacy of etoricoxib in ankylosing spondylitis: results of a fifty-two-week, randomized, controlled study [7].
  • In patients with rheumatoid arthritis, improvements in tender and swollen joint counts and patient and investigator global assessment of disease activity were significantly greater in etoricoxib than in placebo recipients in two studies [1].
  • Novel coxibs (i.e. etoricoxib, valdecoxib, parecoxib and lumiracoxib) with enhanced biochemical cyclooxygenase (COX)-2 selectivity over that of rofecoxib and celecoxib have been recently developed [8].
  • Rofecoxib and etoricoxib (100 nM) also caused a marked increase (>35%, p<0.001) in non-enzymatic generation of isoprostanes, as measured by mass spectroscopy [9].
 

Chemical compound and disease context of Etoricoxib

 

Biological context of Etoricoxib

 

Anatomical context of Etoricoxib

 

Associations of Etoricoxib with other chemical compounds

  • In squirrel monkeys, etoricoxib reversed LPS-induced pyresis by 81% within 2 h of administration at a dose of 3 mg/kg and showed no effect in a fecal 51Cr excretion model of gastropathy at 100 mg/kg/day for 5 days, in contrast to lower doses of diclofenac or naproxen [22].
  • RESULTS: In the endoscopy study, the cumulative incidence of ulcers >/=3 mm at 12 wk in the ibuprofen group (17%) was significantly higher than in the etoricoxib group (8.1%, p < 0.001); similar results were seen for ulcers >/=5 mm [4].
  • The specificity of etoricoxib for COX-2 has been found to be approximately 3-fold greater than that of rofecoxib and valdecoxib and approximately 14-fold more than celecoxib in human whole blood assays [23].
  • Here, we investigated COX-2-independent effects of etoricoxib and lumiracoxib [24].
  • Compared with oxycodone/acetaminophen patients, etoricoxib patients experienced a longer analgesic duration, had a smaller percentage requiring rescue opioids during 6 and 24 h, and required less rescue analgesia during 6 and 24 h [12].
 

Gene context of Etoricoxib

 

Analytical, diagnostic and therapeutic context of Etoricoxib

  • OBJECTIVES: To evaluate the clinical efficacy and tolerability of etoricoxib in the treatment of osteoarthritis (OA) of the knee and define the clinically active dose range for further clinical trials [2].
  • After 3 months of etoricoxib therapy, 8 of 76 (10.53%) of the study group had aggravation of their underlying IBD and stopped the drug therapy, while 68 of 76 (89.5%) completed the study [5].
  • In the pharmacokinetic/pharmacodynamic analysis (n approximately 120), there was a linear relationship between plasma etoricoxib concentrations and pain relief scores up to the maximum observed concentration, followed by a decline in plasma concentrations with persistent analgesia [26].
  • Renal effects of etoricoxib and comparator nonsteroidal anti-inflammatory drugs in controlled clinical trials [11].
  • Based on qualitative X-ray powder diffraction (XRPD) and quantitative Raman data, significant effects on the rate of hydration were observed with the addition of small amounts of amorphous etoricoxib [27].

References

  1. Etoricoxib. Cochrane, D.J., Jarvis, B., Keating, G.M. Drugs (2002) [Pubmed]
  2. Results of a randomized, dose-ranging trial of etoricoxib in patients with osteoarthritis. Gottesdiener, K., Schnitzer, T., Fisher, C., Bockow, B., Markenson, J., Ko, A., DeTora, L., Curtis, S., Geissler, L., Gertz, B.J. Rheumatology (Oxford, England) (2002) [Pubmed]
  3. Complementary studies of the gastrointestinal safety of the cyclo-oxygenase-2-selective inhibitor etoricoxib. Hunt, R.H., Harper, S., Callegari, P., Yu, C., Quan, H., Evans, J., James, C., Bowen, B., Rashid, F. Aliment. Pharmacol. Ther. (2003) [Pubmed]
  4. The gastrointestinal safety of the COX-2 selective inhibitor etoricoxib assessed by both endoscopy and analysis of upper gastrointestinal events. Hunt, R.H., Harper, S., Watson, D.J., Yu, C., Quan, H., Lee, M., Evans, J.K., Oxenius, B. Am. J. Gastroenterol. (2003) [Pubmed]
  5. The gastrointestinal safety and effect on disease activity of etoricoxib, a selective cox-2 inhibitor in inflammatory bowel diseases. El Miedany, Y., Youssef, S., Ahmed, I., El Gaafary, M. Am. J. Gastroenterol. (2006) [Pubmed]
  6. Evaluation of the efficacy and safety of etoricoxib in the treatment of hemophilic arthropathy. Tsoukas, C., Eyster, M.E., Shingo, S., Mukhopadhyay, S., Giallella, K.M., Curtis, S.P., Reicin, A.S., Melian, A. Blood (2006) [Pubmed]
  7. Evaluation of the efficacy of etoricoxib in ankylosing spondylitis: results of a fifty-two-week, randomized, controlled study. van der Heijde, D., Baraf, H.S., Ramos-Remus, C., Calin, A., Weaver, A.L., Schiff, M., James, M., Markind, J.E., Reicin, A.S., Melian, A., Dougados, M. Arthritis Rheum. (2005) [Pubmed]
  8. Clinical pharmacology of novel selective COX-2 inhibitors. Tacconelli, S., Capone, M.L., Patrignani, P. Curr. Pharm. Des. (2004) [Pubmed]
  9. Sulfone COX-2 inhibitors increase susceptibility of human LDL and plasma to oxidative modification: comparison to sulfonamide COX-2 inhibitors and NSAIDs. Walter, M.F., Jacob, R.F., Day, C.A., Dahlborg, R., Weng, Y., Mason, R.P. Atherosclerosis (2004) [Pubmed]
  10. Evaluation of the comparative efficacy of etoricoxib and ibuprofen for treatment of patients with osteoarthritis: A randomized, double-blind, placebo-controlled trial. Wiesenhutter, C.W., Boice, J.A., Ko, A., Sheldon, E.A., Murphy, F.T., Wittmer, B.A., Aversano, M.L., Reicin, A.S. Mayo Clin. Proc. (2005) [Pubmed]
  11. Renal effects of etoricoxib and comparator nonsteroidal anti-inflammatory drugs in controlled clinical trials. Curtis, S.P., Ng, J., Yu, Q., Shingo, S., Bergman, G., McCormick, C.L., Reicin, A.S. Clinical therapeutics. (2004) [Pubmed]
  12. The analgesic efficacy of etoricoxib compared with oxycodone/acetaminophen in an acute postoperative pain model: a randomized, double-blind clinical trial. Chang, D.J., Desjardins, P.J., King, T.R., Erb, T., Geba, G.P. Anesth. Analg. (2004) [Pubmed]
  13. A comparison of the therapeutic efficacy and tolerability of etoricoxib and diclofenac in patients with osteoarthritis. Zacher, J., Feldman, D., Gerli, R., Scott, D., Hou, S.M., Uebelhart, D., Rodger, I.W., Ozturk, Z.E. Current medical research and opinion. (2003) [Pubmed]
  14. Analysis of interaction between etoricoxib and tramadol against mechanical hyperalgesia of spinal cord injury in rats. Singh, V.P., Patil, C.S., Kulkarni, S.K. Life Sci. (2006) [Pubmed]
  15. Pharmacokinetics of etoricoxib in patients with renal impairment. Agrawal, N.G., Matthews, C.Z., Mazenko, R.S., Kline, W.F., Woolf, E.J., Porras, A.G., Geer, L.A., Wong, P.H., Cho, M., Cote, J., Marbury, T.C., Moncrief, J.W., Alcorn, H., Swan, S., Sack, M.R., Robson, R.A., Petty, K.J., Schwartz, J.I., Gottesdiener, K.M. Journal of clinical pharmacology. (2004) [Pubmed]
  16. Single- and multiple-dose pharmacokinetics of etoricoxib, a selective inhibitor of cyclooxygenase-2, in man. Agrawal, N.G., Porras, A.G., Matthews, C.Z., Rose, M.J., Woolf, E.J., Musser, B.J., Dynder, A.L., Mazina, K.E., Lasseter, K.C., Hunt, T.L., Schwartz, J.I., McCrea, J.B., Gottesdiener, K.M. Journal of clinical pharmacology. (2003) [Pubmed]
  17. Characterization of etoricoxib, a novel, selective COX-2 inhibitor. Dallob, A., Hawkey, C.J., Greenberg, H., Wight, N., De Schepper, P., Waldman, S., Wong, P., DeTora, L., Gertz, B., Agrawal, N., Wagner, J., Gottesdiener, K. Journal of clinical pharmacology. (2003) [Pubmed]
  18. Safety of etoricoxib, a specific cyclooxygenase-2 inhibitor, in asthmatic patients with aspirin-exacerbated respiratory disease. El Miedany, Y., Youssef, S., Ahmed, I., El Gaafary, M. Ann. Allergy Asthma Immunol. (2006) [Pubmed]
  19. Role of human liver cytochrome P4503A in the metabolism of etoricoxib, a novel cyclooxygenase-2 selective inhibitor. Kassahun, K., McIntosh, I.S., Shou, M., Walsh, D.J., Rodeheffer, C., Slaughter, D.E., Geer, L.A., Halpin, R.A., Agrawal, N., Rodrigues, A.D. Drug Metab. Dispos. (2001) [Pubmed]
  20. Absorption, metabolism, and excretion of etoricoxib, a potent and selective cyclooxygenase-2 inhibitor, in healthy male volunteers. Rodrigues, A.D., Halpin, R.A., Geer, L.A., Cui, D., Woolf, E.J., Matthews, C.Z., Gottesdiener, K.M., Larson, P.J., Lasseter, K.C., Agrawal, N.G. Drug Metab. Dispos. (2003) [Pubmed]
  21. Protective effects of etoricoxib, a selective inhibitor of cyclooxygenase-2, in experimental periodontitis in rats. Holzhausen, M., Spolidorio, D.M., Muscará, M.N., Hebling, J., Spolidorio, L.C. J. Periodont. Res. (2005) [Pubmed]
  22. Etoricoxib (MK-0663): preclinical profile and comparison with other agents that selectively inhibit cyclooxygenase-2. Riendeau, D., Percival, M.D., Brideau, C., Charleson, S., Dubé, D., Ethier, D., Falgueyret, J.P., Friesen, R.W., Gordon, R., Greig, G., Guay, J., Mancini, J., Ouellet, M., Wong, E., Xu, L., Boyce, S., Visco, D., Girard, Y., Prasit, P., Zamboni, R., Rodger, I.W., Gresser, M., Ford-Hutchinson, A.W., Young, R.N., Chan, C.C. J. Pharmacol. Exp. Ther. (2001) [Pubmed]
  23. A mechanistic perspective on the specificity and extent of COX-2 inhibition in pregnancy. Chan, V.S. Drug safety : an international journal of medical toxicology and drug experience. (2004) [Pubmed]
  24. Different COX-independent effects of the COX-2 inhibitors etoricoxib and lumiracoxib. Niederberger, E., Manderscheid, C., Geisslinger, G. Biochem. Biophys. Res. Commun. (2006) [Pubmed]
  25. Use of gastroprotective agents and discontinuations due to dyspepsia with the selective cyclooxygenase-2 inhibitor etoricoxib compared with non-selective NSAIDs. Watson, D.J., Bolognese, J.A., Yu, C., Krupa, D., Curtis, S. Current medical research and opinion. (2004) [Pubmed]
  26. Etoricoxib in acute pain associated with dental surgery: a randomized, double-blind, placebo- and active comparator-controlled dose-ranging study. Malmstrom, K., Sapre, A., Couglin, H., Agrawal, N.G., Mazenko, R.S., Fricke, J.R. Clinical therapeutics. (2004) [Pubmed]
  27. Investigating the hydrate conversion propensity of different etoricoxib lots. Dalton, C.R., Clas, S.D., Singh, J., Khougaz, K., Bilbeisi, R. Journal of pharmaceutical sciences. (2006) [Pubmed]
 
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