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Chemical Compound Review

NAPROXEN     (2S)-2-(6-methoxynaphthalen- 2-yl)propanoic...

Synonyms: Anexopen, Artrixen, Artroxen, Bipronyl, Clinosyn, ...
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Disease relevance of Naprosyn


Psychiatry related information on Naprosyn


High impact information on Naprosyn


Chemical compound and disease context of Naprosyn


Biological context of Naprosyn


Anatomical context of Naprosyn


Associations of Naprosyn with other chemical compounds


Gene context of Naprosyn

  • Because neither tenidap nor naproxen inhibited SAA synthesis by cytokine-stimulated Hep3B cells and because they differ most significantly in their effect on IL-6 production, the results support a role for IL-6 in the continued stimulation of SAA production during RA [31].
  • Tenidap inhibited production of IL-6 greater than TNF greater than IL-1; the effect of naproxen on production of all three cytokines was lesser and least on IL-6 [31].
  • Dual COX-1 and COX-2 inhibition with naproxen was demonstrated to be effective for the treatment of painful TMJs, as seen by significant improvement in clinical signs and symptoms of TMJ DD with reduction compared to celecoxib and placebo [32].
  • Naphthalene metabolism by CYP3A4 and naproxen metabolism by CYP2C9 demonstrated nonhyperbolic enzyme kinetics suggestive of a low Km, low Vmax component for the first substrate molecule and a high Km, high Vmax component for the second substrate molecule [33].
  • In contrast, standard NSAIDs, such as naproxen, inhibited both COX isoforms to an equal degree at therapeutically relevant concentrations [34].

Analytical, diagnostic and therapeutic context of Naprosyn


  1. Comparison of upper gastrointestinal toxicity of rofecoxib and naproxen in patients with rheumatoid arthritis. VIGOR Study Group. Bombardier, C., Laine, L., Reicin, A., Shapiro, D., Burgos-Vargas, R., Davis, B., Day, R., Ferraz, M.B., Hawkey, C.J., Hochberg, M.C., Kvien, T.K., Schnitzer, T.J. N. Engl. J. Med. (2000) [Pubmed]
  2. Preventing recurrent upper gastrointestinal bleeding in patients with Helicobacter pylori infection who are taking low-dose aspirin or naproxen. Chan, F.K., Chung, S.C., Suen, B.Y., Lee, Y.T., Leung, W.K., Leung, V.K., Wu, J.C., Lau, J.Y., Hui, Y., Lai, M.S., Chan, H.L., Sung, J.J. N. Engl. J. Med. (2001) [Pubmed]
  3. Multiple myeloma in naproxen-induced acute renal failure. Wu, M.J., Kumar, K.S., Kulkarni, G., Kaiser, H. N. Engl. J. Med. (1987) [Pubmed]
  4. Pulmonary infiltrates associated with naproxen. Buscaglia, A.J., Cowden, F.E., Brill, H. JAMA (1984) [Pubmed]
  5. Anti-inflammatory and upper gastrointestinal effects of celecoxib in rheumatoid arthritis: a randomized controlled trial. Simon, L.S., Weaver, A.L., Graham, D.Y., Kivitz, A.J., Lipsky, P.E., Hubbard, R.C., Isakson, P.C., Verburg, K.M., Yu, S.S., Zhao, W.W., Geis, G.S. JAMA (1999) [Pubmed]
  6. Amelioration of ergotamine withdrawal symptoms with naproxen. Mathew, N.T. Headache. (1987) [Pubmed]
  7. The effect of alcohol abuse on the risk of NSAID-related gastrointestinal events. Neutel, C.I., Appel, W.C. Annals of epidemiology. (2000) [Pubmed]
  8. Meta-analysis: cardiovascular events associated with nonsteroidal anti-inflammatory drugs. Salpeter, S.R., Gregor, P., Ormiston, T.M., Whitlock, R., Raina, P., Thabane, L., Topol, E.J. Am. J. Med. (2006) [Pubmed]
  9. The analgesic and anti-inflammatory profile of (+/-)-5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2a]pyrrole-1-carboxylic acid (RS-37619). Rooks, W.H., Tomolonis, A.J., Maloney, P.J., Wallach, M.B., Schuler, M.E. Agents Actions (1982) [Pubmed]
  10. Factors influencing adolescents' responses to regimens of naproxen for dysmenorrhea. DuRant, R.H., Jay, M.S., Shoffitt, T., Linder, C.W., Taylor, W. Am. J. Dis. Child. (1985) [Pubmed]
  11. Famotidine for the prevention of gastric and duodenal ulcers caused by nonsteroidal antiinflammatory drugs. Taha, A.S., Hudson, N., Hawkey, C.J., Swannell, A.J., Trye, P.N., Cottrell, J., Mann, S.G., Simon, T.J., Sturrock, R.D., Russell, R.I. N. Engl. J. Med. (1996) [Pubmed]
  12. Possible naproxen-induced relapse of subacute cutaneous lupus erythematosus. Parodi, A., Rivara, G., Guarrera, M. JAMA (1992) [Pubmed]
  13. Naproxen and agranulocytosis. Nygard, N., Starkebaum, G. JAMA (1987) [Pubmed]
  14. Sulindac. A potentially renal-sparing nonsteroidal anti-inflammatory drug. Bunning, R.D., Barth, W.F. JAMA (1982) [Pubmed]
  15. Risks of bleeding peptic ulcer associated with individual non-steroidal anti-inflammatory drugs. Langman, M.J., Weil, J., Wainwright, P., Lawson, D.H., Rawlins, M.D., Logan, R.F., Murphy, M., Vessey, M.P., Colin-Jones, D.G. Lancet (1994) [Pubmed]
  16. Prevention of NSAID-induced gastric ulcer with misoprostol: multicentre, double-blind, placebo-controlled trial. Graham, D.Y., Agrawal, N.M., Roth, S.H. Lancet (1988) [Pubmed]
  17. Duodenal and gastric ulcer prevention with misoprostol in arthritis patients taking NSAIDs. Misoprostol Study Group. Graham, D.Y., White, R.H., Moreland, L.W., Schubert, T.T., Katz, R., Jaszewski, R., Tindall, E., Triadafilopoulos, G., Stromatt, S.C., Teoh, L.S. Ann. Intern. Med. (1993) [Pubmed]
  18. Effects of naproxen on experimental rhinovirus colds. A randomized, double-blind, controlled trial. Sperber, S.J., Hendley, J.O., Hayden, F.G., Riker, D.K., Sorrentino, J.V., Gwaltney, J.M. Ann. Intern. Med. (1992) [Pubmed]
  19. Effect of non-steroidal anti-inflammatory drugs on control of hypertension by beta-blockers and diuretics. Wong, D.G., Spence, J.D., Lamki, L., Freeman, D., McDonald, J.W. Lancet (1986) [Pubmed]
  20. Late phase of nitroglycerin-induced coronary vasodilatation blunted by inhibition of prostaglandin synthesis. Trimarco, B., Cuocolo, A., Van Dorne, D., Ricciardelli, B., Volpe, M., De Simone, A., Condorelli, M. Circulation (1985) [Pubmed]
  21. Effect of inhibitors of prostaglandin synthesis on induced diuresis in cirrhosis. Mirouze, D., Zipser, R.D., Reynolds, T.B. Hepatology (1983) [Pubmed]
  22. Lipocortin 1 mediates dexamethasone-induced growth arrest of the A549 lung adenocarcinoma cell line. Croxtall, J.D., Flower, R.J. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  23. Targeting naproxen coupled to human serum albumin to nonparenchymal cells reduces endotoxin-induced mortality in rats with biliary cirrhosis. Albrecht, C., Meijer, D.K., Lebbe, C., Sägesser, H., Melgert, B.N., Poelstra, K., Reichen, J. Hepatology (1997) [Pubmed]
  24. Immunomodulatory effects of treatment with naproxen in patients with rheumatic disease. Ceuppens, J.L., Robaeys, G., Verdickt, W., Vertessen, S., Deckmyn, H., Dequeker, J. Arthritis Rheum. (1986) [Pubmed]
  25. Effects of naproxen on connective tissue changes in the adjuvant arthritic rat. Ackerman, N.R., Rooks, W.H., Shott, L., Genant, H., Maloney, P., West, E. Arthritis Rheum. (1979) [Pubmed]
  26. Bradykinin-stimulated electrolyte secretion in rabbit and guinea pig intestine. Involvement of arachidonic acid metabolites. Musch, M.W., Kachur, J.F., Miller, R.J., Field, M., Stoff, J.S. J. Clin. Invest. (1983) [Pubmed]
  27. Randomised trial of eradication of Helicobacter pylori before non-steroidal anti-inflammatory drug therapy to prevent peptic ulcers. Chan, F.K., Sung, J.J., Chung, S.C., To, K.F., Yung, M.Y., Leung, V.K., Lee, Y.T., Chan, C.S., Li, E.K., Woo, J. Lancet (1997) [Pubmed]
  28. Coronary flow regulation in patients with ischemic heart disease: release of purines and prostacyclin and the effect of inhibitors of prostaglandin formation. Edlund, A., Berglund, B., van Dorne, D., Kaijser, L., Nowak, J., Patrono, C., Sollevi, A., Wennmalm, A. Circulation (1985) [Pubmed]
  29. Selectivity of nonsteroidal antiinflammatory drugs as inhibitors of constitutive and inducible cyclooxygenase. Mitchell, J.A., Akarasereenont, P., Thiemermann, C., Flower, R.J., Vane, J.R. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  30. Sensitivity of a health status measure to short-term clinical changes in arthritis. Anderson, J.J., Firschein, H.E., Meenan, R.F. Arthritis Rheum. (1989) [Pubmed]
  31. Modification of proinflammatory cytokine production by the antirheumatic agents tenidap and naproxen. A possible correlate with clinical acute phase response. Sipe, J.D., Bartle, L.M., Loose, L.D. J. Immunol. (1992) [Pubmed]
  32. Treatment of painful temporomandibular joints with a cyclooxygenase-2 inhibitor: a randomized placebo-controlled comparison of celecoxib to naproxen. Ta, L.E., Dionne, R.A. Pain (2004) [Pubmed]
  33. Evaluation of atypical cytochrome P450 kinetics with two-substrate models: evidence that multiple substrates can simultaneously bind to cytochrome P450 active sites. Korzekwa, K.R., Krishnamachary, N., Shou, M., Ogai, A., Parise, R.A., Rettie, A.E., Gonzalez, F.J., Tracy, T.S. Biochemistry (1998) [Pubmed]
  34. Differentiating among nonsteroidal antiinflammatory drugs by pharmacokinetic and pharmacodynamic profiles. Fenner, H. Semin. Arthritis Rheum. (1997) [Pubmed]
  35. Risks of clinically significant upper gastrointestinal events with etodolac and naproxen: a historical cohort analysis. Weideman, R.A., Kelly, K.C., Kazi, S., Cung, A., Roberts, K.W., Smith, H.J., Sarosi, G.A., Little, B.B., Cryer, B. Gastroenterology (2004) [Pubmed]
  36. Tramadol allows reduction of naproxen dose among patients with naproxen-responsive osteoarthritis pain: a randomized, double-blind, placebo-controlled study. Schnitzer, T.J., Kamin, M., Olson, W.H. Arthritis Rheum. (1999) [Pubmed]
  37. FDA Arthritis Advisory Committee Meeting: juvenile rheumatoid arthritis drug evaluation guidelines; over-the-counter naproxen? Paulus, H.E. Arthritis Rheum. (1994) [Pubmed]
  38. Selective inhibition of COX-2 in humans is associated with less gastrointestinal injury: a comparison of nimesulide and naproxen. Shah, A.A., Thjodleifsson, B., Murray, F.E., Kay, E., Barry, M., Sigthorsson, G., Gudjonsson, H., Oddsson, E., Price, A.B., Fitzgerald, D.J., Bjarnason, I. Gut (2001) [Pubmed]
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