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Chemical Compound Review

refecoxib     4-(4-methylsulfonylphenyl)-3- phenyl-5H...

Synonyms: rofecoxib, Ceoxx, Vioxx, CHEMBL122, SureCN3050, ...
Kevin Horgan,  Simon,  Guglielmi,  Kruklitis, Robert Ridell,  Lipetz, Antonio Rossi,  Patrignani, Paolo Maione,  Hinz,  Arbogast, Douglas Watson, Massimo Di Maio, Marianna Alacqua, Gianluca Trifirò, Lorenzo Cavagna, Roberto Caporali, Carlo Maurizio Montecucco, Salvatore Moretti, Domenico Ugo Tari, Mariella Galdo, Achille P. Caputi, Vincenzo Arcoraci, John A. Baron,  Holzapfel, Francesco Carozza,  Brune,  Riddell,  Griffin,  Bolognese,  Capone,  Stern,  Rassen,  Moretta, Francesco Rosetti,  Baron, Robert S. Sandler,  Schnitzer, Alessandro Morabito,  Kvien,  Kapoor,  Thal, Domenico Galetta, Bettina Oxenius,  Tanaka,  Bath,  Young,  Lutz, Hui Quan,  Ouyang,  Bolognese, Santi Barbera,  Cano,  Kivitz,  Stein,  Henry, Antonio Testa,  Hawkey, Cesare Gridelli,  Brookhart,  Kaiser,  Beck, Dion Morton, Teresa Gamucci,  Quan,  Hall, Vittorio Gebbia,  Quan, Francesco Perrone,  Solomon,  Baccante,  Shapiro,  Collantes-Estevez,  Davis, Jim Bolognese, Ciro Gallo,  Sano,  Fraek, Francesco Cognetti,  Antonucci, Fortunato Ciardiello, Adolfo Favaretto,  Sandler,  Di Febbo,  Sterman,  Farlow,  Schwartz,  Johanson,  Whissell,  Morton,  Harper, Yaron Niv, Bruno Daniele,  Laine,  Sciulli,  Hochberg,  Sanders,  Neuhofer,  Bresalier, Angel Lanas,  Ricciotti,  Bombardier, Robert Bresalier, Anna Ceribelli,  Day,  Hee,  Germond,  Schneeweiss,  Oxenius,  Schnitzer,  Aisen,  Laine,  Horgan,  Schafer,  Dormann,  Lopez,  Reicin,  Loftus, Tomas J. Cook, Susan Loftus,  Wang,  Davis,  Noble,  Ferraz,  DeLong,  Jin,  Grundman, Robert Schoen,  Pfeiffer,  Albelda,  Tacconelli, Carol Burke,  Ray,  Porreca,  Fernandez-Perez,  Lanas,  Burgos-Vargas,  Thomas,  Stuppia,  Daugherty,  
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Disease relevance of rofecoxib

  • Upper gastrointestinal toxicity of rofecoxib and naproxen [1].
  • The incidence of myocardial infarction was lower among patients in the naproxen group than among those in the rofecoxib group (0.1 percent vs. 0.4 percent; relative risk, 0.2; 95 percent confidence interval, 0.1 to 0.7); the overall mortality rate and the rate of death from cardiovascular causes were similar in the two groups [2].
  • OBJECTIVE: To compare the incidence of PUBs in patients with osteoarthritis treated with rofecoxib vs NSAIDs [3].
  • METHODS: We used a systematic chemical approach to modify the structures of celecoxib and rofecoxib to produce a series of compounds that were tested for their effects on the viability of human prostate cancer PC-3 cells and their ability to induce apoptosis in these cells [4].
  • Is the demonstration of adenoma reduction with rofecoxib a pyrrhic victory [5]?
  • Among patients with a history of colorectal adenomas, the long-term use of 25 mg/day of rofecoxib was associated with an increased risk of clinically relevant upper gastrointestinal events when compared with placebo [6].
  • There was no channeling in the usage of selective COX-2 inhibitors toward patients with a high risk of GI and low risk of cardiovascular disease following the withdrawal of rofecoxib [7].

Psychiatry related information on rofecoxib


High impact information on rofecoxib


Chemical compound and disease context of rofecoxib


Biological context of rofecoxib


Anatomical context of rofecoxib


Associations of rofecoxib with other chemical compounds

  • METHODS: We randomly assigned 8076 patients who were at least 50 years of age (or at least 40 years of age and receiving long-term glucocorticoid therapy) and who had rheumatoid arthritis to receive either 50 mg of rofecoxib daily or 500 mg of naproxen twice daily [2].
  • Rofecoxib, a COX-2 inhibitor, does not inhibit human gastric mucosal prostaglandin production [28].
  • Selective inhibition of cyclooxygenase 2-dependent prostacyclin (by rofecoxib or etoricoxib) was associated with increased urinary excretion of 11-dehydro-TXB(2) in carriers of TLR4 polymorphisms, but not in wild-type, suggesting a restrainable effect of prostacyclin on platelet function in vivo in this setting [29].
  • Using celecoxib as the reference exposure showed an increase in the MI risk for rofecoxib (risk difference [RD] 1.40, 95% confidence interval [95% CI] -0.20, 3.01) and diclofenac (RD 6.07, 95% CI -0.02, 12.15) [30].
  • SUBJECTS AND METHODS: In this randomized, double-blind group study, gastrointestinal blood loss was assessed by measurement of fecal (51)chromium radioactivity during a 1-week placebo baseline period and during 4 weeks of treatment with rofecoxib (25 mg or 50 mg once daily), ibuprofen (800 mg three times daily), or placebo in 67 healthy subjects [31].
  • Neither PCI gemcitabine nor rofecoxib prolonged survival in the patients in this study [32].
  • The disappearance of rofecoxib was associated with replacement drugs such as newly marketed dexibuprofen and aceclofenac, whereas nimesulide use coincidentally decreased [33].

Gene context of rofecoxib


Analytical, diagnostic and therapeutic context of rofecoxib

  • A randomized trial of rofecoxib for the chemoprevention of colorectal adenomas [36].
  • Between Jan 1, 1999, and June 30, 2001, we did a retrospective cohort study of individuals on the expanded Tennessee Medicaid programme (TennCare), in which we assessed occurrence of serious coronary heart disease (CHD) in non-users (n=202916) and in users of rofecoxib and other NSAIDs (rofecoxib n=24 132, other n=151 728) [37].
  • After 30 days, mortality in the control group was 90%, whereas only one mouse (5%) treated with rofecoxib had died after 30 days [34].
  • In this study, we determined that inhibition of COX-2 by oral administration of Rofecoxib significantly slowed but did not cure the growth of small tumors in mesothelioma-bearing mice [38].
  • Patients who experienced increased pain on withdrawal of analgesia were randomized to receive AZD3582 125 mg, 375 mg, or 750 mg twice a day; rofecoxib 25 mg once a day; naproxen 500 mg twice a day; or placebo for 6 weeks [39].


  1. Upper gastrointestinal toxicity of rofecoxib and naproxen. Gupta, S. N. Engl. J. Med. (2001) [Pubmed]
  2. 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]
  3. Adverse upper gastrointestinal effects of rofecoxib compared with NSAIDs. Langman, M.J., Jensen, D.M., Watson, D.J., Harper, S.E., Zhao, P.L., Quan, H., Bolognese, J.A., Simon, T.J. JAMA (1999) [Pubmed]
  4. Using cyclooxygenase-2 inhibitors as molecular platforms to develop a new class of apoptosis-inducing agents. Zhu, J., Song, X., Lin, H.P., Young, D.C., Yan, S., Marquez, V.E., Chen, C.S. J. Natl. Cancer Inst. (2002) [Pubmed]
  5. Is the demonstration of adenoma reduction with rofecoxib a pyrrhic victory? Lynch, P.M. Gastroenterology (2006) [Pubmed]
  6. Peptic ulcer and bleeding events associated with rofecoxib in a 3-year colorectal adenoma chemoprevention trial. Lanas, A., Baron, J.A., Sandler, R.S., Horgan, K., Bolognese, J., Oxenius, B., Quan, H., Watson, D., Cook, T.J., Schoen, R., Burke, C., Loftus, S., Niv, Y., Ridell, R., Morton, D., Bresalier, R. Gastroenterology (2007) [Pubmed]
  7. Changes in the characteristics of patients prescribed selective cyclooxygenase 2 inhibitors after the 2004 withdrawal of rofecoxib. Setakis, E., Leufkens, H.G., van Staa, T.P. Arthritis Rheum. (2008) [Pubmed]
  8. Chronic COX-2 inhibition reduces medullary HSP70 expression and induces papillary apoptosis in dehydrated rats. Neuhofer, W., Holzapfel, K., Fraek, M.L., Ouyang, N., Lutz, J., Beck, F.X. Kidney Int. (2004) [Pubmed]
  9. Anti-inflammatory treatment with acetylsalicylate or rofecoxib is not neuroprotective in Huntington's disease transgenic mice. Norflus, F., Nanje, A., Gutekunst, C.A., Shi, G., Cohen, J., Bejarano, M., Fox, J., Ferrante, R.J., Hersch, S.M. Neurobiol. Dis. (2004) [Pubmed]
  10. The selective cyclooxygenase-2 inhibitor rofecoxib suppresses brain inflammation and protects cholinergic neurons from excitotoxic degeneration in vivo. Scali, C., Giovannini, M.G., Prosperi, C., Bellucci, A., Pepeu, G., Casamenti, F. Neuroscience (2003) [Pubmed]
  11. Psychotropic effects of COX-2 inhibitors--a possible new approach for the treatment of psychiatric disorders. Müller, N., Riedel, M., Schwarz, M.J. Pharmacopsychiatry (2004) [Pubmed]
  12. Improved control of osteoarthritis pain and self-reported health status in non-responders to celecoxib switched to rofecoxib: results of PAVIA, an open-label post-marketing survey in Spain. Collantes-Estevez, E., Fernandez-Perez, C. Current medical research and opinion. (2003) [Pubmed]
  13. Upper gastrointestinal toxicity of rofecoxib and naproxen. Delgado Fernández, M., Zambrana García, J.L., Diez García, F. N. Engl. J. Med. (2001) [Pubmed]
  14. Inhibition of angiogenesis by nonsteroidal anti-inflammatory drugs: insight into mechanisms and implications for cancer growth and ulcer healing. Jones, M.K., Wang, H., Peskar, B.M., Levin, E., Itani, R.M., Sarfeh, I.J., Tarnawski, A.S. Nat. Med. (1999) [Pubmed]
  15. Effects of rofecoxib or naproxen vs placebo on Alzheimer disease progression: a randomized controlled trial. Aisen, P.S., Schafer, K.A., Grundman, M., Pfeiffer, E., Sano, M., Davis, K.L., Farlow, M.R., Jin, S., Thomas, R.G., Thal, L.J. JAMA (2003) [Pubmed]
  16. A randomized trial comparing the effect of rofecoxib, a cyclooxygenase 2-specific inhibitor, with that of ibuprofen on the gastroduodenal mucosa of patients with osteoarthritis.Rofecoxib Osteoarthritis Endoscopy Study Group. Laine, L., Harper, S., Simon, T., Bath, R., Johanson, J., Schwartz, H., Stern, S., Quan, H., Bolognese, J. Gastroenterology (1999) [Pubmed]
  17. Rofecoxib inhibits cyclooxygenase 2 expression and activity and reduces cell proliferation in Barrett's esophagus. Kaur, B.S., Khamnehei, N., Iravani, M., Namburu, S.S., Lin, O., Triadafilopoulos, G. Gastroenterology (2002) [Pubmed]
  18. Chemoprevention of intestinal polyposis in the Apcdelta716 mouse by rofecoxib, a specific cyclooxygenase-2 inhibitor. Oshima, M., Murai, N., Kargman, S., Arguello, M., Luk, P., Kwong, E., Taketo, M.M., Evans, J.F. Cancer Res. (2001) [Pubmed]
  19. Rofecoxib, a specific inhibitor of cyclooxygenase 2, with clinical efficacy comparable with that of diclofenac sodium: results of a one-year, randomized, clinical trial in patients with osteoarthritis of the knee and hip. Rofecoxib Phase III Protocol 035 Study Group. Cannon, G.W., Caldwell, J.R., Holt, P., McLean, B., Seidenberg, B., Bolognese, J., Ehrich, E., Mukhopadhyay, S., Daniels, B. Arthritis Rheum. (2000) [Pubmed]
  20. Phase II clinical trial results involving treatment with low-dose daily oral cyclophosphamide, weekly vinblastine, and rofecoxib in patients with advanced solid tumors. Young, S.D., Whissell, M., Noble, J.C., Cano, P.O., Lopez, P.G., Germond, C.J. Clin. Cancer Res. (2006) [Pubmed]
  21. Acute tubulointerstitial nephritis associated with the selective COX-2 enzyme inhibitor, rofecoxib. Rocha, J.L., Fernández-Alonso, J. Lancet (2001) [Pubmed]
  22. Celecoxib-induced apoptosis in rat cholangiocarcinoma cells mediated by Akt inactivation and Bax translocation. Zhang, Z., Lai, G.H., Sirica, A.E. Hepatology (2004) [Pubmed]
  23. More pronounced inhibition of cyclooxygenase 2, increase in blood pressure, and reduction of heart rate by treatment with diclofenac compared with celecoxib and rofecoxib. Hinz, B., Dormann, H., Brune, K. Arthritis Rheum. (2006) [Pubmed]
  24. A selective COX-2 inhibitor suppresses chronic pancreatitis in an animal model (WBN/Kob rats): significant reduction of macrophage infiltration and fibrosis. Reding, T., Bimmler, D., Perren, A., Sun, L.K., Fortunato, F., Storni, F., Graf, R. Gut (2006) [Pubmed]
  25. Central retinal vein occlusion in a patient with rheumatoid arthritis taking rofecoxib. Meyer, C., Gähler, R. Lancet (2002) [Pubmed]
  26. The effect of the selective cyclooxygenase-2 inhibitor rofecoxib on human colorectal cancer liver metastases. Fenwick, S.W., Toogood, G.J., Lodge, J.P., Hull, M.A. Gastroenterology (2003) [Pubmed]
  27. Celecoxib exhibits the greatest potency amongst cyclooxygenase (COX) inhibitors for growth inhibition of COX-2-negative hematopoietic and epithelial cell lines. Waskewich, C., Blumenthal, R.D., Li, H., Stein, R., Goldenberg, D.M., Burton, J. Cancer Res. (2002) [Pubmed]
  28. Rofecoxib, a COX-2 inhibitor, does not inhibit human gastric mucosal prostaglandin production. Wight, N.J., Gottesdiener, K., Garlick, N.M., Atherton, C.T., Novak, S., Gertz, B.J., Calder, N.A., Cote, J., Wong, P., Dallob, A., Hawkey, C.J. Gastroenterology (2001) [Pubmed]
  29. Reduced thromboxane biosynthesis in carriers of toll-like receptor 4 polymorphisms in vivo. Patrignani, P., Di Febbo, C., Tacconelli, S., Moretta, V., Baccante, G., Sciulli, M.G., Ricciotti, E., Capone, M.L., Antonucci, I., Guglielmi, M.D., Stuppia, L., Porreca, E. Blood (2006) [Pubmed]
  30. Simultaneous assessment of short-term gastrointestinal benefits and cardiovascular risks of selective cyclooxygenase 2 inhibitors and nonselective nonsteroidal antiinflammatory drugs: an instrumental variable analysis. Schneeweiss, S., Solomon, D.H., Wang, P.S., Rassen, J., Brookhart, M.A. Arthritis Rheum. (2006) [Pubmed]
  31. A randomized trial measuring fecal blood loss after treatment with rofecoxib, ibuprofen, or placebo in healthy subjects. Hunt, R.H., Bowen, B., Mortensen, E.R., Simon, T.J., James, C., Cagliola, A., Quan, H., Bolognese, J.A. Am. J. Med. (2000) [Pubmed]
  32. Factorial phase III randomised trial of rofecoxib and prolonged constant infusion of gemcitabine in advanced non-small-cell lung cancer: the GEmcitabine-COxib in NSCLC (GECO) study. Gridelli, C., Gallo, C., Ceribelli, A., Gebbia, V., Gamucci, T., Ciardiello, F., Carozza, F., Favaretto, A., Daniele, B., Galetta, D., Barbera, S., Rosetti, F., Rossi, A., Maione, P., Cognetti, F., Testa, A., Di Maio, M., Morabito, A., Perrone, F. Lancet Oncol. (2007) [Pubmed]
  33. Prescribing pattern of drugs in the treatment of osteoarthritis in Italian general practice: the effect of rofecoxib withdrawal. Alacqua, M., Trifirò, G., Cavagna, L., Caporali, R., Montecucco, C.M., Moretti, S., Tari, D.U., Galdo, M., Caputi, A.P., Arcoraci, V. Arthritis Rheum. (2008) [Pubmed]
  34. Inhibition of cyclooxygenase-2 by rofecoxib attenuates the growth and metastatic potential of colorectal carcinoma in mice. Yao, M., Kargman, S., Lam, E.C., Kelly, C.R., Zheng, Y., Luk, P., Kwong, E., Evans, J.F., Wolfe, M.M. Cancer Res. (2003) [Pubmed]
  35. Prostaglandin E2 enhances pancreatic cancer invasiveness through an Ets-1-dependent induction of matrix metalloproteinase-2. Ito, H., Duxbury, M., Benoit, E., Clancy, T.E., Zinner, M.J., Ashley, S.W., Whang, E.E. Cancer Res. (2004) [Pubmed]
  36. A randomized trial of rofecoxib for the chemoprevention of colorectal adenomas. Baron, J.A., Sandler, R.S., Bresalier, R.S., Quan, H., Riddell, R., Lanas, A., Bolognese, J.A., Oxenius, B., Horgan, K., Loftus, S., Morton, D.G. Gastroenterology (2006) [Pubmed]
  37. COX-2 selective non-steroidal anti-inflammatory drugs and risk of serious coronary heart disease. Ray, W.A., Stein, C.M., Daugherty, J.R., Hall, K., Arbogast, P.G., Griffin, M.R. Lancet (2002) [Pubmed]
  38. Use of cyclooxygenase-2 inhibition to enhance the efficacy of immunotherapy. DeLong, P., Tanaka, T., Kruklitis, R., Henry, A.C., Kapoor, V., Kaiser, L.R., Sterman, D.H., Albelda, S.M. Cancer Res. (2003) [Pubmed]
  39. Comparison of the COX-inhibiting nitric oxide donator AZD3582 and rofecoxib in treating the signs and symptoms of Osteoarthritis of the knee. Schnitzer, T.J., Kivitz, A.J., Lipetz, R.S., Sanders, N., Hee, A. Arthritis Rheum. (2005) [Pubmed]
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