Evolution of nonsteroidal anti-inflammatory drugs (NSAIDs): Cyclooxygenase (COX) inhibition and beyond

Journal of Pharmacy and Pharmaceutical Sciences

Volumn 11, Issue 2, 2008, Pages

  Praveen Rao, P N ^a,c   Knaus, Edward E ^b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF ALBERTA   (Canada)

^c UNIVERSITY OF WATERLOO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 69949158726     PISSN: None     EISSN: 14821826     Source Type: Journal    
DOI: None     Document Type: Article

References (145)

1. J. R. Vane. The fight against rheumatism: from willow bark to COX-1 sparing drugs. J Physiol Pharmacol, 51:573-586, 2000 and reference cited therein.
2. J. R. Vane. Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs. Nat New Biol, 43:232-235, 1971.
3. J. R. Vane. The mode of action of aspirin and similar compounds. J Allergy Clin Immunol, 58:691-712, 1976.
4. S. Moncada, S. H. Ferreira and J. R. Vane. Prostaglandins, aspirin-like drugs and the oedema of inflammation. Nature, 246:217-219, 1973.
5. R. Tamblyn, L. Berkson, W. D. Dauphinee, D. Gayton, R. Grad, A. Huang, L. Isaac, P. McLeod, and L. Snell. Unnecessary prescribing of NSAIDs and the management of NSAIDrelated gastropathy in medical practice. Ann Intern Med, 127:429-438, (1997) and references cited therein.
6. J. L. Masferrer, B. S. Zweifel, K. Seibert and P. Needleman. Selective regulation of cellular cyclooxygenase by dexamethasone and endotoxin in mice. J Clin Invest, 86:1375-1379, 1990.
7. W. L. Xie, J. G. Chipman, D. L. Robertson, R. L. Erikson and D. L. Simmons. Expression of a mitogen-responsive gene encoding prostaglandin synthase is regulated by mRNA splicing. Proc Natl Acad Sci USA, 88:2692-2696, 1991.
8. D. A. Kujubu, and H. R. Herschman. Dexamethasone inhibits mitogen induction of the TIS10 prostaglandin synthase/cyclooxygenase gene. J Biol Chem, 267:7991-7994, 1992.
9. E. A. Meade, W. L. Smith and D. L. DeWitt. Differential inhibition of prostaglandin endoperoxide synthase (cyclooxygenase) isozymes by aspirin and other non-steroidal anti-inflammatory drugs. J Biol Chem, 268:6610-6614, 1993.
10. J. R. Vane, Y. S. Bakhle and R. M. Botting. Cyclooxygenases 1 and 2. Ann Rev Pharmacol Toxicol, 38:97-120, 1998 and references cited therein.
11. G. A. Fitzgerald and C. Patrono. The coxibs, selective inhibitors of cyclooxygenase-2. N Eng J Med, 345:433-442, 2001.
12. T. D. Penning, J. J. Talley, S. R. Bertenshaw, J. S. Carter, P. W. Collins, S. Docter, M. J. Graneto, L. F. Lee, J. W. Malecha, J. M. Miyashiro, R. S. Rogers, D. J. Rogier, S. S. Yu, G. D. Anderson, E. G. Burton, J. N. Cogburn, S. A. Gregory, C. M. Koboldt, W. E. Perkins, K. Seibert, A. W. Veenhuizen, Y. Y. Zhang and P. C. Isakson. Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1Hpyrazol-1-yl]benzenesulfonamide (SC-58635, celecoxib). J Med Chem, 40:1347-1365, 1997.
13. P. Prasit, Z. Wang, C. Brideau, C. C. Chan, S. Charleson, W. Cromlish, D. Ethier, J. F. Evans, A. W. Ford-Hutchinson, J. Y. Gauthier, R. Gordon, J. Guay, M. Gresser, S. Kargman, B. Kennedy, Y. Leblanc, S. Leger, J. Mancini, G. P. O'Neill, M. Ouellet, M. D. Percival, H. Perrier, D. Riendeau, I. Rodger, R. Zamboni, S. Boyce, N. Rupniak, M. Forrest, D. Visco and D. Patrick. The discovery of rofecoxib, [MK 966, VIOXX, 4-(4'-methylsulfonylphenyl)-3-phenyl-2(5H)-furanone], an orally active cyclooxygenase-2 inhibitor. Bioorg Med Chem Lett, 9:1773-1778, 1999.
14. G. A. Fitzgerald. COX-2 and beyond: Approaches to prostaglandin inhibition in human disease. Nat Rev Drug Dis, 2:879-890, 2003.
15. I. Melnikova. Future of COX-2 inhibitors. Nat Rev Drug Dis, 4:453-454, 2005.
16. D. Mukherjee, S. E. Nissen and E. J. Topol. Risk of cardiovascular events associated with selective COX-2 inhibitors. JAMA, 286:954-959, 2001 and references cited therein.
17. D. H. Solomon, S. Schneeweiss, R. J. Glynn, Y. Kiyota, R. Levin, H. Mogun and J. Avorn. Relationship between selective cyclooxygenase-2 inhibitors and acute myocardial infarction in older adults. Circulation, 109:2068-2073, 2004.
18. R. S. Bresalier, R. S. Sandler, H. Quan, J. A. Bolognese, B. Oxenius, K. Horgan, C. Lines, R. Riddell, D. Morton, A. Lanas, M. A. Konstam and J. A. Baron. Cardiovascular events associated with rofecoxib in a colorectal adenoma chemoprevention trial. N Engl J Med, 352:1092-1102, 2005.
19. S. D. Solomon, J. J. McMurray, M. A. Pfeffer, J. Wittes, R. Fowler, P. Finn, W. F. Anderson, A. Zauber, E. Hawk and M. Bertagnolli. Cardiovascular risk associated with celecoxib in a clinical trial for colorectal adenoma prevention. N Engl J Med, 352:1071-1080, 2005.
20. http://www.merck.com/newsroom/vioxx/
21. J.-M. Dogné, C. T. Supuran and D. Pratico. Adverse cardiovascular effects of the coxibs. J Med Chem, 48:2251-2257, 2005.
22. http://www.fda.gov/cder/drug/infopage/COX2/default.htm
23. R. Watson. European medicines agency gives favorable ruling on NSAIDs. BMJ, 333:873, 2006.
24. C. D. Furberg. Decision by regulatory agencies: are they evidence-based?. Trials, 8:13, 2007.
25. E. M. Antman, J. S. Bennett, A. Daugherty, C. Furberg, H. Roberts and K. A. Taubert. Use of nonsteroidal antiinflammatory drugs: an update for clinicians: a scientific statement from the american heart association. Circulation, 115:1634-1642, 2007.
26. Abramovitz, M., Metters, K.M. Prostanoid receptors. Ann. Rep. Med. Chem., 33:223-231, 1998.
27. W. L. Smith, D. L. DeWitt and R. M. Garavito. Cyclooxygenases: structural, cellular, and molecular biology. Ann Rev Biochem, 69:145-182, 2000.
28. T. Miyamoto, M. Ogino, S. Yamamoto and O. Hayaishin. Purification of prostaglandin endoperoxide synthetase from bovine vesicular gland microsomes. J Biol Chem, 259:2629-2636, 1976.
29. D. L. DeWitt and W. L. Smith. Primary structure of prostaglandin G/H synthase from sheep vesicular gland determined from the complementary DNA sequence. Proc Natl Acad Sci USA, 85:1412-1416, 1988.
30. J. P. Merlie, D. Fagan, J. Mudd and P. Needleman. Isolation and characterization of the complementary DNA for sheep seminal vesicle prostaglandin endoperoxide synthase (cyclooxygenase). J Biol Chem, 263:3550-3553, 1988.
31. C. Yokoyama, T. Takai and T. Tanabe. Primary structure of sheep prostaglandin endoperoxide synthase deduced from cDNA sequence. FEBS Lett, 231:347-351, 1988.
32. D. Picot, P. J. Loll and R. M. Garavito. The xray crystal structure of the membrane protein prostaglandin H2 synthase-1. Nature, 367:243-249, 1994.
33. W. L. Smith and D. L. DeWitt. Prostaglandin endoperoxide H synthases-1 and-2. Adv Immunol, 62:167-215, (1996).
34. H. Lim, B. C. Paria, S. K. Das, J. E. Dinchuk, R. Langenbach, J. M. Trzaskos and S. K. Dey. Multiple female reproductive failures in cyclooxygenase-2 deficient mice. Cell, 91:197-208, 1997.
35. H. F. Cheng, J. L. Wang, M. Z. Zhang, Y. Miyazaki, I. Ichikawa, J. A. McKanna and R. C. Harris. Angiotensin II attenuates renal cortical cyclooxygenase-2 expression. J Clin Invest, 103:953-961, 1999.
36. C. D. Breder, D. L. DeWitt and R. P. Kraig. Characterization of inducible cyclooxygenase in rat brain. J Comp Neurol, 355:296-315, 1995.
37. C. C. Pilbeam, P. M. Fall, C. B. Alander and L. G. Raisz. Differential effects of nonsteroidal antiinflammatory drugs on constitutive and inducible prostglandin G/H synthase in cultured bone cells. J Bone Miner Res, 12:1198-1203, 1997.
38. M. C. Allison, A. G. Howatson, C. J. Torrance, F. D. Lee and R. L. Russel. Gastroinestinal damage associated with the use of nonsteroidal antiiflammatory drugs. N Engl J Med, 327, 749-754, 1992.
39. C. E. Eberhart and R. N. DuBois. Eicosanoids and gastrointestinal tract. Gastroenterology, 109:285-301, 1995.
40. C. J. Smith, Y. Zhang, C. M. Koboldt, J. Muhammad, B. S. Zweifel, A. Shaffer, J. J. Talley, J. L. Masferrer, K. Seibert and P. C. Isakson. Pharmacological analysis of cyclooxygenase-1 in inflammation. Proc Natl Acad Sci USA, 95:13313-13318, 1998.
41. S. H. Lee, E. Soyoola, P. Chanmungam, S. Hart, W. Sun, H. Zhong, S. Liou, D. Simmons and D. Hwang. Selective expression of mitogeninducible cyclooxygenase in macrophages stimulated with lipopolysaccharide. J Biol Chem, 267:25943-25948, 1992.
42. K. Seibert, Y. Hang, K. Leahy, S. Hauser, J. Masferrer, W. Perkins, L. Lee and P. Isakson. Pharmacological and biochemical demonstration of the role of cyclooxygenase-2 in inflammation and pain. Proc Natl Acad Sci USA, 91:12013-12017, 1994.
43. P. Davies, P. J. Bailey, M. M. Goldenberg, A. W. Ford-Hutchinson. The role of arachidonic acid oxygenation products in pain and inflammation. Ann Rev Immunol, 2:335-357, 1984.
44. S. Karman, S. Charleson, M. Cartwright, J. Frank, D. Riendeau, J. Mancini, J. Evans and G. O'Neill. Characterization of prostaglandin G/H synthase 1 and 2 in rat, dog, monkey and human gastrointestinal tracts. Gastroenterology, 111:445-454, 1996.
45. K. C. Zimmermann, M. Sarbia, K. Schor and A. A. Weber. Constitutive cyclooxygenase-2 expression in healthy human and rabbit gastric mucosa. Mol Pharmacol, 54:536-540, 1998.
46. H. Mizuno, C. Sakamoto, K. Matsuda, K. Wada, T. Uchida, H. Noguchi, T. Akamatsu and M. Kasuga. Induction of cyclooxygenase-2 in gastric mucosal lesions and its inhibition by specific antagonist delays healing in mice. Gastroenterology, 112:387-397, 1997.
47. C. Bombardier, L. Laine, A. Reicin, D. Shapiro, R. Burgos-Vargas, B. Davis, R. Day, M. B. Ferraz, C. J. Hawkey, M. C. Hochberg, T. K. Kvien and T. J. Schnitzer. VIGOR Study Group. Comparison of upper gastrointestinal toxicity of rofecoxib and naproxen in patients with rheumatoid arthritis. N Engl J Med, 343:1520-1528, 2000.
48. F. E. Silverstein, G. Faich, J. L. Goldstein, L. S. Simon, T. Pincus, A. Whelton, R/ Makuch, G. Eisen, N. M. Agrawal, W. F. Stenson, A. M. Burr, W. W. Zhao, J. D. Kent, J. B. Lefkowith, K. M. Verburg and G. S. Geis. Gastrointestinal toxicity with celecoxib vs nonsteroidal antiinflammatory drugs for osteoarthritis and rheumatoid arthritis: the CLASS study: A randomized controlled trial. JAMA, 284:1247-1255, 2000.
49. T. J. Schnitzer, G. R. Burmester, E. Mysler, M. C. Hochberg, M. Doherty, E. Ehrsam, X. Gitton, G. Krammer, B. Mellein, P. Matchaba, A. Gimona, and C. J. Hawkey. TARGET Study Group. 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, 2004.
50. M. Katori and M. Majima. Cyclooxygenase-2: its rich diversity roles and possible application of its selective inhibitors. Inflamm Res 49:367-392, 2000.
51. J. E. Dinchuk, B. D. Car, R. J. Focht, J. J. Johnston, B. D. Jaffee, M. B. Covington, N. Contel, V. M. Eng, R. J. Collins, P. M. Czerniak, S. A. Gorry and J. M. Trzaskos. Renal abnormality and an altered inflammatory response in mice lacking cyclooxygenase-II. Nature, 378:406-409, 1995.
52. S. G. Morham, R. Lagenbach, C. D. Loftin, H. F. Tiano and N. O. Vouloumanos. Prostaglandin synthase 2 gene disruption causes severe renal pathology in mouse. Cell, 83:473-482, 1995.
53. W. Ye, H. Zhang, E. Hillas, D. E. Kohan, R. L. Miller, R. D. Nelson, M. Honeggar and T. Yang. Expression and function of COX isoforms in renal medulla: evidence for regulation of salt sensitivity and blood pressure. Am J Renal Physiol, 290:F542-F549, 2006.
54. J. Zhang, E. L. Ding and Y. Song. Adverse effects of cyclooxygenase 2 inhibitors on renal and arrhythmia events: meta-analysis of randomized trials. JAMA, 296:1619-1632, 2006.
55. R. C. Harris and M. D. Breyer. Update on cyclooxygenase-2 inhibitors. Clin J Am Soc Nephrol,1:236-245, 2006.
56. B. F. McAdam, F. Catella-Lawson, I. A. Mardini, S. Kapoor, J. A. Lawson and G. A. FitzGerald. Systemic biosynthesis of prostacyclin by cyclooxygenase (COX)-2: the human pharmacology of a selective inhibitor of COX-2. Proc Natl Acad Sci USA, 96:272-277, 1999.
57. C. D. Loftin, D. B. Trivedi, H. F. Tiano, J. A. Clark, S. G. Morham, M. D. Breyer, M. Nguyen, B. M. Hawkins, J. L. Golet, O. Smithies, B. H. Koller and R. Lagenbach. Failure of ductus arteiosus closure and remodeling in neonatal mice deficient in cyclooxygenase-1 and cycloxygenase-2. Proc Natl Acad Sci USA, 98:1059-1064, 2001.
58. S. R. Adderley and D. J. FitzGerald. Oxidative damage of cardiomyocytes is limited by extracellular regulated kinases 1/2 mediated induction of cyclooxygenanse-2. J Biol Chem, 274:5038-5046, 1999.
59. J. A. Mitchell and T. D. Warner. COX isoforms in the cardiovascular system: understanding the activities of nonsteroidal anti-inflammatory drugs. Nat Rev Drug Dis, 5:75-86, 2006.
60. Y. Cheng, M. Wang, Y. Yu, J. Lawson, C. D. Funk and G. A. Fitzgerald. Cyclooxygenases, microsomal prostaglandin E synthase-1, and cardiovascular function. J Clin Invest, 116:1391-1399, 2006.
61. W. R. Waddell and R. W. Loughry. Sulindac for polyposis of the colon. J Surg Oncol, 24: 83-87, 1983.
62. S. Kanaoka, T. Takai and K. Yoshida. Cyclooxygenase-2 and tumor biology. Adv Clin Chem, 43:59-78, 2007.
63. J. X. Zhu, X. Q. Song, H. P. Lin, D. C. Young, S. Q. Yan, V. E. Marquez and C. S. Chen. Using cyclooxygenase-2 inhibitors as molecular platforms to develop a new class of apoptosisinducing agents. J Natl Cancer Inst, 95:1745-1757, 2002.
64. S. Grösch, T. J. Maier, S. Schiffmann and G. Geisslinger. Cyclooxygenase-2 (COX-2)-independent anticarcinogenic effects of selective COX-2 inhibitors. J Natl Cancer Inst, 98:736-747, 2006.
65. A. L. Hsu, T. T. Ching, D. S. Wang, X. Song, V. M. Rangnekar and C. S. Chen. The cyclooxygenase-2 inhibitor celecoxib induces apoptosis by blocking akt activation in human prostate cancer cells independently of bcl-2. J Biol Chem, 275:1397-1403, 2000.
66. Z. Liao, K. A. Mason and L. Milas. Cyclooxygenase-2 and its inhibition in cancer: is there a role?. Drugs, 67:821-845, 2007.
67. R. S. Bresalier, R. S. Sandler, H. Quan, J. A. Bolognese, B. Oxenius, K. Horgan, C. Lines, R. Riddell, D. Morton and A. Lanas. Cardiovascular events associated with rofecoxib in a colorectal adenoma chemoprevention trial. N Engl J Med, 352:1092-1102, 2005.
68. J. C. Breitner, K. A. Welsh, M. J. Helms, P. C. Gaskell, B. A. Gau, A. D. Roses, M. A. Pericak-Vance and A. M. Saunder. Delayed onset of Alzheimer's disease with nonsteroidal antiinflammatory and histamine H2 blocking drugs. Neurobiol Aging, 16:523-530, 1995.
69. T. A. Sandson and O. Felician. The potential application of cyclo-oxygenase type 2 inhibitors to Alzheimer's disease. Expert Opin Investig Drugs, 7:519-26, 1998.
70. P. S. Aisen, K. A. Schafer, M. Grundman, E. Pfeiffer, M. Sano, K. L. Davis, M. R. Farlow, S. Jin, R. G. Thomas and L. J. Thal. Effects of rofecoxib or naproxen vs placebo on Alzheimer's disease progression: a randomized controlled trial. JAMA, 289:2819-2826, 2003.
71. L. A. Kotilinek, M. A. Westerman, Q. Wang, K. Panizzon, G. P. Lim, A. Simonyi, S. Lesne, A. Falinska, L. H. Younkin, S. G. Younkin, M. Rowan, J. Cleary, R. A. Wallis, G. Y. Sun, G. Cole, S. Frautschy, R. Anwyl and K. H. Ashe. Cyclooxygenase-2 inhibition improves amyloid-{beta}-mediated suppression of memory and synaptic plasticity. Brain, 131:651-664, 2008.
72. L. Ho, W. Qin, B. S. Stetka and G. M. Pasinetti. Is there a future for cyclo-oxygenase inhibitors in Alzheimer's disease? CNS Drugs, 20:85-98, 2006.
73. Z. H. Feng, T. G. Wang, D. D. Li, P. Fung, B. C. Wilson, B. Liu, S. F. Ali, R. Lagenbach and J. S. Hong. Cyclooxygenase-2 deficient mice are resistant to 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced damage of dopaminergic neurons in the substantia nigra. Neurosci Lett, 329:354-358 2002.
74. P. Teismann, K. Tieu, D. K. Choi, D. C. Wu, A/ Naini, S. Hunot, M. Vila, V. Jackson-Lewis and S. Przedborski. Cyclooxygenase-2 is instrumental in Parkinson's disease neurodegeneration. Proc Natl Acad Sci USA, 100:5473-5478, 2003.
75. A. B. Reksidler, M. M. Lima, S. M. Zanata, H. B. Machado, C. da Cunha, R. Andreatini, S. Tufik and M. A. Vital. The COX-2 inhibitor parecoxib produces neuroprotective effects in MPTP-lesioned rats. Eur J Pharmacol, 560:163-175, 2007.
76. N. V. Chandrasekharan, H. Dai, K. L. Roos, N. K. Evanson, J. Tomsik, T. S. Elton and D. L. Simmons. COX-3, a cyclooxygenase-1 variant inhibited by acetaminophen and other analgesic/antipyretic drugs: cloning, structure and expression. Proc Natl Acad Sci USA, 99:13926-13931, 2002.
77. R. M. Botting. Mechanism of action of acetaminophen: is there a cyclooxygenase 3? Clin Infect Dis, 31:S202-S210, 2000.
78. B. Kis, J. A. Snipes and D. W. Busija. Acetaminophen and the cyclooxygenase-3 puzzle: sorting out facts, fictions, and uncertainties. J Pharmacol Exp Ther, 315:1-7, 2005.
79. B. Hinz, O. Cheremina and K. Brune. Acetaminophen (paracetamol) is a selective cyclooxygenase-2 inhibitor in man. FASEB J, 22:383-390, 2008.
80. C. Luong, A. Miller, J. Barnett, J. Chow, C. Ramesha and M. F. Browner. Flexibility of the NSAID binding site in the structure of human cyclooxygenase-2. Nat Struct Biol, 3:927-933, 1996.
81. R. Kurumbail, A. Stevens, J. Gierse, J. McDonald, R. A. Stegeman, J. Y. Pak, D. Gildehaus, J. M. Miyashiro, T. D. Penning, K. Seibert, P. C. Isakson and W. C. Stallings. Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents. Nature, 384:644-648, 1996.
82. D. K. Bhattacharya, M. Lecomte, C. J. Rieke, R. M. Garavito and W. L. Smith. Involvement of arginine 120, glutamate 524 and tyrosine 355 in the binding of arachidonate and 2-phenylpropionic acid inhibitors to the cyclooxygenase active site of ovine prostglandin endoperoxide H synthase-1. J Biol Chem, 271, 2179-2184, 1996.
83. J. A. Mancini, D. Riendeau, J. P. Falgueyret, P. J. Vickers and G. P. O'Neill. Arginine 120 of prostaglandin G/H synthase-1 is required for the inhibition by nonsteroidal anti-inflammatory drugs containing a carboxylic acid moiety. J Biol Chem, 270, 29372-29377, 1995.
84. M. Pairet and J. van Ryn. Experimental models used to investigate the differential inhibition of cyclooxygenase-1 and cyclooxygenase-2 by non-steroidal-anti-inflammatory drugs. Inflamm Res, S-93-S101, 1998.
85. D. Riendeau, S. Charleson, W. Cromlish, J. A. Mancini, E. Wong and J. Guay. Comparison of the cyclooxygenase-1 inhibitory properties of nonsteroidal anti-inflammatory drugs (NSAIDs) and selective COX-2 inhibitors, using sensitive microsomal and platelet assays. Can J Phys Pharmacol, 75:1088-1095, 1997.
86. T. D. Warner, F. Giuliano, I. Vojnovic, A. Bukasa, J. A. Mitchell and J. R. Vane. Nonsteroid drug selectivities for cyclooxygenase-1 rather than cyclo-oxygenase-2 are associated with human gastrointestinal toxicity: a full in vitro analysis. Proc Natl Acad Sci USA, 96:7563-7568, 1999.
87. R. W. Friesen, C. Brideau, C. C. Chan, S. Charleson, D. Deschenes, D. Dube, D. Ethier, R. Fortin, J. Y. Gauthier, Y. Girard, R. Gordon, G. M. Greig, D. Riendeau, C. Savoie, Z. Wang, E. Wong, D. Visco, L. J. Xu and R. N. Young. 2-Pyridinyl-3-(4-methylsulfonyl)phenylpyridines: selective and orally active cyclooxygenase-2 inhibitors. Bioorg Med Chem Lett, 8:2777-2782, 1998.
88. R. Esser, C. Berry, Z. Du, J. Dawson, A. Fox, R. A. Fujimoto, W. Haston, E. F. Kimble, J. Koehler, J. Peppard, E. Quadros, J. Quintavalla, K. Toscano, L. Urban, J. van Duzer, X. Zhang, S. Zhou and P. J. Marshall. Preclinical pharmacology of lumiracoxib: a novel selective inhibitor of cyclooxygenase-2. Br J Pharmacol, 44:538-550, 2005.
89. J. J. Talley. Selective inhibitors of cyclooxygenase-2 (COX-2). Prog Med Chem Res, 36: 201-234, 1999.
90. R. Huff, P. Collins, S. Kramer, K. Seibert, C. Koboldt, S. Gregory and P. A. Isakson. Structural feature of N-[2-(cyclohexyloxy)-4-nitrophenyl] methanesulfonamide (NS-398) that governs its selectivity and affinity for cyclooxygenase 2 (COX-2). Inflamm Res, 44: S145-S146, 1995.
91. D. J. P. Pinto, R. A. Copeland, M. B. Covington, W. J. Pitts, D. G. Batt, M. J. Orwat, G. Lam, A. Joshi, Y. C. Chan, S. Wang, J. M. Trzaskos, R. L. Magolda and D. M. Kornhauser. Chemistry and pharmacokinetics of diarylthiophenes and terphenyls as selective COX-2 inhibitors. Bioorg Med Chem Lett, 6:2907-2912, 1996.
92. Y. Leblanc, J. Y. Gauthier, D. Ethier, J. Guay, J. Mancini, D. Riendeau, P. Tagari, P. Vickers, E. Wong and P. Prasit. Synthesis and biological evaluation of 2,3-diarylthiophenes as selective COX-2 and COX-1 inhibitors. Bioorg Med Chem Lett, 5:2123-2128, 1995.
93. S. R. Bertenshaw, J. J. Talley, D. J. Rogier, M. J. Graneto, R. S. Rogers, S. W. Kramer, T. D. Penning, C. M. Koboldt, A. W. Veenhuizen, Y. Zhang and W. E. Perkins. 3,4-Diarylthiophenes are selective COX-2 inhibitors. Bioorg Med Chem Lett, 5:2919-2122, 1995.
94. Li, J. J.; Anderson, G. D.; Gregory, S. A.; Huang, H. C.; Isakson, P. C.; Koboldt, C. M.; Logusch, E. W.; Norton, M. B.; Perkins, W. E.; Reinhard, E. J.; Seibert, K.; Veenhuizen, A. W. 1,2-Diarylcyclopentenes as selective cyclooxygenase-2 inhibitors and orally active antiinflammatory agents. J Med Chem, 38:4570-4578, (1998).
95. A. G. Habeeb, P. N. P. Rao and E. E. Knaus. Design and synthesis of celecoxib and rofecoxib analogues as selective cyclooxygenase-2 (COX-2) inhibitors: replacement of sulfonamide and methylsulfonyl pharmacophores by an azido bioisostere. J Med Chem, 44:3039-3042, 2001.
96. J. M. Uddin, P. N. P. Rao and E. E. Knaus. Design and synthesis of novel celecoxib analogs as selective cyclooxygenase-2 (COX-2) inhibitors: replacement of the sulfonamide pharmacophore by a sulfonylazide bioisostere. Bioorg Med Chem, 11:5273-5280, 2003.
97. O. Llorens, J. L. Perez, A. Palomer and D. Mauleon. Structural basis for dynamic mechanism of ligand binding to COX. Bioorg Med Chem Lett, 9:2779-2784, 1999.
98. M. Pal, M. Madan, S. Padakanti, V. R. Pattabiraman, S. Kalleda, A. Vanguri, R. Mullangi, N. V. Mamidi, S. R. Casturi, A. Malde, B. Gopalakrishnan and K. R. Yeleswarapu. Synthesis and cyclooxygenase-2 inhibiting property of 1,5-diarylpyrazoles with substituted benzenesulfonamide moiety as pharmacophore: preparation of sodium salt for injectable formulation. J Med Chem, 46:3975-3984, 2003.
99. S. K. Singh, S. Vobbalareddy, S. R. Kalleda, S. R. Casturi, S. R. Datla, R. N. Mamidi, R. Mullangi, R. Ramanujam, K. R. Yeleswarapu and J. Iqbal. Identification of 2-hydroxymethyl-4-[5-(4-methoxyphenyl)-3-trifluoromethylpyrazol-1-yl]-N-propionylbenzenesulfonamide sodium as a potential COX-2 inhibitor for oral and parenteral administration. Bioorg Med Chem, 14:8626-8634, 2006.
100. J. J. Talley, D. L. Brown, J. S. Carter, M. J. Graneto, C. M. Koboldt, J. L. Masferrer, W. E. Perkins, R. S. Rogers, A. F. Shaffer, Y. Y. Zhang, B. S. Zweifel and K. Seibert. 4-[5-Methyl-3-phenylisoxazol-4-yl]-benzenesulfonamide, valdecoxib: a potent and selective inhibitor of COX-2. J Med Chem, 43:775-777, 2000.
101. M. L. Chavez and C. J. DeKorte. Valdecoxib: a review. Clin Ther, 25:817-851, 2003.
102. C. B. Joubert, E. Lorthiois and F. Moreau. To market, to market. Ann Rep Med Chem, 38:347-374, 2003.
103. A. G. Habeeb, P. N. P. Rao and E. E. Knaus. Design and syntheses of diarylisoxazoles: novel inhibitors of cyclooxygenase-2 (COX-2) with analgesic-antiinflammatory activities. Drug Dev Res, 51:273-286, 2001.
104. C. C. Chan, S. Boyce, C. Brideau, S. Charleson, W. Cromlish, D. Ethier, J. Evans, A. W. Ford-Hutchinson, M. J. Forrest, J. Y. Gauthier, R. Gordon, M. Gresser, J. Guay, S. Kargman, B. Kennedy, Y. Leblanc, S. Leger, J. Mancini, G. P. O'Neill, M. Ouellet, D. Patrick, M. D. Percival, H. Perrier, P. Prasit, I. Rodger, P. Tagari, M. Therien, P. Vickers, D. Visco, Z. Wang, J. Webb, E. Wong, L. J. Xu, R. N. Young, R. Zamboni and D. Riendeau. Rofecoxib [Vioxx, MK-0966; 4-(4'-methylsulfonylphenyl)-3-phenyl-2-(5H)-furanone]: a potent and orally active cyclooxygenase-2 inhibitor. Pharmacological and biochemical profiles. J Pharmacol Exp Ther, 290:551-560, 1999.
105. Y. Leblanc, P. Roy, Z. Wang, C. S. Li, N. Chauret, D. A. Nicoll-Griffith, J. M. Silva, Y. Aubin, J. A. Yergey, C. C. Chan, D. Riendeau, C. Brideau, R. Gordon, L. Xu, J. Webb, D. M. Visco and P. Prasit. Discovery of a potent and selective COX-2 inhibitor in the alkoxy lactone series with optimized metabolic profile. Bioorg Med Chem Lett, 12:3317-3320, 2002.
106. W. C. Black, C. Brideau, C. C. Chan, S. Charleson, W. Cromlish, R. Gordon, E. L. Grimm, G. Hughes, S. Leger, C. S. Li, D. Riendeau, M. Therien, Z. Wang, L. J. Xu and P. Prasit. 3,4-Diaryl-5-hydroxyfuranones: highly selective inhibitors of cyclooxygenase-2 with aqueous solubility. Bioorg Med Chem Lett, 13:1195-1198, 2003.
107. M. A. Rahim, P. N. P. Rao and E. E. Knaus. Isomeric acetoxy analogues of rofecoxib: a novel class of highly potent and selective cyclooxygenase-2 inhibitors. Bioorg Med Chem Lett, 12:2753-2756, 2002.
108. N. Chauret, J. A. Yergey, C. Brideau, R. W. Friesen, J. Mancini, D. Riendeau, J. Silva, A. Styhler, L. A. Trimble and D. A. Nicoll-Griffith. In vitro metabolism considerations, including activity testing of metabolites, in the discovery and selection of the COX-2 inhibitor etoricoxib (MK-0663). Bioorg Med Chem Lett, 11:1059-1062, 2001.
109. C. P. Cannon, S. P. Curtis, G. A. FitzGerald, H. Krum, A. Kaur, J. A. Bolognese, A. S. Reicin, C. Bombardier, M. E. Weinblatt, D. van der Heijde, E. Erdmann and L. Laine. Cardiovascular outcomes with etoricoxib and diclofenac in patients with osteoarthritis and rheumatoid arthritis in the multinational etoricoxib and diclofenac arthritis long-term (MEDAL) programme: a randomised comparison. Lancet, 368:1771-81, 2006.
110. C. S. Li, C. Brideau, C. C. Chan, C. Savoie, D. Claveau, S. Charleson, R. Gordon, G. Greig, J. Y. Gauthier, C. K. Lau, D. Riendeau, M. Therien, E. Wong and P. Prasit. Pyridazinones as selective cyclooxygenase-2 inhibitors. Bioorg Med Chem Lett, 13:597-600, 2003.
111. P. N. P. Rao, A. Amini, H. Li, A. G. Habeeb and E. E. Knaus. Design, synthesis and biological evaluation of 6-substituted-3-(4-methanesulfonylphenyl)-4-phenylpyran-2-ones: a novel class of diarylheterocyclic selective cyclooxygenase-2 inhibitors J Med Chem, 46:4872-4882, 2003.
112. P. N. P. Rao, M. J. Uddin and E. E. Knaus. Design, synthesis, and structure-activity relationship studies of 3,4,6-triphenylpyran-2-ones as selective cyclooxygenase-2 inhibitors. J Med Chem, 47:3972-3990, 2004.
113. Y. H. Joo, J. K. Kwan, S. H. Kang, M. S. Noh, J. Y. Ha, J. K. Kyu, K. M. Min, C. H. Hoon and S. Chung. 2,3-Diarylbenzopyran derivatives as a novel class of selective cyclooxygenase-2 inhibitors. Bioorg Med Chem Lett, 13:413-417, 2003.
114. S. Moncada. Nitric oxide in the vasculature: physiology and pathophysiology. Ann N Y Acad Sci, 811:60-67, 1997.
115. J. L. Wallace, L. J. Ignarro and S. Fiorucci. Potential cardioprotective actions of NOreleasing aspirin. Nat. Rev. Drug Disc, 1: 375-382, 2002.
116. A. G. Herman and S. Moncada. Therapeutic potential of nitric oxide donors in the prevention and treatment of atherosclerosis. Eur Heart J, 26:1945-1955, 2005.
117. C. Charlier and C. Michaux. Dual inhibition of cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX) as a new strategy to provide safer nonsteroidal anti-inflammatory drugs. Eur J Med Chem, 38: 645-659, 2003 and references sited therein.
118. J. Hu, P. E. Van den Steen, Q. X. Sang and G. Opdenakker. Matrix metalloproteinase inhibitors as therapy for inflammatory and vascular diseases. Nat Rev Drug Disc, 6:480-497, 2007.
119. M. A. Palladino, F. R. Bahjat, E. A. Theodorakis and L. L. Moldaver. Anti-TNF-α therapies: the next generation. Nat Rev Drug Disc, 2:736-746, 2003.
120. J. L. Wallace, B. Reuter, C. Cicala, W. McKnight, G. Cirino and M. B. Gisham. Novel nonsteroidal antiinflammatory drug derivatives with markedly reduced ulcerogenic properties in rats. Gastroenterology, 107:173-179, 1994.
121. J. L. Wallace, B. Reuter, C. Cicala, W. McKnight, M. B. Grisham and G. A. Cirino. Diclofenac derivative without ulcerogenic properties. J Pharmacol, 257: 249-255, 1994.
122. S. N. Elliott, W. McKnight, G. Cirino and J. L. Wallace. A nitric oxide-releasing nonsteroidal antiinflammatory drug accelerates gastric ulcer healing in rats. Gastroenterology, 109:524-530, 1995.
123. M. N. Muscara, W. McNight, P. Del Soldato and J. L. Wallace. Effects of a nitric oxidereleasing naproxen derivative on hypertension and gastric damage induced by chronic nitric oxide inhibition in the rat. Pharmacol Lett, 62:235-240, 1998.
124. R. E. Kartasasmita, S. Laufer and J. Lehmann. NO-donors (VII [I]): synthesis and cyclooxygenase inhibitory properties of N-and S-nitrooxypivaloyl-cysteine derivatives of naproxen-a novel type of No-NSAID. Arch Pharm, 335:363-366, 2002.
125. U. K. Bandarage, L. Chen, X. Fang, D. S. Garvey, A. Glavin, D. R. Janero, L. G. Letts, G. J. Mercer, J. K. Saha, J. D. Schroeder, M. J. Shumway and S. W. Tam. Nitrosothiol esters of diclofenac: synthesis and pharmacological chracterization as gastrointestinal-sparing prodrugs. J Med Chem, 43: 4005-4016, 2000.
126. R. R. Ranatunge, M. Augustyniak, U. K. Bandarage, R. A. Earl, J. L. Ellis, D. S. Garvey, D. R. Janero, L. G. Letts, A. M. Martino, D. R. Murty, M. G. Murty, S. K. Richardson, J. Schroeder, M. J. Shumway, S. W. Tam, A. M. Trocha and D. V. Young. Synthesis and selective cyclooxygenase-2 inhibitory activity of a series of novel, nitric oxide donorcontaining pyrazoles. J Med Chem, 47:2180-2193, 2004.
127. C. Velázquez, P. N. P. Rao, R. McDonald and E. E. Knaus. Synthesis and biological evaluation of 3,4-diphenyl-1,2,5-oxadiazole-2-oxides and 3,4-diphenyl-1,2,5-oxadiazoles as potential hybrid COX-2 inhibitor/nitric oxide donor agents. Bioorg Med Chem, 13:2749-2757, 2005.
128. T. Csont and P. Ferdinandy. Cardioprotective effects of glyceryl trinitrate: beyond vascular nitrate tolerance. Pharmacol Ther, 105:57-68, 2005.
129. C. Velázquez, P. N. P. Rao, R. McDonald and E. E. Knaus. Novel nonsteroidal antiinflammatory drugs possessing a nitric oxide donor diazen-1-ium-1,2-diolate moiety: design, synthesis, biological evaluation, and nitric oxide release studies. J Med Chem, 48:4061-4067, 2005.
130. L. Lazzarato, M. Donnola, B. Rolando, E. Marini, C. Cena, G. Coruzzi, E. Guaita, G. Morini, R. Fruttero, A. Gasco and S. Biondi. Searching for new NO-donor aspirin-like molecules: a new class of nitrooxy-acyl derivatives of salicylic acid. J Med Chem, 51:1894-1903, 2008.
131. K. Chegaev, L. Lazzarato, P. Tosco, C. Cena, E. Marini, B. Rolando, P. A. Carrupt, R. Fruttero and A. Gasco. NO-donor COX-2 inhibitors. new nitrooxy-substituted 1,5-diarylimidazoles endowed with COX-2 inhibitory and vasodilator properties. J Med Chem, 50:1449-1457, 2007.
132. G. de Gaetano, M. B. Donati and C. Cerletti. Prevention of thrombosis and vascular inflammation: benefits and limitations of selective or combined COX-1, COX-2 and 5-LOX inhibitors. Trends Pharmacol Sci, 24:245-252, 2003.
133. J. L. Wallace, C. M. Keenan and D. N. Granger. Gastric ulceration induced by nonsteroidal antiinflammatory drugs is a neutrophil-dependent process. Am J Physiol, 259:G462-G467, 1990.
134. S. A. Laufer, J. Augustin, G. Dannhardt and W. Kiefer. (6,7-Diaryldihydropyrrolizin-5-yl)acetic acids, a novel class of potent dual inhibitors of both cyclooxygenase and 5-lipoxygenase. J Med Chem, 37:1894-1897, 1994.
135. S. Fiorucci, R. Meli, M. Bucci and G. Cirino. Dual inhibitors of cyclooxygenase and 5-lipoxygenase. A new avenue in antiinflammatory therapy?. Biochem Pharmacol, 62:1433-1438, 2001.
136. A. F. Cicero and L. Laghi. Activity and potential role of licofelone in the management of osteoarthritis. Clin Interv Aging, 2:73-79, 2007.
137. J. M. Alvero-Gracia. Licofelone-clinical update on a novel LOX/COX inhibitor for the treatment osteoarthritis. Rheumatology, 43:i21-i25, 2004.
138. S. Barbey, L. Goossens, T. Taverne, J. Cornet, V. Choesmel, C. Rouaud, G. Gimeno, S. Yannic-Arnoult, C. Michaux, C. Charlier, R. Houssin and J. P. Henichart. Synthesis and activity of a new methoxytetrahydropyran derivative as dual cyclooxygenase-2/5-lipoxygenase inhibitor. Bioorg Med Chem Lett, 12: 779-782, 2002.
139. H. Kuhn and V. B. O'Donnell. Inflammation and immune regulation by 12/15-lipoxygenases. Prog Lipid Res, 45:334-356, 2006.
140. P. N. P. Rao, Q. H. Chen and E. E. Knaus. Synthesis and structure-activity relationship studies of 1,3-diarylprop-2-yn-1-ones: dual inhibitors of cyclooxygenases and lipoxygenases. J Med Chem, 49: 1668-1683, 2006.
141. A. Moreau, P. N. P. Rao and E. E. Knaus. Synthesis and biological evaluation of acyclic triaryl (Z)-olefins possessing a 3,5-di-tert-butyl-4-hydroxyphenyl pharmacophore: dual inhibitors of cyclooxygenases and lipoxygenases. Bioorg Med Chem Lett, 14:5340-5350, 2006.
142. A. A. Geronikaki, A. A. Lagunin, D. I. Hadjipavlou-Litina, P. T. Eleftheriou, D. A. Filimonov, V. V. Poroikov, I. Alam and A. K. Saxena. Computer-aided discovery of antiinflammatory thiazolidinones with dual cyclooxygenase/lipoxygenase inhibition. J Med Chem, 51:1601-1609, 2008.
143. M. V. Reddy, V. K. Billa, V. R. Pallela, M. R. Mallireddigari, R. Boominathan, J. L. Gabriel and E. P. Reddy. Design, synthesis, and biological evaluation of 1-(4-sulfamylphenyl)-3-trifluoromethyl-5-indolyl pyrazolines as cyclooxygenase-2 (COX-2) and lipoxygenase (LOX) inhibitors. Bioorg Med Chem, 16:3907-3916, 2008.
144. Q. H. Chen, P. N. P. Rao and E. E. Knaus. Synthesis and biological evaluation of a novel class of rofecoxib analogues as dual inhibitors of cyclooxygenases (COXs) and lipoxygenases (LOXs). Bioorg Med Chem Lett, 14:7898-7909, 2006.
145. M. Wong, D. Ziring, Y. Korin, S. Desai, S. Kim, J. Lin, D. Gjertson, J. Braun, E. Reed and R. R. Singh. TNF-α blockade in human diseases: mechanisms and future directions. Clin Immunol, 126:121-136, 2008.