Cyclooxygenase-2: A new therapeutic target

Indian Journal of Pharmacology

Volumn 31, Issue 5, 1999, Pages 322-332

  Sengupta, S ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

COX 2 inhibitors; Cyclooxygenase; NSAIDs

Indexed keywords

3 (3 FLUOROPHENYL) 5,5 DIMETHYL 4 (4 METHYLSULFONYLPHENYL) 2(5H) FURANONE; 5 (4 FLUOROPHENYL) 1 [(4 METHYLSULFONYL)PHENYL] 3 TRIFLUOROMETHYLPYRAZOLE; 5 BROMO 2 (4 FLUOROPHENYL) 3 (4 METHYLSULFONYLPHENYL)THIOPHENE; 6 (2,4 DIFLUOROPHENYLTHIO) 5 METHANESULFONAMIDO 1 INDANONE; ACETYLSALICYLIC ACID; ARACHIDONIC ACID; CELECOXIB; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; DICLOFENAC; ETODOLAC; IBUPROFEN; KETOPROFEN; MELOXICAM; NABUMETONE; NAPROXEN; NIMESULIDE; NONSTEROID ANTIINFLAMMATORY AGENT; PIROXICAM; PROSTAGLANDIN; PROSTAGLANDIN SYNTHASE; ROFECOXIB;

ALZHEIMER DISEASE; CANCER; CLINICAL TRIAL; DISEASE MODEL; DOSE TIME EFFECT RELATION; DRUG ABSORPTION; DRUG EFFICACY; DRUG INHIBITION; DYSPEPSIA; ENZYME ACTIVITY; ENZYME INHIBITION; GASTROINTESTINAL TOXICITY; HUMAN; INFLAMMATION; NONHUMAN; ORAL DRUG ADMINISTRATION; OSTEOARTHRITIS; PARENTERAL DRUG ADMINISTRATION; PROSTAGLANDIN SYNTHESIS; RASH; RECTAL DRUG ADMINISTRATION; REVIEW; RHEUMATOID ARTHRITIS; TOPICAL DRUG ADMINISTRATION;

EID: 0032717008     PISSN: 02537613     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (96)

1. Vane JR, Botting RM. New insights into the mode of action of anti-inflammatory drugs. Inflamm Res 1995:44:1-10.
2. Roth SH. NSAID gastropathy. A new understanding. Arch Intern Med 1996:156:1623-8.
3. Murray MD, Brater DC. Renal toxicity of the nonsteroidal anti-inflammatory drugs. Annu Rev Pharmacol Toxicol 1993;33:435-65.
4. Fu JY, Masferrer JL, Seibert K, Raz A, Needleman P.The induction and suppression of prostaglandin H2 synthase (cyclooxygenase) in human monocytes. J Biol Chem 1990:265:16737-40.
5. Masferrer JL, Zweifel BS. Seibert K, Needleman P. Selective regulation of cellular cyclooxygenase by dexamethasone and endotoxin in mice. J Clin Invest 1990:86:1375-9.
6. XieWL, ChipmanJG, RobertsonDL, EriksonRL, Simmons DL. Expression of a mitogen-responsive gene encoding prostaglandin synthase is regulated by mRNA splicing. Proc Natl Acad Sei USA! 991 ;88:2692-6.
7. Sirois J, Richards JS. Purification and characterization of a novel, distinct isoform of prostaglandin endoperoxide synthase induced by human chorionic gonadotropin in granulosa cells of rat preovulatory follicles. J Biol Chem 1992;267:6382-8.
8. Funk CD, Funk LB, Kennedy ME. Pong AS. Fitzgerald GA. Human platelet/erythroleukemia cell prostaglandin G/H synthase: cDNA cloning, expression, and gene chromosomal assignment. FASEBJ 1991:5:2304-12.
9. Harris RC, McKanna JA, Akai Y, Jacobson HR, Dubois RN, Breyer MD. Cyclooxygenase-2 is associated with the macula densa of rat kidney and increases with salt restriction. J Clin Invest 1994:94:2504-10.
10. Kargman S, Charleson S, Cartwright M, Frank J, Riendeau D, Mancini J, Evans J, O'Neill G. Characterization of Prostaglandin G/H Synthase 1 and 2 in rat, dog, monkey, and human gastrointestinal tracts. Gastroenterology 1996:111:445-54.
11. Maslinska D, Gajewski M. Some aspects of the inflammatory process. Folia Neuropathol 1998:36:199-204.
12. Santos AR, Vedana EM, De Freitas GA. Antinociceptive effect of meloxicam, in neurogenic and inflammatory nociceptive models in mice. Inflamm Res 1998:47:302-307.
13. Lora M, Morisset S, Menard HA, Leduc R, de BrumFernandes AJ. Expression of recombinant human cyclooxygenase isoenzymes in transfected COS-7 cells in vitro and inhibition by tenoxicam, indomethacin and aspirin. Prostaglandlns Leukot Essent Fatty Acids 1997; 56:361-7.
14. Dequeker J, Hawkey C, Kahan A, Steinbruck K. Alegre C, Baumelou E, Begaud B, Isomaki H, Littlejohn G. Mau J, Papazoglou S. Improvement in gastrointestinal tolerability of the selective cyclooxygenase (COXJ-2 inhibitor, meloxicam, compared with piroxicam: results of the Safety and Efficacy Large-scale Evaluation of COX-inhibiting Therapies (SELECT) trial in osteoarthritis. Br J Rheumatol 1998:37:946-51.
15. Ward A, Brogden RN. Nimesulide. A preliminary review of its pharmacological properties and therapeutic efficacy in inflammation and pain states. Drugs 1988:36:732-53.
16. Gans KR, Balks EA, Galbraith W, Haber Sb, Kerr JS, Newton RC et al. Pharmacologie profile of DuP697 (5 bromo24-fluorophenyl-3-4-methysulfonylphenyl-thiophene a novel antiinflammatory agent. Pharmacologist 1987;29:183.
17. Penning TD, Talley JJ, Bertenshaw SR, Carter JS, Collins PW et al. Synthesis and biological evaluation of the 1,5diarylpyrazole class of cyclooxygenase-2 Inhibitors: identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1Hpyrazol-1-yl]benze nesulfonamide (SC-58635, celecoxib). J Med Chem 1997;40:1347-65.
18. .Luong C, Miller A, Barnett J. Chow J, Ramesha C, Browner MF. Flexibility of the NSAID binding site in the structure of human cyclooxygenase-2. Nat Struct Bid 1996;3:927-3.
19. Kurumbail RG, Stevens AM, Gierse JK, McDonald JJ, Stegeman RA et al. Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents. Nature 1996:384:644-8 .Published erratum appears in Nature 1997:385:555.
20. Picot D, Loll PJ, Garavito RM. The X-ray crystal structure of the membrane protein prostaglandin H2 synthase-1. Nature 1994:367:243-9.
21. Wong E, Bayly C, Waterman HL, Riendeau D, Mancini JA. Conversion of prostaglandin G/H synthase-1 into an enzyme sensitive to PGHS-2-selective inhibitors by a double His513 Arg and Ile523 val mutation. J Biol Chem 1997;272:9280-6.
22. Mancini JA, Riendeau D, Falgueyret JP, Vickers PJ, O'Neill GPJ. Arginine 120 of prostaglandin G/H synthase-1 is required for the inhibition by nonsteroidal anti-inflammatory drugs containing a carboxylic acid moiety. Biol Chem 1995:270:29372-7.
23. Bhattacharyya DK, Lecomte M, Rieke CJ, Garavito M, Smith WL. Involvement of arginine 120, glutamate 524, and tyrosine 355 in the binding of arachidonate and 2phenylpropionic acid inhibitors to the cyclooxygenase active site of ovine prostaglandin endoperoxide H syntnase1. J Biol Chem 1996;271:2179-84.
24. Arias-Negrete S, Keller K, Chadee K. Proinflammatory cytokines regulate cyclooxygenase-2 mRNA expression in human macrophages. Biochem Biophys Res Commun 1995;208:582-89.
25. Akarasereenont P, Mitchell JA, Bakhle YS, Thiemermann C. Vane JR. Comparison of the induction of cyclooxygenase and nitric oxide synthase by endotoxin in endothelial cells and macrophages. Eur J Pharmaco! 1995;273: 121-8.
26. Forster W. Parratt JR. The case of low-dose aspirin for the prevention of myocardial infarction: but how low is low? Cardiovasc Drugs Ther 1997;10:727-34.
27. HarrisRC.McKannaJA.AkaiY,JacobsonHR.DuboisRN, Breyer MD. Cyclooxygenase-2 is associated with the macula densa of rat kidney and increases with salt restriction. J Clin Invest 1994;94:2504-10.
28. Vane JR. Sotting RM. Biological properties of cyclcoxygenase products. In Lipid mediators, ed. F.Cunningham. London. Academic (1994):61-97.
29. Kargman S, Charleson S. Cartwright M, Frank J, Riendeau D, Mancini J, Evans J, O'Neiil G. Characterization of Prostaglandin G/H Synthase 1 and 2 in rat, dog, monkey, and human gastrointestinal tracts. Gastroanterology 1996;111 : 445-54.
30. Cohn SM, Schloemann S, Tessner T, Seibert K, Stenson WF. Crypt stem cell survival in the mouse intestinal epithelium is regulated by prostaglandins synthesized through cyclooxygenase-1. J Clin Invest 1997;99:1367-79.
31. Ristimaki A, Honkanen N, Jankala H, Sipponen P, Harkonen M. Expression of cyclooxygenase-2 in human gastric carcinoma. Cancer Res 1997:57:1276-80.
32. Breder CD, Saper CB. Expression of inducible cyclooxygenase mRNA in the mouse brain after systemic administration of bacterial lipopolysaccharide. Brain Res 1996; 713:64-9.
33. Luo J, Lang JA, Miller MW . Transforming growth factor betal regulates the expression of cyclooxygenase in cultured cortical astrocytes and neurons. J Neurochem 1998:71:526-34.
34. Yamagata K, Andreasson Kl, Kaufmann WE, Barnes CA, Worley PF. Expression of a mitogen-inducible cyclooxygenase in brain neurons: regulation by synaptic activity and glucocorticoids. Neuron 1993:11:371-86.
35. Breder CD, Dewitt D, Kraig RP. Characterization of inducible cyclooxygenase in rat brain. J Comp Neurol 1995:355: 296-15.
36. Cao C, Matsumura K, Yamagata K, Watanabe Y. Endothelial cells of the rat brain vasculature express cyclooxy-genase-2 mRNA in response to systemic interleukin-1 beta: a possible site of prostaglandin synthesis responsible for 'fever. Brain Res 1996;733:263-72.
37. Beiche F, Scheuerer S, Brune K, Geisslinger G, GoppeltStruebe M. Up-regulation of cyclooxygenase-2 mRNA in the rat spinal cord following peripheral inflammation. FEBS Lett 1996:390:165-9.
38. Sengupta S, Velpandian T, Sapra P, Mathur P, Gupta SK. Comparative analgesic efficacy of nimesulide and diclofenac gels after topical application on the skin. Skin Pharmacol Appl Skin Physiol 1998;11:273-8.
39. Gibb W, Sun M. Localization of prostaglandin H synthase type 2 protein and mRNA in term human fetal membranes and decidua. J Endocrinol 1996;150:497-503.
40. Spaziani EP, Lantz ME, Benoît RR, O'Brien WF.The induction of cyclooxygenase-2 (COX-2) in intact human amnion tissue by interleukin-4. Prostaglandins 1996;51: 215-23.
41. Sawdy R, Slater D, Fisk N, Edmonds DK, Bennett P. Use of a cyclooxygenase type-2-selective non-steroidal antiinflammatory agent to prevent preterm delivery. Lancet 1997:350:265-6.
42. Thun MJ, Namboodiri MM, Calle EE, Flanders WD. Heath CW Jr. Aspirin use and risk of fatal cancer. Cancer Res 1993;53:1322-7.
43. Oshima M, Dinchuk JE, Kargman SL, Oshima H, Hancock B et al. Suppression of intestinal polyposis in Ape delta716 knockout mice by inhibition of cyclooxygenase 2{COX-2). Cell 1996;B7:803-9.
44. Prescott SM, White RL Self-promotion? Intimate connections between APC and prostaglandin H synthase-2. Cell 1996:87:783-6.
45. Morita I, Schindler M, Regier MK, Otto JC, Hori T et al. Different intraceilular locations for prostaglandin endo-peroxide H synthase-1 and -2. J Biol Chem 1995;270:109028.
46. Forman BM.Tontonoz P, Chen J, Brun RP, Spiegelman BM, Evans RM. 15-Deoxy-delta 12, 14-prostaglandin J2 is a ligand for the adipocyte determination factor PPAR gamma. Cell 1995;83:803-12.
47. Mangelsdorf DJ, Evans RM. The RXR heterodimers and orphan receptors. Cell 1995:83:841-50.
48. Parrel ML, Harris RE, Joarder FS, Ross MS, Clausen KP, Robertson FM. Cyclooxygenase-2 gene expression in human breast cancer. Int J Oncol 1997;10:503-10.
49. Tsuji M, Dubois RN. Alterations in cellular adhesions and apoptosis in epithelial cells overexpressing prostaglandin endoperoxide synthase2. Cell 1995:83:493-501.
50. Breitner JC.The role of anti-inflammatory drugs in the prevention and treatment of Alzheimer's disease. Annu Rev Med 1996:47:401-11.
51. Stewart WF, Kawas C, Corrada M, Metter EJ. Risk of Alzheimer's disease and duration of NSAID use. Neurology 1997;48:626-32.
52. Cochran FR, VitekMP. Neuroinflammatory mechanisms in Alzheimer's disease: new opportunities for drug discovery. Expert Opin Invest Drugs 1996:5:449-55.
53. Chang JW, Coleman PD, O'Banion MK. Prostaglandin G/H synthase-2 (cyclooxygenase-2) mRNA expression is decreased in Alzheimer's disease. Neurobiol Aging 1996:17:801-8.
54. Crofford LJ. Wilder RL, Ristimaki AP, Sano H, Remmers EF, Epps HR, Hla T. Cyclooxygenase-1 and -2 expression in rheumatoid synovial tissues. Effects of interleukin-1 beta, phorbol ester, and corticosteroids. J Clin Invest 1994:93:1095-101.
55. Riendeau D, Percival MD, Boyce S, Brideau C, Charleson S et al. Biochemical and pharmacological profile of a tetrasubstituted furanone as a highly selective COX-2 inhibitor. Br J Pharmacol 1997:121:105-17.
56. Engeihardt G, Bogel R. Schnitzler C, Utzmann R. Meloxicam: influence on arachidonic acid metabolism. Part II. In vivo findings. Biochem Pharmacol 1996:51:29-38.
57. Englehart G. Meloxicam, a potent inhibitor of adjuvan arthritis in the rat. Scand J Rheumatol 1994;98:Abstr no 110.
58. Fürst DE, Meloxicam: selective COX-2 inhibition in clinical practice. Semin Arthritis Rheum 1997;26:21-7.
59. Bosch HC, Sigmund R, Hettich M. Efficacy and tolerability of intramuscular and oral meloxicam in patients with acute lumbago: a comparison with intramuscular and oral piroxicam. CurrMed Res Opin 1997:14:29-38.
60. Hawkey C, Kahan A, Steinbruck K, Alegre C, Baumelou E et al. Gastrointestinal tolerability of meloxicam compared to diclofenac in osteoarthritis patients. International MELISSA Study Group. Meloxicam Large-scale International Study Safety Assessment. Br J Rheumatol 1998;37: 937-45. Published erratum appears in Br J Rheumatol 1998:37:1142.
61. Dequeker J, Hawkey C, Kahan A, Steinbruck K, Alegre C eraJ. Improvement in gastrointestinal tolerability of the selective cyclooxygenase (COX)-2 inhibitor, meloxicam, compared with piroxicam: results of the Safety and Efficacy Large-scale Evaluation of COX-inhibiting Therapies (SELECT) trial in osteoarthritis. Br J Rheumatol 38; 37:94651.
62. Turck D, Busch U, Heinzel G, Narjes H. Clinical pharma-cokinetics of meloxicam. Arzneimittelforschung 1997;47: 253-8.
63. Chesne C, Guyomard C. Guillouzo A, Schmid J, Ludwig E, Sauter T. Metabolism of Meloxicam in human liver involves cytochromes P4502C9 and 3A4. Xenobiotica 1998;28:113.
64. Grossman CJ, Wiseman J, Lucas FS, Trevethick MA, Birch PJ. Inhibition of constitutive and inducible cyclooxy-genase activity in human platelets and mononuclear cells by NSAIDs and Cox 2 inhibitors. Inflamm Res 1995;44:2537.
65. Bevilacqua M, Vago T, Beretta A. Nimesulide as inhibitor of Superoxide anions (O2-) production by human polymorphonuciear leukocytes. Pain Rep rod 1988;31:265-72.
66. Pelletier JP, Martel-Pelletier J. Effects of nimesulide and naproxen on the degradation and metalloprotease synthesis of human osteoarthritic cartilage. Drugs 1993;46:34-9.
67. Berti F, Rossoni G, Buschi A, Villa LM, Robuschi M ef aJ. Nimesulide, a non steroidal anti-inflammatory drug, displays antianaphylatic and antihistaminic activity in guinea pig. Drug Invest 1991;3:39-47.
68. Dreiser RL, Reibenfeld D. Nimesulide in the treatment of osteoarthritis: double blind studies in comparison with piroxicam, ketoprofen and placebo. Drugs 1993;46:191-5.
69. Corli O, Cozzolino A, Scaricabarozzi I. Nimesulide and diclofenac in the control of cancer-related pain. Comparison between oral and rectal administration. Drugs 1993; 46:152-5.
70. Gupta SK, Prakash J, Awor L, Joshi S, Velpandian T. Antiinflammatory activity of topical nimesulide gel in various experimental models. Inflamm Res 1996;45:590-2.
71. Sengupta S, Velpandian T, Kabir SR, Gupta SK. Analgesic efficacy and pharmacokinetics of topical nimesulide gel in healthy human volunteers: double-blind comparison with piroxicam, diclofenac and placebo. Eut J Clin Pharmacol 1998;54:541-7.
72. Gupta SK, Bhardwaj RK, Tyagi P, Sengupta S, Velpandian T. Anti-inflammatory activity and pharmacokinetic profile of a new parenteral formulation of nimesulide. Pharmacol Res 1999:39:137-41.
73. Amodeo C, De Marco M, Gambarini G. A clinical study of the efficacy and tolerance of nimesulide compared to flurbiprofen and sodium diclofenac in the prevention and treatment of postoperative pain and inflammatory symptoms in dentistry. Minerva Stomatol 1992;41:567-76.
74. Gupta SK, Velpandian T, Mathur P, Sengupta S. Comparative analgesic activity of nimesulide and diclofenac by intramuscular route: correlation with pharmacokinetic pro-file of nimesulide. Pharmacology 1998;56:137-43.
75. Gupta SK, Velpandian T, Sengupta S, Mathur P, Sapra P. Influence of piperine on nimesulide induced antinociception. PhytotherRes 1998:12:266-9.
76. Davis R, Brogden RN Nimesulide. An update of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy. Drugs 1994:48:431-54. Published erratum appears in Drugs 1994;48:793.
77. Cipollini M, Mecozzi P, Altilia F. Endoscopie assessment of the effects of nimesulide on gastric mucosa: comparison with indomethacin. Curr Ther Res 1989;45:1042-8.
78. Jouzeau JY, Terlain B, Abid A, Nedelec E, Netter P. Cyclooxygenase isoenzymes. How recent findings affect thinking about nonsteroidal anti-inflammatory drugs. Drugs 1997:53:563-82.
79. Chan CC, Boyce S, Brideau C, Ford-Hutchinson AW, Gordon R et al. Pharmacology of a selective cyclooxygenase-2 inhibitor, L-745.337: a novel nonsteroidal antiinflammatory agent with an ulcerogenic sparing effect in rat and nonhuman primate stomach. J Pharmacol Exp Ther 1995:274:1531-7.
80. Bertenshaw SR, Talley JJ, Rogier DJ, Graneto MJ, Rogers RS ef aJ. 3,4-Diarylthiophenes are selective COX-2 inhibitors. Biorg med Chem Lett 1995;5:2919-22.
81. Gans KR, Galbraith W, Roman RJ, Haber SB, Kerr JS et al. Anti-inflammatory and safety profile of DuP 697, a novel orally effective prostaglandin synthesis inhibitor. J Pharmacol Exp Ther 1990:254:180-7.
82. Riendeau D, Percival MD, Boyce S, Brideau C, Charleson S ef aJ. Biochemical and pharmacological profile of a tetrasubstituted furanone as a highly selective COX-2 inhibitor. BrJ Pharmacol 1997:121:105-17.
83. Lanza FL, Simon T, Quan H, Bolognese J, Rack MF et al. Selective inhibition of cyclooxygenase2 (COX2) with MK0966 (250mg q.d) is associated with less gastrointestinal damage than aspirin (ASA) 650mg qid or ibuprofen (IBU) 800mg tid. Gastroenterology 1997:112:194.
84. Ehrich E, Mehlisch D, Perkins S, Brown P, Wittreich J et al. Efficacy of MK-966, a highly selective inhibitor of COX-2, is an effective analgesic in an acute postsurgical pain model. J Invest Med 1996:44:293.
85. Glaser K, Sung ML, O'Neill K, Belfast M, Hartman D et al. Etodolac selectively inhibits human prostaglandin G/H synthase 2 (PGHS-2) versus human PGHS-1. Eur J Pharmacol 1995;281:107-11.
86. Dvornik DM. Tissue selective inhibition of prostaglandin biosynthesis by etodolac. J Rheumatol Suppl 1997;47:40-7.
87. Laine L, Sloane R, Ferretti M, Cominelli F. A randomized double-blind comparison of placebo, elodolac, and naproxen on gastrointestinal injury and prostaglandin production. Gastrointest Endosc 1995;42:428-33.
88. SchnitzerTJ, Constantine G. Etodolac (Lodine) in the treatment of osteoarthritis: recent studies. Rheumatol Suppl 1997:47:23-31.
89. Neustadt DH. Double blind evaluation of the long-term effects of etodolac versus ibuprofen in patients with rheumatoid arthritis. J Rheumatol Suppl 1997:47:17-22.
90. Wilcox GM, Porensky RS. Acute colitis associated with etodolac. J Clin Gastroenterol 1997;25:367-8.
91. Penning TD, Talley JJ, Bertenshaw SR, Carter JS, Collins PW et aJ.Synthesis and biological evaluation of the 1,5diarylpyrazole class of cyclooxygenase-2 inhibitors: identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1Hpyrazol-1-yl]benze nesulfonamide (SC-58635, celecoxib). Med Chem 1997;40:1347-65.
92. Simon LS, Lanza FL, Lipsky PE, Hubbard RC, Talwalker S et al. Preliminary study of the safety and efficacy of SC58635, a novel cyclooxygenase 2 inhibitor: efficacy and safety in two placebo-controlled trials in osteoarthritis and rheumatoid arthritis, and studies of gastrointestinal and platelet effects. Arthritis Rheum 1998:41:1591-602.
93. Lipsky PE, Isakson PC. Outcome of specific COX-2 inhibition in rheumatoid arthritis. J Rheumatol 1997;24:9-14.
94. KawamoriT, RaoCV, Seibert K, ReddyBS.Chemopreventive activity of celecoxib, a specific cyclooxygenase-2 inhibitor, against colon carcinogenesis. Cancer Res 1998; 58:409-12.
95. Dinchuk JE, Car BD, Focht RJ, Johnston JJ, Jaffee BD et al. Renal abnormalities and an altered inflammatory response in mice lacking cyclooxygenase II. Nature 1995:378:406-9.
96. Majima M, Isono M, Ikeda Y, Hayashi I, Hatanaka K et al. Significant roles of inducible cyclooxygenase (COX)-2 in angiogenesis in rat sponge implants. Jpn J Pharmacol 1997:75:105-14.