Profile and mechanisms of gastrointestinal and other side effects of nonsteroidal anti-inflammatory drugs (NSAIDs)

American Journal of Medicine

Volumn 107, Issue 6 SUPPL. 1, 1999, Pages 27-35

  Rainsford, K D ^a  

^a SHEFFIELD HALLAM UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLSALICYLIC ACID; AZAPROPAZONE; CELECOXIB; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; DICLOFENAC; FENBUFEN; FENOPROFEN; FLUFENAMIC ACID; FLURBIPROFEN; IBUPROFEN; INDOMETACIN; KETOPROFEN; MELOXICAM; NABUMETONE; NAPROXEN; NIMESULIDE; NONSTEROID ANTIINFLAMMATORY AGENT; PHENYLBUTAZONE; ROFECOXIB; SALICYLIC ACID DERIVATIVE;

CARTILAGE DEGENERATION; CONFERENCE PAPER; DIGESTIVE SYSTEM FUNCTION DISORDER; DRUG SPECIFICITY; ENZYME INHIBITION; GASTROINTESTINAL HEMORRHAGE; HUMAN; OSTEOARTHRITIS; PKA; PRIORITY JOURNAL; PROSTAGLANDIN SYNTHESIS; PROTEOGLYCAN SYNTHESIS; STRUCTURE ACTIVITY RELATION; ULCER;

EID: 0033452430     PISSN: 00029343     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0002-9343(99)00365-4     Document Type: Conference Paper

References (76)

1. Rainsford KD, Velo GP, eds. Side-Effects of Anti-Inflammatory Drugs - 4. Dordrecht: Kluwer Academic Publishers, 1992.
2. Rainsford KD, ed. New Developments in Anti-Rheumatic Therapy. Boca Raton, FL: CRC Press, 1996.
3. Rashad S, Revell P, Hemingway A, Low F, Rainsford K, Walker FS. Effect of non-steroidal anti-inflammatory drugs on the course of osteoarthritis. Lancet. 1989;2:519-522.
4. Rashad S, Rainsford K, Revell P, Low F, Hemingway A, Walker F. The effects of NSAIDS on the course of osteoarthritis. In: Bálint G, Gömör B, Hódinka L, eds. Rheumatology: State of the Art. Amsterdam: Elsevier, 1992:184-188.
5. Jones AC, Doherty M. The treatment of osteoarthritis. Br J Clin Pharmacol. 1992;33:357-363.
6. Jouzeau J-Y, Terlain B, Abid A, Nédélec E, Netter P. Cyclooxygenase isoenzymes: how recent findings affect thinking about nonsteroidal anti-inflammatory drugs. Drugs. 1997; 53:563-582.
7. Donnelly MT, Hawkey CJ. Review article: COX-II inhibitors - a new generation of safer NSAIDs? Aliment Pharmacol Ther. 1997;11:227-236.
8. Hawkey CJ. COX-2 inhibitors. Lancet. 1999;353:307-314.
9. Dubois RN, Abramson SB, Crofford L, Gupta RA, Simon LS, Van de Putte LBA, Lipsky PE. Cyclooxygenase in biology and disease. FASEB J. 1998;12:1063-1070.
10. Davis R, Brogden RN. Nimesulide: an update of its pharmacodynamic and pharmacokinetic properties and therapeutic efficacy. Drugs. 1994;48:431-454.
11. Rainsford KD. An analysis from clinico-epidemiological data of the principal adverse events from the COX-2 selective NSAID, nimesulide, with particular reference to hepatic injury. Inflammopharmacology. 1998;6:203-221.
12. Rabasseda X. Safety profile of nimesulide: ten years of clinical experience. Drugs of Today. 1997;33(suppl I):1-10.
13. Garcia Rodriguez LA, Cattaruzzi C, Trancon MG, Agostinis L. Risk of hospitalization for upper gastrointestinal tract bleeding associated with ketolorac, other nonsteroidal anti-inflamamtory drugs, calcium antagonists and other antihypertensive drugs. Arch Intern Med. 1998;158:33-39.
14. Menniti-Ippolito F, Maggini M, Raschetti R, Da Cas R, Traversa G, Walker AM. Ketorolac use in outpatients and gastrointestinal hospitalization: a comparison with other non-steroidal anti-inflammatory drugs in Italy. Eur J Clin Pharmacol. 1998;54:393-397.
15. MacDonald TM, Morant SV, Robinson GC, Shield MJ, McGilchrist MM, Murray FE, McDevitt DG. Association of upper gastrointestinal toxicity of non-steroidal anti-inflammatory drugs with the continued exposure: cohort study. BMJ. 1997;315:1333-1337.
16. Henry DA, Drew A, Beuzeville S. Adverse drug reactions in the gastrointestinal system attributed to ibuprofen. In: Rainsford KD, Powanda MC, eds. Proceedings of the International Conference Held at The South San Francisco Conference Center, San Francisco, CA, USA, on 17th March 1997. Dordrecht, Boston, London: Kluwer Academic Publishers, 1997:19-45.
17. Rainsford KD. Protection from gastrointestinal side-effects by azapropazone by its incorporation into a glucose-sodium acid citrate formulation. Aliment Pharmacol Ther. 1991;5:419-433.
18. Rainsford KD, Willis C. Relationship of gastric mucosal damage induced in pigs by anti-inflammatory drugs to their effects on prostaglandin production. Dig Dis Sci. 1982;27: 624-635.
19. Rainsford KD, Fox SA, Osborne DJ. Comparative effects of some non-steroidal anti-inflammatory drugs on the ultrastructural integrity and prostaglandin levels in the rat gastric mucosa: relationship to drug uptake. Scand J Gastroenterol. 1984;19(suppl 101):55-68.
20. Rainsford KD, ed. Azapropazone: Over 20 Years of Clinical Use, 2nd ed. Dordrecht: Kluwer Academic Publishers, 1991.
21. McCormack K, Brune K. Classical absorption theory and the development of gastric mucosal damage associated with the non-steroidal anti-inflammatory drugs. Arch Toxicol. 1987;60:261-269.
22. Fini A, Laus M, Orienti I, Zecchi V. Dissolution and partition thermodynamic functions of some nonsteroidal antiinflammatory drugs. J Pharm Sci. 1986;75:23-25.
23. McCormack K, Brune K. The amphiprotic character of azapropazone and its relevance to the gastric mucosa. Arch Toxicol. 1990;64:1-6.
24. Kivinen A, Vikholm I, Tarpila S. A film balance study of the monolayer-forming properties of dietary phospholipids and the interaction with NSAIDs on the monolayers. Int J Pharmaceut. 1994;108:109-115.
25. Dean FM. hP, the component of logP controlling structure-activity relatonships amongst nonsteroidal antiinflammatory drugs. J Pharm Pharmacol. 1996;48:233-239.
26. Barbato F, La Rotonda MI, Quaglia F. Interactions of non-steroidal antiinflammatory drugs with phospholipids: comparison between octanol/buffer partition coefficients and chromatographic indexes on immobilized artificial membranes. J Pharm Sci. 1997;86:225-229.
27. Rainsford KD. Structure-activity relationships of non-steroidal anti-inflammatory drugs, I: gastric ulcerogenic activity. Agents Actions. 1978;8:587-605.
28. Whitehouse MW, Rainsford KD. Esterification of acidic anti-inflammatory drugs suppresses their gastro-toxicity without adversely affecting their anti-inflammatory activity in rats. J Pharm Pharmacol. 1980;32:795-796.
29. Rainsford KD. Comparison of the gastric ulcerogenic activity of new non-steroidal anti-inflammatory drugs in stressed rats. Br J Pharmacol. 1981;73:79c-80c.
30. Rainsford KD. Gastric ulcerogenicity of nonsteroidal anti-inflammatory drugs in mice with mucosa sensitized by cholinomimetic treatment. J Pharm Pharmacol. 1987;39:669-672.
31. Dearden JC, Nicholson RM. Correlation between gastric irritancy and anti-inflammatory activity of nonsteroidal anti-inflammatory drugs. J Pharm Pharmacol. 1984;36:713-715.
32. Mangan FR, Flack JD, Jackson D. Preclinical overview of nabumetone: pharmacology, bioavailability, metabolism, and toxicology. Am J Med. 1987;83(suppl 4B):6-10.
33. Melarange R, Gentry C, O'Connell C, Blower PR, Neil C, Kelvin AS, Toseland CDN. Antiinflammatory and gastrointestinal effects of nabumetone or its active metabolite 6-methoxy-2-naphthylacetic acid (6MNA): comparative studies with indomethacin. Dig Dis Sci. 1992;37:1847-1852.
34. x List Monographs. Mosby Inc., 1998. www. rxlist.com/cgi/generic/nabume.htm.
35. Deschamps-Labat L, Pehourcq F, Jagou M, Bannwarth B. Relationship between lipophilicity and binding to human serum albumin of arylpropionic acid non-steroidal anti-inflammatory drugs. J Pharmaceut Biomed Anal. 1997;16: 223-229.
36. Hoerter D, Dressman JB. Influence of physicochemical properties on dissolution of drugs in the gastrointestinal tract. Adv Drug Deliv Rev. 1997;25:3-14.
37. Lichtenberger LM, Graziani LA, Dial EJ, Butler BD, Hills BA. Role of surface-active phospholipids in gastric cytoprotection. Science. 1983;219:1327-1329.
38. Luega A, Mourelle M, Guarner F, Domingo A, Salas A, Malagelada JR. Phosphatidylcholines as mediators of adaptive cytoprotection of the rat duodenum. Gastroenterology. 1994;107:720-727.
39. Goddard PJ, Kao YJ, Lichtenberger LM. Luminal surface hydrophobicity of canine gastric mucosa is dependent on a surface mucous gel. Gastroenterology. 1990;98:361-370.
40. Kao YJ, Goddard PJ, Lichtenberger LM. Morphological effects of aspirin and prostaglandin on the canine gastric mucosal surface. Gastroenterology. 1990;98:562-606.
41. Hills BA, Kirwood CA. Gastric mucosal barrier to hydrogen ions imparted by gastric surfactant in vitro. Gut. 1992;33: 1039-1041.
42. 2-induced secretion of surfactant phospholipid by isolated gastric mucous cells. Gastroenterology. 1991;100:1232-1240.
43. Goddard PJ, Hills BA, Lichtenberger LM. Does aspirin damage canine gastric mucosa by reducing its surface hydrophobicity? Am J Physiol. 1987;15:G421-G430.
44. Lichtenberger LM, Wang ZM, Romero JJ, Ulloa C, Perez JC, Giraud MN, Barreto JC. Non-steroidal anti-inflammatory drugs (NSAIDs) associate with zwitterionic phospholipids: insight into the mechanism and reversal of NSAID-induced gastrointestinal injury. Nat Med. 1995;1:154-158.
45. Lugea A, Antolin M, Mourelle M, Guarner F, Malagelada J-R. Deranged hydrophobic barrier of the rat gastroduodenal mucosa after parenteral non-steroidal anti-inflammatory drugs. Gastroenterology. 1997;112:1931-1939.
46. Griswold DE, Adams JL. Constitutive cyclooxygenase (COX-1) and inducible cyclooxygenase (COX-2): rationale for selective inhibition and progress to date. Med Res Rev. 1996;16:181-206.
47. Wallace JL. Selective COX-2 inhibitors: is the water becoming muddy? TIPS. 1999;20:4-6.
48. Hawkey CJ. COX-2 inhibitors. Lancet. 1999;353:307-314.
49. Wu KK. Biochemical pharmacology of nonsteroidal anti-inflammatory drugs. Biochem Pharmacol. 1998;55:543-547.
50. Rainsford KD, Tsang S, Hunt RH, Al-Jehani N. Effects of non-steroidal anti-inflammatory drugs on prostaglandin H synthase isoenzyme 2 (cyclo-oxygenase 2) production by porcine gastric mucosa in organ culture. Inflammopharmacology. 1995;3:299-310.
51. Fenner H. Differentiating among non-steroidal anti-inflammatory drugs by pharmacokinetic and pharmacodynamic profiles. Semin Arthritis Rheum. 1997;26(suppl 1):28-33.
52. Kurumbail RG, Stevens AM, Gierse JK, McDonald JJ, Stegeman RA, Pak JY, Gildehaus D, Miyashiro JM, Penning TD, Seibert K, lsakson PC, Stallings WC. Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents. Nature. 1996;384:644-648.
53. 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. Nature Struct Biol. 1996;3:927-933.
54. 509 in time-dependent inhibition of human prostaglandin H synthase-2 cyclooxygenase activity by isoform-selective agents. J Biol Chem. 1996;271:19134-19139.
55. Gierse JK, McDonald JJ, Hause SD, Rangwala SH, Koboldt CM, Seibert K. A single amino acid difference between cyclooxygenase-1 (COX-1) and -2 (COX-2) reverses the selectivity of COX-2 specific inhibitors. J Biol Chem. 1996; 271:15810-15814.
56. Bhattacharyya DK, Lecomte M, Rieke CJ, Garavito RM, Smith W. Involvement of arginine 120, glutamate 524, and tyrosine 355 in the binding of arachidonate and 2-phenyl-propionic acid inhibitors to the cyclooxygenase active site of bovine prostaglandin endoperoxide H synthase-1. J Biol Chem. 1996;271:2179-2184.
57. Riendeau D, Percival MD, Boyce S, et al. Biochemical and pharmacological profile of a tetrasubstituted furanone as a highly selective COX-2 inhibitor. Br J Pharmacol. 1997;121: 105-117.
58. McAdam BF, Catella-Lawson F, Mardini IA, Kapoor S, Lawson JA, Fitzgerald GA. Systemic biosynthesis of prostacyclin by cyclooxygenase (COX)-2: the human pharmacology of a selective inhibitor of COX-2. Proc Natl Acad Sci USA. 1999;96:272-277.
59. Swinney DC, Mak AY, Barnett J, Ramesha CS. Differential allosteric regulation of prostaglandin H synthase 1 and 2 by arachidonic acid. J Biol Chem. 1997;272:12393-12398.
60. Greig GM, Francis DA, Falgueyret J-P, Quellet M, Percival MD, Roy P, Bayly C, Mancini JA, O'Neill GP. The interaction of arginine 106 of human prostaglandin G/H synthase-2 with inhibitors is not a universal component of inhibition mediated by non-steroidal anti-inflammatory drugs. Mol Pharmacol. 1997;52:829-838.
61. Vane JR, Bakhle YS, Botting RM. Cyclooxygenase 1 and 2. Annu Rev Pharmacol Toxicol. 1998;38:97-120.
62. Rainsford KD, ed. Ibuprofen: A Critical Bibliographic Review. London: Taylor & Francis, 1999.
63. Jeremy JY, Mikhailidis DP, Barradas MA, Kirk RM, Dandona P. Effects of the prodrug nabumetone and its active metabolite, 6-MNA, on human and rat gastric mucosal prostanoids and platelet function. Drugs. 1990;40:53-56.
64. Freed MI, Audet PR, Zariffa N, et al. Comparative effects of nabumetone, sulindac and indomethacin on urinary prostaglandin excretion and platelet function in volunteers. J Clin Pharmacol. 1994;34:1098-1108.
65. Rainsford KD, Willis C. Relationship of gastric mucosal damage induced in pigs by anti-inflammatory drugs to their effects on prostaglandin production. Dig Dis Sci. 1982;27: 624-635.
66. Rainsford KD, Willis CM, Walker SA, Robins PG. Electron microscopic observatons comparing the gastric mucosal damage induced in rats and pigs by benoxaprofen with aspirin, reflecting their differing actions as prostaglandin synthesis inhibitors. Br J Ex Pathol. 1982;63: 25-34.
67. Rainsford KD, Fox J, Hong H, Milne GWA. Gastroulcerogenicity of enantiomeric NSAIDs: relation to cyclooxygenase. In: Xth Symposium of the European League Against Rheumatism (EULAR). Vienna, Austria, November 19-22, 1997.
68. Mangan FR. Nabumetone. In: Lewis AJ, Furst DE, eds. Nonsteroidal Anti-Inflammatory Drugs: Mechanisms and Clinical Use. New York, Basel: Marcel Dekker, Inc., 1987.
69. Friedel HA, Langtry HD, Buckley MM. Nabumetone: a reappraisal of its pharmacology and therapeutic use in rheumatic diseases. Drugs. 1993;45:131-156.
70. Melarange R, Gentry C, Durie M, O'Connell C, Blower PR. Gastrointestinal irritancy, anti-inflammatory activity, and prostanoid inhibition in the rat: differentiation of effects between nabumetone and etodolac. Dig Dis Sci. 1994;39: 601-608.
71. Bjarnason I, Fehilly B, Smethurst P, Menzies IS, Levi AJ. Importance of local versus systemic effects of non-steroidal anti-inflammatory drugs in increasing small intestinal permeability in man. Gut. 1991;32:275-277.
72. Maleev A, Vlahov V, Gruev I, Dierdorf D, Kostova N, Bacracheva N. Liver insufficiency as a factor modifying the pharmacokinetic characteristic of the preparation of nabumetone. Int J Clin Pharmacol Ther Toxicol. 1986;24:425-429.
73. Brett MA, Buscher G, Ellrich E, Greb WH, Kurth H-J, Ruelander G, Schmerenbeck B, Haddock R, Thawley A. Lack of enterohepatic circulation of the active metabolite of nabumetone in humans. J Rheumatol. 1992;19(suppl 36):81-82.
74. 2, and production of interleukins 1,6 and 8 in human and porcine explants in organ culture. J Pharm Pharmacol. 1997;49:991-998.
75. Rainsford KD, Ginsburg I, Gadd SJ. A comparison between the effects of meloxicam and other NSAIDs on the production of oxyradicals by human polymorphonuclear leukocytes. Inflammopharmacology. 1997;5:9-19.
76. Barracchini A, Franceschini N, Amicosante G, et al. Can non-steroidal anti-inflammatory drugs act as metalloproteinase modulators? An in vitro study of inhibition of collagenaseactivity. J Pharm Pharmacol. 1998; 50: 1417-1423.