Single oral dose study of two isosorbide-based aspirin prodrugs in the dog

Journal of Pharmacy and Pharmacology

Volumn 55, Issue 10, 2003, Pages 1351-1357

  Gilmer, John F ^a   Murphy, Michael A ^a   Shannon, Jean A ^a   Breen, Colm G ^a   Ryder, Sheila A ^a   Clancy, John M ^a  

^a TRINITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLSALICYLIC ACID; ACETYLSALICYLIC ACID 3 (NITROXYMETHYL)PHENYL ESTER; ADENOSINE DIPHOSPHATE; ARACHIDONIC ACID; COLLAGEN; ISOSORBIDE DERIVATIVE; ISOSORBIDE DIASPIRINATE; ISOSORBIDE MONONITRATE; PRODRUG; THROMBOXANE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; BLOOD CLOTTING; COMPARATIVE STUDY; CONTROLLED STUDY; DISSOLUTION; DOSE RESPONSE; DRUG ABSORPTION; DRUG DISTRIBUTION; DRUG EFFECT; DRUG EFFICACY; DRUG INHIBITION; DRUG RELEASE; FEMALE; MALE; NONHUMAN; PROTEIN BLOOD LEVEL; PROTEIN EXPRESSION; PROTEIN SYNTHESIS; QUANTITATIVE ANALYSIS; THROMBOCYTE AGGREGATION; THROMBOCYTE AGGREGATION INHIBITION; THROMBOCYTE FUNCTION;

ADMINISTRATION, ORAL; ANIMALS; ARACHIDONIC ACID; ASPIRIN; COLLAGEN; DOGS; FEMALE; ISOSORBIDE; MALE; PLATELET AGGREGATION; PLATELET AGGREGATION INHIBITORS; PLATELET FUNCTION TESTS;

EID: 0142214462     PISSN: 00223573     EISSN: None     Source Type: Journal    
DOI: 10.1211/0022357022007     Document Type: Article

References (37)

1. Bonina, F., Puglia, C., Santagati, N. A., Saija, A., Tomaino, A., Tita, B. (2002) Oligoethylene ester derivatives of ketoprofen, naproxen and diclofenac as oral prodrugs: A pharmacological evaluation. Pharmazie 57: 552-555
2. Born, G. V. R. (1962) Aggregation of blood platelets by adenosine diphosphate and its reversal. Nature 194: 927-929
3. Brideau, C., Kargman, S., Liu, S., Dallob, A. L., Ehrich, E. W., Rodger, I. W., Chan, C. C. (1996) A human whole blood assay for clinical evaluation of biochemical efficacy of cyclooxygenase inhibitors. Inflamm. Res. 45: 68-74
4. Cardinal, D. C., Flower, R. J. (1980) The electronic aggregometer: A novel device for assessing platelet behaviour in whole blood. J. Pharmacol. Method 3: 135-158
5. Chignard, M., Varagaftig, B. (1976) Dog platelets fail to aggregate when they form aggregating substances upon stimulation with arachidonic acid. Eur. J. Pharmacol. 38: 7-18
6. Cryer, B., Luk, G., Feldman, M. (1995) Effects of very low doses of aspirin (ASA) on gastric, duodenal and rectal prostaglandins (PGs) & mucosal injury. Gastroenterology 108: A77
7. Del Soldato, P., Sorrentino, R., Pinto, A. (1999) NO-aspirins: A class of new anti-inflammatory and antithrombotic agents. Trends Pharmacol. Sci. 20: 319-323
8. Gardiner, P. S., Gilmer, J. F. (2003) The medicinal chemistry implications of the anti-cancer effects of aspirin and the NSAIDs. Mini-rev. Med. Chem. 3: 441-450
9. Gilmer, J. F., Moriarty, L. M., McCafferty, D. F., Clancy, J. M. (2001) Synthesis, hydrolysis kinetics and antiplatelet effects of isosorbide mononitrate derivatives of aspirin. Eur. J. Pharm. Sci. 14: 221-227
10. Gilmer, J. F., Moriarty, L. M., Lally, M. N., Clancy, J. M. (2002) Isosorbide-based aspirin prodrugs part II: Hydrolysis kinetics of isosorbide diaspirinate. Eur. J. Pharm. Sci. 16: 297-304
11. Giovannucci, E. (1999) The prevention of colorectal cancer by aspirin use. Biomed Pharmacother. 53: 303-308
12. Grauer, G. F., Rose, B. F., Toolan, L. A., Thrall, M. A. H., Colgan. S. P. (1992) Effects of low dose aspirin and specific thromboxane synthetase inhibition on whole blood platelet aggregation and adenosine triphosphate secretion in healthy dogs. Am. J. Vet. Res. 53: 1631-1635
13. Hawkey, C. J. (1996) Non-steroidal anti-inflammatory drug gastropathy: Causes and treatment. Scand. J. Gastroenterol. Suppl. 220: 124-127
14. Jones, G. (1985) Decreased toxicity and adverse reaction via prodrugs. In: Bundgaard H. (ed.) Design of Prodrugs. Elsevier, Amsterdam, 199-241
15. Jüttner, C., Rodríguez, M., Fragío, C. (2000) Optimal conditions for simultaneous measurement of platelet aggregation and ATP secretion in canine whole blood. Res. Vet. Sci. 68: 27-32
16. Kelly, J. P., Kaufman, D. W., Jurgelon, J. M., Sheehan, J., Koff, R. S., Shapiro, S. (1996) Risk of aspirin-associated major upper-gastrointestinal bleeding with enteric-coated or buffered product. Lancet 348: 1413-1416
17. Kurata, J. H., Abbey, D. E. (1990) The effect of chronic aspirin use on duodenal and gastric ulcer hospitalisation. J. Clin. Gastroenterol. 12: 260-266
18. Kurata, M., Ishizuka, N., Matsuzawa, M., Haruta, K., Takeda, K. (1995) A comparative study of whole-blood platelet aggregation in laboratory animals: Its species differences and comparison with turbidimetric method. Comp. Biochem. Physiol. 112: 359-365
19. Lofttson, T., Kaminski, J. J., Bodor, N. (1981) Improved delivery through biological membranes VIII: Design, synthesis, and in vivo testing of true prodrugs of aspirin. J. Pharm. Sci. 70: 743-749
20. Mahfouz, N. M., Omar, F. A., Aboul-Fadl, T. (1999) Cyclic amide derivatives as potential prodrugs II: N-hydroxymethylsuccinimide/isatin esters of some NSAIDs as prodrugs with an improved therapeutic index. Eur. J. Med. Chem. 34: 551-562
21. Major, R. M., Taylor, T., Chasseaud, L. F., Darragh, A., Lambe, R. F. (1984) Isosorbide 5-mononitrate kinetics. Clin. Pharmacol. Ther. 35: 653-659
22. McGoff, M. A., Allen, B. T., Der, T. (1989) Mechanisms of vascular graft thrombosis: Role of altered canine platelet sensitivity to thromboxane. Thromb. Res. 55: 147-154
23. McKellar, Q. A., Nolan, A. M., Galbraith, E. A. (1990) Serum thromboxane generation by platelets in several domestic animal species. Br. J. Vet. 146: 398-404
24. Minuz, P., Lechi, C., Zuliani, V., Gaino, S., Tommasoli, R., Lechi, A. (1998) NO-aspirins: Anti-thrombotic activity of derivatives of acetylsalicylic acid releasing nitric oxide. Cardio. Drug Rev. 16: 31-47
25. Nielsen, N. M. and Bungaard, H. (1989) Evaluation of glycolamide esters and various other esters of aspirin as true aspirin prodrugs. J. Med. Chem. 32: 727-734
26. Oshima, T., McCluskey, E. R., Honda, A., Needleman, P. (1984) Pharmacological manipulation of canine cyclooxygenase and thromboxane synthase in vivo: Differential renal and platelet recovery rates. J. Pharmacol. Exp. Ther. 229: 598-602
27. Patrigani, P., Panara, M. R., Greco, A., Fusco, O., Natoli, C., Iacobelli, S., Ciplollone, F., Ganci, A., Creminon, C., Maclouf, J., Patrono, C. (1994) Biochemical and pharmacological characterization of the cyclooxygenase activity of human prostaglandin endoperoxides synthases. J. Pharmacol. Exp. Ther. 271: 1705-1712
28. Patrono, C. (1994) Aspirin as an antiplatelet drug. N. Engl. J. Med. 330: 1287-1294
29. Rainsford, K. D. (1989) Mechanisms of gastrointestinal toxicity of non-steroidal anti-inflammatory drugs. Scand. J. Gastroenterol. Suppl. 163: 9-16
30. Rao, G. H. R., Johnson, G. J., Reddy, R. K., White, J. G. (1981) Rapid return of cyclooxygenase active platelet in dogs after a single oral dose of aspirin. Prostaglandins 22: 761-772
31. Sponer, G., Kuhnle, H. F., Strein, K., Bartsch, W., Endele, R., Dietmann, K. (1984) Pharmacokinetic aspects of isosorbide-5-mononitrate in dogs. J. Pharmacol. Exp. Ther. 228: 235-239
32. St Pierre, T., Jencks, W. P. (1968) Intramolecular catalysis in the reactions of nucleophilic reagents with aspirin. J. Am. Chem. Soc. 90: 3817-3827
33. Takeuchi, K., Ukawa, H., Konaka, A., Kitamura, M., Sugawa, Y. (1998) Effect of nitric oxide-releasing aspirin derivative on gastric functional and ulcerogenic responses in rats: Comparison with plain aspirin. J. Pharmacol. Exp. Ther. 286: 115-121
34. Tammara, V. K., Narurkar, M. M., Crider, A. M., Khan, M. A. (1994) Morpholinoalkyl ester prodrugs of diclofenac: Synthesis, in vitro and in vivo evaluation. J. Pharm. Sci. 83: 644-648
35. Tashima, K., Fujita, A., Umeda, M., Takeuchi, K. (2000) Lack of gastric toxicity of nitric oxide releasing aspirin, NCX-4016, in the stomach of diabetic rats. Life Sci. 67: 1639-1652
36. Yamanaka, S., Miura, K., Yukimura, T., Yamamoto, K. (1993) 11-Dehydro thromboxane B2: A reliable parameter of thromboxane A2 production in dogs. Prostaglandins 45: 221-228
37. Zandi, P. P., Anthony, J. C., Hayden, K. M., Mehta, K., Mayer, L., Breitner, J. C. (2002) Reduced incidence of AD with NSAID but not H2 receptor antagonists: The Cache County Study. Neurology 59: 880-886