Synthesis, identification, characterization, stability, solubility, and protein binding of ester derivatives of salicylic acid and diflunisal

International Journal of Pharmaceutics

Volumn 153, Issue 1, 1997, Pages 25-39

  Hung, Daniel Y ^a   Mellick, George D ^a   Prankerd, Richard J ^a   Roberts, Michael S ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

Aspirin analogues; Diflunisal esters; In vitro non enzymatic hydrolysis; Intrinsic solubility; Melting point; Protein binding; Synthesis

Indexed keywords

DIFLUNISAL; SALICYLIC ACID DERIVATIVE;

ARTICLE; DRUG PROTEIN BINDING; DRUG SOLUBILITY; DRUG STABILITY; DRUG SYNTHESIS; ESTERIFICATION; MELTING POINT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL;

EID: 0030786444     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0378-5173(97)00075-6     Document Type: Article

References (26)

1. Aarons, L., Clifton, P., Rowland, M., 1980. Aspirin binding and the effect of albumin on spontaneous and enzyme-catalysed hydrolysis. J. Pharm. Pharmacol. 32, 537-543.
2. Ali, M., McDonald, J.W.D., Theissen, J.J., Coates, P.E., 1980. Plasma acetylsalicylate and salicylate and platelet cyclooxygenase activity following plain and enteric-coated aspirin. Stroke 11, 9-13.
3. Bailey, P.S., Bailey, C.A., 1981. Organic Chemistry, Allyn and Bacon, New York, pp. 57-58.
4. Cossum, P.A., Roberts, M.S., Kilpatrick, D., Yong, A.C., 1986. Distribution and metabolism of nitroglycerin and its metabolites in vascular beds of sheep. J. Pharm. Sci. 75, 731-737.
5. Davis, S.S., Higuchi, T., Rytting, J.H., 1972. Determination of thermodynamics of the methylene group in solutions of drug molecules. J. Pharm. Pharmac., 24, Suppl. 30P-46P.
6. Forster, S., Buckton, G., Beezer, A.E., 1991. The importance of chain length on the wettability and solubility of organic homologs. Int. J. Pharm. 72, 29-34.
7. Foye, W.O., 1989. Principles of Medicinal Chemistry, 3rd ed., Lea & Febiger, Philadelphia, 863.
8. Harris, P.A., Riegelman, S., 1969. Influence of the route of administration on the area under the plasma concentration-time curve. J. Pharm. Sci. 58, 71-75.
9. Isaacs, N.S., 1987. Physical Organic Chemistry, Longmans, Essex, pp. 297-301.
10. Iwamoto, K., Takei, M., Watanabe, J., 1982. Gastrointestinal and hepatic first-pass metabolism of aspirin in rats. J. Pharm. Pharmacol. 34, 176-180.
11. Jusko, W.J., Gretch, M., 1976. Plasma and tissue protein binding of drugs in pharmacokinetics. Drug Metabolism Rev. 5, 43-140.
12. Lecomte, M., Laneuville, O., Ji, C., Dewitt, D.L., Smith, W.L., 1994. Acetylation of human prostaglandin endoperoxide synthase-2 by aspirin. J. Biochem., 269 13 207-13 215.
13. Leo, A., Jow, P.Y., Silipo, C., Hansch, C., 1975. Calculation of hydrophobic constant (log P) from Pi and f constants. J. Med. Chem. 18, 865-868.
14. Levy, G.A., 1966. Glucuronic Acid, Academic Press, New York, p. 301.
15. Martin, A.N., 1983. Physical Pharmacy, 3rd ed., Lea & Febiger, Philadelphia, Ch. 13.
16. McLeod, L.J., Roberts, M.S., Seville, P.R., 1988. Low-dose enteric-coated aspirin as an antiplatelet preparation. Aust. NZ. J. Med. 148, 207.
17. Mellick, G.D., Roberts, M.S., 1996. The disposition of aspirin and salicylic acid in the isolated perfused rat liver: The effect of normal and retrograde flow on availability and mean transit times. J. Pharm. Pharmacol. 48, 738-743.
18. Roberts, M.S., Joyce, R.M., McLeod, L.J., Vial, J.H., Seville, P.R., 1986. Slow-release aspirin and prostaglandin inhibition. Lancet 1, 1153-1154.
19. Siebert, D.J., Bochner, F., Imhoff, D.M., Watts, S., Lloyd, J.V., Field, J., Gabb, B.W., 1983. Aspirin kinetics and platelet aggregation in man. Clin. Pharmacol. Ther. 33, 367-374.
20. The SALT Collaborative Group, Swedish Aspirin Low-dose Trial (SALT) of 75 mg aspirin as secondary prophylaxis after cerebrovascular ischaemic events. 1991. Lancet, 338, 1345-1349.
21. Vial, J.H., Roberts, M.S., McLeod, L.J., Seville, P.R., 1990. Selective inhibition of platelet cyclooxygenase with controlled release, low-dose aspirin. Aust. NZ. J. Med. 20, 652-656.
22. Wientjes, M.G., Levy, G., 1988. Nonlinear pharmacokinetics of aspirin in rats. J. Pharmacol. Exp. Ther. 245, 809-815.
23. Windholz, M (Ed.), 1983. The Merck Index, 10th ed., Merck, Rahway, p. 865.
24. Yacobi, A., Lai, C.M., Levy, G., 1977. Comparative pharmacokinetics of coumarin anticoagulants XXI: effect of plasma protein binding on distribution kinetics of warfarin in rats. J. Pharm. Sci. 66, 567-572.
25. Yalkowsky, S.H., Flynn, G.L., Slunick, T.G., 1972. Importance of chain length on physiochemical and crystalline properties of organic homologues. J. Pharm. Sci., 852-857.
26. Yalkowsky, S.H., 1981. Techniques of Solubilization of Drugs, Marcel Dekker, New York, Ch. 1.