A study of the relationship between the structure and physicochemical parameters of a homologous series of oxprenolol esters at various pH values and temperatures

Journal of Pharmaceutical Sciences

Volumn 86, Issue 10, 1997, Pages 1085-1091

  Jordan, C Geraldine M ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG VEHICLE; ESTER DERIVATIVE; EYE DROPS; OXPRENOLOL; PRODRUG; PROPRANOLOL; TIMOLOL;

ARTICLE; DRUG BIOAVAILABILITY; DRUG DEGRADATION; DRUG DELIVERY SYSTEM; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; LIPOPHILICITY; MASS SPECTROMETRY; PARTITION COEFFICIENT; PH; PHYSICAL CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; SHELF LIFE; TEMPERATURE;

EID: 0030964624     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1021/js970112x     Document Type: Article

References (37)

1. Huang, H.-S.; Schoenwald, R. D.; Lach, J. L. Corneal Penetration Behaviour of β-Blocking Agents. II: Assessment of Barrier Contributions. J. Pharm. Sci. 1983a, 72, 1272-1279.
2. Huang, H.-S.; Schoenwald, R. D.; Lach, J. L. Corneal Penetration Bhaviour of β-Bocking Aents. III: In Vitro In Vivo Correlations. J. Pharm. Sci. 1983b, 72, 1279-1281.
3. Schoenwald, R. D.; Huang, H-S. Corneal Penetration Behaviour of β-Blocking Agents. I: Physicochemical factors. J. Pharm. Sci. 1983, 72, 1266-1272.
4. Vale, J.; Gibbs, A. C. C.; Phillips, C. I. Topical Propranolol and Ocular Tension in the Human. Br. J. Ophthalmol. 1972, 56, 770-775.
5. Bodor, N.; Visor, G. Formation of Adrenaline in the Iris-Ciliary Body from Adrenalone Diesters. Exp. Eye Res. 1984, 38, 621-626.
6. Bundgaard, H.; Falch, E.; Larsen, C.; Mosher, G. L.; Mikkelson, T. J. Pilocarpine Acid Esters as Novel Sequentially Labile Pilocarpine Prodrugs for Improved Ocular Delivery. J. Med. Chem. 1985, 28, 979-981.
7. Bundgaard, H. Design of Prodrugs: Bioreversible Derivatives for Various Functional Groups and Chemical Entities. In Design of Prodrugs; Bundgaard, H., Ed.; Elsevier: Amsterdam, 1985; pp 1-92.
8. Velde, T. M.; Kaiser, F. E. Ophthalmic Timolol Treatment Causing Altered Hypoglycemic Response in a Diabetic Patient. Arch. Intern. Med. 1983, 143, 1627.
9. Munroe, W. P.; Rindone, J. P.; Kershner, R. M. Systemic Side Effects Associated with Ophthalmic Administration of Timolol. Drug Intell. Clin. Pharm. 1985, 19, 85-89.
10. Nelson, W. L.; Fraunfelder, F. T.; Sills, J. M.; Arrowsmith, J. B.; Kuritsky, J.N. Adverse Respiratory and Cardiovascular Events Attributed to Timolol Ophthalmic Solution, 1978-1985. Am. J. Ophthalmol. 1986, 102, 606-611.
11. Buur, A.; Bundgaard, H.; Lee, V. H. L. Prodrugs of Propranolol: Hydrolysis and Intramolecular Aminolysis of Various Propranolol Esters and an Oxazolidin-2-One Derivative. Int. J. Pharm. 1988, 42, 51-60.
12. Irwin, W. J.; Belaid, K. A. Drug-Delivery by Ion-Exchange. Hydrolysis and Rearrangement of Ester Pro-Drugs of Propranolol. Int. J. Pharm. 1988, 46, 57-67.
13. Quigley, J. M.; Jordan, C. G. M.; Timoney, R. F. Synthesis, Hydrolysis Kinetics and Lipophilicity of O-Acyl Esters of Propranolol. Int. J. Pharm. 1994, 101, 145-163.
14. Bundgaard, H.; Buur, A.; Chang, S.-C.; Lee, V. H. L. Prodrugs of Timolol for Improved Ocular Delivery: Synthesis, Hydrolysis Kinetics and Lipophilicity of Various Timolol Esters. Int. J. Pharm. 1986, 33, 15-26.
15. Chang, S.-C.; Bundgaard, H.; Buur, A.; Lee, V. H. L. Improved Corneal Penetration of Timolol by Prodrugs as a Means to Reduce Systemic Drug Load. Invest. Ophthalmol. Vis. Sci. 1987, 28, 487-491.
16. Leger, J. M.; Gadret, M.; Carpy, A. Structure Cristalline du Chlorhydrate d'Oxprenolol [Chlorhydrae d'Isopropylamino-1-(o-allyloxy)phenoxy-3-Propanol-2]. Acta Crystallogr. 1977, B33, 2156-2159.
17. Day, M. D.; Roach, A. G. Cardiovascular Effects of β-Adrenoceptor Blocking Agents after Intracerebroventricular Administration in Conscious Normotensive Cats. Clin. Exp. Pharmacol. Physiol. 1974, 1, 333-339.
18. Forrest, W. A. A Multi-Centre Assessment of the Role of Oxprenolol in the Treatment of Hypertensive Patients. Curr. Med. Res. Opinion 1976, 3, 662-667.
19. Nelson, W. L.; Burke, T. R. Absolute Configuration of Glycerol Derivatives. 5. Oxprenolol Enantiomers. J. Org. Chem. 1978, 43, 3641-3645.
20. Jordan, C. G. M.; Quigley, J. M.; Timoney, R. F. Synthesis, Hydrolysis Kinetics and Lipophilicity of O-Acyl Esters of Oxprenolol. Int. J. Pharm. 1992, 84, 175-189.
21. Clarke, F. H. Ionization Constants by Curve Fitting: Application to the Determination of Partition Coefficients. J. Pharm. Sci. 1984, 73, 226-230.
22. Clarke, F. H.; Cahoon, N. M. Ionization Constants by Curve Fitting: Detrmination of Partition and Distribution Coefficients of Acids and Bases and their Ions. J. Pharm. Sci. 1987, 76, 611-619.
23. as and Partition and Drug Distribution Coefficients of Narcotics and Narcotic Antagonists and their pH and Temperature Dependence. J. Med. Chem. 1975, 18, 647-655.
24. Charton, M. Steric Effects. 1: Esterification and Acid-Catalysed Hydrolysis of Esters. J. Am. Chem. Soc. 1975, 97, 1552-1556.
25. Charton, M. Steric Effects. 7: Additional v Constants. J. Org. Chem. 1976, 41, 2217-2220.
26. Charton, M. The Prediction of Chemical Lability through Substituent. In Design of Biopharmaceutical Properties through Prodrugs and Analogs, Roche, E. B., Ed.; American Pharmaceutical Association: Washington, DC, 1977; pp 228-280.
27. Zaslowsky, J. A.; Fisher, E. The Hydrolysis of β-Diethyl-Aminoethyl Acetate. J. Phys. Chem. 1963, 67, 959-961.
28. Bruice, P. Y.; Mautner, H. G. Inter- and Intramolecular Catalysis and the Involvement of Tetrahedral Partitioning in the Hydrolysis of Benzoycholine, Benzoylthionocfholine and their Dimethylamino Analogs. J. Am. Chem. Soc. 1973, 95, 1582-1586.
29. Kennon, L. Use of Models in Determining Chemical Pharmaceutical Stability. J. Pharm. Sci. 1964, 53, 815-818.
30. Cruickshank, J. M. The Clinical Importance of Cardioselectivity and Lipophilicity in Beta Blockers. Am. Heart. J. 1980, 100, 160-178.
31. Woods, P. B.; Robinson, M. L. An Investigation of the Comparative Liposolubilities of β-Adrenoceptor Blocking Agents. J. Pharm. Pharmacol. 1981, 33, 172-173.
32. Betageri, G. V.; Rogers, J. A. Thermodynamics of Partitioning of β-Blockers in the n-Octanol Buffer and Liposome Systems. Int. J. Pharm. 1987, 36, 165-173.
33. Mannhold, R.; Dross, K. P.; Rekker, R. F. Drug Lipophilicity in QSAR Practice I: A Comparison of Experimental with Calculative Approaches. Quant. Struct.-Act. Relat. 1990, 9, 21-28.
34. Recanatini, M. Comparison between Measured and Calculated Partition Coefficients of β-Receptor Antagonists. In QSAR: Quantitative Structure-Activity Relationships in Drug Design; Frauchere, J.-L., Ed.; Prog. Clin. Drug Res. 1989, 291, 75-78.
35. Burgot, G.; Serrand, P.; Burgot, J.-L. Thermodynamics of Partitioning in the n-Octanol/Water System of some β-Blockers. Int. J. Pharm. 1990, 63, 73-76.
36. Irwin, W. J.; Belaid, K. A. Drug-Delivery by Ion-Exchange.II: Physicochemical Properties of Ester Prodrugs of Propranolol. Drug Dev. Ind. Pharm. 1987, 13, 2033-2045.
37. Hafkenscheid, T. L.; Tomlinson, E. Correlations Between Alkane/Water and Octan-1-ol/Water Distribution Coefficients and Isocratic Reversed-Phase Liquid Chromatographic Factors of Acids, Bases and Neutrals. Int. J. Pharm. 1983, 16, 225-239.