Chemical delivery systems: Evaluation of physicochemical properties and enzymatic stability of phenylephrone derivatives

Pharmaceutical Development and Technology

Volumn 4, Issue 2, 1999, Pages 189-198

  Goskonda, Venkat R ^a   Khan, Mansoor A ^a   Bodor, Nicholas S ^b   Reddy, Indra K ^a,c  

^a UNIVERSITY OF LOUISIANA AT MONROE   (United States)

^b UNIVERSITY OF FLORIDA HEALTH   (United States)

^c School of Pharmacy   (United States)

Author keywords

Bioreversible; Capacity factor; CDS; Mydriatics; Phenylephrone; Stability

Indexed keywords

BUFFER; PHENYLEPHRINE; PHENYLEPHRONE; PHENYLEPHRONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG HALF LIFE; DRUG STABILITY; DRUG SYNTHESIS; ENZYME MODIFICATION; HUMAN; HYDROLYSIS; MYDRIASIS; NONHUMAN; PRIORITY JOURNAL; RAT;

EID: 0032947312     PISSN: 10837450     EISSN: None     Source Type: Journal    
DOI: 10.1081/PDT-100101353     Document Type: Article

References (27)

1. N. Bodor, The use of retrometabolic drug design concepts in ophthalmic drug discovery, in Ocular Therapeutics and Drug Delivery (I. K. Reddy, ed.), Technomic, PA, 1996, pp. 335-361.
2. I. K. Reddy and N. S. Bodor, Novel approaches to design and deliver safe and effective anti-glaucoma agents to the eye, Adv. Drug Del. Rev., 14, 251-267 (1994).
3. N. Bodor, Novel approaches to the design of safer drugs: Soft drugs and site specific chemical delivery systems, in Advances in Drug Research (B. Testa, ed.), Academic Press, London, 1984, pp. 255-331.
4. N. Bodor and M. E. Brewster, Problems of delivery of drugs to the brain, Pharm. Ther., 19, 337-386 (1983).
5. R. D. Schoenwald, Chemical delivery systems with enhanced pharmacokinetic properties, in Ophthalmic Drug Delivery Systems (A. K. Mitra, ed.), Marcel Dekker, New York, 1993, pp. 307-330.
6. A. A. El-Koussi and N. Bodor, Formulation of propranolol in the iris-ciliary body from its propranolol ketoxime precursor - a potential antiglaucoma drug, Int. J. Pharm., 53, 189-194 (1989).
7. D. M. Maurice and S. Mishima, Ocular pharmacokinetics, in Pharmacology of the Eye (M. L. Sears, ed.), Springer, New York, 1984, pp. 19-116.
8. N. D. Das and H. Shichi, Enzymes of mercapturate synthesis and other drug-metabolizing reactions - specific localization in the eye, Exp. Eye Res., 33, 525-533 (1981).
9. N. Bodor and G. Visor, Formation of adrenaline in the iris-ciliary body from adrenalone diesters, Exp. Eye Res., 38, 621-626 (1984).
10. N. Bodor, J. J. Kaminski, and R. G. Roller, Improved delivery through biological membranes. VI. Potent sympathomimetic adrenalone derivatives, Int. J. Pharm., 1, 189-196 (1978).
11. N. Bodor and G. Visor, Improved delivery through biological membranes. XVII. A site-specific chemical delivery system as short-acting mydriatic agent, Pharm. Res., 168-172 (1984).
12. M. V. W. Bergamini, D. L. Murray, and P. D. Krause, Pivalyl phenylephrine (PPE), mydriatic prodrug of phenylephrine with reduced cardiovascular effects, Invest. Ophthalmol. Vis. Sci., 20, 137-191 (1979).
13. V. Kumar, R. D. Schoenwald, D. S. Chien, A. J. Packer, and W. W. Choi, Systemic absorption and cardiovascular effects of phenylephrine eyedrops, Am. J. Ophthalmol., 99, 180-184 (1985).
14. V. K. Tammara and M. A. Crider, Prodrugs: A chemical approach to ocular drug delivery, in Ocular Therapeutics and Drug Delivery (I. K. Reddy, ed.), Technomic, PA, 1996, pp. 285-334.
15. J. S. Mindel, S. T. Shaikewitz, and S. M. Podos, Is phenylephrine pivalate a prodrug? Arch. Ophthalmol., 98, 2220-2223 (1980).
16. S. S. Yuan and N. Bodor, Synthesis and activity of R-(-)-m-trimethylacetoxy-alpha-[(methylamino)methyl] benzyl alcohol hydrochloride: a prodrug form of (R)-(-)-phenylephrine, J. Pharm. Sci., 65, 929-931 (1976).
17. R. D. Schoenwald, J. C. Folk, V. Kumar, and J. C. Piper, In vivo comparison of phenylephrine and phenylephrine oxazolidine instilled in the monkey eye, J. Ocular Pharmacol., 3(4), 333-340 (1987).
18. I. K. Reddy, Design and evaluation of site-specific Chemical Delivery Systems to the eye, Ph.D. Dissertation, University of Florida, Gainesville, FL, 1989.
19. C. Martorell, A. C. Calpena, E. Escribano, J. M. Poblet, and J. Freixas, Influence of the Chromatographic capacity factor (log k′) as an index of lipophilicity in the antibacterial activity of a series of 6-fluoroquinolones. Relationship between physico-chemical and structural properties and their hydrophobicity, J. Chromatogr. A, 655, 177-184 (1993).
20. P. Boudeville, M. Bona, and J. L. Burgot, Correlations between n-octanol/water partition coefficients and RP-HPLC capacity factors of 1,2-dithiole-3-thiones and 1,2-dithiol-3-ones, J. Pharm. Sci., 85(9), 990-998 (1996).
21. S. Yang, J. G. Bumgarner, L. F. R. Kruk, and M. G. Khaledi, Quantitative structure-activity relationship studies with micellar electrokinetic chromatography. Influence of surfactant type and mixed micelles on estimation of hydrophobicity and bioavailability, J. Chromatogr. A, 721, 323-335 (1996)
22. H. Bundgaard and J. Moss, Prodrugs of peptides. 6. Bioreversible derivatives of thyrotropin-releasing hormone (TRH) with increased lipophilicity and resistance to cleavage by the TRH-specific serum enzyme, Pharm. Res., 7, 885-892 (1990).
23. L. B. Hansen, L. L. Christrup, and H. Bundgaard, Ketobemidone prodrugs for buccal delivery, Acta Pharm. Nord., 3, 77-82 (1991).
24. B. J. Aungst, J. A. Blake, N. J. Rogers, H. Saitoh, M. A. Hussain, C. L. Ensinger, and J. R. Pruitt, Prodrugs to improve the oral bioavailability of a diacidic nonpeptide angiotensin II antagonist, Pharm. Res., 12, 763-767 (1995).
25. H. Bundgaard and G. J. Rasmussen, Prodrugs of peptides. 11. Chemical and enzymatic hydrolysis kinetics of N-acyloxymethyl derivatives of a peptide-like bond, Pharm. Res., 8, 1238-1242 (1991).
26. J. E. Harkness and J. E. Wagner, The Biology of Medicine of Rabbits and Rodents, 2nd ed., Lea and Febiger, Philadelphia, 1983.
27. J. U. Patel, R. J. Prankerd, and K. B. Sloan, A prodrug approach to increasing the oral potency of phenolic drug. 1. Synthesis, characterization, and stability of an o-(imidomethyl) derivative of 17β-estradiol, J. Pharm. Sci., 83, 1477-1481, 1994.