Ester prodrugs of a potent analgesic, morphine-6-sulfate: Syntheses, spectroscopic and physicochemical properties

International Journal of Pharmaceutics

Volumn 163, Issue 1-2, 1998, Pages 177-190

  Preechagoon, Detpon ^a   Brereton, Ian ^a   Staatz, Christine ^a   Prankerd, Richard ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

3 Acyl prodrugs; Aqueous solubility; HPLC capacity factors; Hydrolysis kinetics; Lipophilicity; Morphine; Morphine 6 sulfate; Nuclear magnetic resonance; Oil solubility

Indexed keywords

MORPHINE SULFATE; PRODRUG;

ANALGESIA; AQUEOUS SOLUTION; ARTICLE; CRYSTALLIZATION; DRUG POTENCY; DRUG SYNTHESIS; ENZYME KINETICS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; LIPOPHILICITY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; SOLUBILIZATION;

EID: 0032542786     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0378-5173(97)00381-5     Document Type: Article

References (27)

1. Bechalany A., Röthlisberger T., Tayar N.E., Testa B. Comparison of various non-polar stationary phases used for assessing lipophilicity. J. Chromatogr. 473:1989;115-124.
2. Brock C.P., Kottayil S., Butterfield D.A., Crooks P.A. A dihydromorphine-6-O-sulfate. Acta Crystallogr. (C) Cryst. Struct. Commun. 52(1):1996;122-125.
3. Brown C.E., Roerig S.C., Burger V.T., Cody R.B. Jr., Fujimoto J.M. Analgesic potency of morphine 3- and 6-sulfates after intracerebroventricular administration in mice: relationship to structural characteristics defined by mass spectrometry and nuclear magnetic resonance. J. Pharm. Sci. 74:1985;821-825.
4. Brown C.E., Roerig S.C., Fujimoto J.M., Burger V.T. The structure of morphine differs between the crystalline state and aqueous solution. J. Chem. Soc. Chem. Commun. 1:1983;1506-1508.
5. Carrupt P.A., Testa B., Bechalany A., Tayer N.E., Descas P., Perrissoud D. Morphine 6-glucuronide and morphine 3-glucuronide as molecular chamelons with unexpected lipophilicity. J. Med. Chem. 34:1991;1272-1275.
6. Connors, K.A., Amidon, G.L., Stella, V.J., 1986. Chemical Stability of Pharmaceuticals, 2nd ed. Wiley-Interscience, New York, p. 374.
7. Davis, S.S., Higuchi, T., Rytting, J.H., 1974. Determination of thermodynamics of functional groups in solutions of drug molecules. In: Bean, H.S., Beckett, A.H., Carless, J.E. (Eds.), Advances in Pharmaceutical Sciences, vol. 4, Academic Press, London, pp. 73-261.
8. Eliel E.L., Morris-Natschke S. Conformational analogies of morphine agonists and antagonists as revealed by carbon-13 NMR spectroscopy. Org. Magn. Reson. 22:1984;258-262.
9. 1 and bicarbonate concentration in plasma. Clin. Chem. 33:1987;13-20.
10. Hafkenscheid T.L., Tomlinson E. Correlations between alkane/water and octan-1-ol/water distribution coefficients and isocratic reversed-phase liquid chromatographic capacity factors of acids, bases and neutrals. Int. J. Pharm. 16:1983;225-239.
11. Hafkenscheid T.L., Tomlinson E. Relationships between hydrophobic (lipophilic) properties of bases and their retention in reversed-phase liquid chromatography using aqueous methanol mobile phases. J. Chromatogr. 292:1984;305-317.
12. Hammers W.E., Meurs G.J., De Ligny C.L. Correlations between liquid chromatographic capacity ratio data on lichrosorb RP-18 and partition coefficients in the octanol-water system. J. Chromatogr. 247:1982;1-13.
13. Hite, G. J., 1989. Analgesics. In: Foye, W.O. (Ed), Principles of Medicinal Chemistry, Lea & Febiger, Philadelphia, PA, pp. 247-275.
14. Houdi A.A., Kottayil S.G., Butterfield D.A., Crooks P.A. Potent central activity of morphine-6-O-sulfate (M6S) and morphine-3-O-acetyl-6-O-sulfate (M3A6S) [Abstr. MNPC5015]. Pharm. Res. 9:1992;S-103.
15. Houdi A.A., Kottayil S., Crooks P.A., Butterfield D.A. 3-O-Acetylmorphine-6-O-sulfate: A potent centrally acting morphine derivative. Pharmacol. Biochem. Behav. 53:1996;665-671.
16. Jinno K., Kawasaki K. Computer-assisted retention prediction system for reversed-phase micro high-performance liquid chromatography. J. Chromatogr. 316:1984;1-23.
17. Krowech G., Caldera-munoz P.S., Straub K., Castagnoli N. Jr., Correia M.A. Morphine metabolism revisited. III. Confirmation of a novel metabolic pathway. Chem. Biol.-Interact. 58:1986;29-40.
18. Mori M., Oguri K., Yoshimura H., Shimomura K., Kamata O., Ueki S. Chemical synthesis and analgesic effect of morphine ethereal sulfates. Life Sci. 11:1972;525-533.
19. Neville G.A. High-resolution proton magnetic resonance spectra of morphine and its three O-acetyl derivatives. Magn. Reson. Chem. 25:1987;31-35.
20. Osborne R., Joel S., Trew D., Slevin M. Morphine and metabolite behavior after different routes of administration: demonstration of the importance of the active metabolite morphine-6-glucuronide. Clin. Pharmacol. Ther. 47:1990;12-19.
21. Prankerd, R.J., 1985. Physical Properties and Biological Activities of Barbiturates. PhD thesis, University of Otago, Dunedin, NZ.
22. Prankerd R.J., McKeown R.H. Physico-chemical properties of barbituric acids. II: partition coefficients of 5,5-disubstituted barbituric acids at 25°C. Int. J. Pharm. 83:1992;25-37.
23. Preechagoon, D., Smith, M.T., Prankerd, R.J., 1997. Int. J. Pharm. (submitted for publication).
24. Shimomura K., Kamata O., Ueki S., Ida S., Oguri K., Yoshimura H., Tsukamoto H. Analgesic effect of morphine glucuronide. Tohoku J. Exp. Med. 105:1971;45-52.
25. Smith M.T., Watt J.A., Cramond T. Morphine-3-glucuronide: a potent antagonist of morphine analgesia. Life Sci. 47:1990;579-585.
26. Sy W.W., By A.W., Neville G.A., Wilson W.L. Syntheses of 3-O-and 6-O-propanoylmorphine: a reinvestigation and correction. J. Pharm. Sci. 75:1986;787-789.
27. Wright A.W.E., Watt J.A., Kennedy M., Cramond T., Smith M.T. Quantitation of morphine, morphine-3-glucuronide, and morphine-6-glucuronide in plasma and cerebrospinal fluid using solid phase extraction and high performance liquid chromatography with electrochemical detection. Ther. Drug Monit. 16:1994;200-208.