Octanol-, chloroform-, and propylene glycol dipelargonat-water partitioning of morphine-6-glucuronide and other related opiates

Journal of Medicinal Chemistry

Volumn 39, Issue 22, 1996, Pages 4377-4381

  Avdeef, Alex ^a   Barrett, David A ^b   Shaw, P Nicholas ^b   Knaggs, Roger D ^b   Davis, Stanley S ^b  

^a Sirius Analytical Instruments Ltd   (United Kingdom)

^b UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BUPRENORPHINE; CHLOROFORM; CODEINE; DIAMORPHINE; MORPHINE; MORPHINE 3BETA D GLUCURONIDE; MORPHINE 6 ACETATE; MORPHINE 6 GLUCURONIDE; MORPHINE 6BETA D GLUCURONIDE; NORCODEINE; NORMORPHINE; OCTANOL; OPIATE; PROPYLENE GLYCOL; SOLVENT; UNCLASSIFIED DRUG; WATER;

ARTICLE; LIPOPHILICITY; PARTITION COEFFICIENT; PH; PKA; POTENTIOMETRY;

BIOLOGICAL TRANSPORT; CHEMISTRY, PHYSICAL; CHLOROFORM; HYDROGEN-ION CONCENTRATION; MORPHINE DERIVATIVES; NARCOTICS; OCTANOLS; POTENTIOMETRY; SOLUTIONS; SOLVENTS;

EID: 0029911418     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960073m     Document Type: Article

References (27)

1. World Health Organization. Cancer Pain Relief Program. WHO: Geneva, 1986.
2. Glare, P. A.; Walsh, T. D. Clinical Pharmacokinetics of Morphine. Ther. Drug Monit. 1991, 13, 1-23.
3. Yoshimura, H.; Ida, S.; Oguri, K.; Tsukamoto, H. Biochemical Basis for Analgesic Activity of Morphine-6-Glucuronide - I. Penetration of M6G in the Brain of Rats. Biochem. Pharmacol. 1973, 22, 1423-1430.
4. Shimomura, K.; Kamata, O.; Ueki, S.; Ida, S.; Oguri, K.; Yoshimura, H.; Tsukamoto, H. Analgesic Effect of Morphine Glucuronides. Tohoku J. Exp. Med. 1971, 105, 45-52.
5. Oguri, K.; Yamada-Mori, I.; Shigezane, J.; Hirano, T.; Yoshimura, H. Enhanced Binding of Morphine and Nalorphine to Opiod δ Receptor by Glucuronate and Sulfate Conjugation at the 6-Position. Life Sci. 1987, 41, 1457-1464.
6. Abbott, F.; Palmour, R. M6G: Analgesic Effects and Receptor Binding Profile in Rats. Life Sci. 1988, 43, 1685-1695.
7. Gong, Q.-L.; Hedner, T.; Hedner, J.; Björkman, R.; Nordberg, G. Antinociceptive and Ventilatory Effects of the Morphine Metabolites: Morphine-6-Glucuronide and Morphhine-3-Glucuronide. Eur. J. Pharmacol. 1991, 193, 47-56.
8. Hucks, D.; Thompson, P. I.; McLoughlin, L.; Joel, S. P.; Patel, N.; Grossman, A.; Rees, L. H.; Slevin, M. L. Explanation at the Opioid Receptor Level for Differing Toxicity of Morphine and Morphine-6-Glucuronide. Br. J. Cancer 1992, 65, 122-126.
9. Stain, F.; Barjavel, M. J.; Sandouk, P.; Plotkine, M.; Scherrmann, J.-M.; Bhargava, H. N. Analgesic Response and Plasma and Brain Extracellular Fluid Pharmacokinetics of Morphine and Morphine-6-β-D-Glucuronide in the Rat. J. Pharmacol. Exp. Ther. 1995, 274, 852-857.
10. Aasmundstad, T. A.; Mørland, J.; Paulsen, R. E. Distribution of Morphine 6-Glucuronide and Morphine Across the Blood-Brain Barrier in Awake, Freely Moving Rats Investigated by in Vivo Microdialysis Sampling. J. Pharmacol. Exp. Ther. 1995, 275, 435-441.
11. Barjavel, M. J.; Scherrmann, J.-M.; Bhargava, H. N. Relationship Between Morphine Analgesia and Cortical Extracellular Fluid Levels of Morphine and its Metabolites in the Rat: a Microdialysis Study. Br. J. Pharmacol. 1995, 116, 3205-3210.
12. Polt, R.; Porreca, F.; Szabò, L. Z.; Bilsky, E. J.; Davis, P.; Abbruscato, T. J.; Davis, T. P.; Horvath, R.; Yamamura, H. I.; Hruby, V. J. Glycopeptide Enkaphalin Analogues Produce Analgesia in Mice: Evidence for Penetration of the Blood-Brain Barrier. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 7114-7118.
13. Manners, C. N.; Payling, D. W.; Smith, D. A. Lipophilicity of Zwitterionic Sulphate Conjugates of Tiaramide, Propranolol and 4'-Hydroxypropranolol. Xenobiotica 1989, 19, 1387-1397.
14. Carrupt, P.-A.; Testa, B.; Bechalany, A.; El Tayar, N.; Descas, P.; Perrissoud, D. Morphine 6-Glucuronide and Morphine 3-Glucuronide as Molecular Chameleons with Unexpectedly High Lipophilicity. J. Med. Chem. 1991, 34, 1272-1275.
15. Gaillard, P.; Carrupt, P.-A.; Testa, B. The Conformation-Dependent Lipophilicity of Morphine Glucuronides as Calculated from the Molecular Lipophilicity Potential. Bioorg. Med. Chem. Lett. 1994, 4, 737-742.
16. Murphey, L. J.; Olsen, G. D. Diffusion of Morphine-6-β-D-Glucuronide into the Neonatal Guinea Pig Brain during Drug-Induced Respiratory Depression. J. Pharmacol. Exp. Ther. 1994, 271, 118-124.
17. a Determination of Water-Insoluble Substances. Anal. Chem. 1993, 65, 42-49.
18. Avdeef, A. pH-Metric logP. 1. Difference Plots for Determining Ion-Pair Octanol-Water Partition Coefficients of Multiprotic Substances. Quant. Struct.-Act. Relat. 1992, 11, 510-517.
19. Certificate of Analysis, Morphine-6-β-D-Glucuronide Dihydrate batch no. 036/49 purity determined by HPLC, Ultrafine Chemicals, Manchester, U.K.
20. 2O). Acta Crystallogr. C 1995, 51, 1184-1187.
21. Leahy, D. E.; Taylor, P. J.; Wait, A. R. Model Solvent Systems for QSAR. 1. Propylene Glycol Dipelargonate (PGDP). A New Standard for Use in Partition Coefficient Determination. Quant. Struct.-Act. Relat. 1989, 8, 17-31.
22. Avdeef, A. pH-Metric logP. 2. Refinement of Partition Coefficients and Ionization Constants of Multiprotic Substances. J. Pharm. Sci. 1993, 82, 183-190.
23. Slater, B.; McCormack, A.; Avdeef, A.; Comer, J. E. A. pH-Metric logP. 4. Comparison of Partition Coefficients Determined by HPLC and Potentiometric Methods to Literature Values. J. Pharm. Sci. 1994, 83, 1280-1283.
24. Avdeef, A.; Bucher, J. J. Accurate Measurements of the Concentration of Hydrogen Ions with a Glass Electrode: Calibrations Using the Prideaux and Other Universal Buffer Solutions and a Computer-Controlled Automatic Titrator. Anal. Chem. 1978, 50, 2137-2142.
25. 2. J. Pharm. Sci. 1995, 84, 523-529.
26. Avdeef, A. Assessment of Distribution - pH Profiles. In Methods and Principles in Medicinal Chemistry; Pliska, V., Testa, B., van de Waterbeemd, H., Eds.; VCH Publishers: Weinheim, Germany, 1996; Vol. 5, pp 109-139.
27. Barrett, D. A.; Dyssegaard, A. L. P.; Shaw, P. N. The Effect of Temperature and pH on the Deacetylation of Diamorphine in Aqueous Solution and in Human Plasma. J. Pharm. Pharmacol. 1992, 44, 606-608.