Species-specific lipophilicity of morphine antagonists

European Journal of Pharmaceutical Sciences - Tập 78 - Trang 1-7 - 2015
Károly Mazák1, Sándor Hosztafi1, Béla Noszál1
1Semmelweis University, Department of Pharmaceutical Chemistry, Research Group of Drugs of Abuse and Doping Agents, Hungarian Academy of Sciences, Hőgyes E. u. 9., H-1092 Budapest, Hungary

Tài liệu tham khảo

Abraham, 1997, On the partition of ampholytes: application to blood-brain distribution, J. Pharm. Sci., 86, 310, 10.1021/js960328j Avdeef, 2002, Physicochemical profiling, Curr. Topics Med. Chem., 1, 277, 10.2174/1568026013395100 Bjerrum, 1923, Dissociation constants of polybasic acids and their application to the calculation of molecular dimensions, Z. Phys. Chem., 106, 219, 10.1515/zpch-1923-10615 Box, 2008, Using measured pKa, Log P and solubility to investigate supersaturation and predict BCS class, Curr. Drug Metab., 9, 869, 10.2174/138920008786485155 Caron, 1999, Combined molecular lipophilicity descriptors and their role in understanding intramolecular effects, Pharm. Sci. Technol. Today, 2, 327, 10.1016/S1461-5347(99)00180-7 Charifson, 2014, Acidic and basic drugs in medicinal chemistry: a perspective, J. Med. Chem., 57, 9701, 10.1021/jm501000a Comer, 2001, Lipophilicity profiles: theory and measurement, 275 Dearden, 1988, The measurement of partition coefficients, Quant. Struct.-Act. Relat., 7, 133, 10.1002/qsar.19880070304 Funke, 1986, A 1H and 13C nuclear magnetic resonance study of three quaternary salts of naloxone and oxymorphone, J. Chem. Soc. Perkin, 2, 735, 10.1039/p29860000735 Giaginis, 2008, Alternative measures of lipophilicity: from octanol-water partitioning to IAM retention, J. Pham. Sci., 97, 2984, 10.1002/jps.21244 Goldberg, L.I., Merz, H., Stockhaus, K. Quaternary Derivatives of Noroxymorphone Which Relieve Intestinal Motility. US Patent 4 176 186 (November 27, 1979). Iorio, 1984, Narcotic agonist/antagonist properties of quaternary diastereoisomers derived from oxymorphone and naloxone, Eur. J. Med. Chem. – Chim. Ther., 19, 301 Kaufman, 1975, Microelectrometric titration measurement of pKas and partition and drug distribution coefficients of narcotics and narcotic-antagonists and their pH and temperature-dependence, J. Med. Chem., 18, 647, 10.1021/jm00241a001 Liu, 2011, Lipophilicity and its relationship with passive drug permeation, Pharm. Res., 28, 962, 10.1007/s11095-010-0303-7 Mandić, 2006, Ionization, lipophilicity and solubility properties of repaglinide, J. Pharm. Biomed. Anal., 41, 866, 10.1016/j.jpba.2006.01.056 Mazák, 2012, Lipophilicity of morphine microspecies and their contribution to the lipophilicity profile, Eur. J. Pham. Sci., 45, 205, 10.1016/j.ejps.2011.11.007 Mazák, 2012, Zwitterions can be predominant in membrane penetration of drugs: an experimental proof, J. Med. Chem., 55, 6942, 10.1021/jm3007992 Mazák, 2014, Drug delivery: a process governed by species-specific lipophilicities, Eur. J. Pharm. Sci., 62, 96, 10.1016/j.ejps.2014.05.017 Mazák, 2003, Lipophilicity of vinpocetine and related compounds characterized by reversed-phase thin-layer chromatography, J. Chromatogr. A, 996, 195, 10.1016/S0021-9673(03)00617-4 Mazák, 2009, Structural and physicochemical profiling of morphine and related compounds of therapeutic interest, Mini-Rev. Med. Chem., 9, 984, 10.2174/138955709788681555 Mazák, 2009, Proton speciation and microspeciation of serotonin and 5-hydroxytryptophan, Chem. Biodivers., 6, 578, 10.1002/cbdv.200800087 Mazák, 2012, Thyroxine lipophilicity is dominated by its zwitterionic microspecies, Eur. J. Pharm. Sci., 47, 921, 10.1016/j.ejps.2012.09.009 Noszál, 1990, Acid–base properties of bioligands, 18 Olofson, R.A., Pepe, J.P. US Patent 4 141 897 (February 27, 1979). Pagliara, 1997, Lipophilicity profiles of ampholytes, Chem. Rev., 97, 3385, 10.1021/cr9601019 Takács-Novák, 1999, Ion-pair partition of quaternary ammonium drugs: the influence of counter ions of different lipophilicity, size and flexibility, Pharm. Res., 16, 1633, 10.1023/A:1018977225919 Takács-Novák, 1995, Lipophilicity of amphoteric molecules expressed by the true partition coefficient, Int. J. Pharm., 113, 47, 10.1016/0378-5173(94)00176-6 Testa, 1996, Intramolecular interactions encoded in lipophilicity: their nature and significance, 49 Thomae, 2005, Permeation of aromatic carboxylic acids across lipid bilayers: the pH-partition hypothesis revisited, Biophys. J., 89, 1802, 10.1529/biophysj.105.060871 Völgyi, 2012, Predicting the exposure and antibacterial activity of fluoroquinolones based on physicochemical properties, Eur. J. Pharm. Sci., 47, 21, 10.1016/j.ejps.2012.04.022 Willette, 1998, Analgesic agents, 687 Yaksh, 2010, Opioids, analgesia and pain management, 481