Effect of cyclodextrin concentration on the oral bioavailability of danazol and cinnarizine in rats

René Holm1, Niels Erik Olesen1,2, Rune A. Hartvig2, Erling B. Jørgensen1, Dorrit B. Larsen3, Peter Westh2
1Pharmaceutical Science and CMC Biologics, H. Lundbeck A/S, Ottiliavej 9, DK-2500 Valby, Denmark
2NSM, Research Unit for Functional Biomaterials, Roskilde University, Universitetsvej 1, DK-4000 Roskilde, Denmark
3Discovery ADME, H. Lundbeck A/S, Ottiliavej 9, DK-2500 Valby, Denmark

Tài liệu tham khảo

Loftsson, 1996, Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization, J. Pharm. Sci., 85, 1017, 10.1021/js950534b Rajewski, 1996, Pharmaceutical applications of cyclodextrins. 2. In vivo drug delivery, J. Pharm. Sci., 85, 1142, 10.1021/js960075u Uekama, 1998, Cyclodextrin drug carrier systems, Chem. Rev., 98, 2045, 10.1021/cr970025p Olesen, 2015, Displacement of drugs from cyclodextrin complexes by bile salts: a suggestion of an intestinal drug solubilizing capacity from an in vitro model, J. Pharm. Sci. Holm, 2011, Thermodynamics of complexation of tauro- and glyco-conjugated bile salts with two modified β-cyclodextrins, J. Incl. Phenom. Macrocycl. Chem., 69, 201, 10.1007/s10847-010-9831-3 Holm, 2013, Thermodynamics of the interaction of γ-cyclodextrin and tauro- and glyco-conjugated bile salts, J. Incl. Phenom. Macrocycl. Chem., 75, 223, 10.1007/s10847-012-0165-1 Ono, 2003, Model analysis for oral absorption of a drug/cyclodextrin complex involving competitive inclusion complexes, J. Incl. Phenom. Macrocycl. Chem., 44, 93, 10.1023/A:1023037016997 Loftsson, 2011, Pharmaceutical applications of cyclodextrins: effects on drug permeation through biological membranes, J. Pharm. Pharmacol., 63, 1119, 10.1111/j.2042-7158.2011.01279.x Brewster, 2007, Effect of the unstirred water layer on permeability enhancement by hydrophilic cyclodextrins, Int. J. Pharm., 342, 250, 10.1016/j.ijpharm.2007.04.029 Westerberg, 2005, β‐Cyclodextrin reduces bioavailability of orally administered [3H] benzo [a] pyrene in the rat, J. Pharm. Sci., 94, 114, 10.1002/jps.20198 Olesen, 2015, Does digestibility of cyclodextrins influence the in vivo absorption of benzo[a]pyrene in rats?, J. Pharm. Sci. Larsen, 2008, Lipid-based formulations for danazol containing a digestible surfactant, Labrafil M2125CD: in vivo bioavailability and dynamic in vitro lipolysis, Pharm. Res., 25, 2769, 10.1007/s11095-008-9641-0 Kossena, 2004, A novel cubic phase of medium chain lipid origin for the delivery of poorly water soluble drugs, J. Controlled Release, 99, 217, 10.1016/j.jconrel.2004.06.013 Stella, 1999, Mechanisms of drug release from cyclodextrin complexes, Adv. Drug Delivery Rev., 36, 3, 10.1016/S0169-409X(98)00052-0 Charman, 2006, Alteration of the intravenous pharmacokinetics of a synthetic ozonide antimalarial in the presence of a modified cyclodextrin, J. Pharm. Sci., 95, 256, 10.1002/jps.20534 Badawy, 1996, Characterization and bioavailability of danazol-hydroxypropyl β-cyclodextrin coprecipitates, Int. J. Pharm., 128, 45, 10.1016/0378-5173(95)04214-8 Badawy, 1996, A study of the complexation between danazol and hydrophilic cyclodextrin derivatives, Drug Dev. Ind. Pharm., 22, 959, 10.3109/03639049609065926 Jain, 2001, Hygroscopicity, phase solubility and dissolution of various substituted sulfobutylether β-cyclodextrins (SBE) and danazol–SBE inclusion complexes, Int. J. Pharm., 212, 177, 10.1016/S0378-5173(00)00607-4 Okimoto, 1996, The interaction of charged and uncharged drugs with neutral (HP-β-CD) and anionically charged (SBE7-β-CD) β-cyclodextrins, Pharm. Res., 13, 256, 10.1023/A:1016047215907 Järvinen, 1995, β-Cyclodextrin derivatives, SBE4-β-CD and HP-β-CD, increase the oral bioavailability of cinnarizine in beagle dogs, J. Pharm. Sci., 84, 295, 10.1002/jps.2600840306 Devalapally, 2015, Optimization of PEGylated nanoemulsions for improved pharmacokinetics of BCS class II compounds, Drug Delivery, 22, 467, 10.3109/10717544.2013.869275 Lee, 2013, The effect of administered dose of lipid-based formulations on the in vitro and in vivo performance of cinnarizine as a model poorly water-soluble drug, J. Pharm. Sci., 102, 565, 10.1002/jps.23384 Beig, 2015, The use of captisol (SBE7-β-CD) in oral solubility-enabling formulations: comparison to HPβCD and the solubility–permeability interplay, Eur. J. Pharm. Sci., 77, 73, 10.1016/j.ejps.2015.05.024 Stella, 2008, Cyclodextrins, Toxicol. Pathol., 36, 30, 10.1177/0192623307310945 Beig, 2015, Head-to-head comparison of different solubility-enabling formulations of etoposide and their consequent solubility–permeability interplay, J. Pharm. Sci., 104, 2941, 10.1002/jps.24496 Beig, 2013, Oral delivery of lipophilic drugs: the tradeoff between solubility increase and permeability decrease when using cyclodextrin-based formulations, PLoS One, 8, e68237, 10.1371/journal.pone.0068237 Zuo, 2000, Flutamide-hydroxypropyl-β-cyclodextrin complex: formulation, physical characterization, and absorption studies using the caco-2 in vitro model, J. Pharm. Pharm. Sci, 3, 220 Yavuz, 2010, Alternative oral exemestane formulation: improved dissolution and permeation, Int. J. Pharm., 398, 137, 10.1016/j.ijpharm.2010.07.046 Kuang, 2008, Transport research of ibuprofen/HP-β-CD system in the Caco-2 monolayer model, Chin. J. New Drugs, 34, 1037 Dahan, 2010, The solubility–permeability interplay in using cyclodextrins as pharmaceutical solubilizers: mechanistic modeling and application to progesterone, J. Pharm. Sci., 99, 2739, 10.1002/jps.22033 Liversidge, 1995, Particle size reduction for improvement of oral bioavailability of hydrophobic drugs: I. Absolute oral bioavailability of nanocrystalline danazol in beagle dogs, Int. J. Pharm., 125, 91, 10.1016/0378-5173(95)00122-Y Connors, 1986 Sassene, 2010, Precipitation of a poorly soluble model drug during in vitro lipolysis: characterization and dissolution of the precipitate, J. Pharm. Sci., 99, 4982, 10.1002/jps.22226