Cyclodextrins in pharmaceutical formulations I: structure and physicochemical properties, formation of complexes, and types of complex

Fromming, 1994 1991 Szejtli, 1988 1987 Loftsson, 1991, 2-Hydroxypropyl-β-cyclodextrin: Properties and usage in pharmaceutical formulations, Pharm. Ztg. Wiss., 4/136, 5 Loftsson, 1995, Effects of cyclodextrins on the chemical stability of drugs in aqueous solutions, Drug Stability, 1, 22 Szente, 1993, Cyclodextrins: structure, application, stability and their influence on the stability of active substances, 225 van Doorne, 1993, Interactions between cyclodextrins and ophthalmic drugs, Eur. J. Pharm. Biopharm., 39, 133 Duchene, 1993, New possibilities for the pharmaceutical use of cyclodextrins and their derivatives, Chimicaoggi, 11, 17 French, 1957, The Schardinger dextrins, Adv. Carbohydr. Chem., 12, 189 French, 1965, Studies on the Schardinger Dextrins XII, Arch. Biochem. Biophys., 111, 153, 10.1016/0003-9861(65)90334-6 Saenger, 1980, Cyclodextrin inclusion compounds in research and industry, Angew. Chem. Int. Ed. Engl., 19, 344, 10.1002/anie.198003441 Jones, 1984, Cyclodextrins in pharmaceutical sciences II: pharmaceutical, biopharmaceutical, biological, and analytical aspects, and applications of cyclodextrins and its inclusion compounds, Acta. Pharm. Technol., 30, 213 Szente, 1999, Highly soluble cyclodextrin derivatives: chemistry, properties, and trends in development, Adv. Drug Del. Rev., 36, 17, 10.1016/S0169-409X(98)00092-1 Jambhekar, 2013, Cyclodextrins in pharmacy: background and Introduction, J. Chrono. Drug Deliver., 3, 1 Pitha, 1994, Parenteral hydroxypropyl cyclodextrins: intravenous and intracerebral administration of lipophiles, J. Pharm. Sci., 83, 833, 10.1002/jps.2600830615 Thompson, D.O. and Mosher, G.L. Cydex, Inc. Formulations containing propofol and a sulfoalkyl ether cyclodextrins. US Patent 7034013 B2 Ogawa, 2013, Quetiapine free base complexed with cyclodextrins to improve solubility for parenteral use, Chem. Pharm. Bull., 61, 809, 10.1248/cpb.c13-00157 Morrison, 2013, Cyclodextrin-mediated enhancement of riboflavin solubility and corneal permeability, Mol. Pharm., 10, 756, 10.1021/mp3005963 Taupitz, 2013, Cyclodextrin-water soluble polymer ternary complexes enhance the solubility and dissolution behavior of poorly soluble drugs. Case example: itraconazole, Eur. J. Pharm. Biopharm., 83, 378, 10.1016/j.ejpb.2012.11.003 Wong, 2014, Mechanism of 2-hydrxypropyl-beta-cyclodextrin in the solubilization of frozen formulations, Eur. J. Pharm Sci., 62, 281, 10.1016/j.ejps.2014.05.024 di Cagno, 2014, β-Cyclodextrin-dextran polymers for the solubilization of poorly soluble drugs, Int. J Pharm., 468, 258, 10.1016/j.ijpharm.2014.04.029 Bonnet, 2015, Cyclodextrin nanoassemblies: a promising tool for drug delivery, Drug Discov. Today, 20, 1120, 10.1016/j.drudis.2015.05.008 Arima, 2015, Recent advances in cyclodextrin delivery techniques, Expert Opin. Drug Deliv., 12, 1425, 10.1517/17425247.2015.1026893 Medarevic, 2015, Influence of hydrophilic polymers on the complexation of carbamazepine with hydroxylpropyl-β-cyclodextrin, Eur. J. Pharm. Sci., 78, 273, 10.1016/j.ejps.2015.08.001 Borba, 2015, The effect of mechanical grinding on the formation, crystalline changes, and dissolution behavior of the inclusion complex of telmisartan and β-cycloodextrins, Carbohydr. Polym., 133, 373, 10.1016/j.carbpol.2015.06.098 Loftsson, 2015, Pharmacokinetics of cyclodextrins and drugs after oral and parenteral administration of drug/cyclodextrin complexes, J. Pharm. Pharmacol., 9, 201 Ogawa, 2015, Interaction of fentanyl with various cyclodextrins in aqueous solutions, J. Pharm. Pharmacol., 16 Villers, 1891, Chimie organique, Sur la fermentation de la fécula par l’action du ferment butyrique, C.R. Acad. Sci., 112, 536 Schardinger, 1903, Uber thermophile Bakterien aus verschiedenen Speisen und Milch sowie uber einige Umsetzungsprodukte derselben in kohlenhydrathaltigen Nahrlosungen, darunter kristallisierte Polysaccharide Dextrin aus Starke, Z. Unters. Nahr. u. Genussm., 6, 865 Schardinger, 1903, Title, Wien. Klin. Wochenschr., 16, 474 Freudenberg, K. et al. Company. Inclusion compounds of physiologically active organic compounds. German Patent 895,769 Loftsson, 1996, Pharmaceutical applications of cyclodextrins I: drug solubilization and stabilization, J. Pharm. Sci., 85, 1017, 10.1021/js950534b Rajcwski, 1996, Pharmaceutical applications of cyclodextrins 2: in vivo drug delivery, J. Pharm. Sci., 85, 1142, 10.1021/js960075u Irie, 1997, Pharmaceutical applications of cyclodextrins III: toxicological issues and safety evaluation, J. Pharm. Sci., 86, 147, 10.1021/js960213f Loftsson, 2002, Cyclodextrins and biopharmaceutics classification system of drugs, J. Incl. Phenom. Macros Chem., 44, 63, 10.1023/A:1023088423667 Sohi, 2004, Taste masking technologies in oral pharmaceuticals: recent development and approaches, Drug Develop. Ind. Pharm., 30, 429, 10.1081/DDC-120037477 Havir, R. and Kasraian, K. Pfizer, Inc. Palatable chewable tablet. US Patent 7482022 Anon, 2002 Suzuki, 1994, 2H NMR study of the self-assembly of an azo dye-cyclomaltooctanose (γ-cyclodextrin complex), Carbohydr. Res., 264, 223, 10.1016/0008-6215(94)84019-9 Mele, 1998, Non-covalent association of cyclooligosaccharide (cyclodextrin) with trans-b-carotene in water. Evidence for the formation of large aggregates by light scattering and NMR Spectroscopy, Carbohydr. Res., 310, 261, 10.1016/S0008-6215(98)00193-1 Loftsson, 2002, Cyclodextrins and drug permeability through semi-permeable cellophane membranes, Int. J. Pharm., 232, 35, 10.1016/S0378-5173(01)00895-X Loftsson, 2002, Self-association and cyclodextrin solubilization of drugs, J. Pharm. Sci., 91, 2307, 10.1002/jps.10226 Loftsson, 1994, The effect of water soluble polymers on drug-cyclodextrins complexation, Int. J. Pharm., 110, 169, 10.1016/0378-5173(94)90155-4 Valero, 2003, Effect of PVP K-25 on formation of naproxen-cyclodextrin complex, Int. J. Pharm., 253, 97, 10.1016/S0378-5173(02)00664-6 Loftsson, 1998, The effect of water soluble polymer on the aqueous solubility and complexing abilities of β-cyclodextrin, Int. J. Pharm., 163, 115, 10.1016/S0378-5173(97)00371-2 Stella, 2008, Cyclodextrins, Toxicol. Pathol., 36, 30, 10.1177/0192623307310945 Pitha, 1986, Hydroxypropyl-β-cyclodextrins: preparation and characterization: effects on the solubility of drugs, Int. J. Pharm., 29, 73, 10.1016/0378-5173(86)90201-2 Casella, 1998, Solid-state β-cyclodextrin complexes containing indomethacin, ammonia, and water I. Formation Studies, Int. J. Pharm., 65, 1, 10.1016/S0378-5173(97)00330-X Casella, 1998, Solid-state β-cyclodextrin complexes containing indomethacin, ammonia, and water II. Solubility studies, Int. J. Pharm., 165, 15, 10.1016/S0378-5173(98)00003-9 Jambhekar, 2004, The physicochemical characteristics and bioavailability of indomethacin from β-cyclodextrin, hydroxypropyl β-cyclodextrin, and hydroxyethyl β-cyclodextrin complexes, Int. J. Pharm., 270, 149, 10.1016/j.ijpharm.2003.10.012 Loftsson, 2003, Cyclodextrins in solid dosage forms, Business Brief. Pharmatech., XX, 176 Lina, 2004, Subchronic oral toxicity studies with α-cyclodextrin in rats, Regul. Toxicol. Pharmacol., 39, S14, 10.1016/j.yrtph.2004.05.006 Lina, 2004, Subchronic (13 weeks) oral toxicity studies with α-cyclodextrin in dogs, Regul. Toxicol. Pharmacol., 39, S27, 10.1016/j.yrtph.2004.05.005 Frank, 1976, Cyclodextrin nephrosis in the rat, Am. J. Pathol., 83, 367 Thompson, 1997, Cyclodextrin-enabling excipients; their present and future use in pharmaceuticals, Crit. Rev. Ther. Drug Carrier System., 14, 1 Gould, 2005, 2-Hydroxypropyl-β-cyclodextrin (HP-β-CD): a toxicology review, Food Chem. Toxicol., 43, 1451, 10.1016/j.fct.2005.03.007 Bellinger, 1995, β-Cyclodextrin: 52 weeks toxicity studies in the rat and dog, Food Chem. Toxicol., 367, 10.1016/0278-6915(94)00149-I Munro, 2004, Safety assessment of γ-cyclodextrin, Regul. Toxicol. Pharmacol., 39, S3, 10.1016/j.yrtph.2004.05.008 Brewster, 2007, The use of solubilizing excipients and approaches to generate toxicology vehicles for contemporary drug pipelines, 221 Koutson, 1999, Gastrointestinal tolerance of γ-cyclodextrin in human, Food Addit. Contam., 16, 313, 10.1080/026520399283984 Anon, 1997 Antlsperger, 1996, Toxicological comparison of cyclodextrins, 149 Kiser, 2015, Evaluation of sulfobutylether β-cyclodextrin (SBECD) accumulation and voriconazole pharmacokinetics in critically ill patients undergoing continuous renal replacement therapy, Crit. Care, 19, 32, 10.1186/s13054-015-0753-8 Anon, 2015 von Mach, 2006, Accumulation of the solvent vehicle sulfobutylether β-cyclodextrin sodium in critically ill patients treated with intravenous voriconazole under renal replacement therapy, BMC Clin. Pharmacol., 6, 6, 10.1186/1472-6904-6-6 Anon, 2006 Higuchi, 1965, Phase solubility techniques, Adv. Anal. Chem. Instrum., 4, 117 1991 Brewster, 2007, Cyclodextrins as pharmaceutical solubilizers, Adv. Drug Del. Rev., 59, 645, 10.1016/j.addr.2007.05.012