Effect of mechanochemical inclusion of triamterene into sulfobutylether-β-cyclodextrin and its improved dissolution behavior

References

• Wiebelhaus VD, Weinstock J, Maass AR, et al. The diuretic and natruretic activity of triamterene and several related pteridines in the rat. J Pharmacol Exp Ther. 1965;149(3):397–403. doi: http://jpet.aspetjournals.org/content/149/3/397.
   PubMed Web of Science ®Google Scholar
• Douglas JG, Hollifield JW, Liddle GW. Treatment of low-renin essential hypertension. Comparison of spironolactone and a hydrochlorothiazide-triamterene combination. Jama. 1974;227(5):518–521. PubMed PMID: 4589187; eng.
   PubMed Web of Science ®Google Scholar
• Dittert LW, Higuchi T, Reese DR. Phase solubility technique in studying the formation of complex salts of triamterene. J Pharm Sci. 1964;53:1325–1328. PubMed PMID: 14253586; eng.
   PubMed Web of Science ®Google Scholar
• Pruitt AW, Winkel JS, Dayton PG. Variations in the fate of triameterene. Clin Pharmacol Ther. 1977; May21(5):610–619.
   PubMed Web of Science ®Google Scholar
• Lipinski CA, Lombardo F, Dominy BW, et al. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Delivery Rev. 1997;23(1-3):3–25.
   Web of Science ®Google Scholar
• Curatolo W. Physical chemical properties of oral drug candidates in the discovery and exploratory development settings. Pharm Sci Technol Today. 1998;1(9):387–393.
   Google Scholar
• Kumar S, Bhargava D, Thakkar A, et al. Drug carrier systems for solubility enhancement of BCS class II drugs: a critical review. Crit Rev Ther Drug Carrier Syst. 2013;30(3):217–256. PubMed PMID: 23614647; eng.
   PubMed Web of Science ®Google Scholar
• Heimbach T, Fleisher D, Kaddoumi A, et al. Overcoming poor aqueous solubility of drugs for oral delivery. In Stella VJ, Borchrdt RT, Hageman MJ, editors. Prodrugs: Challenge and rewards part1. Berlin (DE): Springer; 2007. P157–215.
   Google Scholar
• Banerjee R, Bhatt PM, Ravindra NV, et al. Saccharin salts of active pharmaceutical ingredients, their crystal structures, and increased water solubilities. Crystal Growth & Design. 2005;5(6):2299–2309.
   Web of Science ®Google Scholar
• Bruni G, Maietta M, Maggi L, et al. Preparation and physicochemical characterization of acyclovir cocrystals with improved dissolution properties. J Pharm Sci. 2013;102(11):4079–4086.
   PubMed Web of Science ®Google Scholar
• Fischer F, Schmidt MU, Greiser S, et al. The challenging case of the theophylline-benzamide cocrystal. Acta Crystallogr C Struct Chem. 2016;72(Pt 3):217–224.
   PubMedGoogle Scholar
• Vasconcelos T, Sarmento B, Costa P. Solid dispersions as strategy to improve oral bioavailability of poor water soluble drugs. Drug Discov Today. 2007;12(23-24):1068–1075.
   PubMed Web of Science ®Google Scholar
• Sinha S, Ali M, Baboota S, et al. Solid dispersion as an approach for bioavailability enhancement of poorly water-soluble drug ritonavir. AAPS PharmSciTech. 2010;11(2):518–527. Jun PubMed PMID: 20238187; PubMed Central PMCID: PMCPMC2902348.
   PubMed Web of Science ®Google Scholar
• Skwarczynski M, Sohma Y, Noguchi M, et al. No auxiliary, no byproduct strategy for water-soluble prodrugs of taxoids: scope and limitation of O-N intramolecular acyl and acyloxy migration reactions. J Med Chem. 2005;48(7):2655–2666.
   PubMed Web of Science ®Google Scholar
• Stella VJ, Nti-Addae KW. Prodrug strategies to overcome poor water solubility. Adv Drug Deliv Rev. 2007;59(7):677–694.
   PubMed Web of Science ®Google Scholar
• Mallick S. The solid state amorphization of poorly water soluble drugs. Indian J Pharm Sci. 2004;66(6):729–734. doi: https://www.ijpsonline.com/abstract/the-solid-state-amorphization-of-poorly-water-soluble-drugs-742.html.
   Google Scholar
• Wu JZ, Ho PC. Evaluation of the in vitro activity and in vivo bioavailability of realgar nanoparticles prepared by cryo-grinding. Eur J Pharm Sci. 2006;29(1):35–44.
   PubMed Web of Science ®Google Scholar
• Uekama K, Oh K, Otagiri M, et al. Improvement of some pharmaceutical properties of clofibrate by cyclodextrin complexation. Pharm Acta Helv. 1983;58(12):338–342. PubMed PMID: 6657712; eng.
   PubMedGoogle Scholar
• Nakai Y, Yamamoto K, Oguchi T, et al. New methods for preparing cyclodextrin inclusion compounds. IV. enhancement of combining molar ratio by using a ground mixture in heptakis-(2,6-di-O-methyl)-β-cyclodextrin and benzoic acid system. Chem. Pharm. Bull. 1991;39(6):1532–1535.
   Web of Science ®Google Scholar
• Arias-Blanco MJ, Muñoz P, Moyano JR, et al. Preliminary study of different omeprazole-γ-CD co-grinded systems. Int J Pharm. 1996;143(1):113–118.
   Web of Science ®Google Scholar
• Kong R, Zhu X, Meteleva ES, et al. Physicochemical characteristics of the complexes of simvastatin and atorvastatin calcium with hydroxypropyl-β-cyclodextrin produced by mechanochemical activation. J Drug Delivery Sci Technol. 2018;46:436–445.
   Web of Science ®Google Scholar
• Ginés JM, Arias MJ, Novák C, et al. Thermal study of complex formation of triamterene with β-cyclodextrin by spray-drying and co-grinding. J Therm Anal. 1995;45(4):659–666.
   Google Scholar
• Arias MJ, Moyano JR, Ginés JM. Investigation of the triamterene–β-cyclodextrin system prepared by co-grinding. Int J Pharm. 1997;153(2):181–189.
   Google Scholar
• Venuti V, Stancanelli R, Acri G, et al. “Host-guest” interactions in Captisol®/Coumestrol inclusion complex: UV–vis, FTIR-ATR and Raman studies. J Mol Struct. 2017;1146:512–521.
   Web of Science ®Google Scholar
• Deng Y, Pang Y, Guo Y, et al. Host-guest inclusion systems of daidzein with 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) and sulfobutyl ether-β-cyclodextrin (SBE-β-CD): Preparation, binding behaviors and water solubility. J Mol Struct. 2016;1118:307–315.
   Web of Science ®Google Scholar
• Luke DR, Tomaszewski K, Damle B, et al. Review of the basic and clinical pharmacology of sulfobutylether-beta-cyclodextrin (SBECD). J Pharm Sci. 2010;99(8):3291–3301. PubMed PMID: 20213839; eng.
   PubMed Web of Science ®Google Scholar
• Frank DW, Gray JE, Weaver RN. Cyclodextrin nephrosis in the rat. Am J Pathol. 1976; 83(2):367–382. doi: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2032314/. PubMed PMID: 1266946; PubMed Central PMCID: PMCPMC2032314.
   PubMed Web of Science ®Google Scholar
• Maeda H, Ogawa Y, Nakayama H. Inclusion complexes of melatonin with modified cyclodextrins. J Incl Phenom Macrocycl Chem. 2014;78(1-4):217–224.
   Web of Science ®Google Scholar
• Benesi HA, Hildebrand JH. A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J. Am. Chem. Soc. 1949;71(8):2703–2707.
   Web of Science ®Google Scholar
• Job P. Formation and stability of inorganic complexes in solution. Ann Chim. 1928;9:113–203.
   Google Scholar
• The Japanese Pharmacopoeia JP17. 2016. [https://www.mhlw.go.jp/file/06-Seisakujouhou-11120000-Iyakushokuhinkyoku/JP17_REV.pdf]
   Google Scholar
• Higuchi T, Connors KA. Phase-solubility techniques. Advan Anal Chem Instr. 1965; 4:117–212.
   Google Scholar
• He D, Deng P, Yang L, et al. Molecular encapsulation of rifampicin as an inclusion complex of hydroxypropyl-β-cyclodextrin: design; characterization and in vitro dissolution. Colloids Surf B Biointerfaces. 2013;103:580–585.
   PubMed Web of Science ®Google Scholar
• Thi TH, Azaroual N, Flament MP. Characterization and in vitro evaluation of the formoterol/cyclodextrin complex for pulmonary administration by nebulization. Eur J Pharm Biopharm. 2009;72(1):214–218.
   PubMed Web of Science ®Google Scholar
• Jamrógiewicz M, Wielgomas B, Strankowski M. Evaluation of the photoprotective effect of β-cyclodextrin on the emission of volatile degradation products of ranitidine . J Pharm Biomed Anal. 2014;98:113–119.
   PubMed Web of Science ®Google Scholar
• Priotti J, Ferreira MJ, Lamas MC, et al. First solid-state NMR spectroscopy evaluation of complexes of benznidazole with cyclodextrin derivatives. Carbohydr Polym. 2015;131:90–97. PubMed PMID: 26256164.
   PubMed Web of Science ®Google Scholar
• Arrúa EC, Ferreira MJ, Salomon CJ, et al. Elucidating the guest-host interactions and complex formation of praziquantel and cyclodextrin derivatives by (13)C and (15)N solid-state NMR spectroscopy. Int J Pharm. 2015;496(2):812–821.
   PubMedGoogle Scholar
• Ribeiro L, Loftsson T, Ferreira D, et al. Investigation and physicochemical characterization of vinpocetine-sulfobutyl ether beta-cyclodextrin binary and ternary complexes. Chem Pharm Bull. 2003;51(8):914–922.
   PubMed Web of Science ®Google Scholar
• Mura P, Furlanetto S, Cirri M, et al. Interaction of naproxen with ionic cyclodextrins in aqueous solution and in the solid state. J Pharm Biomed Anal. 2005;37(5):987–994.
   PubMed Web of Science ®Google Scholar