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Research Article

Diloxanide furoate binary complexes with β-, methyl-β-, and hydroxypropyl-β-cyclodextrins: inclusion mode, characterization in solution and in solid state and in vitro dissolution studies

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Pages 723-731 | Received 20 Feb 2017, Accepted 28 Jul 2017, Published online: 16 Aug 2017

References

  • Aloisio C, Gomes de Oliveira A, Longhi M. 2014. Characterization, inclusion mode, phase-solubility and in vitro release studies of inclusion binary complexes with cyclodextrins and meglumine using sulfamerazine as model drug. Drug Dev Ind Pharm. 40:919–928.
  • Anguiano-Igea S, Otero-Espinar FJ, Vila-Jato JL, Blanco-Méndez J. 1997. Interaction of clofibrate with cyclodextrin in solution: phase solubility, 1H NMR and molecular modelling studies. Eur J Pharm Sci. 5:215–221.
  • Araújo MV, Barbosa EK, Lázaro G, Conegero LS, Almeida LE, Barreto LS, da Costa NB, Gimenez IF. 2008. Sulfadiazine/hydroxypropyl-β-cyclodextrin host-guest system: characterization, phase-solubility and molecular modeling. Bioorg Med Chem. 16:5788–5794.
  • Barillaro V, Dive G, Bertholet P, Evrard B, Delattre L, Frederich M, Ziémons E, Piel G. 2007. Theoretical and experimental investigations of organic acids/cyclodextrin complexes and their consequences upon the formation of miconazole/cyclodextrin/acid ternary inclusion complexes. Int J Pharm. 347:62–70.
  • Blanco-García E, Guerrero-Callejas F, Blanco-Méndez J, Gómez-Couso H, Luzardo-Álvarez A. 2016. Development of particulate drug formulation against C. parvum: formulation, characterization and in vivo efficacy. Eur J Pharm Sci. 92:74–85.
  • Brewster ME, Loftsson T. 2007. Cyclodextrins as pharmaceutical solubilizers. Adv Drug Deliv Rev. 59:645–666.
  • Budal RM, Da Graça Nascimento M, Dal Magro J, Vázquez tato J, Yunes RA. 2004. Studies on the inclusion complex of diloxanide furoate-β-cyclodextrin. J Incl Phenom Macrocycl Chem. 50:151–155.
  • Castro Hermida JAA, Ares-Mazás MEE, Otero Espinar F, Blanco Méndez J. 2001. Inhibition of Cryptosporidium infection in mice treated with a cyclodextrin inclusion complex with diloxanide furoate. Parasitol Res. 87:449–452.
  • Delrivo A, Zoppi A, Longhi MR. 2012. Interaction of sulfadiazine with cyclodextrins in aqueous solution and solid state. Carbohydr Polym. 87:1980–1988.
  • Duchêne D, Bochot A. 2016. Thirty years with cyclodextrins. Int J Pharm. 514:58–72.
  • Farthing MJG. 2006. Treatment options for the eradication of intestinal protozoa. Nat Clin Pract Gastroenterol Hepatol. 3:436–445.
  • García A, Leonardi D, Vasconi MD, Hinrichsen LI, Lamas MC, Deli MA. 2014. Characterization of albendazole-randomly methylated-β-cyclodextrin inclusion complex and in vivo evaluation of its antihelmitic activity in a murine model of Trichinellosis. PLoS One. 9:e113296.
  • Garnero C, Longhi M. 2007. Study of ascorbic acid interaction with hydroxypropyl-β-cyclodextrin and triethanolamine, separately and in combination. J Pharm Biomed. 45:536–545.
  • Granero GE, Maitre MM, Garnero C, Longhi MR. 2008. Synthesis, characterization and in vitro release studies of a new acetazolamide–HP-β-CD–TEA inclusion complex. Eur J Med Chem. 43:464–470.
  • Higuchi T, Connors K. 1965. Phase solubility techniques. In: Reilly CW, editor. Advances in analytical chemistry and instrumentation. New York (NY): Wiley-Interscience; p. 117–212.
  • Kutyła MJ, Lambert LK, Davies NM, McGeary RP, Shaw PN, Ross BP. 2013. Cyclodextrin-crosslinked poly(acrylic acid): synthesis, physicochemical characterization and controlled release of diflunisal and fluconazole from hydrogels. Int J Pharm. 444:175–184.
  • Loukas YL, Vraka V, Gregoriadis G. 1996. Use of a nonlinear least-squares model for the kinetic determination of the stability constant of cyclodextrin inclusion complexes. Int J Pharm. 144:225–231.
  • Mishal A, Sober D. 2005. Stability indicating reversed-phase liquid chromatographic determination of metronidazole benzoate and diloxanide furoate as bulk drug and in suspension dosage form. J Pharm Biomed Anal. 39:819–823.
  • Mora MJ, Longhi MR, Granero GE. 2010. Synthesis and characterization of binary and ternary complexes of diclofenac with a methyl-β-CD and monoethanolamine and in vitro transdermal evaluation. Eur J Med Chem. 45:4079–4088.
  • Ojarinta R, Heikkinen AT, Sievänen E, Laitinen R. 2017. Dissolution behavior of co-amorphous amino acid-indomethacin mixtures: the ability of amino acids to stabilize the supersaturated state of indomethacin. Eur J Pharm Biopharm. 112:85–95.
  • Onnainty R, Longhi MR, Granero GE. 2011. Complex formation of chlorhexidine gluconate with hydroxypropyl-β-cyclo-dextrin (HP-β-CD) by proton nuclear magnetic resonance spectroscopy (1H NMR). Carbohydr Res. 346:1037–1046.
  • Özdemir N, Erkin J. 2012. Enhancement of dissolution rate and bioavailability of sulfamethoxazole by complexation with β-cyclodextrin. Drug Dev Ind Pharm. 38:331–340.
  • Piel G, Piette M, Barillaro V, Castagne D, Evrard B, Delattre L. 2006. Betamethasone-in-cyclodextrin-in-liposome: the effect of cyclodextrins on encapsulation efficiency and release kinetics. Int J Pharm. 312:75–82.
  • Rekharsky MV, Goldberg RN, Schwarz FP, Tewari YB, Ross PD, Yamashoji Y, Inoue Y. 1995. Thermodynamic and nuclear magnetic resonance study of the interactions of α- and β-cyclodextrin with model substances: phenethylamine, ephedrines, and related substances. J Am Chem Soc. 117:8830–8840.
  • Ribeiro L, Ferreira D, Veiga F. 2003. Physicochemical investigation of the effects of water-soluble polymers on vinpocetine complexation with beta-cyclodextrin and its sulfobutyl ether derivative in solution and solid state. Eur J Pharm Sci. 20:253–266.
  • Taupitz T, Dressman JB, Buchanan CM, Klein S. 2013. Cyclodextrin-water soluble polymer ternary complexes enhance the solubility and dissolution behaviour of poorly soluble drugs. Case example: itraconazole. Eur J Pharm Biopharm. 83:378–387.
  • Veiga F, Pecorelli C, Ribeiro L. 2006. As ciclodextrinas em tecnología farmacéutica. Coimbra: Minerva Coimbra.
  • Yi L, Zhang T, Tao J, Ji G, Wang S. 2009. Preparation, characterization, and pharmacokinetics of the inclusion complex of genipin-β-cyclodextrin. Drug Dev Ind Pharm. 35:1452–1459.
  • Zoppi A, Garnero C, Linck YG, Chattah AK, Monti GA, Longhi MR. 2011. Enalapril:β-CD complex: stability enhancement in solid state. Carbohydr Polym. 86:716–721.

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