Clotrimazole–cyclodextrin based approach for the management and treatment of Candidiasis – A formulation and chemistry-based evaluation

References

• Sobel JD, Faro S, Force RW, et al. Vulvovaginal candidiasis: epidemiologic, diagnostic, and therapeutic considerations. Am J Obstet Gynecol 1998;178:203–211
   PubMed Web of Science ®Google Scholar
• Nyirjesy P, Weitz MV, Grody MH, Lorber B. Over-the-counter and alternative medicines in the treatment of chronic vaginal symptoms. Obstet Gynecol 1997;90:50–53
   PubMed Web of Science ®Google Scholar
• Reef SE, Levine WC, McNeil MM, et al. Treatment options for vulvovaginal candidiasis, 1993. Clin Infect Dis 1995;20:S80–S90
   PubMedGoogle Scholar
• Pedersen M. Effect of hydrotropic substances on the complexation of clotrimazole with β-cyclodextrin. Drug Dev Ind Pharm 1993;19:439–448
   Web of Science ®Google Scholar
• Pedersen M, Bjerregaard S, Jacobsen J, Sorensen AM. A genuine clotrimazole cyclodextrin inclusion complex-isolation, antimycotic activity, toxicity, and an unusual dissoltuion rate. Int J Pharm 1998;176:121–131
   Web of Science ®Google Scholar
• Moreira D, Paula CR. Vulvovaginal candidiasis. Int J Gynecol Obstet 2006;92:266–267
   PubMed Web of Science ®Google Scholar
• Abdel-Moety EM, Khattab FI, Kelani KM, AbouAl-Alamein AM. Chromatographic determination of clotrimazole, ketoconazole and fluconazole in pharmaceutical formulations. Farmaco 2002;57:931–938
   PubMedGoogle Scholar
• Chang JY, Oh YK, Kong HS, et al. Prolonged antifungal effects of clotrimazole-containing mucoadhesive thermosensitive gels on vaginitis. J Control Release 2002;82:39–50
   PubMed Web of Science ®Google Scholar
• Ning M, Gu Z, Pan H, et al. Preparation and in vitro evaluation of liposomal/niosomal delivery systems for antifungal drug clotrimazole. Indian J Exp Biol 2005;43:150–157
   PubMedGoogle Scholar
• Memisoglu E, Bochot A, Ozalp M, et al. Direct formation of nanospheres from amphiphilic beta-cyclodextrin inclusion complexes. Pharm Res 2003;20:117–125
   PubMed Web of Science ®Google Scholar
• Prodduturi S, Urman KL, Otaigbe JU, Repka MA. Stabilization of hot-melt extrusion formulations containing solid solutions using polymer blends. AAPS PharmSciTech 2007;8:E152–E161
   Google Scholar
• Mohammed NN, Majumdar S, Singh A, et al. Klucel EF and ELF polymers for immediate-release oral dosage forms prepared by melt extrusion technology. AAPS PharmSciTech 2012;13:1158–1169
   PubMed Web of Science ®Google Scholar
• Deng W, Majumdar S, Singh A, et al. Stabilization of fenofibrate in low molecular weight hydroxypropylcellulose matrices produced by hot-melt extrusion. Drug Dev Ind Pharm 2013;39:290–298
   PubMed Web of Science ®Google Scholar
• Repka MA, Shah S, Lu J, et al. Melt extrusion: process to product. Expert Opin Drug Deliv 2012;9:105–125
   PubMed Web of Science ®Google Scholar
• Prabagar B, Yoo BK, Woo JS, et al. Enhanced bioavailability of poorly water-soluble clotrimazole by inclusion with beta-cyclodextrin. Arch Pharm Res 2007;30:249–254
   PubMed Web of Science ®Google Scholar
• Bilensoy E, Rouf MA, Vural I, et al. Mucoadhesive, thermosensitive, prolonged-release vaginal gel for clotrimazole:beta-cyclodextrin complex. AAPS PharmSciTech 2006;7:E38
   PubMed Web of Science ®Google Scholar
• Taneri F, Guneri T, Aigner Z, et al. Improvement of the physicochemical properties of clotrimazole by cyclodextrin complexation. J Incl Phenom Macrocyclic Chem 2003;46:1–13
   Web of Science ®Google Scholar
• Tenjarla S, Puranajoti P, Kasina R, Mandal T. Preparation, characterization, and evaluation of miconazole-cyclodextrin complexes for improved oral and topical delivery. J Pharm Sci 1998;87:425–429
   PubMed Web of Science ®Google Scholar
• Brewster ME, Vandecruys R, Peeters J, et al. Comparative interaction of 2-hydroxypropyl-beta-cyclodextrin and sulfobutylether-beta-cyclodextrin with itraconazole: phase-solubility behavior and stabilization of supersaturated drug solutions. Eur J Pharm Sci 2008;34:94–103
   PubMed Web of Science ®Google Scholar
• Rodriguez-Perez AI, Rodriguez-Tenreiro C, Alvarez-Lorenzo C, et al. Sertaconazole/hydroxypropyl-beta-cyclodextrin complexation: isothermal titration calorimetry and solubility approaches. J Pharm Sci 2006;95:1751–1762
   PubMed Web of Science ®Google Scholar
• Justin-Temu M, Damian F, Kinget R, Van Den Mooter G. Intravaginal gels as drug delivery systems. J Womens Health (Larchmt) 2004;13:834–844
   PubMed Web of Science ®Google Scholar
• Deshpande AA, Rhodes CT, Danish M. Intravaginal drug delivery. Drug Dev Ind Pharm 1992;18:1225–1279
   Web of Science ®Google Scholar
• Hussain A, Ahsan F. The vagina as a route for systemic drug delivery. J Control Release 2005;103:301–313
   PubMed Web of Science ®Google Scholar
• Higuchi T, Connors K. Phase-solubility techniques. Adv Anal Chem Instrum 1965;4:212–217
   Google Scholar
• Yokota T, Tonozuka T, Shimura Y, et al. Structures of Thermoactinomyces vulgaris R-47 alpha-amylase II complexed with substrate analogues. Biosci Biotechnol Biochem 2001;65:619–626
   PubMed Web of Science ®Google Scholar
• MacroModel, Version 9.3. New York (NY): Schrödinger, LLC; 2012
   Google Scholar
• Maestro, Version 9.3. New York (NY): Schrödinger, LLC; 2012
   Google Scholar
• LigPrep, Version 9.9. New York (NY): Schrödinger, LLC; 2012
   Google Scholar
• Friesner RA, Banks JL, Murphy RB, et al. Glide: a new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy. J Med Chem 2004;47:1739–1749
   PubMed Web of Science ®Google Scholar
• Frisch MJ, Trucks GW, Schlegel HB, et al. Gaussian. Gaussian 09, Revision D.01. Inc. Wallingford CT; 2009
   Google Scholar
• Hanwell MD, Curtis DE, Lonie DC, et al. Avogadro: an advanced semantic chemical editor, visualization, and analysis platform. J Cheminform 2012;4:17
   PubMed Web of Science ®Google Scholar
• Dennington R, Keith T, Millam J. Gauss View, Version 3. J. Semichem Inc. Shawnee Mission, KS; 2009
   Google Scholar
• Loftsson T, Duchene D. Cyclodextrins and their pharmaceutical applications. Int J Pharm 2007;329:1–11
   PubMed Web of Science ®Google Scholar
• Taneri F, Guneri T, Aigner Z, et al. Thermoanalytical studies on complexes of clotrimazole with cyclodextrins. J Therm Anal Calorimetry 2004;76:471–479
   Web of Science ®Google Scholar
• Navarro M, Cisneros-Fajardo EJ, Lehmann T, et al. Toward a novel metal-based chemotherapy against tropical diseases. 6. Synthesis and characterization of new copper(II) and gold(I) clotrimazole and ketoconazole complexes and evaluation of their activity against Trypanosoma cruzi. Inorg Chem 2001;40:6879–6884
   PubMed Web of Science ®Google Scholar
• Souto EB, Müller RH. Investigation of the factors influencing the incorporation of clotrimazole in SLN and NLC prepared by hot high-pressure homogenization. J Microencapsul 2006;23:377–388
   PubMed Web of Science ®Google Scholar
• Prodduturi S, Manek RV, Kolling WM, et al. Solid-state stability and characterization of hot-melt extruded poly(ethylene oxide) films. J Pharm Sci 2005;94:2232–2245
   PubMed Web of Science ®Google Scholar
• Trapani G, Latrofa A, Franco M, et al. Inclusion complexation of propofol with 2-hydroxypropyl-beta-cyclodextrin: physicochemical, nuclear magnetic resonance spectroscopic studies, and anesthetic properties in rat. J Pharm Sci 1998;87:514–518
   PubMed Web of Science ®Google Scholar
• Zhang G, Musgrave CB. Comparison of DFT methods for molecular orbital eigenvalue calculations. J Phys Chem A 2007;111:1554–1561
   PubMed Web of Science ®Google Scholar
• Costa P, Sousa Lobo JM. Modeling and comparison of dissolution profiles. Eur J Pharm Sci 2001;13:123–133
   PubMed Web of Science ®Google Scholar