1,015
Views
38
CrossRef citations to date
0
Altmetric
Research Article

Effect of hydrophilic additives on the dissolution and pharmacokinetic properties of itraconazole-enteric polymer hot-melt extruded amorphous solid dispersions

, , &
Pages 429-445 | Received 06 Mar 2015, Accepted 16 Jul 2015, Published online: 10 Sep 2015

References

  • Shah S, Maddineni S, Lu J, Repka MA. Melt extrusion with poorly soluble drugs. Int J Pharm 2013;453:233–52
  • Jorgensen WL, Duffy EM. Prediction of drug solubility from structure. Adv Drug Deliv Rev 2002;54:355–66
  • Yalkowsky SH, Valvani SC. Solubility and partitioning I: solubility of nonelectrolytes in water. J Pharm Sci 1980;69:912–22
  • Jain N, Yalkowsky SH. Estimation of the aqueous solubility I: application to organic nonelectrolytes. J Pharm Sci 2001;90:234–52
  • Yalkowsky SH, Pinal R. Estimation of the aqueous solubility of complex organic-compounds. Chemosphere 1993;26:1239–61
  • Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 1997;23:3–25
  • Serajuddin AT. Salt formation to improve drug solubility. Adv Drug Deliv Rev 2007;59:603–16
  • Serajuddin AT. Solid dispersion of poorly water-soluble drugs: early promises, subsequent problems, and recent breakthroughs. J Pharm Sci 1999;88:1058–66
  • Craig DQ. The mechanisms of drug release from solid dispersions in water-soluble polymers. Int J Pharm 2002;231:131–44
  • Overhoff KA, Engstrom JD, Chen B, et al. Novel ultra-rapid freezing particle engineering process for enhancement of dissolution rates of poorly water-soluble drugs. Eur J Pharm Biopharm 2007;65:57–67
  • Shah N, Sandhu H, Phuapradit W, et al. Development of novel microprecipitated bulk powder (MBP) technology for manufacturing stable amorphous formulations of poorly soluble drugs. Int J Pharm 2012;438:53–60
  • Paudel A, Worku ZA, Meeus J, et al. Manufacturing of solid dispersions of poorly water soluble drugs by spray drying: formulation and process considerations. Int J Pharm 2013;453:253–84
  • Lang B, McGinity JW, Williams III RO. Hot-melt extrusion – basic principles and pharmaceutical applications. Drug Dev Ind Pharm 2014;40:1133–55
  • Friesen DT, Shanker R, Crew M, et al. Hydroxypropyl methylcellulose acetate succinate-based spray-dried dispersions: an overview. Mol Pharm 2008;5:1003–19
  • Curatolo W, Nightingale JA, Herbig SM. Utility of hydroxypropylmethylcellulose acetate succinate (HPMCAS) for initiation and maintenance of drug supersaturation in the GI Milieu. Pharm Res 2009;26:1419–31
  • DiNunzio JC, Miller DA, Yang W, et al. Amorphous compositions using concentration enhancing polymers for improved bioavailability of itraconazole. Mol Pharm 2008;5:968–80
  • Engers D, Teng J, Jimenez-Novoa J, et al. A solid-state approach to enable early development compounds: selection and animal bioavailability studies of an itraconazole amorphous solid dispersion. J Pharm Sci 2010;99:3901–22
  • Ghebremeskel AN, Vemavarapu C, Lodaya M. Use of surfactants as plasticizers in preparing solid dispersions of poorly soluble API: stability testing of selected solid dispersions. Pharm Res 2006;23:1928–36
  • Ghebremeskel AN, Vernavarapu C, Lodaya M. Use of surfactants as plasticizers in preparing solid dispersions of poorly soluble API: selection of polymer-surfactant combinations using solubility parameters and testing the processability. Int J Pharm 2007;328:119–29
  • Perlman ME, Shanker RM, Babcock WC, et al. Pharmaceutical Compositions of Amorphous Dispersions of Drugs and Lipophilic Microphase-forming Materials. US Patent Application Publication US 2008/0063708 A1, 2008
  • Serajuddin ATM, Jarowski CI. Effect of diffusion layer Ph and solubility on the dissolution rate of pharmaceutical bases and their hydrochloride salts. 1. Phenazopyridine. J Pharm Sci 1985;74:142–7
  • Miller DA, DiNunzio JC, Yang W, et al. Targeted intestinal delivery of supersaturated itraconazole for improved oral absorption. Pharm Res 2008;25:1450–9
  • DiNunzio JC, Hughey JR, Brough C, et al. Production of advanced solid dispersions for enhanced bioavailability of itraconazole using KinetiSol (R) dispersing. Drug Dev Ind Pharm 2010;36:1064–78
  • Shevchenko A, Bimbo LM, Miroshnyk I, et al. A new cocrystal and salts of itraconazole: comparison of solid-state properties, stability and dissolution behavior. Int J Pharm 2012;436:403–9
  • Stahl PH, Wermuth CG. Handbook of pharmaceutical salts: properties, selection, and use. John Wiley & Sons, Inc.; 2011
  • Tao T, Zhao Y, Wu JJ, Zhou BY. Preparation and evaluation of itraconazole dihydrochloride for the solubility and dissolution rate enhancement. Int J Pharm 2009;367:109–14
  • Dong ZD, Choi DS. Hydroxypropyl methylcellulose acetate succinate: potential drug-excipient incompatibility. AAPS PharmSciTech 2008;9:991–7
  • Stroyer A, McGinity JW, Leopold CS. Solid state interactions between the proton pump inhibitor omeprazole and various enteric coating polymers. J Pharm Sci 2006;95:1342–53
  • Hughey JR, DiNunzio JC, Bennett RC, et al. Dissolution enhancement of a drug exhibiting thermal and acidic decomposition characteristics by fusion processing: a comparative study of hot melt extrusion and KinetiSolA (R) Dispersing. AAPS PharmSciTech 2010;11:760–74
  • Qian F, Huang J, Hussain MA. Drug-polymer solubility and miscibility: stability consideration and practical challenges in amorphous solid dispersion development. J Pharm Sci 2010;99:2941–7
  • Gordon M, Taylor JS. Ideal copolymers and the second-order transitions of synthetic rubbers. i. Non-crystalline copolymers. J Appl Chem 1952;2:493–500
  • Simha R. On a general relation involving glass temperature and coefficients of expansion of polymers. J Chem Phys 1962;37:1003–7
  • Six K, Berghmans H, Leuner C, et al. Characterization of solid dispersions of itraconazole and hydroxypropylmethylcellulose prepared by melt extrusion, part II. Pharm Res 2003;20:1047–54
  • Maniruzzaman M, Rana MM, Boateng JS, et al. Dissolution enhancement of poorly water-soluble APIs processed by hot-melt extrusion using hydrophilic polymers. Drug Dev Ind Pharm 2013;39:218–27
  • Verreck G, Six K, Van den Mooter G, et al. Characterization of solid dispersions of itraconazole and hydroxypropylmethylcellulose prepared by melt extrusion-part I. Int J Pharm 2003;251:165–74
  • Lakshman JP, Cao Y, Kowalski J, Serajuddin ATM. Application of melt extrusion in the development of a physically and chemically stable high-energy amorphous solid dispersion of a poorly water-soluble drug. Mol Pharm 2008;5:994–1002
  • Abu-Diak OA, Jones DS, Andrews GP. Understanding the performance of melt-extruded poly(ethylene oxide)-bicalutamide solid dispersions: characterisation of microstructural properties using thermal, spectroscopic and drug release methods. J Pharm Sci 2012;101:200–13
  • Frank KJ, Rosenblatt KM, Westedt U, et al. Amorphous solid dispersion enhances permeation of poorly soluble ABT-102: true supersaturation vs. apparent solubility enhancement. Int J Pharm 2012;437:288–93
  • Sathigari SK, Radhakrishnan VK, Davis VA, et al. Amorphous-state characterization of efavirenz-polymer hot-melt extrusion systems for dissolution enhancement. J Pharm Sci 2012;101:3456–64
  • Warren DB, Benameur H, Porter CJH, Pouton CW. Using polymeric precipitation inhibitors to improve the absorption of poorly water-soluble drugs: a mechanistic basis for utility. J Drug Target 2010;18:704–31
  • Abu-Diak OA, Jones DS, Andrews GP. An investigation into the dissolution properties of celecoxib melt extrudates: understanding the role of polymer type and concentration in stabilizing supersaturated drug concentrations. Mol Pharm 2011;8:1362–71
  • Peeters J, Neeskens P, Tollenaere JP, et al. Characterization of the interaction of 2-hydroxypropyl-beta-cyclodextrin with itraconazole at pH 2, 4, and 7. J Pharm Sci 2002;91:1414–22
  • Konno H, Taylor LS. Influence of different polymers on the crystallization tendency of molecularly dispersed amorphous felodipine. J Pharm Sci 2006;95:2692–705
  • Yamashita K, Nakate T, Okimoto K, et al. Establishment of new preparation method for solid dispersion formulation of tacrolimus. Int J Pharm 2003;267:79–91
  • Gao P, Rush BD, Pfund WP, et al. Development of a supersaturable SEDDS (S-SEDDS) formulation of paclitaxel with improved oral bioavailability. J Pharm Sci 2003;92:2386–98
  • Miller DA, DiNunzio JC, Yang W, et al. Enhanced in vivo absorption of itraconazole via stabilization of supersaturation following acidic-to-neutral pH transition. Drug Dev Ind Pharm 2008;34:890–902
  • Marsac PJ, Shamblin SL, Taylor LS. Theoretical and practical approaches for prediction of drug-polymer miscibility and solubility. Pharm Res 2006;23:2417–26
  • Guo Y, Luo J, Tan S, et al. The applications of Vitamin E TPGS in drug delivery. Eur J Pharm Sci 2013;49:175–86
  • Collnot EM, Baldes C, Wempe MF, et al. Mechanism of inhibition of P-glycoprotein mediated efflux by vitamin E TPGS: influence on ATPase activity and membrane fluidity. Mol Pharm 2007;4:465–74
  • Follonier N, Doelker E, Cole ET. Various ways of modulating the release of diltiazem hydrochloride from hot-melt extruded sustained-release pellets prepared using polymeric materials. J Control Release 1995;36:243–50
  • Dvorackova K, Rabiskova M, Masteikova R, et al. Soluble filler as a dissolution profile modulator for slightly soluble drugs in matrix tablets. Drug Dev Ind Pharm 2009;35:930–40
  • Overhoff KA, Moreno A, Miller DA, et al. Solid dispersions of itraconazole and enteric polymers made by ultra-rapid freezing. Int J Pharm 2007;336:122–32
  • Ozaki S, Minamisono T, Yamashita T, et al. Supersaturation-nucleation behavior of poorly soluble drugs and its impact on the oral absorption of drugs in thermodynamically high-energy forms. J Pharm Sci 2012;101:214–22
  • Zhu W, Romanski FS, Meng X, et al. Atomistic simulation study of surfactant and polymer interactions on the surface of a fenofibrate crystal. Eur J Pharm Sci 2011;42:452–61
  • Zeng A, Yuan B, Fu Q, et al. Influence of sodium dodecyl sulfate on swelling, erosion and release behavior of HPMC matrix tablets containing a poorly water-soluble drug. Pharm Dev Technol 2009;14:499–505
  • Petrovic LB, Sovilj VJ, Katona JM, Milanovic JL. Influence of polymer-surfactant interactions on o/w emulsion properties and microcapsule formation. J Colloid Interface Sci 2010;342:333–9
  • Galia E, Nicolaides E, Horter D, et al. Evaluation of various dissolution media for predicting in vivo performance of class I and II drugs. Pharm Res 1998;15:698–705
  • Isoherranen N, Kunze KL, Allen KE, et al. Role of itraconazole metabolites in CYP3A4 inhibition. Drug Metab Dispos 2004;32:1121–31
  • Peng CC, Shi W, Lutz JD, et al. Stereospecific metabolism of itraconazole by CYP3A4: dioxolane ring scission of azole antifungals. Drug Metab Dispos 2012;40:426–35
  • Christiansen A, Backensfeld T, Denner K, Weitschies W. Effects of non-ionic surfactants on cytochrome P450-mediated metabolism in vitro. Eur J Pharm Biopharm 2011;78:166–72

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.