Hot melt extrusion versus spray drying: hot melt extrusion degrades albendazole

References

• Marriner SE, Morris DL, Dickson B, Bogan JA. Pharmacokinetics of albendazole in man. Eur J Clin Pharmacol 1986;30:705–8.
   PubMed Web of Science ®Google Scholar
• Lindenberg M, Kopp S, Dressman JB. Classification of orally administered drugs on the World Health Organization Model list of Essential Medicines according to the biopharmaceutics classification system. Eur J Pharm Biopharm 2004;58:265–78.
   PubMed Web of Science ®Google Scholar
• Jung H, Medina L, García L, et al. Biopharmaceutics: absorption studies of albendazole and some physicochemical properties of the drug and its metabolite albendazole sulphoxide. J Pharm Pharmacol 1998;50:43–8.
   PubMed Web of Science ®Google Scholar
• Daniel-Mwambete K, Torrado S, Cuesta-Bandera C, et al. The effect of solubilization on the oral bioavailability of three benzimidazole carbamate drugs. Int J Pharm 2004;272:29–36.
   PubMed Web of Science ®Google Scholar
• Lange H, Eggers R, Bircher J. Increased systemic availability of albendazole when taken with a fatty meal. Eur J Clin Pharmacol 1988;34:315–7.
   PubMed Web of Science ®Google Scholar
• del Estal JL, Alvarez AI, Villaverde C, et al. Increased systemic bioavailability of albendazol when administered with surfactants in rats. Int J Pharm 1994;102:257–60.
   Web of Science ®Google Scholar
• Pavan Kumar M, Madhusudan Rao Y, Apte S. Improved bioavailability of albendazole following oral administration of nanosuspension in rats. Curr Nanosci 2007;3:191–4.
   Web of Science ®Google Scholar
• Vogt M, Kunath K, Dressman JB. Dissolution enhancement of fenofibrate by micronization, cogrinding and spray-drying: comparison with commercial preparations. Eur J Pharm Biopharm 2008;68:283–8.
   PubMed Web of Science ®Google Scholar
• Ravichandran R. In vivo pharmacokinetic studies of albendazole nanoparticulate oral formulations for improved bioavailability. Int J Green Nanotechnol Biomed 2010;2:B46–53.
   Google Scholar
• Paulekuhn GS, Dressman JB, Saal C. Salt screening and characterization for poorly soluble, weak basic compounds: case study albendazole. Pharmazie 2013;68:555–64.
   PubMed Web of Science ®Google Scholar
• Alanazi FK, El-Badry M, Ahmed MO, Alsarra IA. Improvement of albendazole dissolution by preparing microparticles using spray-drying technique. Sci Pharm 2007;75:63.
   Google Scholar
• Martinez-Marcos L, Lamprou DA, McBurney RT, Halbert GW. A novel hot-melt extrusion formulation of albendazole for increasing dissolution properties. Int J Pharm 2016;499:175–85.
   PubMed Web of Science ®Google Scholar
• Zhou D, Zhang GGZ, Law D, et al. Physical stability of amorphous pharmaceuticals: importance of configurational thermodynamic quantities and molecular mobility. J Pharm Sci 2002;91:1863–72.
   PubMed Web of Science ®Google Scholar
• Friesen DT, Shanker R, Crew M, et al. Hydroxypropyl methylcellulose acetate succinate-based spray-dried dispersions: an overview. Mol Pharm 2008;5:1003–19.
   PubMed Web of Science ®Google Scholar
• Pajula K, Taskinen M, Lehto VP, et al. Predicting the formation and stability of amorphous small molecule binary mixtures from computationally determined Flory − Huggins interaction parameter and phase diagram. Mol Pharm 2010;7:795–804.
   PubMed Web of Science ®Google Scholar
• Tian Y, Booth J, Meehan E, et al. Construction of drug–polymer thermodynamic phase diagrams using Flory–Huggins interaction theory: identifying the relevance of temperature and drug weight fraction to phase separation within solid dispersions. Mol Pharm 2012;10:236–48.
   PubMed Web of Science ®Google Scholar
• Patel RP, Patel MP, Suthar AM. Spray drying technology: an overview. Indian J Sci Technol 2009;2:44–7.
   Google Scholar
• Crowley MM, Zhang F, Repka MA, et al. Pharmaceutical applications of hot-melt extrusion: Part I. Drug Dev Ind Pharm 2007;33:909–26.
   PubMed Web of Science ®Google Scholar
• Keen JM, Martin C, Machado A, et al. Investigation of process temperature and screw speed on properties of a pharmaceutical solid dispersion using corotating and counter-rotating twin-screw extruders. J Pharm Pharmacol 2014;66:204–17.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• 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 KinetiSol® dispersing. AAPS PharmSciTech 2010;11:760–74.
   PubMed Web of Science ®Google Scholar
• am Ende DJ. Achieving a hot melt extrusion design space for the production of solid solutions. Chemical engineering in the pharmaceutical industry. Hoboken (NJ): John Wiley & Sons, Inc.; 2011:819–36.
   Google Scholar
• Huang S, O’Donnell K, Keen J, III, et al. A new extrudable form of hypromellose: AFFINISOLTM HPMC HME. AAPS PharmSciTech 2016;17:106–19.
   PubMed Web of Science ®Google Scholar
• US Pharmacopeia 36-NF31; 2013.
   Google Scholar
• Pobudkowska A, Domańska U. Study of pH-dependent drugs solubility in water. Chem Ind Chem Eng Q 2014;20:115–26.
   Web of Science ®Google Scholar
• FDA. Stability testing: drug substance stress testing. Int. Conf. Harmon. Tech. Requir. Regist. Pharm. Hum. Use; 2003; Rockv., MD, USA.
   Google Scholar
• Forster A, Hempenstall J, Tucker I, Rades T. Selection of excipients for melt extrusion with two poorly water-soluble drugs by solubility parameter calculation and thermal analysis. Int J Pharm 2001;226:147–61.
   PubMed Web of Science ®Google Scholar
• Flory PJ. Thermodynamics of high polymer solutions. J Chem Phys 1942;10:51–61.
   Google Scholar
• Huggins ML. Thermodynamic properties of solutions of long-chain compounds, Vol. 43. 1. New York: Annals of the New York Academy of Sciences; 1942.
   Google Scholar
• Marsac PJ, Shamblin SL, Taylor LS. Theoretical and practical approaches for prediction of drug–polymer miscibility and solubility. Pharm Res 2006;23:2417–26.
   PubMed Web of Science ®Google Scholar
• Marsac PJ, Li T, Taylor LS. Estimation of drug–polymer miscibility and solubility in amorphous solid dispersions using experimentally determined interaction parameters. Pharm Res 2009;26:139–51.
   PubMed Web of Science ®Google Scholar
• Rubinstein M, Colby RH. Polymer physics. Oxford: Oxford University Press; 2007.
   Google Scholar
• 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.
   Web of Science ®Google Scholar
• Albendazole Tablets, in US Pharmacopeia 36-NF 31, US Pharmacopeia, US Pharmacopeial Convention, Rockville, MD; 2013.
   Google Scholar
• Venkatesan P. Albendazole. J Antimicrob Chemother 1998;41:145–7.
   PubMed Web of Science ®Google Scholar
• Nogrady T, Weaver DF. Medicinal chemistry: a molecular and biochemical approach. 3rd edn. New York (NY): Oxford University Press; 2005.
   Google Scholar
• Blessy M, Patel RD, Prajapati PN, Agrawal YK. Development of forced degradation and stability indicating studies of drugs—a review. J Pharm Anal 2014;4:159–65.
   PubMedGoogle Scholar
• Shah N, Sandhu H, Choi DS, et al. Amorphous solid dispersions: theory and practice. New York: Springer; 2014.
   Google Scholar
• Craig DQ, Royall PG, Kett VL, Hopton ML. The relevance of the amorphous state to pharmaceutical dosage forms: glassy drugs and freeze dried systems. Int J Pharm 1999;179:179–207.
   PubMed Web of Science ®Google Scholar
• Yoshioka S, Aso Y. Correlations between molecular mobility and chemical stability during storage of amorphous pharmaceuticals. J Pharm Sci 2007;96:960–81.
   PubMed Web of Science ®Google Scholar
• Greenhalgh DJ, Williams AC, Timmins P, York P. Solubility parameters as predictors of miscibility in solid dispersions. J Pharm Sci 1999;88:1182–90.
   PubMed Web of Science ®Google Scholar
• Zhao Y, Inbar P, Chokshi HP, et al. Prediction of the thermal phase diagram of amorphous solid dispersions by Flory–Huggins theory. J Pharm Sci 2011;100:3196–207.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• Forster A, Hempenstall J, Rades T. Characterization of glass solutions of poorly water-soluble drugs produced by melt extrusion with hydrophilic amorphous polymers. J Pharm Pharmacol 2001;53:303–15.
   PubMed Web of Science ®Google Scholar
• Polymer extrusion. 2nd edn. Munchen: Hanser Publishers; 1990.
   Google Scholar
• Govindasamy S, Campanella OH, Oates CG. High moisture twin-screw extrusion of sago starch: 1. Influence on granule morphology and structure. Carbohydr Polym 1996;30:275–86.
   Web of Science ®Google Scholar
• Anandharamakrishnan C. Computational fluid dynamics applications in food processing. New York: Springer Science & Business Media; 2013.
   Google Scholar
• Masters K. Impact of spray dryer design on powder properties. Drying 1991;91:56–73.
   Google Scholar
• Anandharamakrishnan C, Rielly CD, Stapley AGF. Effects of process variables on the denaturation of whey proteins during spray drying. Dry Technol 2007;25:799–807.
   Web of Science ®Google Scholar
• Clas SD, Faizer R, O’Connor R, Vadas E. Quantification of crystallinity in blends of lyophilized and crystalline MK-0591 using X-ray powder diffraction. Int J Pharm 1995;121:73–9.
   Web of Science ®Google Scholar
• de Villiers MM, Wurster DE, Van der Watt JG, Ketkar A. X-ray powder diffraction determination of the relative amount of crystalline acetaminophen in solid dispersions with polyvinylpyrrolidone. Int J Pharm 1998;163:219–24.
   Web of Science ®Google Scholar
• Utracki LA. Polymer alloys and blends: thermodynamics and rheology. Munich: Hanser; 1990.
   Google Scholar
• Van den Mooter G, Wuyts M, Blaton N, et al. Physical stabilization of amorphous ketoconazole in solid dispersions with polyvinylpyrrolidone K25. Eur J Pharm Sci 2001;12:261–9.
   PubMed Web of Science ®Google Scholar
• Harmon P, Li L, Marsac PJ, et al. Amorphous solid dispersions: analytical challenges and opportunities. AAPS Newsmag 2009;12:14–20.
   Google Scholar
• Rumondor AC, Taylor LS. Effect of polymer hygroscopicity on the phase behavior of amorphous solid dispersions in the presence of moisture. Mol Pharm 2010;7:477–90.
   PubMed Web of Science ®Google Scholar
• Yu L. Amorphous pharmaceutical solids: preparation, characterization and stabilization. Adv Drug Deliv Rev 2001;48:27–42.
   PubMed Web of Science ®Google Scholar
• Turnbull D. On the relation between crystallization rate and liquid structure. J Phys Chem 1962;66:609–13.
   Web of Science ®Google Scholar
• Savjani KT, Gajjar AK, Savjani JK. Drug solubility: importance and enhancement techniques. ISRN Pharm 2012;2012:195727. doi: 10.5402/2012/195727.
   PubMedGoogle Scholar
• Shozo M, Midori O, Tanekazu N. Unusual solubility and dissolution behavior of pharmaceutical hydrochloride salts in chloride-containing media. Int J Pharm 1980;6:77–85.
   Google Scholar
• Hancock BC, Zografi G. The relationship between the glass transition temperature and the water content of amorphous pharmaceutical solids. Pharm Res 1994;11:471–7.
   PubMed Web of Science ®Google Scholar
• Taupitz T, Dressman JB, Klein S. New formulation approaches to improve solubility and drug release from fixed dose combinations: case examples pioglitazone/glimepiride and ezetimibe/simvastatin. Eur J Pharm Biopharm 2013;84:208–18.
   PubMed Web of Science ®Google Scholar