Overview of milling techniques for improving the solubility of poorly water-soluble drugs

Asian Journal of Pharmaceutical Sciences - Tập 10 - Trang 255-274 - 2015
Zhi Hui Loh1, Asim Kumar Samanta2, Paul Wan Sia Heng1
1GEANUS Pharmaceutical Processing Research Laboratory, Department of Pharmacy, National University of Singapore, 18 Science Drive 4, Singapore 117543, Singapore
2Janssen India, Department of PDMS-SMMD-AD, Johnson & Johnson Ltd., Higi House, Opp Ralli Wolf, LBS Marg, Mulund (W), Mumbai 400080, India

Tài liệu tham khảo

Noyes, 1897, The rate of solution of solid substances in their own solutions, J Am Chem Soc, 19, 930, 10.1021/ja02086a003 Aulton, 2002, Dissolution and solubility, 15 Ashford, 2002, Assessment of biopharmaceutical properties, 253 Lipinski, 1997, Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings, Adv Drug Deliv Rev, 23, 3, 10.1016/S0169-409X(96)00423-1 Lipinski, 2000, Drug-like properties and the causes of poor solubility and poor permeability, J Pharmacol Toxicol, 44, 235, 10.1016/S1056-8719(00)00107-6 Amidon, 1995, A theoretical basis for a biopharmaceutic drug classification: the correlation of in vitro drug product dissolution and in vivo bioavailability, Pharm Res, 12, 413, 10.1023/A:1016212804288 Muller, 2004, Challenges and solutions for the delivery of biotech drugs – a review of drug nanocrystal technology and lipid nanoparticles, J Biotechnol, 113, 151, 10.1016/j.jbiotec.2004.06.007 Loftsson, 1996, Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization, J Pharm Sci, 85, 1017, 10.1021/js950534b Serajuddin, 1999, Solid dispersion of poorly water-soluble drugs: early promises, subsequent problems, and recent breakthroughs, J Pharm Sci, 88, 1058, 10.1021/js980403l Ettmayer, 2004, Lessons learned from marketed and investigational prodrugs, J Med Chem, 47, 2393, 10.1021/jm0303812 Johnson, 2003, Prediction of precipitation-induced phlebitis: a statistical validation of an in vitro model, J Pharm Sci, 92, 1574, 10.1002/jps.10396 Hauss, 2007 Rabinow, 2004, Nanosuspensions in drug delivery, Nat Rev Drug Discov, 3, 785, 10.1038/nrd1494 Machiste, 1995, Characterization of carbamazepine in systems containing a dissolution rate enhancer, Int J Pharm, 126, 65, 10.1016/0378-5173(95)04085-4 Randall, 1995, Particle size distribution, 157 Bisrat, 1988, Physicochemical aspects of drug release. Viii. The relation between particle size and surface specific dissolution rate in agitated suspensions, Int J Pharm, 47, 223, 10.1016/0378-5173(88)90235-9 Ho, 2011, Role of surface chemistry and energetics in high shear wet granulation, Ind Eng Chem Res, 50, 9642, 10.1021/ie2009263 Danesh, 2001, An in situ dissolution study of aspirin crystal planes (100) and (001) by atomic force microscopy, Pharm Res, 18, 299, 10.1023/A:1011046728622 Massol-Chaudeur, 2002, Experimental study of the mixing kinetics of binary pharmaceutical powder, Chem Eng Sci, 57, 4053, 10.1016/S0009-2509(02)00262-2 Mullarney, 2003, The powder flow and compact mechanical properties of sucrose and three high-intensity sweeteners used in chewable tablets, Int J Pharm, 257, 227, 10.1016/S0378-5173(03)00144-3 Shah, 2007, Assessment of segregation potential of powder blends, Pharm Dev Technol, 12, 457, 10.1080/10837450701556834 Swaminathan, 2002, Polydisperse powder mixtures: effect of particle size and shape on mixture stability, Drug Dev Ind Pharm, 28, 41, 10.1081/DDC-120001484 Yin, 2005, Bioavailability enhancement of a cox-2 inhibitor, bms-347070, from a nanocrystalline dispersion prepared by spray-drying, J Pharm Sci, 94, 1598, 10.1002/jps.20366 Dali, 1996, Effect of change in shape factor of a single crystal on its dissolution behavior, Pharm Res, 13, 155, 10.1023/A:1016010207729 Fini, 1995, Influence of crystallization solvent and dissolution behaviour for a diclofenac salt, Int J Pharm, 121, 19, 10.1016/0378-5173(94)00419-6 Kitamori, 1978, Dissolution of nonspherical powders, J Pharm Sci, 67, 1674, 10.1002/jps.2600671210 Lu, 1993, Dissolution modeling: factors affecting the dissolution rates of polydisperse powders, Pharm Res, 10, 1308, 10.1023/A:1018917729477 Núñez, 1994, A general shrinking-particle model for the chemical dissolution of crystalline forms, Hydrometallurgy, 36, 1, 10.1016/0304-386X(94)90038-8 Ma, 2000, New developments in particle characterization by laser diffraction: size and shape, Powder Technol, 111, 66, 10.1016/S0032-5910(00)00242-4 Hickey, 2001, Size reduction and classification, 174 Boldyrev, 2004, Mechanochemical modification and synthesis of drugs, J Mater Sci, 39, 5117, 10.1023/B:JMSC.0000039193.69784.1d Hersey, 1980, Biopharmaceutical implications of technological change, Int J Pharm Tech Prod Manuf, 1, 18 Hutten-Raunch, 1983, Modification of starting materials to improve tablet properties, Pharm Ind, 45, 435 Yu, 2001, Amorphous pharmaceutical solids: preparation, characterization and stabilization, Adv Drug Deliv Rev, 48, 27, 10.1016/S0169-409X(01)00098-9 Shakhtshneider, 1997, Phase transformations and stabilization of metastable states of molecular crystals under mechanical activation, Solid State Ionics, 101–103, 851, 10.1016/S0167-2738(97)00224-5 Dudognon, 2006, Formation of budesonide/α-lactose glass solutions by ball-milling, Solid State Commun, 138, 68, 10.1016/j.ssc.2006.02.007 Kayaert, 2012, Is the amorphous fraction of a dried nanosuspension caused by milling or by drying? A case study with naproxen and cinnarizine, Eur J Pharm Biopharm, 81, 650, 10.1016/j.ejpb.2012.04.020 Karmwar, 2012, Effect of different preparation methods on the dissolution behaviour of amorphous indomethacin, Eur J Pharm Biopharm, 80, 459, 10.1016/j.ejpb.2011.10.006 Guinot, 1999, The use of mtdsc to assess the amorphous phase content of a micronised drug substance, Int J Pharm, 192, 63, 10.1016/S0378-5173(99)00273-2 Elamin, 1994, Increased metastable solubility of milled griseofulvin, depending on the formation of a disordered surface-structure, Int J Pharm, 111, 159, 10.1016/0378-5173(94)00132-4 Weinekötter, 2000, Mixing and degregation processes, 7 Otte, 2011, Assessment of milling-induced disorder of two pharmaceutical compounds, J Pharm Sci, 100, 1793, 10.1002/jps.22415 Van Eerdenbrugh, 2008, Top-down production of drug nanocrystals: nanosuspension stabilization, miniaturization and transformation into solid products, Int J Pharm, 364, 64, 10.1016/j.ijpharm.2008.07.023 Bahl, 2006, Amorphization of indomethacin by co-grinding with neusilin us2: amorphization kinetics, physical stability and mechanism, Pharm Res, 23, 2317, 10.1007/s11095-006-9062-x Choi, 2008, Effect of polymer molecular weight on nanocomminution of poorly soluble drug, Drug Deliv, 15, 347, 10.1080/10717540802039113 Lee, 2008, Characteristics of polymers enabling nano-comminution of water-insoluble drugs, Int J Pharm, 355, 328, 10.1016/j.ijpharm.2007.12.032 Lee, 2005, Amphiphilic amino acid copolymers as stabilizers for the preparation of nanocrystal dispersion, Eur J Pharm Sci, 24, 441, 10.1016/j.ejps.2004.12.010 Choi, 2005, Role of polymeric stabilizers for drug nanocrystal dispersions, Curr Appl Phys, 5, 472, 10.1016/j.cap.2005.01.012 Bhakay, 2011, Novel aspects of wet milling for the production of microsuspensions and nanosuspensions of poorly water-soluble drugs, Drug Dev Ind Pharm, 37, 963, 10.3109/03639045.2010.551775 Ghosh, 2011, Nanosuspension for improving the bioavailability of a poorly soluble drug and screening of stabilizing agents to inhibit crystal growth, Int J Pharm, 409, 260, 10.1016/j.ijpharm.2011.02.051 Van Eerdenbrugh, 2009, A screening study of surface stabilization during the production of drug nanocrystals, J Pharm Sci, 98, 2091, 10.1002/jps.21563 Saleem, 2010, Micronization of a soft material: air-jet and micro-ball milling, AAPS PharmSciTech, 11, 1642, 10.1208/s12249-010-9542-5 Shariare, 2012, Influence of solvent on the morphology and subsequent comminution of ibuprofen crystals by air jet milling, J Pharm Sci, 101, 1108, 10.1002/jps.23003 Shariare, 2011, Effect of crystallisation conditions and feedstock morphology on the aerosolization performance of micronised salbutamol sulphate, Int J Pharm, 415, 62, 10.1016/j.ijpharm.2011.05.043 Brodka-Pfeiffer, 2005, Air jet milling with homogeneous premixes of fenoterol hydrobromide and glucose for the application in dry powder inhalers, Pharm Ind, 67, 713 Jain, 2008, Effect of powder processing on performance of fenofibrate formulations, Eur J Pharm Biopharm, 69, 727, 10.1016/j.ejpb.2007.12.006 Vogt, 2008, Cogrinding enhances the oral bioavailability of emd 57033, a poorly water soluble drug, in dogs, Eur J Pharm Biopharm, 68, 338, 10.1016/j.ejpb.2007.06.011 Han, 2011, Simultaneous micronization and surface modification for improvement of flow and dissolution of drug particles, Int J Pharm, 415, 185, 10.1016/j.ijpharm.2011.05.070 Muller, 1995, Nanosuspensions – a novel formulation for the iv administration of poorly soluble drugs, 491 Hoyer, 2010, Preparation and evaluation of thiomer nanoparticles via high pressure homogenization, J Microencapsul, 27, 487, 10.3109/02652040903518460 Colombo, 2009, Drug mechanochemical activation, J Pharm Sci, 98, 3961, 10.1002/jps.21733 Suryanarayana, 2001, Mechanical alloying and milling, Prog Mater Sci, 46, 1, 10.1016/S0079-6425(99)00010-9 Lantz, 1990, Size reduction, 107 Yamamoto, 1974, Dissolution rate and bioavailability of griseofulvin from a ground mixture with microcrystalline cellulose, J Pharmacokinet Biop, 2, 487, 10.1007/BF01070943 Yamamoto, 1976, Dissolution behavior and bioavailability of phenytoin from a ground mixture with microcrystalline cellulose, J Pharm Sci, 65, 1484, 10.1002/jps.2600651017 Mallick, 2008, Physicochemical characterization of interaction of ibuprofen by solid-state milling with aluminum hydroxide, Drug Dev Ind Pharm, 34, 726, 10.1080/03639040801901868 Balani, 2010, Influence of excipients in comilling on mitigating milling-induced amorphization or structural disorder of crystalline pharmaceutical actives, J Pharm Sci, 99, 2462, 10.1002/jps.21998 Löbmann, 2012, Co-amorphous simvastatin and glipizide combinations show improved physical stability without evidence of intermolecular interactions, Eur J Pharm Biopharm, 81, 159, 10.1016/j.ejpb.2012.02.004 Tozuka, 2011, A novel application of α-glucosyl hesperidin for nanoparticle formation of active pharmaceutical ingredients by dry grinding, Eur J Pharm Biopharm, 79, 559, 10.1016/j.ejpb.2011.07.006 Müller, 2001, Nanosuspensions as particulate drug formulations in therapy: rationale for development and what we can expect for the future, Adv Drug Deliv Rev, 47, 3, 10.1016/S0169-409X(00)00118-6 Peltonen, 2010, Pharmaceutical nanocrystals by nanomilling: critical process parameters, particle fracturing and stabilization methods, J Pharm Pharmacol, 62, 1569, 10.1111/j.2042-7158.2010.01022.x Gulsun, 2011, Design and characterization of nanocrystal formulations containing ezetimibe, Chem Pharm Bull, 59, 41, 10.1248/cpb.59.41 Sievens-Figueroa, 2012, Preparation and characterization of hydroxypropyl methyl cellulose films containing stable BCS class ii drug nanoparticles for pharmaceutical applications, Int J Pharm, 423, 496, 10.1016/j.ijpharm.2011.12.001 Kayaert, 2011, Bead layering as a process to stabilize nanosuspensions: influence of drug hydrophobicity on nanocrystal reagglomeration following in-vitro release from sugar beads, J Pharm Pharmacol, 63, 1446, 10.1111/j.2042-7158.2011.01351.x Kesisoglou, 2007, Nanosizing – oral formulation development and biopharmaceutical evaluation, Adv Drug Deliv Rev, 59, 631, 10.1016/j.addr.2007.05.003 Liversidge, 1995, Particle-size reduction for improvement of oral bioavailability of hydrophobic drugs .1. Absolute oral bioavailability of nanocrystalline danazol in beagle dogs, Int J Pharm, 125, 91, 10.1016/0378-5173(95)00122-Y Merisko-Liversidge, 2003, Nanosizing: a formulation approach for poorly-water-soluble compounds, Eur J Pharm Sci, 18, 113, 10.1016/S0928-0987(02)00251-8 Patravale, 2004, Nanosuspensions: a promising drug delivery strategy, J Pharm Pharmacol, 56, 827, 10.1211/0022357023691 Verhoff FH, Snow RA, Pace GW. Media milling. US Patent 6604698. 2003. Moschwitzer, 2006, New method for the effective production of ultrafine drug nanocrystals, J Nanosci Technol, 6, 3145 Van Eerdenbrugh, 2007, Characterization of physico-chemical properties and pharmaceutical performance of sucrose co-freeze-dried solid nanoparticulate powders of the anti-hiv agent loviride prepared by media milling, Int J Pharm, 338, 198, 10.1016/j.ijpharm.2007.02.005 Park, 2009, Improved efficacy of appetite suppression by lipoic acid particles prepared by nanocomminution, Drug Dev Ind Pharm, 35, 1305, 10.3109/03639040902902385 Ghosh, 2012, Design and characterization of submicron formulation for a poorly soluble drug: the effect of vitamin e tpgs and other solubilizers on skin permeability enhancement, Int J Pharm, 434, 90, 10.1016/j.ijpharm.2012.05.031 Niwa, 2011, Design of dry nanosuspension with highly spontaneous dispersible characteristics to develop solubilized formulation for poorly water-soluble drugs, Pharm Res, 28, 2339, 10.1007/s11095-011-0465-y Nekkanti, 2009, Development and characterization of solid oral dosage form incorporating candesartan nanoparticles solid oral dosage form incorporating drug nanoparticles, Pharm Dev Technol, 14, 290, 10.1080/10837450802585278 Laaksonen, 2011, Intact nanoparticulate indomethacin in fast-dissolving carrier particles by combined wet milling and aerosol flow reactor methods, Pharm Res, 28, 2403, 10.1007/s11095-011-0456-z Tanaka, 2012, Nanoparticulation of probucol, a poorly water-soluble drug, using a novel wet-milling process to improve in vitro dissolution and in vivo oral absorption, Drug Dev Ind Pharm, 38, 1015, 10.3109/03639045.2011.637051 Chan, 2011, Production methods for nanodrug particles using the bottom-up approach, Adv Drug Deliv Rev, 63, 406, 10.1016/j.addr.2011.03.011 Shegokar, 2010, Nanocrystals: industrially feasible multifunctional formulation technology for poorly soluble actives, Int J Pharm, 399, 129, 10.1016/j.ijpharm.2010.07.044 Muller RH, Becker R, Kruss B, et al. Pharmaceutical nanosuspensions for medicament administration as system of increased saturation solubility and rate of solution. US Patent No. 5858410. 1998. Mohr, 1987, High-pressure homogenization. Part i. Liquid-liquid dispersion in turbulence fields of high energy density, J Food Eng, 6, 177, 10.1016/0260-8774(87)90023-9 Pandolfe, 1981, Effect of dispersed and continuous phase viscosity on droplet size of emulsions generated by homogenization, J Disper Sci Technol, 2, 459, 10.1080/01932698108943924 Jahnke, 1998, The theory of high-pressure homogenization, 177 Müller, 1998, Nanosuspensions for the formulation of poorly soluble drugs. I. Preparation by a size-reduction technique, Int J Pharm, 160, 229, 10.1016/S0378-5173(97)00311-6 Schwarz, 1994, Influence of production parameters of solid lipid nanoparticles (SLN) on the suitability for intravenous injection, Eur J Pharm Biopharm, 40 Radtke, 2001, Nanopure pure drug nanoparticles for the formulation of poorly soluble drugs, New Drugs, 3, 62 Kluge, 2012, Co 2-assisted high pressure homogenization: a solvent-free process for polymeric microspheres and drug-polymer composites, Int J Pharm, 436, 394, 10.1016/j.ijpharm.2012.06.048 Kluge, 2012, High pressure homogenization of pharmaceutical solids, J Supercrit Fluid, 66, 380, 10.1016/j.supflu.2012.01.009 Quan, 2012, A novel surface modified nitrendipine nanocrystals with enhancement of bioavailability and stability, Int J Pharm, 430, 366, 10.1016/j.ijpharm.2012.04.025 Ye, 2004, Technical cost modeling for the mechanical milling at cryogenic temperature (cryomilling), Adv Eng Mater, 6, 10.1002/adem.200400074 Salazar, 2012, Nanocrystals: comparison of the size reduction effectiveness of a novel combinative method with conventional top-down approaches, Eur J Pharm Biopharm, 81, 82, 10.1016/j.ejpb.2011.12.015 Sugimoto, 2012, Development of a novel ultra cryo-milling technique for a poorly water-soluble drug using dry ice beads and liquid nitrogen, Int J Pharm, 426, 162, 10.1016/j.ijpharm.2012.01.007 Yang, 2010, Spray-dried microparticles containing polymeric micelles encapsulating hematoporphyrin, AAPS J, 12, 138, 10.1208/s12248-009-9172-6 Shakhtshneider, 1999, Mechanochemical synthesis and mechanical activation of drugs, 271 Sugimoto, 2012, Novel ultra-cryo milling and co-grinding technique in liquid nitrogen to produce dissolution-enhanced nanoparticles for poorly water-soluble drugs, Chem Pharm Bull, 60, 325, 10.1248/cpb.60.325 Jayasankar, 2006, Cocrystal formation during cogrinding and storage is mediated by amorphous phase, Pharm Res, 23, 2381, 10.1007/s11095-006-9110-6 Kogermann, 2011, X-ray powder diffractometry in combination with principal component analysis – a tool for monitoring solid state changes, Eur J Pharm Sci, 43, 278, 10.1016/j.ejps.2011.05.001 Willart, 2008, Solid state amorphization of pharmaceuticals, Mol Pharm, 5, 905, 10.1021/mp800092t Crowley, 2002, Cryogenic grinding of indomethacin polymorphs and solvates: assessment of amorphous phase formation and amorphous phase physical stability, J Pharm Sci, 91, 492, 10.1002/jps.10028 Karmwar, 2011, Investigation of properties and recrystallisation behaviour of amorphous indomethacin samples prepared by different methods, Int J Pharm, 417, 94, 10.1016/j.ijpharm.2010.12.019 Wojnarowska, 2010, Study of the amorphous glibenclamide drug: analysis of the molecular dynamics of quenched and cryomilled material, Mol Pharm, 7, 1692, 10.1021/mp100077c Chieng, 2008, Formation and physical stability of the amorphous phase of ranitidine hydrochloride polymorphs prepared by cryo-milling, Eur J Pharm Biopharm, 68, 771, 10.1016/j.ejpb.2007.09.001 Adrjanowicz, 2011, Effect of cryogrinding on chemical stability of the sparingly water-soluble drug furosemide, Pharm Res, 28, 3220, 10.1007/s11095-011-0496-4 Niwa, 2010, One-step preparation of pharmaceutical nanocrystals using ultra cryo-milling technique in liquid nitrogen, Eur J Pharm Sci, 41, 78, 10.1016/j.ejps.2010.05.019 Feng, 2008, Process induced disorder in crystalline materials: differentiating defective crystals from the amorphous form of griseofulvin, J Pharm Sci, 97, 3207, 10.1002/jps.21219 Ma, 2002, On-line measurement of particle size and shape using laser diffraction, Part Part Syst Char, 18, 243, 10.1002/1521-4117(200112)18:5/6<243::AID-PPSC243>3.0.CO;2-4 Deriemaeker, 2005, Shape and size determination by laser diffraction: average aspect ratio and size distributions by volume; feasibility of data analysis by neural networks, Part Part Syst Char, 22, 5, 10.1002/ppsc.200400960 Ma, 2001, Extending laser diffraction for particle shape characterization: technical aspects and application, Powder Technol, 118, 180, 10.1016/S0032-5910(01)00309-6 Xu, 2003, Comparison of sizing small particles using different technologies, Powder Technol, 132, 145, 10.1016/S0032-5910(03)00048-2 Almeida-Prieto, 2004, Image analysis of the shape of granulated powder grains, J Pharm Sci, 93, 621, 10.1002/jps.10572 Staniforth, 2002, Particle-size reduction, 166 George, 2013, Identifying the correlation between drug/stabilizer properties and critical quality attributes (cqas) of nanosuspension formulation prepared by wet media milling technology, Eur J Pharm Sci, 48, 142, 10.1016/j.ejps.2012.10.004 Bilgili, 2012, A combined microhydrodynamics-polymer adsorption analysis for elucidation of the roles of stabilizers in wet stirred media milling, Int J Pharm, 439, 193, 10.1016/j.ijpharm.2012.09.040 Ghosh, 2012, Optimization of formulation and process parameters for the production of nanosuspension by wet media milling technique: effect of vitamin e tpgs and nanocrystal particle size on oral absorption, Eur J Pharm Sci, 47, 718, 10.1016/j.ejps.2012.08.011 Anhalt, 2012, Development of a new method to assess nanocrystal dissolution based on light scattering, Pharm Res, 29, 2887, 10.1007/s11095-012-0795-4 De Smet, 2012, Development of a nanocrystalline paclitaxel formulation for hipec treatment, Pharm Res, 29, 2398, 10.1007/s11095-012-0765-x Bose, 2012, Application of spray granulation for conversion of a nanosuspension into a dry powder form, Eur J Pharm Sci, 47, 35, 10.1016/j.ejps.2012.04.020 Niwa, 2011, Universal wet-milling technique to prepare oral nanosuspension focused on discovery and preclinical animal studies – development of particle design method, Int J Pharm, 405, 218, 10.1016/j.ijpharm.2010.12.013 Cerdeira, 2010, Miconazole nanosuspensions: influence of formulation variables on particle size reduction and physical stability, Int J Pharm, 396, 210, 10.1016/j.ijpharm.2010.06.020 Jinno, 2008, In vitro-in vivo correlation for wet-milled tablet of poorly water-soluble cilostazol, J Control Release, 130, 29, 10.1016/j.jconrel.2008.05.013 Merisko-Liversidge, 2004, Insulin nanoparticles: a novel formulation approach for poorly water soluble zn-insulin, Pharm Res, 21, 1545, 10.1023/B:PHAM.0000041446.14569.e2 Na, 1999, Physical stability of ethyl diatrizoate nanocrystalline suspension in steam sterilization, Pharm Res, 16, 569, 10.1023/A:1018883431970 Sangwai, 2013, Amorphous ternary cyclodextrin nanocomposites of telmisartan for oral drug delivery: improved solubility and reduced pharmacokinetic variability, Int J Pharm, 453, 423, 10.1016/j.ijpharm.2012.08.034 Scalia, 2012, Comparative evaluation of the effect of permeation enhancers, lipid nanoparticles and colloidal silica on in vivo human skin penetration of quercetin, Skin Pharmacol Phys, 26, 57, 10.1159/000345210 Talekar, 2012, Development and evaluation of pik75 nanosuspension, a phosphatidylinositol- 3-kinase inhibitor, Eur J Pharm Sci, 47, 824, 10.1016/j.ejps.2012.09.015 Rachmawati, 2013, Development of curcumin nanocrystal: physical aspects, J Pharm Sci, 102, 204, 10.1002/jps.23335 Muller, 2012, Development of industrially feasible concentrated 30% and 40% nanoemulsions for intravenous drug delivery, Drug Dev Ind Pharm, 38, 420, 10.3109/03639045.2011.608681 Chu, 2012, Development of intravenous lipid emulsion of tanshinone iia and evaluation of its anti-hepatoma activity in vitro, Int J Pharm, 424, 76, 10.1016/j.ijpharm.2011.12.049 Sun, 2012, Effect of novel stabilizers-cationic polymers on the particle size and physical stability of poorly soluble drug nanocrystals, Nanotechnol Biol Med, 8, 460, 10.1016/j.nano.2011.07.006 Wang, 2012, Emodin loaded solid lipid nanoparticles: preparation, characterization and antitumor activity studies, Int J Pharm, 430, 238, 10.1016/j.ijpharm.2012.03.027 Xu, 2012, Engineering drug ultrafine particles of beclomethasone dipropionate for dry powder inhalation, Int J Pharm, 436, 1, 10.1016/j.ijpharm.2012.06.038 Zhang, 2011, Enhanced bioavailability after oral and pulmonary administration of baicalein nanocrystal, Int J Pharm, 420, 180, 10.1016/j.ijpharm.2011.08.023 Jeon, 2012, Enhanced percutaneous delivery of recombinant human epidermal growth factor employing nano-liposome system, J Microencapsul, 29, 234, 10.3109/02652048.2011.646327 Anwar, 2011, Enhanced bioavailability of nano-sized chitosan-atorvastatin conjugate after oral administration to rats, Eur J Pharm Sci, 44, 241, 10.1016/j.ejps.2011.08.001 Wang, 2012, Enhance the dissolution rate and oral bioavailability of pranlukast by preparing nanosuspensions with high-pressure homogenizing method, Drug Dev Ind Pharm, 38, 1381, 10.3109/03639045.2011.652636 Kakran, 2012, Fabrication of quercetin nanocrystals: comparison of different methods, Eur J Pharm Biopharm, 80, 113, 10.1016/j.ejpb.2011.08.006 He, 2011, Food protein-stabilized nanoemulsions as potential delivery systems for poorly water-soluble drugs: preparation, in vitro characterization, and pharmacokinetics in rats, Int J Nanomed, 6, 521 Kim, 2012, Identification of an emulsifier and conditions for preparing stable nanoemulsions containing the antioxidant astaxanthin, Int J Cosmet Sci, 34, 64, 10.1111/j.1468-2494.2011.00682.x Gonzalez-Mira, 2012, Improved and safe transcorneal delivery of flurbiprofen by nlc and nlc-based hydrogels, J Pharm Sci, 101, 707, 10.1002/jps.22784 Wang, 2013, In vitro and in vivo anticancer activity of a novel puerarin nanosuspension against colon cancer, with high efficacy and low toxicity, Int J Pharm, 441, 728, 10.1016/j.ijpharm.2012.10.021 Yao, 2012, In vitro and in vivo evaluation of camptothecin nanosuspension: a novel formulation with high antitumor efficacy and low toxicity, Int J Pharm, 423, 586, 10.1016/j.ijpharm.2011.11.031 Piao, 2011, In vitro-in vivo study of coq10-loaded lipid nanoparticles in comparison with nanocrystals, Int J Pharm, 419, 255, 10.1016/j.ijpharm.2011.07.016 Kakran, 2012, Long-term stability of quercetin nanocrystals prepared by different methods, J Pharm Pharmacol, 64, 1394, 10.1111/j.2042-7158.2012.01515.x Mitri, 2011, Lutein nanocrystals as antioxidant formulation for oral and dermal delivery, Int J Pharm, 420, 141, 10.1016/j.ijpharm.2011.08.026 Schwarz, 2012, Nanocarriers for dermal drug delivery: influence of preparation method, carrier type and rheological properties, Int J Pharm, 437, 83, 10.1016/j.ijpharm.2012.08.003 Lai, 2011, Nanocrystals as tool to improve piroxicam dissolution rate in novel orally disintegrating tablets, Eur J Pharm Biopharm, 79, 552, 10.1016/j.ejpb.2011.07.005 Duret, 2012, New inhalation-optimized itraconazole nanoparticle-based dry powders for the treatment of invasive pulmonary aspergillosis, Int J Nanomed, 7, 5475, 10.2147/IJN.S34091 Botker, 2011, Assessment of crystalline disorder in cryo-milled samples of indomethacin using atomic pair-wise distribution functions, Int J Pharm, 417, 112, 10.1016/j.ijpharm.2010.12.018 Garmise, 2006, Formulation of a dry powder influenza vaccine for nasal delivery, AAPS Pharm Sci Tech, 7, E1, 10.1208/pt070119