Pharmaceutical nanocrystals by nanomilling: Critical process parameters, particle fracturing and stabilization methods

Journal of Pharmacy and Pharmacology

Volumn 62, Issue 11, 2010, Pages 1569-1579

  Peltonen, Leena ^a   Hirvonen, Jouni ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

Author keywords

nanocrystals; stability; wet milling

Indexed keywords

ADIPIODONE; ANTHRACENE; BETAMETHASONE VALERATE; BUPARVAQUONE; CAMPTOTHECIN; CARBAMAZEPINE; CINNARIZINE; ETOPOSIDE; FUNCTIONAL GROUP; GRISEOFULVIN; HESPERETIN; HYDROCORTISONE ACETATE; IBUPROFEN; INDOMETACIN; ITRACONAZOLE; LOVIRIDE; MEBENDAZOLE; MITOTANE; NANOCRYSTAL; NAPROXEN; NIFEDIPINE; OXCARBAZEPINE; PACLITAXEL; PHENYLBUTAZONE; PHENYTOIN; PREDNISOLONE ACETATE; PROGESTERONE; SIMVASTATIN; TAMOXIFEN; UNINDEXED DRUG;

CHEMICAL REACTION; DRUG FORMULATION; DRUG SOLUBILITY; DRUG STABILITY; FREEZE FRACTURE; HYDROPHOBICITY; MOLECULAR WEIGHT; PARTICLE SIZE; REVIEW; TRANSMISSION ELECTRON MICROSCOPY; UNINDEXED SEQUENCE; VISCOSITY; X RAY POWDER DIFFRACTION;

CHEMISTRY, PHARMACEUTICAL; DRUG COMPOUNDING; DRUG STABILITY; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; NANOPARTICLES; PHARMACEUTICAL PREPARATIONS; SURFACE PROPERTIES;

EID: 78649648146     PISSN: 00223573     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.2042-7158.2010.01022.x     Document Type: Review

References (92)

1. Müller RH, Keck CM,. Challenges and solutions for the delivery of biotech drugs-a review of drug nanocrystal technology and lipid nanoparticles. J Biotechnol 2004; 113: 151-170.
2. Keck CM, Müller RH,. Drug nanocrystals of poorly soluble drugs produced by high pressure homogenization. Eur J Pharm Biopharm 2006; 62: 3-16.
3. Merisko-Liversidge E, Liversidge G,. Drug nanoparticles: formulating poorly water-soluble compounds. Tox Pathol 2008; 36: 43-38.
4. Trotta M, et al. Emulsions containing partially water- miscible solvents for the preparation of drug nanosuspensions. J Control Release 2001; 76: 119-128.
5. Elder EJ, et al. Preparation, characterization, and scale-up of ketoconazole with enhanced dissolution and bioavailability. Drug Dev Ind Pharm 2007; 33: 755-765.
6. Rogers TL, et al. Development and characterization of a scalable controlled precipitation process to enhance the dissolution of poorly water-soluble drugs. Pharm Res 2004; 21: 2048-2057.
7. Liversidge GG, Cundy KC,. Particle size reduction for improvement of oral bioavailability of hydrophobic drugs: I. Absolute oral bioavailability of nanocrystalline danazol in beagle dogs. Int J Pharm 1995; 125: 91-97.
8. Wu Y, et al. The role of biopharmaceutics in the development of a clinical nanoparticle formulation of MK-0869: a beagle dog model predicts improved bioavailability and diminished food effect on absorption in human. Int J Pharm 2004; 285: 135-146.
9. Van Eerdenbrugh B, et al. A screening study of surface stabilization during the production of drug nanocrystals. J Pharm Sci 2009; 98: 2091-2103.
10. Langguth P, et al. Nanosuspension formulations for low-soluble drugs: pharmacokinetic evaluation using spironolactone as model compound. Drug Dev Ind Pharm 2005; 31: 319-329.
11. Mishra PR, et al. Production and characterization of hesperetin nanosuspensions for dermal delivery. Int J Pharm 2009; 371: 182-189.
12. Elan,.
13. SkyePharma,.
14. Kocbek P, et al. Preparation and evaluation of nanosuspensions for enhancing the dissolution of poorly soluble drugs. Int J Pharm 2006; 312: 179-186.
15. Verma S, et al. A comparative study of top-down and bottom-up approaches for the preparation of micro/nanosuspensions. Int J Pharm 2009; 380: 216-222.
16. Rabinow BE,. Nanosuspension in drug delivery. Nat Rev Drug Discovery 2004; 3: 785-796.
17. Lee J, et al. Characteristics of polymers enabling nano-comminution of water-insoluble drugs. Int J Pharm 2008; 355: 328-336.
18. Merisko-Liversidge E, et al. Formulation and antitumor activity evaluation of nanocrystalline suspensions of poorly soluble anticancer drugs. Pharm Res 1996; 13: 272-278.
19. Merisko-Liversidge E, et al. Nanosizing: a formulation approach for poorly-water-soluble compounds. Eur J Pharm Sci 2003; 18: 113-120.
20. Date AA, Petravale VB,. Current strategies for engineering drug nanoparticles. Curr Opin Colloid Interface Sci 2004; 9: 222-235.
21. Van Eerdenbrugh B, et al. Top-down production of drug nanocrystals: nanosuspension stabilization, miniaturization and transformation into solid products. Int J Pharm 2008; 364: 64-75.
22. Junghaus J-U, Müller RH,. Nanocrystal technology, drug delivery and clinical applications. Int J Nanomedicine 2008; 3: 295-310.
23. Merisko-Liversidge E, et al. Insulin nanoparticles: a novel formulation approach for poorly water soluble Zn-insulin. Pharm Res 2004; 21: 1545-1553.
24. Gao L, et al. Drug nanocrystals for the formulation of poorly soluble drugs and its application as a potential drug delivery system. J Nanopart Res 2008; 10: 845-862.
25. Choi J-Y, et al. Role of polymeric stabilizers for drug nanocrystal dispersions. Curr Appl Phys 2005; 5: 472-474.
26. Lee J,. Intrinsic adhesion force of lubricants to steel surfaces. J Pharm Sci 2004; 93: 2310-2318.
27. Van Eerdenbrugh B, et al. 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 2007; 338: 198-206.
28. Lee J,. Drug nano- and microparticles processed into solid dosage forms: physical properties. J Pharm Sci 2003; 92: 2057-2068.
29. Na GC, et al. Physical stability of ethyl diatrizoate nanocrystalline suspension in steam sterilization. Pharm Res 1999; 16: 569-574.
30. Annapragada A, Adjei A,. Numerical simulation of milling processes as an aid to process design. Int J Pharm 1996; 136: 1-11.
31. Deng Z, et al. Understanding a relaxation behavior in a nanoparticle suspension for drug delivery applications. Int J Pharm 2008; 351: 236-243.
32. Müller RH, et al. Nanosuspensions: a formulation approach for poorly soluble and poorly bioavailable drugs. In, Wise DL, ed. Handbook of Pharmaceutical Controlled Release Technology. New York: Marcel Dekker Inc, 2000: 345-358.
33. Sharma P, et al. Effect of wet milling process on the solid state of indomethacin and simvastatin. Int J Pharm 2009; 380: 40-48.
34. Chamarthy SP, Pinal R,. The nature of crystal disorder in milled pharmaceutical materials. Colloids Surf A: Physicochem Eng Asp 2008; 331: 68-75.
35. Crowley KJ, Zografi G,. Cryogenic grinding of indomethacin polymorphs and solvates: assessment of amorphous phase formation and amorphous phase physical stability. J Pharm Sci 2002; 91: 492-507.
36. Eurand,.
37. Joshi V, et al. Increase in the specific surface area of budesonide during storage postmicronization. Pharm Res 2002; 19: 7-12.
38. Gubskaya AV, et al. Effect of cryogrinding on physico-chemical properties of drugs. I. Theophylline: evaluation of particles sizes and the degree of crystallinity, relation to dissolution parameters. Drug Dev Ind Pharm 1995; 21: 1953-1964.
39. Brodka-Pfeiffer K, et al. Influence of mechanical activation on the physical stability of salbutamol sulphate. Eur J Pharm Biopharm 2003; 56: 393-400.
40. Hüttenrauch R, et al. Mechanical activation of pharmaceutical systems. Pharm Res 1985; 2: 302-306.
41. Steckel H, et al. In vitro characterization of jet-milled and in-situ-micronized fluticasone-17-propionate. Int J Pharm 2003; 258: 65-75.
42. Heng JYY, et al. The effects of milling on the surface properties of form I paracetamol crystals. Pharm Res 2006; 23: 1918-1927.
43. Roberts RJ, et al. The relationship between indentation hardness of organic solids and their molecular structure. J Mater Sci 1994; 29: 2289-2296.
44. De Vegt O, et al. Influence of flaws and crystal properties on particle fracture in a jet mill. Powder Technol 2009; 191: 72-77.
45. Burt HM, Mitchell AG,. Crystal defects and dissolution. Int J Pharm 1981; 9: 137-152.
46. Tangsathitkulchai C,. The effect of slurry rheology on fine grinding in a laboratory ball mill. Int J Miner Process 2003; 69: 29-47.
47. Peukert W, et al. Control of aggregation in production and handling of nanoparticles. Chem Eng Process 2005; 44: 245-252.
48. Palla BJ, Shah DO,. Stabilization of high ionic strength slurries using the synergistic effects of a mixed surfactant system. J Colloid Interface Sci 2000; 223: 102-111.
49. Grau MJ, et al. Nanosuspensions of poorly soluble drugs-reproducibility of small scale production. Int J Pharm 2000; 196: 155-157.
50. Hecq J, et al. Preparation and characterization of nanocrystals for solubility and dissolution rate enhancement of nifedipine. Int J Pharm 2005; 299: 167-177.
51. Hecq J, et al. Preparation and in vitro/in vivo evaluation of nanosized crystals for dissolution rate enhancement of ucb-35440-3, a highly dosed poorly water-soluble weak base. Eur J Pharm Biopharm 2006; 64: 360-368.
52. Hernández-Trejo N, et al. Characterization of nebulized buparvaquone nanosuspensions-effect of nebulization tehnology. J Drug Target 2005; 13: 499-507.
53. Van Eerdenbrugh B, et al. Drying of crystalline drug nanosuspensions-the importance of surface hydrophobicity on dissolution behavior upon redispersion. Eur J Pharm Sci 2008; 35: 127-135.
54. TM drug formulations. Drug Dev Ind Pharm 1997; 23: 1087-1093.
55. Lee J, et al. Amphiphilic amino acid copolymers as stabilizers for the preparation of nanocrystal dispersion. Eur J Pharm Sci 2005; 24: 441-449.
56. Agarwal A, et al. Stable nanocolloids of poorly soluble drugs with high drug content prepared using the combination of sonication and layer-by-layer technology. J Control Release 2008; 128: 255-260.
57. Douroumis D, Fahr A,. Nano- and micro-particulate formulations of poorly water-soluble drugs by using a novel optimized technique. Eur J Pharm Biopharm 2006; 63: 173-175.
58. Koichi B, et al. New method for delivering a hydrophobic drug for photodynamic therapy using pure nanocrystal form of the drug. Mol Pharm 2009; 4: 289-297.
59. Chen X, et al. Flocculation of polymer stabilized nanocrystal suspensions to produce redispersible powders. Drug Dev Ind Pharm 2009; 35: 283-296.
60. Matteucci ME, et al. Drug nanoparticles by antisolvent precipitation. Mixing energy versus surfactant stabilization. Langmuir 2006; 22: 8951-8959.
61. Makhlof A, et al. Cyclodextrins as stabilizers for the preparation of drug nanocrystals by the emulsion solvent diffusion method. Int J Pharm 2008; 357: 280-285.
62. Palla BJ, Shah DO,. Stabilization of high ionic strength slurries using surfactant mixtures: molecular factors that determine optimal stability. J Colloid Interface Sci 2002; 256: 143-152.
63. Müller RH, et al. Manufacturing of nanoparticles by milling and homogenization techniques. In, Gupta RB, Kompela UB, ed. Nanoparticle technology for drug delivery. New York: Taylor & Francis Group, 2006: 21-28.
64. Müller RH, Junghanns J-UAH,. Drug nanocrystals/nanosuspensions for the delivery of poorly soluble drugs. In, Torchilin V, ed. Nanoparticulates as Drug Carriers. London: Imperial College Press, 2006: 307-328.
65. Farrokhpay S,. A review of polymeric dispersant stabilisation of titania pigment. Adv Colloid Interface Sci 2009; 151: 24-32.
66. Decher G,. Fuzzy nanoassemblies: toward layered polymeric multicomposites. Science 1997; 277: 1232-1237.
67. Hirsjärvi S, et al. Layer-by-layer polyelectrolyte coating of low molecular weight poly(lactic acid) nanoparticles. Colloids Surf B: Biointerf 2006; 49: 93-99.
68. 2 suspensions: effect of dissociation and type of polyelectrolyte. J Colloid Interface Sci 2000; 228: 73-81.
69. Lee J, Cheng Y,. Critical freezing rate in freeze drying nanocrystal dispersions. J Control Release 2006; 111: 185-192.
70. York P, et al. Characterisation of the surface energetics of milled dl-propranolol hydrochloride using inverse gas chromatography and molecular modeling. Int J Pharm 1998; 174: 179-186.
71. Prasad KVR, et al. Dissolution kinetics of paracetamol single crystals. Int J Pharm 2002; 238: 29-41.
72. Watanabe A, et al. Crystal habits and dissolution behavior of aspirin. Chem Pharm Bull 1982; 30: 2958-2963.
73. Korlakunte VR, et al. Dissolution kinetics of paracetamol single crystals. Int J Pharm 2002; 238: 29-41.
74. Mukuta T, et al. Influence of impurities on the solution-mediated phase transformation of an active pharmaceutical ingredient. Cryst Growth Des 2005; 5: 1429-1436.
75. Lechuga-Ballesteros D, Rodriguez-Hornedo N,. Effects of molecular structure and growth kinetics on the morphology of L-alanine crystals. Int J Pharm 1995; 115: 151-160.
76. Rasenack N, et al. Microcrystals for dissolution rate enhancement of poorly water-soluble drugs. Int J Pharm 2003; 254: 137-145.
77. Zimmermann A, et al. Adsorption of pharmaceutical excipients onto microcrystals of siramesine hydrochloride: effects on physicochemical properties. Eur J Pharm Biopharm 2009; 71: 109-116.
78. Parsons GE, et al. The use of surface energy and polarity determinations to predict physical stability of non-polar non-aqueous suspension. Int J Pharm 1992; 83: 163-170.
79. Liu X, et al. Size effect on melting temperature of nano-structured drugs. Mat Chem Phys 2007; 103: 1-4.
80. Matijasic G, et al. Suspension rheology during wet comminution in planetary ball mill. Chem Eng Res Des 2008; 86: 384-389.
81. Fuerstenau DW, Abouzeid A-ZM,. The energy efficiency of ball milling in comminution. Int J Miner Process 2002; 67: 161-185.
82. Tian F, et al. The influence of various excipients on the conversion kinetics of carbamazepine polymorphs in aqueous suspension. J Pharm Pharmacol 2007; 59: 193-201.
83. Sabnis S, et al. Use of chitosan in compressed tablets of diclofenac sodium: inhibition of drug release in an acidic environment. Pharm Dev Technol 1997; 2: 243-255.
84. Law SL, Kayes JP,. Adsorption of non-ionic water-soluble cellulose polymers at the solid-water interface and their effect on suspension stability. Int J Pharm 1983; 15: 251-260.
85. Rosen MJ,. Surfactants and interfacial phenomena. New York: Wiley, 1989.
86. Badia A, et al. Structure and dynamics in alkanethiolate monolayers self-assembled on gold nanoparticles: a DSC, FT-IR, and deuterium NMR study. J. Am Chem Soc 1997; 119: 2682-2692.
87. Peltonen L, Yliruusi J,. Surface pressure, hysteresis, interfacial tension, and cmc of four sorbitan monesters at water-air, water-hexane, and hexane-air interfaces. J Colloid Interface Sci 2000; 227: 1-6.
88. Piao L, et al. The simple and facile methods to improve dispersion stability of nanoparticles: different chain length alkylcarboxylate mixtures. J Colloid Interface Sci 2009; 334: 208-211.
89. Ploehn HJ, Russel WB,. Interactions between colloidal particles and soluble polymers. Adv Chem Eng 1990; 15: 137-228.
90. Cerdeira A, et al. Particle size reduction by nanomilling correlates with polymer and surfactant adsorption on nanoparticles. Proceedings in 36th Annual Meeting & Exposition of the Controlled Release Society, July 18-22, 2009, Copenhagen.
91. Berglund KD, et al. Coadsorption of sodium dodecyl sulfate with hydrophobically modified nonionic cellulose polymers. 1. Role of polymer hydrophobic modification. Langmuir 2003; 19: 2705-2713.
92. Berglund KD, et al. Coadsorption of sodium dodecyl sulfate with hydrophobically modified nonionic cellulose polymers. 2. Role of surface selectivity in adsorption hysteresis. Langmuir 2003; 19: 2714-2721.