Nano-sized crystalline drug production by milling technology

Current Pharmaceutical Design

Volumn 19, Issue 35, 2013, Pages 6246-6258

  Moribe, Kunikazu ^a   Ueda, Keisuke ^a   Limwikrant, Waree ^b   Higashi, Kenjirou ^a   Yamamoto, Keiji ^a  

^a CHIBA UNIVERSITY   (Japan)

^b MAHIDOL UNIVERSITY   (Thailand)

Author keywords

Comminution; Drug dissolution; Grinding; High pressure homogenizer; Milling; Nanoparticle

Indexed keywords

ALBENDAZOLE; ARSENIC TRIOXIDE; AZITHROMYCIN; BEZAFIBRATE; CLARITHROMYCIN; CURCUMIN; DANAZOL; DICLOFENAC; ETRAVIRINE; FENOFIBRATE; FLURBIPROFEN; FUROSEMIDE; GLIBENCLAMIDE; GRISEOFULVIN; HYDROCORTISONE; IBUPROFEN; INDOMETACIN; ITRACONAZOLE; MEFENAMIC ACID; MICONAZOLE; NANOPARTICLE; NAPROXEN; NIFEDIPINE; OMEPRAZOLE; PACLITAXEL; PHENYTOIN; PRANLUKAST; PRANOPROFEN; PROBUCOL; QUERCETIN; TOLBUTAMIDE; UG 588; UNCLASSIFIED DRUG;

AREA UNDER THE CURVE; CRYSTAL STRUCTURE; CRYSTALLIZATION; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG DELIVERY SYSTEM; DRUG FORMULATION; DRUG SCREENING; DRUG SOLUBILITY; GENERAL DEVICE; HYDROPHOBICITY; MICROFLUIDICS; NANOMILLING TECNOLOGY; NANOTECHNOLOGY; NONHUMAN; PARTICLE SIZE; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROCESS OPTIMIZATION; REVIEW; ZETA POTENTIAL;

ANIMALS; CRYSTALLIZATION; DRUG COMPOUNDING; DRUG DESIGN; EXCIPIENTS; HUMANS; NANOPARTICLES; PARTICLE SIZE; PHARMACEUTICAL PREPARATIONS; QUALITY CONTROL; SOLUBILITY; TECHNOLOGY, PHARMACEUTICAL;

EID: 84887925688     PISSN: 13816128     EISSN: 18734286     Source Type: Journal    
DOI: 10.2174/1381612811319350003     Document Type: Review

References (84)

1. Osawa E. Monodisperse single nanodiamond particulates. Pure Appl Chem 2008; 80: 1365-79.
2. Funk JE, Dinger DR. Chapter 25 Milling or Comminution. Predictive process control of crowded particulate suspension. Kluwer Academic Publishers 2001; pp373-94.
3. Chin CP, Wu HS, Wang SS. New approach to pesticide delivery using nanosuspensions: Research and applications. Ind Eng Chem Res 2011; 50: 7637-43.
4. Yu CC, Lee CL, Pan TM. A novel formulation approach for preparation of nanoparticulate red mold rice. J Agr Food Chem 2006; 54: 6845-51.
5. Liao CD, Hung WL, Jan KC, Yeh AI, Ho CT, Hwang LS. Nano/sub-microsized lignan glycosides from sesame meal exhibit higher transport and absorption efficiency in Caco-2 cell monolayer. Food Chem 2010; 119: 896-902.
6. Morimoto Y, Hirohashi M, Ogami A, et al. Inflammogenic effect of well-characterized fullerenes in inhalation and intratracheal instillation studies. Part Fibre Toxicol 2010; 7: 4.
7. Warheit DB, Laurence BR, Reed KL, Roach DH, Webb TR. Comparative pulmonary toxicity assessment of single-wall carbon nanotubes in rats. Toxicol Sci 2004; 77: 117-25.
8. Colombo I, Grassi G, Grassi M. Drug mechanochemical activation. J Pharm Sci 2009; 98: 3961-86.
9. Asahi T, Sugiyama T, Masuhara H. Laser fabrication and spectroscopy of organic nanoparticles. Acc Chem Res 2008; 41: 1790-8.
10. Stein J, T Fuchs, Mattern C. Advanced milling and containment technologies for superfine active pharmaceutical ingredients. Chem Eng Technol 2010; 33: 1464-70.
11. Yamamoto K, Limwikrant W, Moribe K. Analysis of molecular interactions in solid dosage forms; challenge to molecular pharmaceutics. Chem Pharm Bull 2011; 59: 147-54.
12. Kesisoglou F, Panmai S, Wu Y. Nanosizing--oral formulation development and biopharmaceutical evaluation. Adv Drug Deliv Rev 2007; 59: 631-44.
13. Merisko-Liversidge EM, Liversidge GG. Drug nanoparticles: formulating poorly water-soluble compounds. Toxicol Pathol 2008; 36: 43-8.
14. Peltonen L, Hirvonen J. Pharmaceutical nanocrystals by nanomilling: critical process parameters, particle fracturing and stabilization methods. J Pharm Pharmacol 2010; 62: 1569-79.
15. Van Eerdenbrugh B, Van den Mooter G, Augustijns P. Top-down production of drug nanocrystals: nanosuspension stabilization, miniaturization and transformation into solid products. Int J Pharm 2008; 364: 64-75.
16. Merisko-Liversidge EM, Liversidge GG. Nanosizing for oral and parenteral drug delivery: A perspective on formulating poorlywater soluble compounds using wet media milling technology. Adv Drug Deliv Rev 2011; 63: 427-40.
17. Müller RH, Gohla S, Keck CM. State of the art of nanocrystals--special features, production, nanotoxicology aspects and intracellular delivery. Eur J Pharm Biopharm 2011; 78: 1-9.
18. Miller WH Jr., Schipper HM, Lee JS, Singer J, Waxman S. Mechanisms of action of arsenic trioxide. Cancer Res 2002; 62: 3893-903.
19. 4 nanoparticles prepared by high-energy milling. Powder Tech 2011; 211: 232-6.
20. Bhakay A, Merwade M, Bilgili E, Dave RN. Novel aspects of wet milling for the production of microsuspensions and nanosuspensions of poorly watersoluble drugs. Drug Dev Ind Pharm 2011; 37: 963-76.
21. Singh SK, Srinivasan KK, Gowthamarajan K, Singare DS, Prakash D, Gaikwad NB. Investigation of preparation parameters of nanosuspension by top-down media milling to improve the dissolution of poorly water-soluble glyburide. Eur J Pharm Biopharm 2011; 78: 441-6.
22. Tanaka Y, Inkyo M, Yumoto R, Nagai J, Takano M, Nagata S. Nanoparticulation of probucol, a poorly water-soluble drug, using a novel wet-milling process to improve in vitro dissolution and in 10vivo oral absorption. Drug Dev Ind Pharm 2012; 38: 1015-23.
23. Tanaka Y, Inkyo M, Yumoto R, Nagai J, Takano M, Nagata S. Nanoparticulation of poorly water soluble drugs using a wet-mill process and physicochemical properties of the nanopowders. Chem Pharm Bull 2009; 57: 1050-7.
24. Plakkot S, de Matas M, York P, Saunders M, Sulaiman B. Comminution of ibuprofen to produce nano-particles for rapid dissolution. Int J Pharm 2011; 415: 307-14.
25. Cerdeira AM, Mazzotti M, Gander B. Role of milling parameters and particle stabilization on nanogrinding of drug substances of similar mechanical properties. Chem Eng Technol 2011; 34: 1427-38.
26. Ghosh I, Bose S, Vippagunta R, Harmon F. Nanosuspension for improving the bioavailability of a poorly soluble drug and screening of stabilizing agents to inhibit crystal growth. Int J Pharm 2011; 409: 260-8.
27. Takatsuka T, Endo T, Jianguo Y, Yuminoki K, Hashimoto N. Nanosizing of poorly water soluble compounds using rotation/revolution mixer. Chem Pharm Bull 2009; 57: 1061-7.
28. Juhnke M, Berghausen J, Timpe C. Accelerated formulation development for nanomilled active pharmaceutical ingredients using a screening approach. Chem. Eng. Technol 2010; 33: 1412-8.
29. Niwa T, Miura S, Danjo K. Universal wet-milling technique to prepare oral nanosuspension focused on discovery and preclinical animal studies-Development of particle design method. Int J Pharm 2011; 405: 218-27.
30. Sigfridsson K, Nordmark A, Theilig S, Lindahl A. A formulation comparison between micro-and nanosuspensions: the importance of particle size for absorption of a model compound, following repeated oral administration to rats during early development. Drug Dev Ind Pharm 2011; 37: 185-92.
31. Sigfridsson K, Lundqvist AJ, Strimfors M. Particle size reduction for improvement of oral absorption of the poorly soluble drug UG558 in rats during early development. Drug Dev Ind Pharm 2009; 35: 1479-86.
32. Ali HS, York P, Ali AM, Blagden N. Hydrocortisone nanosuspensions for ophthalmic delivery: A comparative study between microfluidic nanoprecipitation and wet milling. J Control Release 2011; 149: 175-81.
33. Kim S, Lee J. Folate-targeted drug-delivery systems prepared by nano-comminution. Drug Dev Ind Pharm 2011; 37: 131-8.
34. Laaksonen T, Liu P, Rahikkala A, et al. Intact nanoparticulate indomethacin in fast-dissolving carrier particles by combined wet milling and aerosol flow reactor methods. Pharm Res 2011; 28: 2403-11.
35. Niwa T, Miura S, Danjo K. Design of dry nanosuspension with highly spontaneous dispersible characteristics to develop solubilized formulation for poorly water-soluble drugs. Pharm Res 2011; 28: 2339-49.
36. Niwa T, Nakanishi Y, Danjo K. One-step preparation of pharmaceutical nanocrystals using ultra cryo-milling technique in liquid nitrogen. Eur J Pharm Sci 2010; 41: 78-85.
37. Knieke C, Sommer M, Peukert W. Identifying the apparent and true grinding limit. Powder Technol. 2009; 195: 25-9.
38. Keck CM, Müller RH. Drug nanocrystals of poorly soluble drugs produced by high pressure homogenisation. Eur J Pharm Biopharm 2006; 62: 3-16.
39. Zhang D, Tan T, Gao L, Zhao W, Wang P. Preparation of azithromycin nanosuspensions by high pressure homogenization and its physicochemical characteristics studies. Drug Dev Ind Pharm 2007; 33: 569-75.
40. Lai F, Sinico C, Ennas G, Marongiu F, Marongiu G, Fadda AM. Diclofenac nanosuspensions: Influence of preparation procedure and crystal form on drug dissolution behavior. Int J Pharm 2009; 373: 124-32.
41. Kakran M, Shegokar R, Sahoo NG, Shaal LA, Li L, Müller RH. Fabrication of quercetin nanocrystals: Comparison of different methods. Eur J Pharm Biopharm 2012; 80: 113-21.
42. Verma S, Gokhale R, Burgess DJ. A comparative study of topdown and bottom-up approaches for the preparation of micro/nanosuspensions. Int J Pharm 2009; 380: 216-22.
43. Sun W, Mao S, Shi Y, Li LC, Fang L. Nanonization of itraconazole by high pressure homogenization: stabilizer optimization and effect of particle size on oral absorption. J Pharm Sci 2011; 100: 3365-73.
44. Gao Y, Li Z, Sun M, et al. Preparation and characterization of intravenously injectable curcumin nanosuspension. Drug Deliv 2011; 18: 131-42.
45. Ichimura K, Aoki K, Akiyama H, Horiuchi S, Horie S. Dry grinding of polymer solids with silica nanoparticles to give powdery nanocomposites: mechanochemical effect on thermotropic behaviour and solid-state dissolution of molecular crystals. J Mater Chem 2010; 20: 4784-91.
46. Ichimura K, Aoki K, Akiyama H, Horiuchi S, Nagano S, Horie S. Properties of core-shell structured nanopowders of molecular crystals fabricated by dry grinding. J Mater Chem 2010; 20: 4312-20.
47. Krause B, Villmow T, Boldt R, Mende M, Petzold G, Pötschke P. Influence of dry grinding in a ball mill on the length of multiwalled carbon nanotubes and their dispersion and percolation behaviour in melt mixed polycarbonate composites. Compos Sci Technol 2011; 71: 1145-53.
48. Wu JZ, Ho PC. Evaluation of the in vitro activity and in vivo bioavailabilityof realgar nanoparticles prepared by cryo-grinding. Eur J Pharm Sci 2006; 29: 35-44.
49. H Suzuki, Ogawa M, Hironaka K, Ito K, Sunada H. A nifedipine coground mixture with sodium deoxycholate. I. Colloidal particle formation and solid-state analysis. Drug Dev Ind Pharm 2001; 27: 943-9.
50. H Suzuki, Ogawa M, Hironaka K, Ito K, Sunada H. A nifedipine coground mixture with sodium deoxycholate. II. Dissolution characteristics and stability. Drug Dev Ind Pharm 2001; 27: 951-58.
51. Inoue Y, Yoshimura S, Tozuka Y, et al. Application of ascorbic acid 2-glucoside as a solubilizing agent for clarithromycin: Solubilization and nanoparticle formation. Int J Pharm 2007; 331: 38-45.
52. Tozuka Y, Imono M, Uchiyama H, Takeuchi H. A novel application of β-glucosyl hesperidin for nanoparticle formation of active pharmaceutical ingredients by dry grinding. Eur J Pharm Biopharm 2011; 79: 559-65.
53. Pongpeerapat A, Itoh K, Tozuka Y, Moribe K, Oguchi T, Yamamoto K. Formation and stability of drug nanoparticles obtained from drug/PVP/SDS ternary ground mixture. J Drug Del Sci Tech 2004; 14: 441-7.
54. Pongpeerapat A, Higashi K, Tozuka Y, Moribe K, Yamamoto K. Molecular interaction among probucol/PVP/SDS multicomponent system investigated by solid-state NMR. Pharm Res 2006; 23: 2566-74.
55. C Wanawongthai, Pongpeerapat A, Higashi K, Tozuka Y, Moribe K, Yamamoto K. Nanoparticle formation from probucol/PVP/sodium alkyl sulfate co-ground mixture. Int J Pharm 2009; 376: 169-75.
56. Moribe K, Pongpeerapat A, Tozuka Y, Yamamoto K. Drug nanoparticle formation from drug/HPMC/SDS ternary ground mixtures. Pharmazie 2006; 61: 97-101.
57. Shudo J, Pongpeerapat A, Wanawongthai C, Moribe K, Yamamoto K. In vivo assessment of oral administration of probucol nanoparticles in rats. Biol Pharm Bull 2008; 31: 321-5.
58. Moribe K, Shibata M, Furuishi T, Higashi K, Tomono K, Yamamoto K. Effect of particle size on skin permeation and retention of piroxicam in aqueous suspension. Chem Pharm Bull 2010; 58: 1096-9.
59. Y. Ikeda, K. Higashi, K. Moribe, K. Yamamoto. Enhanced skin permeation of piroxicam and pranoprofen induced from nanoparticles dispersed in propylene glycol aqueous solution. J Drug Del Sci Tech 2012; 22: 131-7.
60. Fukami T, Ishii T, Io T, et al. Nanoparticle processing in the solid state dramatically increases the cell membrane permeation of a cholesterol-lowering drug, probucol. Mol Pharmaceutics 2009; 6: 1029-35.
61. Io T, Fukami T, Yamamoto K, et al. Homogeneous nanoparticles to enhance the efficiency of a hydrophobic drug, antihyperlipidemic probucol, characterized by solid-state NMR. Mol Pharmaceutics 2010; 7: 299-305.
62. Washington C. Drug release from microdisperse systems: A critical review. Int J Pharm 1990; 58: 1-12.
63. Illum L, Khan MA, Mak E, Davis SS. Evaluation of carrier capacity and release characteristics for poly(butyl-2-cyanoactylate) nanoparticles. Int J Pharm 1986; 30: 17-28.
64. Lamprecht A, Bouligand Y, Benoit JP. New lipid nanocapsules exhibit sustained release properties for amiodarone. J Control Release 2002; 84: 59-68.
65. Shabbits J, Chiu G, Mayer L. Development of an in vitro drug release assay that accurately predicts in vivo drug retention for liposome-based delivery systems. J Control Release 2002; 84: 161-70.
66. Pignatello R, Bucolo C, Ferrara P, Maltese A, Puleo A, Puglisi G. Eudragit RS100® nanosuspensions for the ophthalmic controlled delivery of ibuprofen. Eur J Pharm Sci 2002; 16: 53-61.
67. Pignatello R, Bucolo C, Spedalieri C, Maltese A, Puglisi G. Flurbiprofen-loaded acrylate polymer nanosuspensions for ophthalmic application. Biomaterials 2002; 23: 3247-55.
68. Abdel-Mottaleb MMA, Lamprecht A. Standardized in vitro drug release test for colloidal drug carriers using modified USP dissolution apparatus I. Drug Dev Ind Pharm 2011; 37: 178-84.
69. Xia D, Quan P, Piao H, et al. Preparation of stable nitrendipine nanosuspensions using the precipitation-ultrasonication method for enhancement of dissolution and oral bioavailability. Eur J Pharm Sci 2010; 40: 325-34.
70. Yang W, Johnston KP, Williams III RO. Comparison of bioavailability of amorphous versus crystalline itraconazole nanoparticles via pulmonary administration in rats. Eur J Pharm Biopharm 2010; 75: 33-41.
71. Rogers TL, Gillespie IB, Hitt JE, et al. Development and characterization of a scalable controlled precipitation process to enhance the dissolution of poorly water-soluble drugs. Pharm Res 2004; 21: 2048-57.
72. Crisp MT, Tucker CJ, Rogers TL, Williams RO 3rd, Johnston KP. Turbidimetric measurement and prediction of dissolution rates of poorly soluble drug nanocrystals. J Control Release 2007; 117: 351-9.
73. Alhnan MA, Basit AW. Engineering polymer blend microparticles: an investigation into the influence of polymer blend distribution and interaction. Eur J Pharm Sci 2011; 42(1-2): 30-6.
74. Van Eerdenbrugh B, Alonzo DE, Taylor LS. Influence of particle size on the ultraviolet spectrum of particulate-containing solutions: implications for in-situ concentration monitoring using UV/Vis fiber-optic probes. Pharm Res 2011; 28: 1643-52.
75. Heng D, Cutler DJ, Chan HK, Yun J, Raper JA. What is a suitable dissolution method for drug nanoparticles?. Pharm Res 2008; 25: 1696-701.
76. Jinno J, Kamada N, Miyake M, et al. In vitro-in vivo correlation for wet-milled tablet of poorly water-soluble cilostazol. J Control Release 2008; 25: 29-37.
77. Van Eerdenbrugh B, Vermant J, Martens JA, et al. Solubility increases associated with crystalline drug nanoparticles: Methodologies and significance. Mol Pharm 2010; 7: 1858-70.
78. Ramirez EC, Johnston DB, McAloon AJ, Yee W, Singh V. Engineering process and cost model for a conventional corn wet milling facility. Ind Corp Prod 2008; 27: 91-7.
79. Hennart SLA, van Hee P, Drouet V, Domingues MC, Wildeboer WJ, Meesters GMH. Characterization and modeling of a submicron milling process limited by agglomeration phenomena. Chem Eng Sci 2012; 71: 484-95.
80. Gaisford S, Dennison M, Tawfik M, Jones MD. Following mechanical activation of salbutamol sulphate during ball-milling with isothermal calorimetry. Int J Pharm 2010; 393: 74-8.
81. Saraf S. Process optimization for the production of nanoparticles for drug delivery applications. Expert Opin Drug Deliv 2009; 6: 187-96.
82. Pandya VM, Patel JK, Patel DJ. Formulation and optimization of nanosuspensions for enhancing simvastatin dissolution using central composite design. Dissolut Technol 2011; 18: 40-5.
83. Moribe K, Wanawongthai C, Shudo J, Higashi K, Yamamoto K. Morphology and surface States of colloidal probucol nanoparticles evaluated by atomic force microscopy. Chem Pharm Bull 2008; 56: 878-80.
84. Zhang J, Higashi K, Limwikrant W, Moribe K, Yamamoto K. Molecular-level characterization of probucol nanocrystal in water by in situ solid-state NMR spectroscopy. Int J Pharm 2012; 423: 571-6.