Supercritical fluid technique for particle engineering: Drug delivery applications

Reviews in Chemical Engineering

Volumn 21, Issue 1, 2005, Pages 33-69

  Martin Del Valle, E M ^a   Galan, M A ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ANGIOGENIC FACTOR; BASIC FIBROBLAST GROWTH FACTOR; BETA CYCLODEXTRIN; BURSAL DISEASE VIRUS VACCINE; CAMPOSOMES; CAMPTOTHECIN; CISPLATIN; CLONIDINE; CYCLODEXTRIN; DICHLOROMETHANE; DOXORUBICIN; FLUORESCEIN ISOTHIOCYANATE DEXTRAN; GLYCOLIC ACID; LACTIC ACID; LIPOSOME; MEVINOLIN; NAPROXEN; PEPTIDE; PIROXICAM; POLYGLACTIN; POLYLACTIC ACID; POLYMER; PROTEIN; SALICYLIC ACID; STEROID; STIGMASTEROL; TAXOID; TAXOSOMES; THEOPHYLLINE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VINCRISTINE; VIRUS VACCINE;

SUPERCRITICAL FLUID;

CRYSTALLIZATION; DRUG DELIVERY SYSTEM; DRUG DESIGN; DRUG FORMULATION; DRUG MANUFACTURE; DRUG SOLUBILITY; DRUG STABILITY; DRUG STERILITY; ENGINEERING; HUMAN; NONHUMAN; PARTICLE SIZE; REACTION ANALYSIS; REVIEW; SCALE UP; SUPERCRITICAL FLUID; TECHNIQUE;

EID: 14244262410     PISSN: 01678299     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (82)

1. Kiran, E., Debenedetti, P.G. and Peters C.J. "Supercritical Fluids Fundamentals and Applications" Chapter 7. Kluwer Academic Publishers, 2000.
2. Kompella UB, Koushik K. "Preparation of drug delivery systems using supercritical fluid technology". Crit Rev Therapeut Drug Car Sys. 2001;18(2):173-199.
3. Krukonis VJ. "Supercritical fluid nucleation of difficult to comminute solids". Paper 104f presented at AIChE Meeting in San Francisco, California. Nov 1984.
4. Tom JW, Lim GB, Debendetti PG, Prod'homme RK. "Applications of supercritical fluids in controlled release of drugs". In: Brennecke JF, Kiran E, eds. Supercritical Fluid Engineering Science. ACS Symposium Series 514. Washington (DC): American Chemical Society; 1993; 238.
5. Kim JH, Paxton TE, Tomasko DL. "Microencapsulation of naproxen using rapid expansion of supercritical solutions". Biotechnol Prog. 1996; 12(5):650-661.
6. Bastian, P., Bartkowski, R., Kohler, H. and Kissel, T. "Chemoembolization of experimental liver metastases. Part 1:distribution of biodegradable microspheres of different sizes in an animal model for the locoregional therapy". Eur. J. Pharm. And Biopharm. 1998, 46(3), 243-254 (1998).
7. Benoit, J-P., Fainsanta, N. Venier-Julienne, M-C and Meneibed, P. "Development of microspheres for neurological disordes:from basics to clinical applications". J. Controlled release. 2000, 65(1-2) 285-296.
8. Taguchi, T., Ogawa, N., Bunke, B. and Nilsson, B., "The use of degradable starch microspheres with intra arterial for the treatment of primary and secondary liver tumours-results of phase III clinical trial". Reg. Cancer Treat., 1992, 4, 161-165.
9. Cohen, S. and Bernstein, H. (eds.), "Microparticulate systems for the delivery of proteins and vaccines" (Knutson et al. Chapter), Marcel Dekker, New York, 1996.
10. Jallil, R. and Nixon, J.R., "Microencapsulation using poly(L-lactic acid).III. Effect of polymer weight on the microcapsule properties". J. Microencapsulation, 1990, 7(1), 41-52.
11. Langer, R. and Folkman, J., "Polymer for the sustained released of proteins and other macromolecules", Nature, 1976, 263: 797-800.
12. Debenedetti PG, Lim GB, Prud'Homme RK." Preparation of protein microparticles by precipitation". United States Patent No. 6,063,910, 2000.
13. Kamihara H, Asai T, Yamagata M, Taniguchi M, Kobayashi T. "Formation of inclusion complexes between cyclodextrins and aromatic compounds under pressurized carbon dioxide". J Ferment Bioeng. 1990; 69:350-353.
14. Benoit JP, Rolland H, Thies C, Vande VV. "Method of coating particles and coated spherical particles". United States Patent No. 6,087,003, 2000.
15. J.F. Brennecke and C.A. Eckert. "Phase equilibria for supercritical fluid process design", Am. Inst. Chem. Eng. J. 35, 1989, pp. 1409-1427.
16. Mueller BW, Fisher W. "Manufacture of sterile sustained release drug formulations using liqufied gases". W. Germany Patent No. 3,744,329., 1989.
17. Pace GW, Vachon MG, Mishra AK, Henrikson IB, Krukoniz V. "Processes to generate submicron particles of water-insoluble compounds". United States Patent No. 6,177,103., 2001.
18. M. McHugh and V. Krukonis, "Supercritical Fluid Extraction Principles and Practice". (2nd ed.), Butterworth-Heinemann, 1994.
19. P. York et al., In: Proc. Resp. Drug Delivery VI, Hilton Head, USA ,1998, pp. 169-175.
20. Jung, J. and Perrut, M. "Particle design using supercritical fluids: Literature and patent survey", Journal of Supercritical Fluids, (2001), (20), 179-219.
21. K.A. Larson and M.L. King. "Evaluation of supercritical fluid extraction in the pharmaceutical industry" Biotechnol. Prog. 2, 1986, pp. 73-82
22. B.Yu. Shekunov et al., "Crystallization process in turbulent supercritical flows" J. Cryst Growth 198/199, 1999, pp. 1345-1351
23. B.Yu Shekunov et al., Pharm. Res. 15, 1998, p. S162.
24. F. Ruchatz et al. "Residual solvents in biodegradable microparticles. Influence of process parameters on the residual solvent in microparticles produced by the aerosol solvent extraction system (ASES) process." J. Pharm. Sci. 86,1997, pp. 101-105.
25. E.M. Phillips and V.J. Stella. "Rapid expansion from supercritical solutions: application to pharmaceutical processes", Int. J. Pharm. 94 ,1993, pp. 1-10.
26. Ventosa, N., Sala, S. Veciana, J. "DELOS process: a crystallization technique using compressed fluids, 1. Comparison to the GAS crystallization method" Journal of Supercritical fluids, 2003, (26), 33-45
27. Reverchon, E. and Della Porta, G. "Micronization of antibiotics by supercritical assisted atomization" Journal of Supercritical Fluids, 2003, (26), 243-252
28. Sievers, R.E., Huang, E.T.C., Villa, J.A., Engling, G., Brauer, P.R., "Micronization of water-soluble pharmaceuticals and model compounds with a low-temperature Bubble Dryer" Journal of Supercritical Fluids, 2003, (26), 9-16.
29. Debendetti, P.G. in Supercritical Fluids: Fundamentals for Application, (Vol. 273), NATO ASI Series E. 1994.
30. 3". Ind. Eng. Chem. Res., 34, 1995, 4087-4091.
31. McHugh, M. Krukonis, V.J. "Special Applications in Supercritical Fluid Extraction: Principles and Practice", 2nd Edition. Butterworths-Heinemann, Boston, 1994.
32. Weidner, E. et al. in High Pressure Chemical Engineering, Process Technol. Proceedings, 12, Elsevier. 1996.
33. Jung, J. and Perrut, M. "Particle design using supercritical fluids: Literature and patent survey". J. of Supercritical Fluids., 2001, 20 179-219.
34. Palakodaty, S. and York, P., "Phase behavioral effects on particle formation processes using supercritical fluids" Pharm. Res. 16, 1999, pp. 976-985.
35. R.D. Smith, R. Wash, US Patent 4,582,731, April 15, 1986 (Priority 01/09/1983).
36. Matson, D.W., Fulton, J.L., Petersen, R.C., Smith, R.D., "Rapid Expansion of Supercritical Fluid Solutions: Solute Formation of Powders, Thin Films, and Fibers". Ind. Eng. Chem. Res., 26, 1987, 2298-2306.
37. Matson, D.W., Petersen, R.C., Smith, R.D., "Production of Powders and Films from Supercritical Solutions". Journal of Material Science, 22, 1987, 1919-1928.
38. Petersen, R.C., Matson, D.W., Smith, R.D., "The Formation of Polymer Fibers from the Rapid Expansion of Supercritical Fluid Solutions". Polymer Engineering Science, 27, 1987, 1693-1697.
39. R.D. Smith, US Patent 4 734 451, 1988.
40. Lele, A.K., Shine, A.D., "Morphology of Polymers Precipitated from a Supercritical Solvent". AIChE Journal, 38, 5, 1992, 742-752.
41. E.M. Phillips, Stella, V.J. "Rapid Expansion from Supercritical Solutions: Application to Pharmaceutical Processes". International Journal of Pharmaceutics, 1993, 94, 1-10.
42. Reverchon, E., Taddeo, R., "Morphology of Salicylic Acid Crystals Precipitated by Rapid Expansion of a Supercritical Solution". I Fluidi Supercritici e Le Loro Applicazioni. E. Reverchon, A. Schiraldi (Eds.), 20-22 June, Ravello (Italy), 1993, 189-198.
43. E.M. Berends, E.M., Bruinsma, O.S.L., van Rosmalen, G.M., "Supercritical Crystallization with the RESS Process: Experimental and Theoretical Results". Proceedings of the 3rd International Symposium on Supercritical Fluids, Tome 3; G. Brunner, M. Perrut (Eds.), ISBN 2-905-267-23-8, 17 19 October, Strasbourg (France), 1994, 337-342. 4087-4091.
44. Reverchon, E., Pallado, P. "Hydrodynamic Modelling of the RESS Process". Journal of Supercritical Fluids, 1996, (9), 216-221.
45. 2." The 4th International Symposium on Supercritical Fluids, 11-14 May, Sendai (Japan), 1997, 59-62.
46. Mishima, K., Matsuyama, K., Uchiyama, H., Ide, M., "Microcoating of Flavone and 3-Hydroxyflavone with Polymer Using Supercritical Carbon Dioxide". The 4th International Symposium on Supercritical Fluids, 11-14 May, Sendai (Japan), 1997, 267-270.
47. Nagahama, K., Liu, G.T., "Supercritical Fluid Crystallization of Solid Solution". The 4th International Symposium on Supercritical Fluids, 11-14 May, Sendai (Japan), 1997, 43-46.
48. Robertson, J. King, M.B., Seville, J.P.K., Merrifield, D.R., Buxton, P.C., Recrystallisa-tion of Organic Compounds using Near Critical Carbon Dioxide. The 4th International Symposium on Supercritical Fluids, 11-14 May, Sendai (Japan), 1997, 47-50.
49. Godinas, A., Henriksen, B., Krukonis, V., Mishra, K.A., Pace, G.W., Vachon, G.M., Patent US,0089852., 1998
50. Kim J.H., et al. "Microencapsulation of naproxen using rapid expansion of supercritical solutions", Biotechnol. Prog, 1996, 12, pp. 650-661
51. F.E. Wubbolts et al., In: Proc. 5th Int. Symp. Supercrit. Fluids, Soc. Adv. Sup. Fluids, Nice France, 1998.
52. McHugh, M.A., Guckes, T.L., "Separating polymer solutions with supercritical fluids". Macromolecules, 1985, 18, 674-681.
53. Seckner, A.J., McClellan, A.K., McHugh, M.A., "High pressure solution behavior of the polymer-toluene-ethane system". AIChE Journal, 1988, 34, 9-16.
54. Hanna, M., York, P., Patent WO 95/01221, 1994.
55. Liau, I.S., Mc Hugh, M.A. "Supercritical Fluid Technology", Elsevier Science Publishers, Amsterdam, 1985.
56. Tom, J.E. et al. "Supercritical Fluid Engineering Science: Fundamentals and applications" ACS Symp. Series 514, 1993, pp. 238-257.
57. Yeo, S.D., et al. "Formation of microparticulate protein powders using a supercritical fluid antisolvent", Biotechnol. Bioeng., 1993, 45, pp. 341-346 57.
58. Bleich, J. et al. "Aerosol solvent extraction system - a new microparticle production technique" Int. J. Pharm, 1993, 97 pp. 111-117.
59. Dixon, D.J. et al. "Polymeric materials formed by precipitation with a compressed fluid antisolvent" AIChE J., 1993, 39, pp. 127-139.
60. Kiran, E., and Zhuang, W., "Supercritical Fluids: Extraction and pollution prevention" ACS Symp. Ser. 670, 1997, pp. 2-36.
61. Liau, I.S., M.A. Mc Hugh, M.A., Supercritical Fluid Technology" Elsevier Science Publishers, Amsterdam, 1985, 415.
62. Weidner, E., R. Steiner, R., Z. Knez, Z., "Powder Generation from Polyethyleneglycols with Compressible Fluids. High Pressure Chemical Engineering" P. Rudolf von Rohr, and C. Trepp (Eds.), Elsevier Science, 1996.
63. 2-assisted Nebulization of Aqueous Solutions". Proceedings from Respiratory Drug Delivery IV Conference, Hilton Head, South Carolina, 3-8 May, 1998, 417-419. Supercritical Fluids, Chemistry and Materials; M. Poliakoff, M.W. George, S.M. Howdle (Eds.), ISBN 2-905-267-30-5, 10-13 April, Nottingham, 1999.
64. Sievers, R.E., Karst, U., European Patent 0 677 332, 1995. US Patent 5,639,441, 1997.
65. E. Weidner, Z. Knez, Z. Novak, European Patent EP 0 744 992, February 1995 Patent WO 95/21688, July 1995.
66. Steckel H, Thies J, Muller BW. "Micronizing of steroids for pulmonary delivery by supercritical carbon dioxide", Int J Pharm. 1997;152(1):99-110.
67. 2." J Controlled Rel." 2000; 66(2-3): 177-185.
68. Frederiksen L, Anton K, Hoogevest PV, Keller HR, Leuenberger H. "Preparation of liposomes encapsulating water-soluble compounds using supercritical carbon dioxide". J Pharm Sci. 1997; 86(8):921-928.
69. Castor TP, Chu L. "Methods and apparatus for making liposomes containing hydrophobic drugs". United States Patent No. 5,776,486., 1998.
70. Lin SY, Kao YH. "Solid particulates of drug-b-cyclodextrin inclusion complexes directly prepared by a spray-drying technique". Int J Pharm. 1989;56:249-259.
71. Kamihara H, Asai T, Yamagata M, Taniguchi M, Kobayashi T. "Formation of inclusion complexes between cyclodextrins and aromatic compounds under pressurized carbon dioxide". J Ferment Bioeng. 1990;69:350-353.
72. Van Hees T, Piel G, Evrard B, Otte X, Thunus T, Delattre L. "Application of supercritical carbon dioxide for the preparation of a piroxicam-beta-cyclodextrin inclusion compound". Pharm Res. 1999;16(12):1864-1870.
73. Castor TP, Hong GT. Methods for the size reduction of proteins. United States Patent No. 6,051,694., 2000.
74. Tservistas M, Levy MS, Lo-Yim MYA, O'Kennedy RD, York P, Humphery GO, Hoare M. "The formation of plasmid DNA loaded pharmaceutical powders using supercritical fluid technology". Biotech Bioeng. 2000;72(1):12-18.
75. Kumagai H, Hata C, Nakamura K. "CO2 sorption by microbial cells and sterilization by high-pressure CO2". Biosci Biotech Biochem. 1997;61(6):931-935.
76. Thies J, Muller BW. "Size controlled production of biodegradable microparticles with supercritical gases". Eur J Pharm Biopharm. 1998;45(1):67-74.
77. Dillow AK, Langer RS, Foster N, Hrkach JS. Supercritical sterilization method. United States Patent No. 6,149,864., 2000.
78. Winters, M.A., et al., "Precipitation of proteins in supercritical carbon" J. Pharm. Sci. 85, 1996, pp. 586-594.
79. W.J. Schmitt, W.J., "Finely-divided powders by carrier solution injection into a near or supercritical fluid" AIChE J. 1995, 41, pp. 2476-2486.
80. Forbes, R.T. et al. "Supercritical fluid processing of proteins1: Lysozyme precipitation from organic solutions" Proc. IChE World Congress on Particle Technology 3, 1998, Brighton, UK, pp. 180-184.
81. Steckel, H., and Müller. B.W., "Metered-dose inhaler formulation of fluticasone-17-propionate micronized with supercritical carbon dioxide using the alternative propellant HFA-227", Int. J. Pharm, 1998, 173 pp. 25-33.
82. Thies, J. and Müller, B.W., "Size controlled production of biodegradable microparticles with supercritical gases" Eur. J. Pharm. Biopharm., 1998, 45, pp. 67-74.