Supercritical fluid technologies: An innovative approach for manipulating the solid-state of pharmaceuticals

Advanced Drug Delivery Reviews

Volumn 60, Issue 3, 2008, Pages 399-410

  Pasquali, Irene ^a   Bettini, Ruggero ^a   Giordano, Ferdinando ^a  

^a UNIVERSITY OF PARMA   (Italy)

Author keywords

Crystal purity; Polymorphism; Pseudopolymorphism; Solid state chemistry; Supercritical fluids

Indexed keywords

CRYSTAL PURITY; PSEUDOPOLYMORPHISM; SOLID STATE CHEMISTRY;

CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; DRUG DELIVERY; POLYMORPHISM; SUPERCRITICAL FLUIDS;

DRUG PRODUCTS;

4 ACETOXYACETANILIDE; ACETONE; ANTINEOPLASTIC AGENT; CARBAMAZEPINE; CARBON DIOXIDE; CARBOXYMETHYLCELLULOSE; CHLORPROPAMIDE; DEOXYCHOLIC ACID; DICHLOROMETHANE; DICLOFENAC; FLUNISOLIDE; GELUCIRE; IBUPROFEN; MACROGOL 8000; METHANOL; NIFEDIPINE; NITROFURANTOIN; PARACETAMOL; PNU 159548; POVIDONE; SOLID LIPID NANOPARTICLE; SOLVENT; SULFATHIAZOLE; TERBUTALINE SULFATE; THEOPHYLLINE; TOCOFERSOLAN; UNCLASSIFIED DRUG;

CONTROLLED DRUG RELEASE; CRYSTALLIZATION; DRUG DELIVERY SYSTEM; DRUG DESIGN; DRUG PURIFICATION; DRUG SOLUBILITY; DRUG STABILITY; DRUG SYNTHESIS; FREEZE DRYING; GAS; HYDRATION; LIQUID; NEBULIZATION; PHYSICAL CHEMISTRY; PRECIPITATION; PRIORITY JOURNAL; REVIEW; SOLID STATE; SOLUBILIZATION; SPRAY DRYING; SUPERCRITICAL FLUID; THERMOSTABILITY; X RAY POWDER DIFFRACTION;

CARBON DIOXIDE; CHEMISTRY, PHARMACEUTICAL; CHROMATOGRAPHY, SUPERCRITICAL FLUID; CRYSTALLIZATION; DRUG DELIVERY SYSTEMS; PHARMACEUTICAL PREPARATIONS; TECHNOLOGY, PHARMACEUTICAL;

EID: 38949207528     PISSN: 0169409X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.addr.2007.08.030     Document Type: Review

References (79)

1. Food and Drug Administration, Center for Drug Evaluation and Research, Office of Pharmaceutical Science, Rockville, Maryland 20857, 2000.
2. York P. Particle design: a 'Supercritical' issue for the pharma industry. Pharm.Visions (2000) 28-30
3. Morissette S.L., Soukasene S., Levinson D., Cima M.J., and Almarsson Ö. Elucidation of crystal form diversity of the HIV protease inhibitor ritonavir by high-throughput crystallization. Proc. Natl. Acad. Sci. 100 (2003) 2180-2184
4. Chow A.H.L., Tong H.H.Y., and Shekunov B.Y. Control of physical forms of pharmaceutical substances. In: York P., Kompella U.B., and Shekunov B.Y. (Eds). Supercritical fluid technology for drug product development (2004), Marcel Dekker, Inc., New York, USA
5. Grant D.J.W. Theory and origin of polymorphism. In: Brittain H.G. (Ed). Polymorphism in pharmaceutical solids (1999), Marcel Dekker, New York, USA
6. Giron D. Thermal analysis, microcalorimetry and combined techniques for the study of pharmaceuticals. J. Therm. Anal. Calorim. 56 (1999) 1285-1304
7. Carstensen J.T. Amorphates. In: Carstensen J.T. (Ed). Advanced Pharmaceutical Solids (2001), Marcel Dekker, Inc., New York, USA
8. Byrn S.R., Pfeiffer R.R., Stephenson G., Grant D.J.W., and Gleason W.B. Solid-state pharmaceutical chemistry. Chem. Mater. 6 (1994) 1148-1158
9. Vippagunta S.R., Brittain H.G., and Grant D.J.W. Crystalline solids. Adv. Drug Delivery Rev. 48 (2001) 3-26
10. Zhang G.G.Z., Law D., Schmitt E.A., and Qiu Y. Phase transformation considerations during process development and manufacture of solid oral dosage forms. Adv. Drug Delivery Rev. 56 (2004) 371-390
11. Mullins J.D., and Macek T.J. Some pharmaceutical properties of novobiocin. J. Am. Pharm. Ass. 49 (1960) 245-248
12. Elamin A.A., Ahlneck C., Alderbon G., and Nystrom C. Increased metastable solubility of milled griseoufulvin, depending on the formation of a disordered surface-structure. Int. J. Pharm. 11 (1994) 159
13. Vishweshwar P., McMahon J.A., Bis J.A., and Zaworotko M.J. Pharmaceutical co-crystal. J Pharm. Sci. 95 (2006) 499-516
14. Pasquali I., Bettini R., and Giordano F. Solid-state and particle engineering with supercritical fluids in pharmaceutics. Eur. J. Pharm. Sci. 27 (2006) 299-310
15. Murphy D., Rodríguez-Cintrón F., Langevin B., Kelly R.C., and Rodríguez-Hornedo N. Solution-mediated phase transformation of anhydrous to dehydrate carbamazepine and the effect of lattice disorder. Int. J. Pharm. 246 (2002) 121-134
16. Brunner G. Properties of supercritical and near-critical gases and mixtures with sub- and supercritical components. In: Brunner G. (Ed). Gas Extraction. Steinkopff Darmstadt (1994), Springer, New York, USA
17. Chow A.H.L., Tong H.H.Y., and Shekunov B.Y. Preface. In: York P., Kompella U.B., and Shekunov B.Y. (Eds). Supercritical fluid technology for drug product development (2004), Marcel Dekker, Inc, New York, USA
18. Vasukumar K., and Bansal K.A. Supercritical fluid technology in pharmaceutical research. CRIPS 4 (2003) 8-12
19. Sako S., Shibata K., Ohgaki K., and Katayama T. Solubilities of indole, skatole, and 5-methoxyindole in supercritical fluids. J. Supercrit. Fluids 2 (1989) 3-8
20. Nakatani T., Ohgaki K., and Katayama T. Solubilities of indole derivatives in supercritical fluids. J. Supercrit. Fluids 2 (1989) 9-14
21. Hillmann R., and Bächmann K. Extraction of pesticides using supercritical trifluoromethane and carbon dioxide. Short Communication J. Chrom. A 695 (1995) 149-154
22. Carstensen J.T. Crystallization. In: Carstensen J.T. (Ed). Advanced pharmaceutical solids (2001), Marcel Dekker, Inc, New York, USA
23. Hannay J.B., and Hogarth J. Proc. R. Soc. Lond. A 29 (1879) 324-326
24. Krukonis V. Supercritical fluid nucleation of difficult-to-comminute solids. Proc. Annual Meeting AIChE, paper 140 f, T-214 (1984)
25. Phillips E.M., and Stella V.J. Rapid expansion from supercritical solutions: application to pharmaceutical processes. Int. J. Pharm. 94 (1993) 1-10
26. Kayrak D., Akman U., and Hortaçsu Ö. Micronisation of ibuprofen by RESS. J. Supercrit. Fluids 26 (2003) 17-31
27. Kompella U.B., and Koushik K. Preparation of drug delivery systems using supercritical fluid technology. Crit. Rev. Therap. Drug Carrier Systems 18 (2001) 173-199
28. York P. Strategies for particle design using supercritical fluid technologies. PSTT 2 (1999) 430-440
29. Meziani M.J., Pathak P., Beacham F., Allard L.F., and Sun Y.-P. Nanoparticle formation in rapid expansion of water-in-supercritical carbon dioxide microemulsion into liquid solution. J. Supercrit. Fluids 34 (2005) 91-97
30. Gallagher P.M., Coffey M.P., Krukonis V.J., and Klasutis N. Gas antisolvent recrystallization: new process to recrystallize compounds insoluble in supercritical fluids. In: Penniger J.M.L. (Ed). Supercritical fluid science and technology, ACS Symposium Series 406 (1989), American chemical society, Washington, DC 334-354
31. 2. J. Supercrit. Fluids 21 (2001) 257-271
32. Noyes A.A., and Whitney W.R. The rate of solution of solid substances in their own solutions. J. Am. Chem. Soc. 19 (1897) 930-934
33. Nernst W. Theory of reaction velocity in heterogeneous systems. Z. Phys. Chem. 47 (1904) 52-55
34. Brunner E. Reaction velocity in heterogeneous systems. Z. Phys. Chem. 47 (1904) 56-102
35. Eggers R., and Jaeger P. Interfacial phenomena in countercurrent and spray processing using supercritical fluids. In: Brunner G. (Ed). Supercritical fluids as solvents and reaction media (2004) 363-377
36. Shekunov B.Y., Hanna M., and York P. Crystallization process in turbulent supercritical flows. J. Cryst. Growth 198/199 (1999) 1345-1351
37. Werling J.O., and Debenedetti P.G. Numerical modelling of mass transfer in the supercritical antisolvent process. J. Supercrit. Fluids 16 (1999) 167-181
38. USP 28. <467> Organic volatile impurities (2005), The United States Pharmacopoeial Convention, Inc., Rockville 2322-2332
39. Hanna M., and York P. WO 95/01221 (1995)
40. Palakodaty S., and York P. Phase behavioral effects on particle formation processes using supercritical fluids. Pharm. Res. 16 (1999) 976-985
41. Moshashaee S., Bisrat M., Forbes R.T., Nyqvist H., and York P. Supercritical fluid processing of proteins. I. Lysozime precipitation from organic solution. Eur. J. Pharm. Sci. 11 (2000) 29-41
42. York P., Hanna M., Shekunov B.Y., and Humphreys G.O. Microfine particle formation by SEDS (Solution Enhanced Dispersion by Supercritical Fluids): scale up by design. Proc. Resp. Drug Delivery VI (1998) 169-175
43. Charbit G., Badens E., and Boutin O. Methods of particle production. In: York P., Kompella U.B., and Shekunov B.Y. (Eds). Supercritical fluid technology for drug product development (2004), Marcel Dekker Inc., New York, USA
44. Sievers R.E., Karst U., Milewski P.D., Sellers S.P., Miles B.A., Schaefer J.D., Stoldt C.R., and Xu C.Y. Formation of aqueous small droplet aerosol assisted by supercritical carbon dioxide. Aerosol Sci. Technol. 30 (1999) 3-15
45. Reverchôn E. Supercritical-assisted atomization to produce micro- and/or nanoparticles of controlled size and distribution. Ind. Eng. Chem. Res. 41 (2002) 2405-2411
46. Gu C.-H., Young Jr. V., and Grant D.J.W. Polymorph screening: influence of solvents on the solvent-mediated polymorphic transformation. J. Pharm. Sci. 90 (2001) 1878-1890
47. Bettini R., Bonassi L., Castoro V., Rossi A., Zema L., Gazzaniga A., and Giordano F. Solubility and conversion of carbamazepine polymorphs in supercritical carbone dioxide. Eur. J. Pharm. Sci. 13 (2001) 281-286
48. Rustichelli C., Gamberini G., Ferioli V., Gamberini MC., Ficarra R., and Tommasini S. Solid-state study of polymorphic drugs:carmazepine. J. Pharm. Biomed. Anal. 23 (2000) 41-54
49. Bettini R., Zampieri M., Martini A., Fumagalli P., Rossi A., and Giordano F. Treatment of an anticancer drug with supercritical carbon dioxide: residual solvent removal and formation of a new crystal phase. Proc. AAPS annual meeting paper (2002). http://www.aapspharmaceutica.com/search/abstract_view.asp?id=3878&ct=02A bstracts no T2328 http://www.aapspharmaceutica.com/search/abstract_view.asp?id=3878&ct =02Abstracts.
50. Tozuka Y., Kawada D., Oguchi T., and Yamamoto K. Supercritical carbon dioxide treatment as a method for polymorph preparation of deoxycholic acid. Int. J. Pharm. 263 (2003) 45-50
51. Gosselin P.M., Thibert R., Preda M., and McMulen J.N. Polymorphic properties of micronized carbamazepine produced by RESS. Int. J. Pharm. 252 (2003) 225-233
52. Charoenchaitrakool M., Dehghani F., and Foster N.R. Micronization by rapid expansion solution to enhance the dissolution rates of poorly water-soluble pharmaceuticals. Ind. Eng. Chem. Res. 39 (2000) 4794-4802
53. Spilimbergo S., Luca G., Elvassore N., and Bertucco A. Effect of high pressure gases on phase behavior of solid lipids. J. Supercrit. Fluids 38 (2006) 289-294
54. Gilbert D.J., Palakodaty S., York P., Schultz T.W., and Shah D. Isolation of three polymorphic forms of RWJ-337813 using the solution enhanced dispersion by the supercritical fluids (SEDS™) technique. AAPS Pharm. Sci. 3 (2001)
55. 2. Pharm. Res. 18 (2001) 682-688
56. Blagden N., Davey R.J., Lieberman H.F., Williams L., Payne R., Robert R., Rowe R., and Docherty R. Crystal chemistry and solvent effects in polymorphic systems-sulfathiazole. J. Chem. Soc. Farad. Trans. 94 (1998) 1035-1045
57. Edwards A.D., Shekunov B.Y., Kordikowski A., Forbes R.T., and York P. Crystallization of pure anhydrous polymorphs of carbamazepine by Solution Enhanced Dispersion with Supercritical Fluids (SEDS). J. Pharm. Sci. 90 (2001) 1115-1124
58. Moneghini M., Kikic I., Voinovich D., Perissuti B., Alessi P., Cortesi A., Princivalle F., and Solinas D. Study of the solid state of carbamazepine after processing with gas anti-solvent technique. Eur. J. Pharm. Sci. 56 (2003) 281-289
59. Bartolomei M. Solid-state studies on the hemihydrate and the anhydrous forms of flunisolide. J. Pharm. Biomed. Anal. 24 (2000) 81-93
60. Velaga S.P., Berger R., and Carlfors J. Supercritical fluids crystallization of budesonide and flunisolide. Pharm. Res. 19 (2002) 1564-1571
61. Tong H.H.Y., Shekunov B.Y., York P., and Chow A.H.L. Characterization of two polymorphs of salmeterol xinafoate crystallized from supercritical fluids. Pharm. Res. 18 (2001) 852-858
62. Tong H.H.Y., Shekunov B.Y., York P., and Chow A.H.L. Thermal analysis of trace levels of polymorphic impurity in salmeterol xinafoate samples. Pharm. Res. 20 (2003) 1423-1429
63. Tong H.H.Y., Shekunov B.Y., Chow A.H.L., and York P. Influence of polymorphism on the surface energetics of salmeterol xinafoate crystallized from supercritical fluids. Pharm. Res. 19 (2002) 640-648
64. Rehman M., Shekunov B.Y., York P., Lechuga-Ballesteros D., Miller D.P., Tan T., and Colthorpe P. Optimisation of powders for pulmonary delivery using supercritical fluid technology. Eur. J. Pharm. Sci. 22 (2004) 1-17
65. Lee P.I., and Kim C. Probing the mechanisms of drug release from hydrogels. J. Control. Rel. 16 (1991) 229-236
66. Rajabi-Siaboomi A.R., Davies M.C., and Melia C.D. Identification of active molecular structures in thermally dependent release behavior of diclofenac sodium from HMPC matrices. Proc. Int. Symp. Control. Rel. Biact. Mater, 21 (1994) 25
67. Sujja-Areevath J., Munday D.L., Cox P.J., and Khan K.A. Relationship between swelling, erosion and drug release in hydrophilic natural gum mini-matrix formulations. Eur. J. Pharm. Sci. 6 (1998) 207-217
68. Bettini R., Giordano F., Donini C., Massimo G., Catellani P.L., and Colombo P. Swelling force as a result of hydrate formation in diclofenac sodium or nitrofurantoin tablets. S.T.P. Pharm. Sci. 10 (2000) 335-339
69. Marzo A., and Reiner V. Open questions on bioequivalence: the case of multiple peak phenomenon. J. Pharm. Pharmacol. 56 (2003) 281-282
70. 2. J. Therm. Anal. Cal. 77 (2004) 625-638
71. 2 fluid extraction of crystal water from trehalose dihydrate. Efficient production of form II (Tα) phase. Carbohydr. Res. 337 (2002) 1729-1735
72. Weissbuch I., Leiserowitz L., and Lahav M. "Tailor-Made" additives and impurities. In: Mersann A. (Ed). Crystallization Technology Handbook (2001), Marcel Dekker, New York 401-457
73. Vemavarapu C., Mollan M.J., and Needham T.E. Crystal doping aided by rapid expansion of supercritical solutions. AAPS Pharm. Sci. Tech. 3 (2002) 1-15
74. 2. Cryst. Growth Des. 3 (2003) 603-610
75. Sethia S., and Squillante E. Physicochemical characterization of solid dispersions of carbamazepine formulated by supercritical carbon dioxide and conventional solvent evaporation method. J. Pharm. Sci. 91 (2002) 1948-1957
76. Hancock B.C., and Zografi G. Characteristics and significance of the amorphous state in pharmaceutical systems. J. Pharm Sci. 86 (1997) 1
77. Sethia S., and Squillante E. Solid dispersion of carbamazepine in PVP K30 by conventional solvent evaporation and supercritical methods. Int. J. Pharm. 272 (2004) 1-10
78. Thumsi S.G., Nunes A.C., Needham T., and Zia H. The X-ray diffraction analysis and characterization of nifedipine treated with a supercritical solvent. AAPS J. 6 (2004)
79. Pathak P., Meziani M.J., Desai T.D., and Sun Y.-P. Formation and stabilization of ibuprofen nanoparticles in supercritical fluid processing. J. Supercrit. Fluids 37 (2006) 279-286