Instant solubilization of poorly water-soluble drugs by in-situ loading of aqueous phospholipid dispersions suitable for parenteral administration

PDA Journal of Pharmaceutical Science and Technology

Volumn 60, Issue 6, 2006, Pages 366-377

  Van Hoogevest, Peter ^a,b   Rogue, Vincent ^a   Brumec, Marko ^a   Schwebel, Hervé ^a   Grunkemeyer, Jeffry L ^a   Leigh, Mathew L S ^a  

^a Phares Drug Delivery AG   (Switzerland)

^b UNIVERSITY OF BASEL   (Switzerland)

Author keywords

Cyclosporine A; Diazepam; In situ solubilization; Liposomes; Parenteral; Phospholipids; Poorly water soluble drugs

Indexed keywords

CYCLOSPORIN; DIAZEPAM; DRUG; PHOSPHOLIPID;

ARTICLE; CHEMISTRY; INFUSION; PARTICLE SIZE; SOLUBILITY;

CYCLOSPORINE; DIAZEPAM; INFUSIONS, PARENTERAL; PARTICLE SIZE; PHARMACEUTICAL PREPARATIONS; PHOSPHOLIPIDS; SOLUBILITY;

EID: 33847251189     PISSN: 10797440     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (40)

1. Strickley, R. G. Solubilizing excipients in oral and injectable formulations. Pharm. Res. 2004, 21, 201-230.
2. Eckart, J. Fett in der parenteralen Ernährung 4; Experimentelle und klinische Aspekte MCThaltige Fett Emulsionen. W. Zuckschwerdt Verlag: München, Bern, Wien, New York; 1993.
3. Teelmann, K.; Schläppi, B.; Schüpbach, M.; Kistler, A. Preclinical safety evaluation of intravenously administered mixed micelles. Arzneim.-Forsch/Drug Res. 1984, 34 (II), 1517-1523.
4. Barenholz, Y.; Yechiel, E. Method for Reversing Age-related Changes in Heart Muscle Cells. U.S. Patent 6,348,213, February 19, 2002.
5. Forrest, P.; Galletly; D. C. A double-blind comparative study of three formulations of diazepam in volunteers. Anaesth. Intensive Care 1988, 16 (2), 158-163.
6. Guentert, T. W.; Oie, S.; Paalzow, L.; Frey, B. M.; Brandt, R.; Aarons,L. J.; Rowland, M. Interaction of mixed micelles formed from glycocholic acid and lecithin with the protein binding of various drugs. Br. J. Clin. Pharmacol. 1987, 23 (5), 569-577.
7. Galletly, D. C.; Wilson, L. F.; Treuren, B. C.; Boon; B. P. Diazepam mixed micelle - comparison with diazepam in propylene glycol and midazolam. Anaesth. Intensive Care 1985, 13 (4), 352-354.
8. Veerareddy, P. R; Vobalaboina V. Lipid-based formulations of amphotericin B. Drugs Today (Barc). 2004, 40 (2), 33-45.
9. Chowdary, R. K.; Shariff, I.; Dolphin, D. Drug release characteristics of lipid based benzoporphyrin derivative. J. Pharm. Pharmaceut. Sci. 2003, 6 (1), 13-19.
10. Chowdhary, R. K.; Sharif, I.; Chansarkar, N.; Dolphin, D.; Ratkay, L.; Delaney, S.; Meadows, H. Correlation of photosensitizer delivery to lipoproteins and efficacy in tumor and arthritis mouse models; comparison of lipid-based and Pluronic® P123 formulations. J. Pharm. Pharmaceut. Sci. 2003, 6 (2), 198-204.
11. Zuidam, N. J.; Gouw, H. K.; Barenholz, Y.; Crommelin, D. J. Physical (in) stability of liposomes upon chemical hydrolysis: the role of lysophospholipids and fatty acids. Biochim. Biophys. Acta 1995, 1240 (1), 101-110.
12. Zuidam, N. J.; Lee, S. S.; Crommelin, D. J. Sterilization of liposomes by heat treatment. Pharm. Res. 1993, 10 (11), 1591-1596.
13. Grit, M.; Crommelin; D. J. Chemical stability of liposomes: implications for their physical stability. Chem. Phys. Lipids 1993, 64 (1-3), 3-18.
14. Grit, M.; Zuidam, N. J.; Underberg, W. J.; Crommelin, D. J. Hydrolysis of partially saturated egg phosphatidylcholine in aqueous liposome dispersions and the effect of cholesterol incorporation on hydrolysis kinetics. J. Pharm. Pharmacol. 1993, 45 (6), 490-495.
15. Grit, M.; Crommelin, D. J. The effect of aging on the physical stability of liposome dispersions. Chem. Phys. Lipids 1992, 62 (2), 113-122.
16. Crommelin; D.J.. Influence of lipid composition and ionic strength on the physical stability of liposomes. J. Pharm. Sci. 1984, 73 (11), 1559-1563.
17. Wolkers, W. F.; Oldenhof, H.; Tablin; F.; Crowe; J. H. Preservation of dried liposomes in the presence of sugar and phosphate. Biochim. Biophys. Acta 2004, 1661 (2), 125-134.
18. Sun, W. Q.; Leopold, A. C.; Crowe, L. M.; Crowe; J. H. Stability of dry liposomes in sugar glasses. Biophys. J. 1996, 70 (4), 1769-1776.
19. Prankerd, J.; Stella, V. J. The use of oil-in-water emulsions as a vehicle for parenteral drug administration. J. Parenter. Sci. Technol. 1990, 44 (3), 139-149.
20. Bartsch, W.; Sponer, G.; Dietmann, K.; Fuchs, G. Acute toxicity of various solvents in the mouse and rat. Arzneim.-Forsch. 1976, 26 (8), 1581-1583.
21. Royals, M. A.; Fujita, S. M.; Yewey, G. L.; Rodriguez, J.; Schultheiss, P. C.; Dunn, R. L. Biocompatibility of biodegradable in-situ forming implant system in rhesus monkeys. J. Biomed. Mater. Res. 1999, 45, 231-239.
22. Stewart, J. A.; Low, J. B.; Roberts, J. D.; Blow, A. A phase I clinical trial of didemnin B. Cancer 1991, 68 (12), 2550-2554.
23. Volcheck, G. W.; Van Dellen, R. G. Anaphylaxis to intravenous Cyclosporin and tolerance to oral Cyclosporin: case report and review. Ann. Allergy Asthma Immunol. 1998, 80 (2), 159-163.
24. Scherphof, G.; Roerdink, F.; Waite, M.; Parks, J. Disintegration of phosphatidylcholine liposomes in plasma as a result of interaction with high-density lipoproteins. Biochim. Biophys. Acta 1978, 542, 296-307.
25. Guo, L. S.; Hamilton, R. L.; Goerke, J.; Weinstein, J. N.; Havel, R. J. Interaction of unilamellar liposomes with serum lipoproteins and apolipoproteins. J. Lipid Res. 1989, 21 (8), 993-1003.
26. Zborowski, J.; Roerdink, F.; Scherphof, G. Leakage of sucrose from phosphatidylcholine liposomes induced by interaction with serum albumin. Biochim. Biophys. Acta 1977, 497 (1), 183-191.
27. Tall, A. R. Studies on the transfer of phosphatidylcholine from unilamellar vesicles into plasma high density lipoproteins in the rat. J. Lipid Res. 1980, 21 (3), 354-363.
28. Fahr, A.; Van Hoogevest, P.; May, S.; Bergstrand, N.; Leigh, M. L. S. Transfer of lipophilic drugs between liposomal membranes and biological interfaces: Consequences for drug delivery. Eur. J. Pharm. Sci. 2005, 26 (3-4), 251-265.
29. Jones, J. D.; Thompson, T.E. Spontaneous phosphatidylcholine transfer by collision between vesicles at high lipid concentration. Biochemistry 1989, 28, 129-134.
30. Steck, T. L.; Kezdy, F. J.; Lange, Y. An activation-collision mechanism for cholesterol transfer between membranes. J. Biol. Chem. 1988, 263, 13023-13031.
31. Lange, Y.; Molinaro, A. L.; Chauncey, T. R.; Steck, T. L. On the mechanism of transfer of cholesterol between human erythrocytes and plasma. J. Biol. Chem. 1983, 258, 6920-6926.
32. McLean, L. R.; Phillips, M. C. Mechanism of cholesterol and phosphatidylcholine exchange or transfer between unilamellar vesicles. Biochemistry 1981, 20, 2893-2900.
33. McLean, L. R.; Phillips, M. C. Kinetics of phosphatidylcholine and lysophosphatidylcholine exchange between unilamellar vesicles. Biochemistry 1984, 23, 4624-4630.
34. Lidgate, D. M.; Felgner, P. L.; Fleitman, J. S.; Whatley, J.; Fu, R. C. In vitro and in vivo studies evaluating a liposome system for drug solubilization. Pharm. Res. 1988, 5, 759-764.
35. Hosokawa, T.; Yamauchi, M.; Yamamoto, Y.; Iwata, K.; Mochizuki, H.; Kato, Y. Role of the lipid emulsion on an injectable formulation of lipophilic KW-3902, a newly synthesized adenosine A1-receptor antagonist. Biol. Pharm. Bull. 2002, 25, 492-498. (Pubitemid 40036741)
36. Varma, R. K.; Kaushal, R.; Junnarkar, A. Y.; Thomas, G. P.; Naidu, M. U.; Singh, P. P.; Tripathi, R. M.; Shridhar, D. R. Polysorbate 80: a pharmacological study. Arzneim.-Forsch. 1985, 35 (5), 804-808.
37. Masini, E.; Planchenault, J.; Pezziardi, F.; Gautier, P.; Gagnol, J. P. Histamine-releasing properties of Polysorbate 80 in vitro and in vivo: correlation with its hypotensive action in the dog. Agents Actions 1985, 16 (6), 470-477.
38. Bowers, V. D.; Locker, S.; Ames, S.; Jennings, W.; Corry, R. J. The hemodynamic effects of Cremophor-EL. Transplantation 1991, 51 (4), 847-850.
39. Eschalier, A.; Lavarenne, J.; Burtin, C.; Renoux, M.; Chapuy, E.; Rodriguez, M. Cancer study of histamine release induced by acute administration of antitumor agents in dogs. Chemother. Pharmacol. 1988, 21 (3), 246-250.
40. Lorenz, W.; Schmal, A.; Schult, H.; Lang, S.; Ohmann, C.; Weber, D.; Kapp, B.; Luben, L.; Doenicke, A. Histamine release and hypotensive reactions in dogs by solubilizing agents and fatty acids: analysis of various components in Cremophor EL and development of a compound with reduced toxicity. Agents Actions 1982, 12 (1-2), 64-80.