The use of natural and synthetic phospholipids as pharmaceutical excipients

European Journal of Lipid Science and Technology

Volumn 116, Issue 9, 2014, Pages 1088-1107

  van Hoogevest, Peter ^a   Wendel, Armin ^a  

^a Phospholipid Research Center   (Germany)

Author keywords

Emulsifier; Lecithin; Liposomes; Natural phospholipids; Phosphatidylcholine; Solubilizer; Synthetic phospholipids

Indexed keywords

EID: 85027923724     PISSN: 14387697     EISSN: 14389312     Source Type: Journal    
DOI: 10.1002/ejlt.201400219     Document Type: Review

References (86)

1. Shurtleff, W., Aoyagi, A., History of Soy Lecithin, http://www. soyinfocenter.com/HSS/lecithin1.php, 2007.
2. Pepeu, G., Vannucchi, M. G., Di Patre, P. L., in: Hanin, I., Pepeu, G. (Ed.), Phospholipids: Biochemical, Pharmaceutical, and Analytical Considerations [Proceedings of the 5th International Colloquium on Lecithin; Phospholipids: Biochemical, Pharmaceutical, and Analytical Considerations, Held April 10-12, 1989, in Cannes, France] Plenum Press, New York [u. a.] 1990, pp. 43-50.
3. Vertzoni, M., Markopoulos, C., Symillides, M., Goumas, C. et al., Luminal lipid phases after administration of a triglyceride solution of danazol in the fed state and their contribution to the flux of danazol across Caco-2 cell monolayers. Mol. Pharm. 2012, 9, 1189-1198.
4. Hanin, I., Pepeu, G., Phospholipids Biochemical, Pharmaceutical, and Analytical Considerations: [Proceedings of the Fifth International Colloquium on Lecithin; Phospholipids: Biochemical, Pharmaceutical, and Analytical Considerations, held April 10-12, 1989, in Cannes, France], Plenum Press, New York [u.a.] 1990.
5. Merolli, A., Santin, M., Role of phosphatidyl-serine in bone repair and its technological exploitation. Molecules 2009, 14, 5367-5381.
6. Devitt, A., Pierce, S., Oldreive, C., Shingler, W. H., Gregory, C. D., CD14-dependent clearance of apoptotic cells by human macrophages: The role of phosphatidylserine. Cell Death Differ. 2003, 10, 371-382.
7. Lentz, B. R., Exposure of platelet membrane phosphatidylserine regulates blood coagulation. Prog. Lipid Res. 2003, 42, 423-438.
8. Shimojo, T., Abe, M., Ota, M., A method for determination of saturated phosphatidylcholine. J. Lipid Res. 1974, 15, 525-527.
9. McFerron, W., Global soybean production seen bigger than expected by oil world. Bloomberg L.P., 2013.
10. Bundschuh, R., Heinze, C., in: Agrarmärkte 2013, Landesanstalt für Entwicklung der Landwirtschaft und der ländlichen Räume (LEL), Bayrische Landesanstalt für Landwirtschaft (LfL), Schwäbisch Gmünd 2013, pp. 246-274.
11. Data kindly provided by LIPOID GmbH.
12. Wendel, A., In: Kirk, R. E., Othmer, D. F. (Eds.), Kirk-Othmer Encyclopedia of Chemical Technology, John Wiley & Sons, Inc., New York, Chichester, Weinheim, Brisbane, Singapur, Toronto 1995, pp. 191-210.
13. Quinkert, R.-O., Setzer, C., Soybean Lecithins and Phospholipids for Pharmaceutical Applications, Phospholipid Forschungszentrum e. V./Research Center 2010.
14. Egg Lecithins for Pharmaceutical Application, Phospholipid Forschungszentrum e. V./Research Center 2008.
15. Senior, J., Gregoriadis, G., Stability of small unilamellar liposomes in serum and clearance from the circulation: The effect of the phospholipid and cholesterol components. Life Sci. 1982, 30, 2123-2136.
16. Pryde, E. H., In: Szuhaj, B. F., List, G. R. (Eds.), Lecithins, American Oil Chemists' Society, Champaign 1985, pp. 213-246.
17. European Pharmacopoeia. (Ph. Eur.) 8. 0: 2. 5. 4 Iodine value (reference 01/2008 20504).
18. Lekim, D., The resorption of lecithin administered orally and its physiologic implications, in: Soya Lecithin: Nutritional and Clinical Aspects: Proceedings of the First International Colloquium Held in Rome, Italy, Nov. 22, 1980, Cairella, M., Lekim, D. (Eds.), Societa Editrice Universo, Rome 1981, pp. 21-33.
19. Xu, X., Vikbjerg, A. F., Guo, Z., Zhang, L., Acharya, A. K., in: Gunstone, F. D. (Ed.), Phospholipid Technology and Applications, Oily Press, Bridgewater 2008, pp. 41-82.
20. Bornscheuer, U. T., Fettwissenschaft, D. G. F., Enzymes in Lipid Modification, Wiley-VCH, Weinheim 2000.
21. Bittmann, R., in: Cevc, G. (Ed.), Phospholipids Handbook, Marcel Dekker, Inc., New York 1993, pp. 141-232.
22. Ghyczy, M., In: Szuhaj, B. F. (Ed.), Lecithins Sources, Manufacture & Uses, The American Oil Chemists' Soc., Champaign, IL 1989, pp. 131-144.
23. Paltauf, F., Hermetter, A., In: Hanin, I. Pepeu, G. (Eds.), Phospholipids Biochemical, Pharmaceutical, and Analytical Considerations: [Proceedings of the Fifth International Colloquium on Lecithin; Phospholipids: Biochemical, Pharmaceutical, and Analytical Considerations, held April 10-12, 1989, in Cannes, France], Plenum Press, New York [u.a.] 1990, pp. 1-12.
24. Koo, O. M., Rubinstein, I., Onyuksel, H., Role of nanotechnology in targeted drug delivery and imaging: A concise review. Nanomedicine 2005, 1, 193-212.
25. MacDonald, R. C., Rakhmanova, V. A., Choi, K. L., Rosenzweig, H. S., Lahiri, M. K., O-Ethylphosphatidylcholine: A metabolizable cationic phospholipid which is a serumcompatible DNA transfection agent. J. Pharm. Sci. 1999, 88, 896-904.
26. Lux, H., Heise, N., Klenner, T., Hart, D., Opperdoes, F. R., Ether-lipid (alkyl-phospholipid) metabolism and the mechanism of action of ether-lipid analogues in Leishmania. Mol. Biochem. Parasitol. 2000, 111, 1-14.
27. Schumann, G., Van Hoogevest, P., Fankhauser, P., Probst, A. et al., Comparison of free and liposomal MTP-PE: Pharmacological and toxicological aspects, in: Liposomes in the therapy of infectious diseases and cancer: Proceedings of a Ciba-Geigy-Squibb-UCLA Colloquium, held at Lake Tahoe, California, February 16-20, 1988, Lopez-Berestein, G., Fidler, I. J. (Eds.), CIBA-GEIGY Corporation, E.R. Squibb & Sons, University of California, A.R. Liss, New York 1989, p. 191.
28. Eibl, H., Phospholipids as functional constituents of biomembranes. Angew. Chem. Int. Ed. Engl. 1984, 23, 257-271.
29. Ohno, M., Fujita, K., Nakai, H., Kobayashi, S. et al., An enantioselective synthesis of platelet-activating factors, their enantiomers, and their analogues from D-and L-tartaric acids. Chem. Pharm. Bull. 1985, 33, 572-582.
30. Ali, S., Bittman, R., Mixed-chain phosphatidylcholine analogues modified in the choline moiety: Preparation of isomerically pure phospholipids with bulky head groups and one acyl chain twice as long as the other. Chem. Phys. Lipids 1989, 50, 11-21.
31. Mangroo, D., Gerber, G. E., Phospholipid synthesis: Effects of solvents and catalysts on acylation. Chem. Phys. Lipids 1988, 48, 99-108.
32. Mason, J. T., Broccoli, A. V., Huang, C.-H., A method for the synthesis of isomerically pure saturated mixed-chain phosphatidylcholines. Anal. Biochem. 1981, 113, 96-101.
33. Virtanen, J. A., Brotherus, J. R., Renkonen, O., Kates, M., Synthesis of monoacid 2,3-diacyl-sn-glycerols via 1,6-ditrityl-d-mannitol, Chem. Phys. Lipids 1980, 27, 185-190.
34. Peters, U., Bankova, W., Welzel, P., Platelet activating factor synthetic studies. Tetrahedron 1987, 43, 3803-3816.
35. Synthetic Phospholipids and Other Synthetic Lipids, Corden Pharma Switzerland LLC.
36. Crans, D. C., Whitesides, G. M., Glycerol kinase: synthesis of dihydroxyacetone phosphate, sn-glycerol-3-phosphate, and chiral analogs. J. Am. Chem. Soc. 1985, 107, 7019-7027.
37. Hermetter, A., Paltauf, F., A facile procedure for the synthesis of saturated phosphatidylcholines. Chem. Phys. Lipids 1981, 28, 111-115.
38. Warner, T. G., Benson, A. A., An improved method for the preparation of unsaturated phosphatidylcholines: Acylation of sn-glycero-3-phosphorylcholine in the presence of sodium methylsulfinyl methide. J. Lipid Res. 1977, 18, 548-552.
39. Fricker, G., Kromp, T., Wendel, A., Blume, A. et al., Phospholipids and lipid-based formulations in oral drug delivery. Pharm. Res. 2010, 27, 1469-1486.
40. Van Hoogevest, P., Liu, X., Fahr, A., Leigh, M. L. S., Role of phospholipids in the oral and parenteral delivery of poorly water soluble drugs. J. Drug Deliv. Sci. Technol. 2011, 21, 5-133.
41. Inactive, Ingredient Search for Approved Drug Products, U.S. Food and Drug Administration. http://www.accessdata.fda. gov/scripts/cder/iig/index.Cfm
42. Abelcet, RxList Inc. http://www.rxlist.com/abelcet-drug.htm
43. AmBisome1 (amphotericin B) liposome for injection, Astellas Pharma US, Inc. www.ambisome.com
44. Daunoxome (Daunorubicin Citrate)-Summary DrugLib. com. www.druglib.com/druginfo/daunoxome/
45. Doxil, RxList, Inc. www.rxlist.com/doxil-drug.htm
46. Assessment report for MEPACT (EMEA/CHMP/635781/ 2008), European Medicines Agency 2008.
47. Van Hoogevest, P., Fankhauser, P., An industrial liposomal dosage form for muramyltripeptidephosphatidylethanolamine (MTP-PE), in: Liposomes in the therapy of infectious diseases and cancer: Proceedings of a Ciba-Geigy-Squibb-UCLA Colloquium, held at Lake Tahoe, California, February 16-20, 1988, Lopez-Berestein, G. Fidler, I. J. (Eds.), CIBA-GEIGY Corporation, E. R. Squibb & Sons, University of California, A. R. Liss, New York 1989, p. 453.
48. Martin, F., Liposome Drug Products-Product Evolution and Influence of Formulation on Pharmaceutical Properties and Pharmacology, U.S. Food and Drug Administration.
49. Myocet 50mg Pulver, Dispersion und Lösungsmittel für ein Konzentrat zur Herstellung einer Infusionsdispersion TEVA Pharma B.V. http://www.pharmazie.com/graphic/A/50/0-90350.pdf 2013.
50. Visudyne1 Verteporfin for Injection, Valeant Pharmaceuticals North America LLC. http://www.visudyne.com/
51. Regulon Group. www.regulon.com
52. Desai, N. R., Agha, B. J., Kale, K. M., US6074666 2000.
53. Exparel, RxList, Inc. http://www.rxlist.com/exparel-drug. htm
54. DepoDur, RxList, Inc. http://www.rxlist.com/depodur-drug. htm
55. DepoCyt, RxList, Inc. http://www.rxlist.com/depocyt-drug. htm
56. TM, a novel, single-dose extendedrelease epidural morphine, with standard epidural morphine for pain relief after lower abdominal surgery. Anesth. Analg. 2005, 100, 1065-1074. 1010.1213/1001.A NE.0000145009.0000103574.0000145078.
57. Cada, D. J., Levien, T., Baker, D. E., Morphine Sulfate Extended-Release Liposome Injection, Thomas Land, St. Louis, MO, ETATS-UNIS 2004.
58. Driscoll, D., Lipid injectable emulsions: Pharmacopeial and safety issues. Pharm. Res. 2006, 23, 1959-1969.
59. Intralipid, Drugs.com. http://www.drugs.com/pro/intralipid. html
60. Intralipid 10%, RxList, Inc. http://www.rxlist.com/intralipid-10-drug/indications-dosage.htm
61. Diazemuls Emulsion for Injection 5 mg/ml (Diazepam), Actavis Nordic A/S, Actavis Group PTC 2013.
62. Shah, P., Bhalodia, D., Shelat, P., Nanoemulsion: A pharmaceutical review, Syst. Rev. Pharm. 2010, 1, 24-32.
63. Cada, D., Levien, T., Baker, D., Formulary drug reviews-Clevidipine butyrate injectable emulsion. Hosp. Pharm. 2008, 43, 903-912.
64. Hammad, M. A., Müller, B. W., Increasing drug solubility by means of bile salt-phosphatidylcholine-based mixed micelles. Eur. J. Pharm. Biopharm. 1998, 46, 361-367.
65. Gundermann, K.-J., Schneider, E., LipoStabil in: Information Brochure, Rhône-Poulenc Rorer/Nattermann International GmbH 1990.
66. Gregory, T. J., Steinberg, K. P., Spragg, R., Gadek, J. E. et al., Bovine surfactant therapy for patients with acute respiratory distress syndrome. Am. J. Respir. Crit. Care Med. 1997, 155, 1309-1315.
67. Geller, D. E., Weers, J., Heuerding, S., Development of an inhaled dry-powder formulation of tobramycin using Pulmo-Sphere technology. J. Aerosol Med. Pulm. Drug Deliv. 2011, 24, 175-182.
68. VanDevanter, D. R., Geller, D. E., Tobramycin administered by the TOBI((R)) Podhaler((R)) for persons with cystic fibrosis: A review. Med. Devices (Auckl). 2011, 4, 179-188.
69. WHO Food Additives Series No. 5, World Health Organization 1974, p. 234.
70. Commission Regulation (EU) No 231/2012 of March 9, 2012, laying down specifications for food additives listed in Annexes II and III to Regulation (EC) No 1333/2008 of the European Parliament and of the Council European Commission, 2012.
71. Annex I of European Parliament and Council Directive No 95/2/EC of February 20, 1995, on food additives other than colours and sweeteners, European Parliament and Council 1995.
72. Report from the Commission on Dietary Food Additive Intake in the European Union European Commission, http:// ec.europa.eu/food/fs/sfp/addit_flavor/flav15_en.pdf, 2001.
73. 21CFR184.1400 revised as of April 1, 2013, U. S. Food and Drug Administration.
74. 21CFR184.1063 August 1996, U. S. Food and Drug Administration.
75. 21CFR184.1063 revised as of April 1, 2013, U. S. Food and Drug Administration.
76. Edgren, B., Hallberg, D., Hakansson, I., Meng, H. C., Wretlind, A., Long-term tolerance study of two fat emulsions for intravenous nutrition in dogs. Am. J. Clin. Nutr. 1964, 14, 28-236.
77. Le, V. H. H., Giordano, P., Spletzer, J., The mechanism of removal of intravenously injected fat: Its relationship to toxicity. Arch. Surg. 1961, 83, 311-321.
78. Schuberth, O. W. A., Intravenous Infusion of Fat Emulsions, Phosphatides and Emulsifying Agents: Clinical and Experimental Studies (tr.: P.A. Norstedt), Stockh 1961.
79. Mueller, J. F., Iacono, J., In: Henning, N., Berg, G. (Eds.), Fette in der Medizin, las Verlag, München 1967, pp. 7-10.
80. Draft Guidance for Industry: Liposome Drug Products Chemistry, Manufacturing, and Controls; Human Pharmacokinetics and Bioavailability; and Labeling Documentation, U.S. Department of Health and Human Services, Food and Drug Administration, Center for Drug Evaluation and Research (CDER), 2002.
81. Reflection Paper on the Data Requirements for Intravenous Liposomal Products Developed With Reference to an Innovator Liposomal Product (EMA/CHMP/806058/2009/Rev. 02), European Medicines Agency, 2013.
82. European Pharmacopoeia 7.0 general text 5.1.7 Viral Safety.
83. Commission Regulation (EC) No 1881/2006 of December 19, 2006, setting maximum levels for certain contaminants in foodstuffs, European Commission 2006.
84. Walts, A. E., Schena, D. G., Fox, E. M., Davis, J. T., Mischke, M. R., Applications of biocatalysts in the synthesis of phospholipids. Chim. Oggi. 1991, 9, 29-33.
85. Walts, A. E., Schena, D. G., Fox, E. M., Davis, J. T., Mischke, M. R., In: Collins, A. N., Sheldrake, G. N., Crosby, J. (Eds.), Chirality in industry: the commercial manufacture and applications of optically active compounds, Wiley, Chichester [u.a.] 1992, pp. 223-235.
86. Haran, G., Cohen, R., Bar, L. K., Barenholz, Y., Transmembrane ammonium sulfate gradients in liposomes produce efficient and stable entrapment of amphipathic weak bases. Biochim. Biophys. Acta (BBA)-Biomembr. 1993, 1151, 201-215.