Emulsions, microemulsions, and lipid-based drug delivery systems for drug solubilization and delivery-part II: Oral applications

Water-Insoluble Drug Formulation, Second Edition

Volumn , Issue , 2008, Pages 227-254

  Cannon, John B ^a   Long, Michelle A ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85013371167     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (118)

1. Abraham, M.H. and Le, J. (1999) The correlation and prediction of the solubility of compounds in water using an amended solvation energy relationship. J. Pharm. Sci., 88: 868-880.
2. Abrams, L.S., Weintraub, H.S., Patrick, J.E., and McGuire, J.L. (1978) Comparative bioavailability of a lipophilic steroid. J. Pharm. Sci., 67: 1287-1290.
3. Alfons, K. and Engstrom, S. (1998) Drug compatibility with the sponge phases formed in monoolein, water, and propylene glycol or poly(ethylene glycol). J. Pharm. Sci., 87: 1527-1607.
4. Armstrong, N.A. and James, K.C. (1980) Drug release from lipid-based dosage forms. II. Int. J. Pharm., 6: 195-204.
5. Barker, S.A., Yap, S.P., Yuen, K.H., McCoy, C.P., Murphy, J.R., and Craig, D.Q.M. (2003) An investigation into the structure and bioavailability of alpha-tocopherol dispersions in Gelucire. J. Control. Rel., 91: 477-488.
6. Bell, S.J. et al. (1997) The new dietary fats in health and disease. J. Am. Dietetic Assoc., 97: 280-288.
7. Bogman, K., Erne-Brand, F., Alsenz, J., and Drewe, J. (2003) The role of surfactants in the reversal of active transport mediated by multidrug resistance proteins. J. Pharm. Sci. , 92: 1250-1261.
8. Breitenbach, J. (2002) Melt extrusion: from process to drug delivery technology. Eur. J. Pharm. Biopharm., 54: 107-117.
9. Buchanan, M. et al. (2000) Kinetic pathways of multiphase surfactant systems. Phys. Rev. E: Stat. Phys., Plasm., Fluids, Relat. Interdisc. Topics, 62: 6895-6905.
10. Bummer, P.M. (2004) Physical chemical considerations of lipid-based oral drug delivery-solid lipid nanoparticles. Crit. Rev. Therap. Drug Carrier Syst., 21: 1-19.
11. Burcham, D.L. et al. (1997) Improved oral bioavailability of the hypocholesterolemic DMP 565 in dogs following oral dosing in oil and glycol solutions. Biopharm. Drug Disp., 18: 737-742.
12. Cade, D., Cole, E.T., Mayer, J.P., and Wittwer, F. (1986) Liquid filled and sealed hard gelatin capsules. Drug. Dev. Ind. Pharm., 12: 2289-2300.
13. Cannon, J. (2005) Oral solid dosage forms of lipid-based drug delivery systems. Am. Pharm. Rev., 8: 108-113.
14. Cao, Y. et al. (2004) Predictive relationships for the effects of triglyceride ester concentration and water uptake on solubility and partitioning of small molecules into lipid vehicles. J. Pharm. Sci., 93: 2768-2779.
15. Carrigan, P.J. and Bates, T.R. (1973) Biopharmaceutics of drugs administered in lipid containing dosage forms. I. GI absorption of griseofulvin from an oil-in-water emulsion in the rat. J. Pharm. Sci., 62: 1476-1479.
16. Chafetz, L. et al. (1984) Decrease in the rate of capsule dissolution due to formaldehyde from Polysorbate 80 autoxidation. J. Pharm. Sci., 73: 1186-1187.
17. Chambin, O., Bellone, C., Champion, D., Rochat-Gonthier, M.H., and Poucelot, Y. (2000) Dry adsorbed emulsion: I. characterization of an intricate physicochemical structure. J. Pharm. Sci., 89: 991-999.
18. Charman, W.N. (2000) Lipids, lipophilic drugs, and oral drug delivery-some emerging concepts. J. Pharm. Sci., 89: 967-978.
19. Charman, W.N., Rogge, M.C., Boddy, A.W., and Berger, B.M. (1993) Effect of food and a monoglyceride emulsion formulation on danazol bioavailability. J. Clin. Pharmacol., 33: 381-386.
20. Charman, W.N. and Stella, V.J. (1992) Lymphatic Transport of Drugs, CRC Press, Boca Raton, FL.
21. Charman, W.N. et al. (1997) Physicochemical and physiological mechanisms for the effects of food on drug absorption: the role of lipids and pH. J. Pharm. Sci., 86: 269-282.
22. Christensen, J.O. et al. (2004) Solubilisation of poorly water-soluble drugs during in vitro lipolysis of mediumand long-chain triacylglycerols. Eur. J. Pharm. Sci., 23: 287-296.
23. Cole, E. (1999) Liquid filled and sealed hard gelatin capsules. Technical report, Capsugel.
24. Constantinides, P.P. (1995) Lipid microemulsions for improving drug dissolution and oral absorption: physical and biopharmaceutical aspects. Pharm. Res., 12: 1561-1572.
25. Corvelyn, S. and Remon, J.P. (1998) Formulation of a lyophilized dry emulsion tablet for poorly soluble drugs. Int. J. Pharm., 166: 65-74.
26. Embleton, J.K. and Pouton, C.W. (1997) Structure and function of gastro-intestinal lipases. Adv. Drug Del. Rev., 25: 15-32.
27. Fleisher, D. et al. (1999) Drug, meal and formulation interactions influencing drug absorption after oral administration. Clin. Pharmacokinet., 36: 233-254.
28. Friberg, S.E. and Venable, R.L. (1983) Microemulsions. In Encyclopedia of Emulsion Technology, P. Becher, ed., Vol. I, Marcel Dekker, New York, p. 287.
29. Galal, S., El Massik, A.A., Abdallah, O.Y., and Daabis, N.A. (2004) Study of in vitro release of carbamazepine extended release semi-solid matrix filled capsules based on gelucires. Drug Dev. Ind. Pharm., 30: 817-829.
30. Gao, P. et al. (2003) Development of a supersaturable SEDDS (S-SEDDS) formulation of paclitaxel with improved oral bioavailability. J. Pharm. Sci., 92: 2386-2398.
31. Gao, P. et al. (2004) Application of a mixture experimental design in the optimization of a self-emulsifying formulation with a high drug load. Pharm. Dev. Tech., 9: 301-309.
32. Garti, N. et al. (2001) Improved oil solubilization in oil/water food grade microemulsions in the presence of polyols and ethanol. J. Agric. Food Chem., 49: 2552-2562.
33. Gelbart, W.M. and Ben-Shaul, A. (1996) The "new" science of "complex fluids." J. Phys. Chem., 100: 13169-13189.
34. Gershanik, T. and Benita, S. (2000) Self-dispersing lipid formulations for improving oral absorption of lipophilic drugs. Eur. J. Pharm. Biopharm., 50: 179-188.
35. Ginski, M.J. and Polli, J.E. (1999) Prediction of dissolution-absorption relationships from a dissolution/Caco-2 system. Int. J. Pharm., 177: 117-125.
36. Gold, T.B., Bruice, R.G., Lodder, R.A., and Digenis, G.A. (1997) Determination of the extent of formaldehyde-induced cross-linking in hard gelatin capsules by near-infrared spectrophotometry. Pharm. Res., 14: 1046-1050.
37. González, R.C.B. et al. (2002) Improved oral bioavailability of cyclosporin A in male wistar rats comparison of a Solutol HS 15 containing self-dispersing formulation and a microsuspension. Int. J. Pharm., 245: 143-151.
38. Greiner, R.W. and Evans, D.F. (1990) Spontaneous formation of a water-continuous emulsion from a w/o microemulsion. 6: 1793-1796.
39. Griffin, W.C. (1949) Classification of surface-active agents by "HLB." J. Soc. Cos. Chem., 1: 311-326.
40. Hamdani, J., Moes, A., and Amighi, K. (2003) Physical and thermal characterization of precirol and compritol as lipophikic glycerides used for the preparation of controlled-release matrix pellets. Int. J. Pharm., 260: 47-57.
41. Handbook of Pharmaceutical Excipients (1994) American Pharmaceutical Association. The Pharmaceutical Press, London. pp. 371, 375, 379, 473, 481.
42. Hauss, D.J., Fogal, S.E., Ficorilli, J.V., Price, C.A., Roy, T., Jayara, A.A., and Keirns, J.J. (1998) Lipid-based delivery systems for improving the bioavailability and lymphatic transport of a poorly water-soluble LTB4 inhibitor. J. Pharm. Sci., 87: 164-169.
43. Hellweg, T. (2002) Phase structures of microemulsions. Curr. Opin. Coll. Interf. Sci., 7: 50-56.
44. Hernell, O. et al. (1990) Physical-chemical behavior of dietary and biliary lipids during intestinal digestion and absorption. 2. Phase analysis and aggregation states of luminal lipids during duodenal fat digestion in healthy adult human beings. Biochemistry, 29: 2041-2056.
45. Holm, R., Porter, C.J.H., Edwards, G.A., Mullertz, A., Kristensen, H.G., and Charman, W.N. (2003) Examination of oral absorption and lymphatic transport of halofantrine in a triple-cannulated canine model after administration in self-microemulsifying drug delivery systems (SMEDDS) containing structured triglycerides. Eur. J. Pharm. Sci., 20: 91-97.
46. Holt, D.W. and Johnston, A. (1997) Cyclosporin microemulsion. A guide to usage and monitoring. BioDrugs, 7: 175-197.
47. Holt, D.R., Mueller, E.A., Kovarik, J.M., van Bree, J.B., and Kutz, K. (1994) The pharmacokinetics of Sandimmun Neoral: a new oral formulation of cyclosporine. Transplant Proc., 26: 2935-2939.
48. Hörter, D. and Dressman, J.B. (1997) Influence of physicochemical properties on dissolution of drugs in the gastrointestinal tract. Adv. Drug Del. Rev., 25: 3-14.
49. Humberstone, A.J. and Charman, W.N. (1997) Lipid-based vehicles for the oral delivery of poorly water soluble drugs. Adv. Drug Del. Rev., 25: 103-128.
50. Jandacek, R.J. et al. (1987) The rapid hydrolysis and efficient absorption of triglycerides with octanoic acid in the 1 and 3 positions and long-chain fatty acid in the 2 position. Am J. Clin. Nutr., 45: 940-945.
51. Jimerson, R.F. (1986.) Soft gelatin capsule update. Drug. Dev. Ind. Pharm., 12: 1133-1144.
52. Kaminsky, L.S. and Fasco, M.J. (1991) Small intestinal cytochromes P450. Crit. Rev. Toxicol., 21: 407-422.
53. Kataoka, M. et al. (2006) Effect of food intake on the oral absorption of poorly water-soluble drugs: in vitro assessment of drug dissolution and permeation assay system. J. Pharm. Sci., 95: 2051-2061.
54. Kaukonen, A.M. et al. (2004) Drug solubilization behavior during in vitro digestion of simple triglyceride lipid solution formulations. Pharm. Res., 21: 245-253.
55. Khoo, S.-M. et al. (1998) Formulation design and bioavailability assessment of lipidic self-emulsifying formulations of halofantrine. Int. J. Pharm., 167: 155-164.
56. Khoo, S.-M. et al. (2000) The formulation of halofantrine as either non-solubilizing PEG 6000 or solubilizing lipid based solid dispersions: physical stability and absolute bioavailability assessment. Int. J. Pharm., 205: 65-78.
57. Kossena, G.A. et al. (2003) Separation and characterization of the colloidal phases produced on digestion of common formulation lipids and assessment of their impact on the apparent solubility of selected poorly water-soluble drugs. J. Pharm. Sci., 92: 634-648.
58. Kossena, G.A. et al. (2005) Influence of the intermediate digestion phases of common formulation lipids on the absorption of a poorly water-soluble drug. J. Pharm. Sci., 94: 481-492.
59. Kuentz, M. and Röthlisberger, D. (2002) Determination of the optimal amount of water in liquid-fill masses for hard gelatin capsules by means of texture analysis and experimental design. Int. J. Pharm., 236: 145-152.
60. Laughlin, R. (1994) The Aqueous Phase Behavior of Surfactants, Academic Press, London.
61. Lawrence, M.J. (1996) Microemulsions as drug-delivery vehicles. Curr. Opin. Coll. Interface Sci., 1: 826-832.
62. Lide, D.R., ed. (1993) CRC Handbook of Chemistry and Physics, 74th edition, CRC Press, Boca Raton FL, pp. 8-46.
63. Lombardin, P., Seiller, M., Leverd, E., Goutay, E., Bougaret, J., and Grossiord (2000) Study of thixotropic bases for the filling of hard capsules. STP Pharm. Sci., 10: 429-437.
64. López-Montilla, J.C. et al. (2002) Spontaneous emulsification: mechanisms, physicochemical aspects, modeling, and applications. J. Disp. Sci. Tech., 23: 219-268.
65. Lovell, M.W., Johnson, H.W., Hui, H.-W., Cannon, J.B., Gupta, P.K., and Hsu, C.C. (1994) Less-painful emulsion formulations for intravenous administration of clarithromycin. Int. J. Pharm., 109: 45-57.
66. MacGregor, K.J. et al. (1997) Influence of lipolysis on drug absorption from the gastro-intestinal tract. Adv. Drug Del. Rev., 25: 33-46.
67. Malcolmson, C. et al. (1998) Effect of oil on the level of solubilization of testosterone propionate into nonionic oil-in-water microemulsions. J. Pharm. Sci., 87: 109-116.
68. Mehnert, W. and Mader, K. (2001) Solid lipid nanoparticles: production, characterization, and applications. Adv. Drug Del. Rev., 47: 165-196.
69. Miller, C.A. (1988) Spontaneous emulsification produced by diffusion-a review. Coll. Surf., 29: 89-102.
70. Mu, H. and Høy, C.-E. (2004) The digestion of dietary triacylglycerols. Prog. Lipid Res., 43: 105-133.
71. Mueller, E.A. et al. (1994a) Improved dose linearity of cyclosporine pharmacokinetics from a microemulsion formulation. Pharm. Res., 11: 301-304.
72. Mueller, E.A. et al. (1994b) Pharmacokinetics and tolerability of a microemulsion formulation of cyclosporine in renal allograft recipients-a concentration-controlled comparison with the commercial formulation. Transplantation, 57: 1178-1182.
73. Myers, R.A. and Stella, V.J. 1992. Factors affecting the lymphatic transport of penclomedine (NSC-338720), alipophilic cytotoxic drug: Comparison to DDT and hexachlorobenzene. Int. J. Pharm., 80: 51-62.
74. Nazzal, S., Nutan, M., Palamakula, A., Shah, R., Zaghloul, A.A., and Khan, M.A. (2002) Optimization of a self-nanoemulsified tablet dosage form of Ubiquinone using response surface methodology: effect of formulation ingredients. Int. J. Pharm., 240: 103-114.
75. Nicolaides, E. et al. (1999) Forecasting the in vivo performance of four low solubility drugs from their in vitro dissolution data. Pharm. Res., 16: 1877-1883.
76. Nishimi, T. and Miller, C.A. (2000) Spontaneous emulsification of oil in aerosol-OT/ water/hydrocarbon systems. Langmuir, 16: 9233-9241.
77. Norkskog, B.K. et al. (2001) An examination of the factors affecting intestinal lymphatic transport of dietary lipids. Adv. Drug Del. Rev., 50: 21-44.
78. Patton, J.S. et al. (1985) The light microscopy of triglyceride digestion. Food Microstruct., 4: 29-41.
79. Physicians Desk Reference (2007) PDR® Electronic Library, Thomson MICROMEDEX.
80. Porter, C.J.H. et al. (2004) Use of in vitro lipid digestion data to explain the in vivo performance of triglyceride-based oral lipid formulations of poorly water-soluble drugs: studies with halofantrine. J. Pharm. Sci., 93: 1110-1121.
81. Porter, C.J.H. and Charman, W.N. (1997) Uptake of drugs into the intestinal lymphatics after oral administration. Adv. Drug Del. Rev., 25: 71-89.
82. Porter, C.J.H. and Charman, W.N. (2001) In vitro assessment of oral lipid based formulations. Adv. Drug Del. Rev., 50: S127-S147.
83. Pouton, C.W. (1997) Formulation of self-emulsifying drug delivery systems. Adv. Drug Del. Rev., 25: 47-58.
84. Pouton, C.W. (2000) Lipid formulations for oral administration of drugs: non-emulsifying, self-emulsifying and "self-micro emulsifying" drug delivery systems. Eur. J. Pharm. Sci., 11 (Suppl. 2): S93-S98.
85. Rang, M-J. and Miller, C.A. (1999) Spontaneous emulsification of oils containing hydrocarbon, nonionic surfactant, and oleyl alcohol. J. Coll. Interface Sci., 209: 179-192.
86. Rege, B.D., Kao, J.P., and Polli, J.E. (2002) Effects of nonionic surfactants on membrane transporters in Caco-2 cell monolayers. Eur. J. Pharm. Sci., 16: 237-246.
87. Ritschel, W.A. (1996) Microemulsion technology in the reformulation of cyclosporine: the reason behind the pharmacokinetic properties of Neoral. Clin. Transplant., 10: 364-373.
88. Robson, H., Craig, D.Q.M., and Deutsch, D. (2000) An investigation into the release of cefuroxime axetil from taste-masked stearic acid microspheres. II. The effects of buffer composition on drug release. Int. J. Pharm., 195: 137-145.
89. Ruelle, P. and Kesselring, U.W. (1994) Solubility predictions for solid nitriles and tertiary amides based on the mobile order theory. Pharm. Res., 11: 201-205.
90. Seelig, A. and Landwojtowicz, E. (2000) Structure-activity relationship of P-glycoprotein substrates and modifiers. Eur. J. Pharm. Sci., 12: 31-40.
91. Serajuddin, A.T.M. et al. (1986) Water migration from soft gelatin capsule shell to fill material and its effect on drug solubility. J. Pharm. Sci., 75: 62-64.
92. Serajuddin, A.T.M. et al. (1988) Effect of vehicle amphiphilicity on the dissolution and bioavailability of a poorly water-soluble drug from solid dispersions. J. Pharm. Sci., 77: 414-417.
93. Shahidzadeh, N. et al. (2000) Dynamics of spontaneous emulsification for fabrication of oil in water emulsions. Langmuir, 16: 9703-9708.
94. Shen, H. et al. (2001) From interaction of lipidic vehicles with intestinal epithelial cell membranes to the formation and secretion of chylomicrons. Adv. Drug Del. Rev., 50: S103-S125.
95. Shively, M.L. and Thompson, D.C. (1995) Oral bioavailability of vancomycin solid-state emulsions. Int. J. Pharm., 117: 119-122.
96. Staggers, J.E. et al. (1990) Physical-chemical behavior of dietary and biliary lipids during intestinal digestion and absorption. 1. Phase behavior and aggregation states of model lipid systems patterned after aqueous duodenal contents of healthy adult human beings. Biochemistry, 29: 2028-2040.
97. Strey, R. (1994) Microemulsion microstructure and interfacial curvature. Coll. Polym. Sci., 272: 1005-1019.
98. Strickley, R.G. (2004) Solubilizing excipients in oral and injectable formulations. Pharm. Res., 21: 201-230.
99. Tahibi, S.E. and Gupta, S.L. (2000) Soft gelatin capsules development. In R. Liu, ed. Water Insoluble Drug Formulation, Interpharm Press, Engle wood, CO. pp. 609-633.
100. Takahashi, M., Mochizuki, M., Wada, K., Itoh, T., and Goto, M. (1994) Studies on dissolution tests of soft gelatin capsules. Part 5. Rotating dialysis cell method. Chem. Pharm. Bull., 42: 1672-1675.
101. Takeuchi, H., Saski, H., Niwa, T., Hino, T., Kawashima, Y., Uesugi, K., Kayano, M., and Miyake, Y. (1991) Preparation of a powdered redispersible vitamin E acetate emulsion by spray-drying. Chem. Pharm. Bull., 39: 1528-1531.
102. Thomson, A.B.R. et al. (1993) Lipid absorption: passing through the unstirred layers, brush-border membrane, and beyond. Can. J. Physiol. Pharmacol., 71: 531-555.
103. Traul, K.A., Driedger, A., Ingle, D.L., and Nakhasf, D. (2000) Review of the toxicologic properties of medium-chain triglycerides. Food Chem. Toxicol., 38: 79-98.
104. Trotta, M. (1999) Influence of phase transformation on indomethacin release from microemulsions. J. Contr. Rel., 60: 399-405.
105. Trull, A.K. et al. (1993) Cyclosporine absorption from microemulsion formulation in liver transplant recipient. Lancet, 341: 433.
106. Tuleu, C., Khela, M.K., Evans, D.F., Jones, B.E., Nagata, S., andBasit, A.W. (2007)Ascintigraphic investigation of the disintegration behavior of capsules in fasting subjects: a comparison of hypromellose capsules containing carrageenan as a gelling agent and standard gelatin capsules. Eur. J. Pharm. Sci., 30: 251-255.
107. Turnberg, L.A. and Riley, S.A. (1985) Digestion and absorption of nutrients and vitamins. In Handbook of Physiology, Oxford Press, New York. pp. 977-1008.
108. Van Os, N.M. et al. (1993) Physio-chemical Properties of Selected Anionic, Cationic and Nonionic Surfactants. Elsevier Science Publishers, Amsterdam. p. 301.
109. Verkijk, M., Vecht, J., Gielkens, H.A.J., Lamers, C., and Masclee, A. (1997) Effects of medium-chain and long-chain triglycerides on antroduodenal motility and small bowel transit time in man. Dig. Diseases Sci., 42: 1933-1939.
110. Von Corswant, C. et al. (1997) Microemulsions based on soybean phosphatidylcholine and triglycerides. Phase behavior and microstructure. Langmuir, 13: 5061-5070.
111. Wacher, V.J., Wu, C.-Y., and Benet, L.Z. (1995) Overlapping substrate specificities and tissue distribution of cytochrome P450 3A and P-glycoprotein: implications for drug delivery and activity in cancer chemotherapy. Mol. Carcinog., 13129-13134.
112. Walker, S.E., Ganley, J.A., Bedford, K., and Eaves, T. (1980) The filling of molten and thixotropic formulations into hard gelatin capsules. J. Pharm. Pharmacol., 32: 389-393.
113. Wang, R.B., Kuo, C.L., Lien, L.L., and Lien, E.J. (2003) Structure activity relationship: analysis of P-glycoprotein substrates and inhibitors. J. Clin. Pharm. Ther., 28: 203-228.
114. Wasan, K.M. (2001) Formulation and physiological and biopharmaceutical issues in the development of oral lipid-based drug delivery systems. Drug Dev. Ind. Pharm., 27: 267-276.
115. Wu, C.-Y. and Benet, L.Z. (2005) Predicting drug disposition via application of BCS: transport/ absorption/elimination interplay and development of a biopharmaceutics drug disposition classification system. Pharm. Res., 22: 11-23.
116. Yu, L., Bridgers, A., Polli, J., Vickers, A., Long, S., Roy, A., Winnike, R., and Coffin, M. (1999) Vitamin E-TPGS increases absorption flux of an HIV protease inhibitor by enhancing its solubility and permeability. Pharm. Res., 16: 1812-1817.
117. Zangenberg, N.H. et al. (2001) A dynamic in vitro lipolysis model I. Controlling the rate of lipolysis by continuous addition of calcium. Eur. J. Pharmaceut. Sci., 14: 115-122.
118. Zourab, S.M. and Miller, C.A. (1995) Equilibrium and dynamic behavior for systems containing nonionic surfactants, n-hexadecane, triolein and oleyl alcohol. Coll. Surf., 95: 173-183.