Lipid-based vehicles for the oral delivery of poorly water soluble drugs

Advanced Drug Delivery Reviews

Volumn 25, Issue 1, 1997, Pages 103-128

  Humberstone, Andrew J ^a   Charman, William N ^a  

^a MONASH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION; DRUG INTERACTIONS; EMULSIFICATION; LIPIDS; PHYSIOLOGY; SOLUTIONS;

POORLY WATER SOLUBLE DRUGS; SELF EMULSIFYING DRUG DELIVERY SYSTEMS (SEDDS);

DRUG INFUSION;

EID: 0031125683     PISSN: 0169409X     EISSN: None     Source Type: None    
DOI: 10.1016/S0169-409X(96)00494-2     Document Type: Review

References (105)

1. C.L. Bisgaier R.M. Glickman Intestinal synthesis, secretion and transport of lipoproteins Annu. Rev. Physiol. 45 1983 625 636
2. A.B.R. Thomson M. Keelan M.L. Garg M.T. Clandinin Intestinal aspects of lipid absorption: in review Can. J. Physiol. Pharmacol. 67 1989 179 191
3. P. Tso Intestinal lipid absorption L.R. Johnson Physiology of the Gastrointestinal Tract 1994 Raven Press New York 1867 1908
4. M.C. Carey D.M. Small C.M. Bliss Lipid digestion and absorption Annu. Rev. Physiol. 45 1983 651 677
5. M. Hamosh J.W. Scanlon D. Ganot M. Likel K.B. Scanlon P. Hamosh Fat digestion in the newborn: characterization of lipase in gastric aspirates of premature and term infants J. Clin. Invest. 67 1981 838 846
6. T.H. Liao P. Hamosh M. Hamosh Fat digestion by lingual lipase: mechanism of lipolysis in the stomach and upper small intestine Pediatr. Res. 18 1984 402 409
7. M.E. Lowe The structure and function of pancreatic enzymes L.R. Johnson Physiology of the Gastrointestinal Tract 1994 Raven Press New York 1531 1542
8. 2 and fatty acid for the digestion of dietary fat Gastroenterology 78 1980 954 962
9. S. Bernback L. Blackberg O. Hernell Fatty acids generated by gastric lipase promote human milk triacylglycerol digestion by pancreatic colipase-dependent lipase Biochim. Biophys. Acta 1001 1989 286 293
10. M. Rautureau A. Bisalli J.C. Rimbaud Bile salts and lipids in the aqueous intraluminal phase during the digestion of a standard meal in man Clin. Biol. 5 1981 417 425
11. M.C. Carey D.M. Small The characteristics of mixed micellar solutions with particular reference to man Am. J. Med. 49 1970 590 608
12. M.C. Carey D.M. Small Micelle formation by bile salts Arch. Intern. Med. 130 1972 506 527
13. V. Bakatselou R.C. Oppenheim J.B. Dressman Solubilisation and wetting effects of bile salts on the dissolution of steroids Pharm. Res. 8 1991 1461 1469
14. L.J. Naylor V. Bakatselou J.B. Dressman Comparison of the mechanism of dissolution of hydro-cortisone in simple and mixed micelle systems Pharm. Res. 10 1993 865 870
15. A.F. Hofmann B. Borgstrom Physico-chemical state of lipids in intestinal content during their digestion and absorption Fed. Proc. 21 1962 43 50
16. A.F. Hofmann B. Borgstrom The intraluminal phase of fat digestion in man: The lipid content of the micellar and oil phases of intestinal content obtained during fat digestion and absorption J. Clin. Invest. 43 1964 247 257
17. J.E. Staggers O. Hernell R.J. Stafford M.C. Carey Physical-chemical behaviour of dietary and biliary lipids during intestinal digestion and absorption. 1. Phase behaviour and aggregation states of model lipid systems patterned after aqueous duodenal contents of healthy adult human beings Biochemistry 29 1990 2028 2040
18. O. Hernell J.E. Staggers M.C. Carey Physical-chemical behaviour 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 1990 2041 2056
19. H. Westergaard J.M. Dietschy The mechanism whereby bile acid micelles increase the rate of fatty acid and cholesterol uptake into the mucosal cell J. Clin. Invest. 58 1976 97 108
20. N.E. Hoffmann The relationship between uptake in vitro of oleic acid and micellar solubilization Biochim. Biophys. Acta 196 1970 193 203
21. W.J. Simmonds The role of micellar solubilisation in lipid absorption Aust. J. Exp. Biol. Med. Sci. 50 1972 403 421
22. M.L. Lucas W. Schneider F.J. Haberich J.A. Blair Direct measurement by pH microelectrode in rat proximal jejunum Proc. Royal Soc. B. 192 1975 39 48
23. Y. Shiau Mechanism of intestinal fatty acid uptake in the rat: the role of an acidic microclimate J. Physiol. 421 1990 463 474
24. J.Y. Kiyasu B. Bloom I.L. Chaikoff The portal transport of absorbed fatty acids J. Biol. Chem. 199 1952 415 419
25. G.B. McDonald M. Weidman Partitioning of polar fatty acids into lymph and portal vein after intestinal absorption in the rat Q. J. Exp. Physiol. 72 1987 153 159
26. G.B. McDonald D.R. Saunders M. Weidman L. Fisher Portal venous transport of long-chain fatty acids absorbed from rat intestine Am. J. Physiol. 239 1980 G141 G150
27. J.R. Senior K.J. Isselbacher Direct esterification of monoglycerides with palmityl coenzyme A by intestinal epithelial subcellular fractions J. Biol. Chem. 237 1962 1454 1459
28. D.B. Zilversmit The composition and structure of lymph chylomicrons in dog, rat and man J. Clin. Invest. 44 1965 1610 1622
29. W.N. Charman V.J. Stella Estimating the maximal potential for intestinal lymphatic transport of lipophilic drug molecules Int. J. Pharm. 34 1986 175 178
30. W.N. Charman Lipid vehicle and formulation effects on intestinal lymphatic drug transport W.N. Charman V.J. Stella Lymphatic Transport of Drugs 1992 CRC Boca Raton 113 179
31. T.J. Raub S.L. Douglas G.W. Melchior W.N. Charman W. Morozowich Methodologies for assessing intestinal lymphatic transport W.N. Charman V.J. Stella Lymphatic Transport of Drugs 1992 CRC Press Boca Raton 63 111
32. W.N. Charman C.J.H. Porter Lipophilic pro-drugs designed for intestinal lymphatic transport Adv. Drug Deliv. Rev. 19 1996 149 169
33. J.N. Hunt M.T. Knox A relation between the chain length of fatty acids and the slowing of gastric emptying J. Physiol. 194 1968 327 336
34. R. Khosla L.C. Feely S.S. Davis Gastrointestinal transit of non-disintegrating tablets in fed subjects Int. J. Pharm. 53 1989 107 117
35. R. Khosla S.S. Davis Gastric emptying and small and large bowel transit of non-disintegrating tablets in fasted subjects Int. J. Pharm. 52 1989 1 10
36. M. Gibaldi S. Feldman Mechanisms of surfactant effects on drug absorption J. Pharm. Sci. 59 1970 579 589
37. E.K. Anderberg T. Lindmark P. Artursson Sodium caprate elicits dilatations in human intestinal tight junctions and enhances drug absorption by the paracellular route Pharm. Res. 10 1993 857 864
38. B.J. Aungst Novel formulation strategies for improving oral bioavailability of drugs with poor membrane permeation or presystemic metabolism J. Pharm. Sci. 82 1993 979 987
39. E.S. Swenson W.B. Milisen W. Curatolo Intestinal permeability enhancement: efficacy, acute local toxicity and reversibility Pharm. Res. 11 1994 1132 1142
40. W. Curatolo R. Ochoa Safety assessment of intestinal permeability enhancers A.G. de Boer Drug Absorption Enhancement 1994 Harwood Academic Switzerland 367 389
41. P.R. Kvietys R.D. Speian M.B. Grisham P. Tso Jejunal mucosal injury and restitution: role of hydrolytic products of food digestion Am. J. Physiol. 261 1991 G384 G391
42. N.A. Armstrong K.C. James Drug release from lipid based dosage forms Part 2 Int. J. Pharm. 6 1980 195 204
43. S. Chakrabarti F.M. Belpaire Bioavailability of phenytoin in lipid containing dosage forms in rats J. Pharm. Pharmacol. 30 1978 330 331
44. J.T. Hargrove W.S. Maxson A.C. Wentz Absorption of oral progesterone is influenced by vehicle and particle size Am. J. Obstet. Gynecol. 161 1989 948 951
45. L.S. Abrams H.S. Weintraub J.E. Patrick J.L. McGuire Comparitive bioavailability of a lipophilic steroid J. Pharm. Sci. 67 1978 1287 1290
46. Y. Yamaoka R.D. Roberts V.J. Stella Low-melting phenytoin prodrugs as alternative oral delivery modes for phenytoin: a model for other high-melting sparingly water-soluble drugs J. Pharm. Sci. 72 1983 400 405
47. V. Stella J. Haslam N. Yata H. Okada S. Lindenbaum T. Higuchi Enhancement of bioavailability of a Hydrophobie amine antimalarial by formulation with oleic acid in a soft gelatin capsule J. Pharm. Sci. 67 1978 1375 1377
48. T. Tokumura Y. Tsushima K. Tatsuishi M. Kayano Y. Machida T. Nagai Enhancement of the oral bioavailability of cinnarizine in oleic acid in beagle dogs J. Pharm. Sci. 76 1987 286 288
49. P.J. Carrigan T.R. Bates 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 1973 1476 1479
50. R.A. Volpenhein D.R. Webb R.J. Jandacek Effect of nonabsorbable lipid, sucrose polyester, on the absorption of DDT by the rat J. Tox. Environ. Health 6 1980 679 683
51. K. Rozman L. Ballhorn T. Rozman Mineral oil in the diet enhances fecal excretion of DDT in the Rhesus monkey Drug Chem. Toxicol. 6 1983 311 316
52. D.C. Bloedow W.L. Hayton Effects of lipids on bioavailability of sulfisoxazole acetyl, dicumerol and griseofulvin in rats J. Pharm. Sci. 65 1976 328 334
53. T.F. Patton P. Gilford Effect of various vehicles and vehicle volumes on oral absorption of triamterene in rats J. Pharm. Sci. 70 1981 1131 1134
54. Y. Yamahira T. Noguchi H. Takenaka T. Maeda Biopharmaceutical studies of lipid containing oral dosage forms: relationship between drug absorption rate and digestibility of vehicles Int. J. Pharm. 3 1979 23 31
55. R.A. Myers V.J. Stella Systemic bioavailability of penclomedine (NSC-338720) from oil-in-water emulsions administered intraduodenally to rats Int. J. Pharm. 78 1992 217 226
56. J. Reymond H. Sucker In vitro model for cyclosporin intestinal absorption in lipid vehicles Pharm. Res. 5 1988 673 676
57. J. Reymond H. Sucker J. Vonderscher In vivo model for cyclosporin intestinal absorption in lipid vehicles Pharm. Res. 5 1988 677 679
58. W.A. Ritschel Microemulsions for improved peptide absorption from the gastrointestinal tract Meth. Find. Exp. Clin. Pharmacol. 13 1991 205 220
59. M.U. Mehta R. Venkataramanan G.J. Burckart R.J. Ptachcinski B. Dalamos S. Stachak D.H. Van Theil S. Iwatsuki T.E. Starzl Effect of bil e on cyclosporin absorption in liver transplant patients Br. J. Clin. Pharmacol. 25 1988 579 584
60. K.J. Palin C.M. Wilson The effect of different oils on the absorption af probucol in the rat J. Pharm. Pharmacol. 36 1984 641 643
61. 3 from two different lipid vehicles in man: comparison of peanut oil and medium chain triglyceride Biopharm. Drug Dispos. 11 1990 807 815
62. H.E. Gallo-Torres J. Ludorf M. Brin The effect of medium-chain triglycerides on the bioavailability of vitamin E Int. J. Vit. Nutr. Res. 48 1978 240 249
63. T.R. Bates P.J. Carrigan Apparent absorption kinetics of micronized griseofulvin after its oral administration on single- and multiple-dose regimens to rats as a corn oil-in-water emulsion and aqueous suspension J. Pharm. Sci. 64 1975 1475 1481
64. T.R. Bates J.A. Sequeira Bioavailability of micronized griseofulvin from corn oil-in-water emulsion, aqueous suspension and commercial tablet dosage forms in humans J. Pharm. Sci. 64 1975 793 797
65. N.J. Greenberger J.B. Rodgers K.J. Isselbacher Absorption of medium and long chain triglycerides: factors influencing their hydrolysis and transport J. Clin. Invest. 45 1966 217 227
66. W.A. Ritschel S. Adolph G.B. Ritschel T. Schroeder Improvement of peroral absorption of cyclosporin by microemulsions Meth. Find. Exp. Clin. Pharmacol. 12 1990 127 134
67. F.J. Alvarez V.J. Stella The role of calcium ions and bile salts on the pancreatic lipase-catalysed hydrolysis of trglyceride emulsions stabilised with lecithin Pharm. Res. 6 1989 449 457
68. T. Kimura E. Fukui A. Kageyu Y. Kurohara T. Nakayama Y. Monta K. Shibusawa S. Ohsawa Y. Takeda Enhancement of oral bioavailability of d -α-tocopherol acetate by lecithin-dispersed aqueous preparations containing medium-chain triglyceridies in rats Chem. Pharm. Bull. 37 1989 439 441
69. E. Fukui H. Kurohara A. Kageyu Y. Kurosaki T. Nakayama T. Kimura Enhancing effect of medium-chain triglycerides on intestinal absorption of d -α- tocopherol acetate from lecithin-dispersed preparations in the rat J. Pharmacobio-Dyn. 12 1989 80 86
70. A.T. Serajuddin P. Sheen D. Mufson D.F. Bernstein M.A. Augustine Physicochemical basis of increased bioavailability of a poorly water-soluble drug following oral administration as organic solutions J. Pharm. Sci. 77 1988 325 329
71. B.D. Tarr S.H. Yalkowsky Enhanced intestinal absorption of cyclosporin in rats through the reduction of emulsion droplet size Pharm. Res. 6 1989 40 43
72. E.A. Mueller J.M. Kovarik J.B. Van Bree W. Tetzloff K. Kutz Improved dose linearity of cyclosporin pharmacokinetics from a microemulsion formulation Pharm. Res. 11 1994 301 304
73. E.A. Mueller J.M. Kovarik J.B. Van Bree J. Grevel K. Kutz Influence of a fat-rich meal on the pharmacokinetics of a new oral formulation of cyclosporin in a crossover comparison with the market formulation Pharm. Res. 11 1994 151 155
74. J.M. Kovarik E.A. Mueller J.B. Van Bree W. Tetzloff K. Kutz Reduced inter- and intra-individual variability in cyclosporin pharmacokinetics from a microemulsion formulation J. Pharm. Sci. 83 1994 444 446
75. I.S. Sketris V. McAlister M.R. Wright Increased cyclosporin bioavailability from a microemulsion formulation in a liver transplant recipient Ann. Pharmacother. 28 1994 962 963
76. A.K. Trull K.K.C. Tan L. Tan G.J.M. Alexander N.V. Jamieson Absorption of cyclosporin from conventional and new microemulsion oral formulations in liver transplant recipients with external biliary diversion Br. J. Clin. Pharmacol. 39 1995 627 631
77. W.N. Charman M.C. Rogge A.W. Boddy B.M. Berger Effect of food and a monoglyceride emulsion formulation on danazoi bioavailability J. Clin. Pharmacol. 33 1993 381 386
78. S.K. Gupta R.C. Manfro S.J. Tomlanovich J.G. Gambertoglio M.R. Garovoy L.Z. Benet Effect of food on the pharmacokinetics of cyclosporin in healthy subjects following oral and intravenous administration J. Clin. Pharmacol. 30 1990 643 653
79. ®: A new oral formulation of cyclosporin Transplant. Proc. 26 1994 2935 2939
80. D. Attwood Microemulsions J. Kreuter Colloidal Drug Delivery Systems 1994 Marcel Dekker, Inc New York 31 71
81. P.P. Constantinides Lipid microemulsions for improving drug dissolution and oral absorption: physical and biopharmaceutical aspects Pharm. Res. 12 1995 1561 1572
82. M.J. Groves D.A. de Galindez The self-emulsifying action of mixed surfactants in oil Acta Pharm. Suec. 13 1976 361 372
83. M.J. Groves R.M.A. Mustafa J.E. Carless Phase studies of mixed phosphated surfactants, n -hexane and water J. Pharm. Pharmacol. 26 1974 616 623
84. M.J. Groves R.M.A. Mustafa Measurement of the ‘spontaneity’ of self-emulsifiable oils J. Pharm. Pharmacol. 26 1974 671 681
85. C.W. Pouton Self-emulsifying drug delivery systems: assessment of their efficiency of emulsification Int. J. Pharmaceut. 27 1985 335 348
86. M.G. Wakerly C.W. Pouton B.J. Meakin F.S. Morton Self-emulsification of vegetable oil-nonsurfactant mixtures: a proposed mechanism of action Am. Chem. Soc. Symp. Ser. 311 1986 242 255
87. S.A. Charman W.N. Charman M.C. Rogge T.D. ai[Wilson F.J. Dutko C.W. Pouton Self-emulsifying drug delivery systems: formulation and biopharmaceutical evaluation of an investigational lipophilic compound Pharm. Res. 9 1992 87 93
88. D.Q.M. Craig H.S.R. Lievens K.G. Pitt D.E. Storey An investigation into the physico-chemical properties of self-emulsifying systems using low frequency dielectric spectroscopy, surface tension measurements and particle size analysis Int. J. Pharmaceut. 96 1993 147 155
89. B receptor antagonist in dogs Pharm. Res. 8 1991 S 272 (Abstract)
90. N.H. Shah M.T. Carvajal C.I. Patel M.H. Infeld A.W. Malick Self-emulsifying drug delivery systems (SEDDS) with polyglycolyzed glycerides for improving in vitro dissolution and oral absorption of lipophilic drugs Int. J. Pharmaceut. 106 1994 15 23
91. J.L. Ford The current status of solid dispersions Pharm. Acta Helv. 61 1986 69 88
92. K.S. Chang C.I. Jarowski Solid dispersion of morphine-tristearin with reduced presystemic inactivation in rats J. Pharm. Sci. 69 1980 466 469
93. F.A. Kincl H.W. Rudel Increasing intestinal absorption of drags by formulation Arch. Pharm. (Weinheim) 319 1986 615 624
94. S. Venkataram J.A. Rogers Characteristics of drug-phospholipid coprecipitates I: Physical properties and dissolution behaviour of griseofulvin-dimyristoylphos-phatidylcholine systems J. Pharm. Sci. 73 1984 757 761
95. S. Venkataram J.A. Rogers Characteristics of drug-phosphoipid coprecipitates II: Unavailability studies of griseofulvin in rats J. Pharm. Sci. 77 1988 933 936
96. G.K. Vudathala J.A. Rogers Oral bioavailability of griseofulvin from aged griseofulvin: lipid coprecipitates: in vivo studies in rats J. Pharm. Sci. 81 1992 1166 1169
97. A.T.M. Serajuddin P. Sheen D. Mufson D.F. Bernstein M.A. Augustine Effect of vehicle amphilicity on the dissolution and bioavailability of a poorly water-soluble drug from solid dispersions J. Pharm. Sci. 77 1988 414 417
98. P.C. Sheen S.I. Kim J.J. Petillo A.T. Serajuddin Bioavailability of a poorly water-soluble drag from tablet and solid dispersion in humans J. Pharm. Sci. 80 1991 712 714
99. J. Drewe R. Meier J. Vonderscher D. Kiss U. Posanski T. Kissel K. Gyr Enhancement of the oral absorption of cyclosporin in man Br. J. Clin. Pharmacol. 34 1992 60 64
100. R. Kinget H. De Greef Absorption characteristics of novel 8-MOP semi-solid-lipid-matrix formulations: In vitro-in vivo correlation Int. J. Pharm. 110 1994 65 73
101. G.K. Vudathala J.A. Rogers Effect of cholesterol on the aging of griseofulvin-phospholipid coprecipitates Int. J. Pharmaceut. 69 1991 13 19
102. C.Y. Wu L.Z. Benet M.F. Hebert S.K. Gupta M. Rowland D.Y. Gomez V.J. Wacher Differentiation of absorption, first-pass gut and hepatic metabolism in man: studies with cyclosporin Clin. Pharmacol. Ther. 58 1995 492 497
103. L.Z. Benet C.Y. Wu M.F. Hebert V.J. Wacher Intestinal drag metabolism and antitransport processes: A potential paradigm shift in oral drag delivery J. Control. Rel. 39 1996 139 143
104. T. Chang L.Z. Benet M.F. Hebert The effect of water soluble vitamin E on cyclosporin pharmacokinetics in healthy volunteers Clin. Pharm. Ther. 59 1996 297 303
105. M.M. Nerurkar P.S. Burton R.T. Borchardt The use of surfactants to enhance the permeability of peptides through Caco-2 cells by inhibition of an apically polarized efflux system Pharm. Res 13 1996 528 534