Stable drug encapsulation in micelles and microemulsions

International Journal of Pharmaceutics

Volumn 345, Issue 1-2, 2007, Pages 9-25

  Narang, Ajit S ^a   Delmarre, David ^b   Gao, Danchen ^c  

^a BRISTOL MYERS SQUIBB   (United States)

^b CAPSUGEL   (France)

^c Anchen Pharmaceuticals Inc   (United States)

Author keywords

Bioavailability; Hydrophobic drugs; Micelles; Microemulsions; Precipitation; SEDDS; Self emulsifying; Self microemulsifying; SMEDDS; Solubilization

Indexed keywords

ALCOHOL; ALPHA TOCOPHEROL; AMPRENAVIR; ARACHIS OIL; ATORVASTATIN; BEXAROTENE; CALCITRIOL; CAPTEX 355; CORN OIL; CREMOPHOR; CRILLET 4; CYCLOSPORIN A; DEXTRO ALPHA TOCOPHERYL POLYETHYLENE GLYCOL 1000 SUCCINATE; DRONABINOL; DRUG VEHICLE; ESTOL; GELUCIRE; GLYCEROL; LABRAFAC; LABRAFIL M 2125CS; LABRAFIL M1944CS; MACROGOL; OLEIC ACID; OLIVE OIL; PECEOL; POLIDOCANOL; POLOXAMER; POLYOXYETHYLATED GLYCERIDE; POLYOXYETHYLATED OLECI GLYCERIDE; POLYSORBATE 20; POLYSORBATE 40; POLYSORBATE 60; POLYSORBATE 80; PROPOLIS; PROPYLENE GLYCOL; RICINOMACROGOL; RITONAVIR; SESAME SEED OIL; SORBITAN OLEATE; SOYBEAN OIL; SURFACTANT; UNCLASSIFIED DRUG; VEGETABLE OIL;

CRYSTALLIZATION; DISPERSION; DRUG BIOAVAILABILITY; DRUG DELIVERY SYSTEM; DRUG FORMULATION; DRUG STRUCTURE; DRUG TRANSPORT; EMULSION; ENCAPSULATION; HUMAN; LIPOLYSIS; MICELLE; MICROEMULSION; NONHUMAN; PRECIPITATION; PREDICTION; PRIORITY JOURNAL; REVIEW; SOLUTION AND SOLUBILITY;

ANIMALS; BIOLOGICAL AVAILABILITY; CRYSTALLIZATION; DRUG COMPOUNDING; DRUG DELIVERY SYSTEMS; EMULSIONS; HUMANS; MICELLES; PEPTIDES; PHARMACEUTICAL SOLUTIONS; PHARMACOKINETICS; PROTEINS; SOLUBILITY;

EID: 36148996510     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2007.08.057     Document Type: Review

References (77)

1. Aramaki K., Hayashi T., Katsuragi T., Ishitobi M., and Kunieda H. Effect of adding an amphiphilic solubilization improver, sucrose distearate, on the solubilization capacity of nonionic microemulsions. J. Colloid Interface Sci. 236 (2001) 14-19
2. Beattie J. Monodisperse colloids of transition metal and lanthanide compounds. Pure Appl. Chem. 61 (1989) 937-941
3. Brime B., Moreno M.A., Frutos G., Ballesteros M.P., and Frutos P. Amphotericin B in oil-water lecithin-based microemulsions: formulation and toxicity evaluation. J. Pharm. Sci. 91 (2002) 1178-1185
4. Celebi N., Turkyilmaz A., Gonul B., and Ozogul C. Effects of epidermal growth factor microemulsion formulation on the healing of stress-induced gastric ulcers in rats. J. Control Release 83 (2002) 197-210
5. Cho Y.W., and Flynn M. Oral delivery of insulin. Lancet 2 (1989) 1518-1519
6. Cilek A., Celebi N., Tirnaksiz F., and Tay A. A lecithin-based microemulsion of rh-insulin with aprotinin for oral administration: investigation of hypoglycemic effects in non-diabetic and STZ-induced diabetic rats. Int. J. Pharm. 298 (2005) 176-185
7. Constantinides P.P. Lipid microemulsions for improving drug dissolution and oral absorption: physical and biopharmaceutical aspects. Pharm. Res. 12 (1995) 1561-1572
8. Cooney G.F., Jeevanandam V., Choudhury S., Feutren G., Mueller E.A., and Eisen H.J. Comparative bioavailability of Neoral and Sandimmune in cardiac transplant recipients over 1 year. Transplant. Proc. 30 (1998) 1892-1894
9. Dahan A., and Hoffman A. Use of a dynamic in vitro lipolysis model to rationalize oral formulation development for poor water soluble drugs: correlation with in vivo data and the relationship to intra-enterocyte processes in rats. Pharm. Res. 23 (2006) 2165-2174
10. Davey R., Hilton A., Garside J., de la Fuente M., Edmondson M., and Rainsford P. Crystallisation of oil-in-water emulsions. Amphiphile directed nucleation in aqueous emulsions of m-chloronitrobenzene. J. Chem. Soc. Faraday Trans. 92 (1996) 1927-1933
11. de Smidt P.C., Campanero M.A., and Troconiz I.F. Intestinal absorption of penclomedine from lipid vehicles in the conscious rat: contribution of emulsification versus digestibility. Int. J. Pharm. 270 (2004) 109-118
12. Flanagan J., and Singh H. Microemulsions: a potential delivery system for bioactives in food. Crit. Rev. Food Sci. Nutr. 46 (2006) 221-237
13. Furedi-Milhofer H., Garti N., and Kamyshny A. Crystallization from microemulsions-a novel method for the preparation of new crystal forms of aspartame. J. Cryst. Growth 198/199 (1999) 1365-1370
14. Furedi-Milhofer H., Kamishny A., Yano J., Aserin A., and Garti N. Crystallization of organic compounds in reverse micelles. III. Solubilization of aspartame. Langmuir 19 (2003) 5984-5990
15. Gao P., Guyton M.E., Huang T., Bauer J.M., Stefanski K.J., and Lu Q. Enhanced oral bioavailability of a poorly water soluble drug PNU-91325 by supersaturatable formulations. Drug Dev. Ind. Pharm. 30 (2004) 221-229
16. Gao P., Rush B.D., Pfund W.P., Huang T., Bauer J.M., Morozowich W., Kuo M.S., and Hageman M.J. Development of a supersaturable SEDDS (S-SEDDS) formulation of paclitaxel with improved oral bioavailability. J. Pharm. Sci. 92 (2003) 2386-2398
17. Garti N., Avrahami M., and Aserin A. Improved solubilization of celecoxib in U-type nonionic microemulsions and their structural transitions with progressive aqueous dilution. J. Colloid Interface Sci. 299 (2006) 352-365
18. Garti N., Yaghmur A., Leser M.E., Clement V., and Watzke H.J. Improved oil solubilization in oil/water food grade microemulsions in the presence of polyols and ethanol. J. Agric. Food Chem. 49 (2001) 2552-2562
19. Gursoy R.N., and Benita S. Self-emulsifying drug delivery systems (SEDDS) for improved oral delivery of lipophilic drugs. Biomed. Pharmacother. 58 (2004) 173-182
20. Hasegawa A., Taguchi M., Suzuki R., Miyata T., Nakagawa H., and Sugimoto I. Supersaturation mechanism of drugs from solid dispersions with enteric coating agents. Chem. Pharm. Bull. (Tokyo) 36 (1988) 4941-4950
21. Hauss D.J., Fogal S.E., Ficorilli J.V., Price C.A., Roy T., Jayaraj A.A., and Keirns J.J. Lipid-based delivery systems for improving the bioavailability and lymphatic transport of a poorly water-soluble LTB4 inhibitor. J. Pharm. Sci. 87 (1998) 164-169
22. Hou M.J., and Shah D.O. Effects of molecular structure of the interface and continuous phase on solubilization of water in water/oil microemulsions. Langmuir 3 (1987) 1086-1096
23. Hugger E.D., Novak B.L., Burton P.S., Audus K.L., and Borchardt R.T. A comparison of commonly used polyethoxylated pharmaceutical excipients on their ability to inhibit P-glycoprotein activity in vitro. J. Pharm. Sci. 91 (2002) 1991-2002
24. Huie C.W. Recent applications of microemulsion electrokinetic chromatography. Electrophoresis 27 (2006) 60-75
25. Humberstone A.J., and Charman W.N. Lipid-based vehicles for the oral delivery of poorly water soluble drugs. Adv. Drug Deliv. Rev. 25 (1997) 103-128
26. Ishihama Y., Oda Y., Uchikawa K., and Asakawa N. Correlation of octanol-water partition coefficients with capacity factors measured by micellar electrokinetic chromatography. Chem. Pharm. Bull. (Tokyo) 42 (1994) 1525-1527
27. Johannessen E., Walderhaug H., and Balinov B. Aqueous microemulsions of a fluorinated surfactant and oil studied by PFG-NMR: transformation from threadlike to spherical micelles. Langmuir 20 (2004) 336-341
28. Julianto T., Yuen K.H., and Noor A.M. Improved bioavailability of vitamin E with a self emulsifying formulation. Int. J. Pharm. 200 (2000) 53-57
29. Khoo S.M., Humberstone A.J., Porter C.J., Edwards G.A., and Charman W.N. Formulation design and bioavailability assessment of lipidic self-emulsifying formulations of halofantrine. Int. J. Pharm. 167 (1998) 155-164
30. Kraeling M.E., and Ritschel W.A. Development of a colonic release capsule dosage form and the absorption of insulin. Methods Find. Exp. Clin. Pharmacol. 14 (1992) 199-209
31. Lamer V., and Dinegar R. Theory, production and mechanism of formation of monodispersed hydrosols. J. Am. Chem. Soc. 72 (1950) 4847-4854
32. Lawrence M.J., and Rees G.D. Microemulsion-based media as novel drug delivery systems. Adv. Drug Deliv. Rev. 45 (2000) 89-101
33. Leodidis E.B., and Hatton T.A. Amino acids in AOT reversed micelles. 1. Determination of interfacial partition coefficients using the phase-transfer method. J. Phys. Chem. 94 (1990) 6400-6411
34. Leodidis E.B., and Hatton T.A. Amino acids in AOT reversed micelles. 2. The hydrophobic effect and hydrogen bonding as driving forces for interfacial solubilization. J. Phys. Chem. 94 (1990) 6411-6420
35. Leodidis E.B., and Hatton T.A. Amino acids in reversed micelles. 3. Dependence of the interfacial partition coefficient on excess phase salinity and interfacial curvature. J. Phys. Chem. 95 (1991) 5943-5956
36. Leodidis E.B., and Hatton T.A. Amino acids in reversed micelles. 4. Amino acids as cosurfactants. J. Phys. Chem. 95 (1991) 5957-5965
37. Li P., Tabibi S.E., and Yalkowsky S.H. Solubilization of flavopiridol by pH control combined with cosolvents, surfactants, or complexants. J. Pharm. Sci. 88 (1999) 945-947
38. Li P., Tabibi S.E., and Yalkowsky S.H. Solubilization of ionized and un-ionized flavopiridol by ethanol and polysorbate 20. J. Pharm. Sci. 88 (1999) 507-509
39. Li P., Vishnuvajjala R., Tabibi S.E., and Yalkowsky S.H. Evaluation of in vitro precipitation methods. J. Pharm. Sci. 87 (1998) 196-199
40. Lindenberg M., Kopp S., and Dressman J.B. Classification of orally administered drugs on the World Health Organization Model list of essential medicines according to the biopharmaceutics classification system. Eur. J. Pharm. Biopharm. 58 (2004) 265-278
41. Lyons K.C., Charman W.N., Miller R., and Porter C.J. Factors limiting the oral bioavailability of N-acetylglucosaminyl-N-acetylmuramyl dipeptide (GMDP) and enhancement of absorption in rats by delivery in a water-in-oil microemulsion. Int. J. Pharm. 199 (2000) 17-28
42. Madamwar D., and Thakar A. Entrapment of enzyme in water-restricted microenvironment for enzyme-mediated catalysis under microemulsion-based organogels. Appl. Biochem. Biotechnol. 118 (2004) 361-369
43. Malcolmson C., Barlow D.J., and Lawrence M.J. Light-scattering studies of testosterone enanthate containing soybean oil/C18:1E10/water oil-in-water microemulsions. J. Pharm. Sci. 91 (2002) 2317-2331
44. Malcolmson C., Satra C., Kantaria S., Sidhu A., and Lawrence M.J. Effect of oil on the level of solubilization of testosterone propionate into nonionic oil-in-water microemulsions. J. Pharm. Sci. 87 (1998) 109-116
45. Moreno M.A., Ballesteros M.P., and Frutos P. Lecithin-based oil-in-water microemulsions for parenteral use: pseudoternary phase diagrams, characterization and toxicity studies. J. Pharm. Sci. 92 (2003) 1428-1437
46. Mrestani Y., Neubert R.H., and Krause A. Partition behaviour of drugs in microemulsions measured by electrokinetic chromatography. Pharm. Res. 15 (1998) 799-801
47. Neubert R.H., Schmalfuss U., Wolf R., and Wohlrab W.A. Microemulsions as colloidal vehicle systems for dermal drug delivery. Part V. Microemulsions without and with glycolipid as penetration enhancer. J. Pharm. Sci. 94 (2005) 821-827
48. Ni N., El-Sayed M.M., Sanghvi T., and Yalkowsky S.H. Estimation of the effect of NaCl on the solubility of organic compounds in aqueous solutions. J. Pharm. Sci. 89 (2000) 1620-1625
49. Peltola S., Saarinen-Savolainen P., Kiesvaara J., Suhonen T.M., and Urtti A. Microemulsions for topical delivery of estradiol. Int. J. Pharm. 254 (2003) 99-107
50. Podlogar F., Gasperlin M., Tomsic M., Jamnik A., and Rogac M.B. Structural characterisation of water-Tween 40/Imwitor 308-isopropyl myristate microemulsions using different experimental methods. Int. J. Pharm. 276 (2004) 115-128
51. Porter C.J., and Charman W.N. In vitro assessment of oral lipid based formulations. Adv. Drug Deliv. Rev. 50 Suppl. 1 (2001) S127-S147
52. Porter C.J., Kaukonen A.M., Boyd B.J., Edwards G.A., and Charman W.N. Susceptibility to lipase-mediated digestion reduces the oral bioavailability of danazol after administration as a medium-chain lipid-based microemulsion formulation. Pharm. Res. 21 (2004) 1405-1412
53. Pouton C.W. Formulation of self-emulsifying drug delivery systems. Adv. Drug Deliv. Rev. 25 (1997) 47-58
54. Pouton C.W. Lipid formulations for oral administration of drugs: non-emulsifying, self-emulsifying and 'self-microemulsifying' drug delivery systems. Eur. J. Pharm. Sci. 11 Suppl. 2 (2000) S93-S98
55. Prince L.M. Microemulsions versus micelles. J. Colloid Interface Sci. 52 (1975) 182-188
56. Raghavan S.L., Kiepfer B., Davis A.F., Kazarian S.G., and Hadgraft J. Membrane transport of hydrocortisone acetate from supersaturated solutions; the role of polymers. Int. J. Pharm. 221 (2001) 95-105
57. Raghavan S.L., Trividic A., Davis A.F., and Hadgraft J. Effect of cellulose polymers on supersaturation and in vitro membrane transport of hydrocortisone acetate. Int. J. Pharm. 193 (2000) 231-237
58. Raghavan S.L., Trividic A., Davis A.F., and Hadgraft J. Crystallization of hydrocortisone acetate: influence of polymers. Int. J. Pharm. 212 (2001) 213-221
59. Scherlund M., Malmsten M., Holmqvist P., and Brodin A. Thermosetting microemulsions and mixed micellar solutions as drug delivery systems for periodontal anesthesia. Int. J. Pharm. 194 (2000) 103-116
60. Schuleit M., and Luisi P.L. Enzyme immobilization in silica-hardened organogels. Biotechnol. Bioeng. 72 (2001) 249-253
61. Sek L., Boyd B.J., Charman W.N., and Porter C.J. Examination of the impact of a range of Pluronic surfactants on the in-vitro solubilisation behaviour and oral bioavailability of lipidic formulations of atovaquone. J. Pharm. Pharmacol. 58 (2006) 809-820
62. Sek L., Porter C.J., Kaukonen A.M., and Charman W.N. Evaluation of the in-vitro digestion profiles of long and medium chain glycerides and the phase behaviour of their lipolytic products. J. Pharm. Pharmacol. 54 (2002) 29-41
63. Shen H., and Zhong M. Preparation and evaluation of self-microemulsifying drug delivery systems (SMEDDS) containing atorvastatin. J. Pharm. Pharmacol. 58 (2006) 1183-1191
64. Shukla A., Janich M., Jahn K., Krause A., Kiselev M.A., and Neubert R.H. Investigation of pharmaceutical oil/water microemulsions by small-angle scattering. Pharm. Res. 19 (2002) 881-886
65. Shukla A., Janich M., Jahn K., and Neubert R.H. Microemulsions for dermal drug delivery studied by dynamic light scattering: effect of interparticle interactions in oil-in-water microemulsions. J. Pharm. Sci. 92 (2003) 730-738
66. Simonelli A.P., Mehta S.C., and Higuchi W.I. Inhibition of sulfathiazole crystal growth by polyvinylpyrrolidone. J. Pharm. Sci. 59 (1970) 633-638
67. Spernath A., Aserin A., and Garti N. Fully dilutable microemulsions embedded with phospholipids and stabilized by short-chain organic acids and polyols. J. Colloid Interface Sci. 299 (2006) 900-909
68. Spernath A., Yaghmur A., Aserin A., Hoffman R.E., and Garti N. Food-grade microemulsions based on nonionic emulsifiers: media to enhance lycopene solubilization. J. Agric. Food Chem. 50 (2002) 6917-6922
69. Spernath A., Yaghmur A., Aserin A., Hoffman R.E., and Garti N. Self-diffusion nuclear magnetic resonance, microstructure transitions, and solubilization capacity of phytosterols and cholesterol in Winsor IV food-grade microemulsions. J. Agric. Food Chem. 51 (2003) 2359-2364
70. Spiclin P., Homar M., Zupancic-Valant A., and Gasperlin M. Sodium ascorbyl phosphate in topical microemulsions. Int. J. Pharm. 256 (2003) 65-73
71. Strickley R.G. Solubilizing excipients in oral and injectable formulations. Pharm. Res. 21 (2004) 201-230
72. Testard F., and Zemb T. Excess of solubilization and curvature in nonionic microemulsions. J. Colloid Interface Sci. 219 (1999) 11-19
73. Trull A.K., Tan K.K., Tan L., Alexander G.J., and Jamieson N.V. 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
74. Vaze A., Parizo M., and Rusling J.F. Enhanced rates of electrolytic styrene epoxidation catalyzed by cross-linked myoglobin-poly(l-lysine) films in bicontinuous microemulsions. Langmuir 20 (2004) 10943-10948
75. Yano J., Furedi-Milhofer H., Wachtel E., and Garti N. Crystallization of organic compounds in reversed micelles. I. Solubilization of amino acids in water-isooctane-AOT microemulsions. Langmuir 16 (2000) 9996-10004
76. Yap S.P., and Yuen K.H. Influence of lipolysis and droplet size on tocotrienol absorption from self-emulsifying formulations. Int. J. Pharm. 281 (2004) 67-78
77. Zheng J.Y., and Fulu M.Y. Decrease of genital organ weights and plasma testosterone levels in rats following oral administration of leuprolide microemulsion. Int. J. Pharm. 307 (2006) 209-215