A novel excipient, 1-perfluorohexyloctane shows limited utility for the oral delivery of poorly water-soluble drugs

European Journal of Pharmaceutical Sciences

Volumn 42, Issue 4, 2011, Pages 416-422

  Holm, René ^a   Jørgensen, Erling Bonne ^a   Harborg, Michael ^a,b   Larsen, Rune ^a,b   Holm, Per ^a   Müllertz, Anette ^b   Jacobsen, Jette ^b  

^a H LUNDBECK A S   (Denmark)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

1 Perfluorohexyloctane; Bioavailability; Lipid based formulation; Poorly water soluble drugs; Semi fluorinated alkane

Indexed keywords

ANTINEOPLASTIC AGENT; CINNARIZINE; CREMOPHOR; DANAZOL; ESTRADIOL; FENOFIBRATE; GELUCIRE; GRISEOFULVIN; HALOFANTRINE; LABRASOL; LIDOCAINE; MEDIUM CHAIN TRIACYLGLYCEROL; PERFLUOROHEXYLOCTANE; POLYSORBATE 80; PREDNISOLONE; PROBUCOL; ROLIPRAM; SIRAMESINE; SORBITAN LAURATE; SORBITAN OLEATE; SOYBEAN OIL; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; AREA UNDER THE CURVE; ARTICLE; DRUG BIOAVAILABILITY; DRUG DELIVERY SYSTEM; DRUG FORMULATION; DRUG SOLUBILITY; IN VITRO STUDY; LIPOLYSIS; MALE; MAXIMUM PLASMA CONCENTRATION; NONHUMAN; PRIORITY JOURNAL; RAT;

ADMINISTRATION, ORAL; ANIMALS; BIOLOGICAL AVAILABILITY; CHEMISTRY, PHARMACEUTICAL; EXCIPIENTS; FLUOROCARBONS; LIPOLYSIS; MALE; PHARMACEUTICAL PREPARATIONS; PHENANTHRENES; RATS; RATS, SPRAGUE-DAWLEY; SOLUBILITY; SURFACE-ACTIVE AGENTS; TRIGLYCERIDES;

EID: 79952282344     PISSN: 09280987     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejps.2011.01.007     Document Type: Article

References (57)

1. H. Araya, S. Nagao, M. Tomita, and M. Hayashi The novel formulation design of self-emulsifying drug delivery systems (SEDDS) typo O/W microemulsion I: enhancing effects on oral bioavailability of poorly water soluble compounds in rats and beagle dogs Drug Metab. Pharmacokinet. 20 2005 244 256
2. N. Balandraud-Pieri, P.-E. Queneau, F.-X. Caroli-Bosc, P. Bertault-Pérs, A.-M. Montet, A. Durand, and J.-C. Montet Effects of tauroursodeoxycholate solutions on cyclosporin A bioavalability in rats Drug Metab. Dispos. 25 1997 912 916 (Pubitemid 27357687)
3. A. Bondi van der Walls volumes and radii J. Phys. Chem. 68 1964 441 451
4. M. Broniatowski, and P. Dynarowicz-Latka Semifluorinated alkanes - primitive surfactants of fascinating properties Adv. Colloids Interface Sci. 138 2008 63 83
5. S.M. Caliph, W.N. Charman, and C.J.H. Porter Effect of short-, medium-, and long-chain fatty acid-based vehicles on the absolute oral bioavailability and intestinal lymphatic transport of halofantrine and assessment of mass balance in lymph-cannulated and non-cannulated rats J. Pharm. Sci. 89 2000 1073 1084
6. C. Cecutti, A. Novelli, I. Rico, and A. Lattes A new formulation for blood substitutes J. Disp. Sci. Technol. 11 1990 115 123
7. J.O. Christensen, K. Schultz, B. Møllgaard, H.G. Kristensen, and A. Müllertz Solubilisation of poorly water-soluble drugs during in vitro lipolysis of medium- and long chain triacylglycerols Eur. J. Pharm. Sci. 23 2004 287 296 (Pubitemid 39369884)
8. M.J. Colthurst, R.L. Williams, P.S. Hiscott, and I. Grierson Biomaterials used in the posterior segment of the eye Biomaterials 21 2000 649 665 (Pubitemid 30109156)
9. J.F. Cuiné, C.L. Mcevoy, W.N. Charman, C.W. Pouton, G.A. Edwards, H. Benameur, and C.J.H. Porter Evaluation of the impact of surfactant digestion on the bioavailability of danazol after oral administration of lipidic self-emulsifying formulations to dogs J. Pharm. Sci. 97 2008 995 1012 (Pubitemid 351293898)
10. E.W. Cook, and J.S. Pierce Toxicology of fluoro-olefins Nature 242 1973 337 338
11. P.C. de Smidt, M.A. Campanero, and I.F. Trocóniz Intestinal absorption of penclomedine from lipid vehicles in the conscious rat: contribution of emulsification versus digestibility Int. J. Pharm. 270 2004 109 118 (Pubitemid 38077092)
12. D.F. Eaton, and B.E. Smart Are fluorocarbon chains stiffer than hydrocarbon chains - dynamics of end-to-end cyclization in a C8F16 segment monitored by fluorescence J. Am. Chem. Soc. 112 1990 2821 2823
13. A. Fahr, and X. Liu Drug delivery strategies for poorly water-soluble drugs Exp. Opin. Drug Del. 4 2007 403 416 (Pubitemid 47249138)
14. S.C. Gad, C.D. Cassidy, N. Aubert, B. Spainhour, and H. Robbe Nonclinical vehicle use in studies by multiple routes in multiple species Int. J. Toxicol. 25 2006 499 521 (Pubitemid 44888807)
15. Z.-G. Gao, H.-G. Choi, H.-J. Shin, K.-M. Park, S.-J. Lim, K.-J. Hwang, and C.-K. Kim Physicochemical characterization and evaluation of a microemulsion system for oral delivery of cyclosporin A Int. J. Pharm. 161 1998 75 86 (Pubitemid 28080661)
16. R.N. Gursoy, and S. Benita Self-emulsifying drug delivery systems (SEDDS) for improved oral delivery of lipophilic drugs Biomed. Pharmacother. 58 2004 173 182 (Pubitemid 38479922)
17. D.J. Hauss Oral lipid-based formulations Adv. Drug Del. Rev. 59 2007 667 676 (Pubitemid 47285409)
18. H. Hoerauf, K. Kobuch, J. Dresp, and D.H. Menz Combined use of partially fluorinated alkanes, perfluorocarbon liquids and silicon oil: an experimental study Graefe's Arch. Clin. Exp. Ophtalmol. 243 2001 474 477
19. R. Holm, C.J.H. Porter, A. Müllertz, H.G. Kristensen, and W.N. Charman Intestinal lymphatic transport of halofantrine dosed in a structured triglyceride vehicle to conscious rats Pharm. Res. 19 2002 1354 1361
20. D.W. Holt, E.A. Mueller, J.M. Kovarik, J.B. van Bree, and K. Kutz The pharmacokinetics of sandimmun neoral: a new oral formulation of cyclosporine Transplant. Proc. 26 1994 2935 2939 (Pubitemid 24329372)
21. A.J. Humberstone, G.J. Currie, C.J.H. Porter, M.J. Scanlon, and W.N. Charman Simplified liquid-chromatography assay for the quantitation of halofantrine and desbutylhalofantrine in plasma and identification of a degradation product of desbutylhalofantrine formed under alkaline conditions J. Pharm. Biomed. Anal. 13 1995 265 272
22. K. Iwanaga, T. Kushibiki, M. Miyzaki, and M. Kakemi Disposition of lipid-based formulation in the intestinal tract affects the absorption of poorly water-soluble drugs Biol. Pharm. Bull. 29 2006 508 512
23. A.M. Kaukonen, B.J. Boyd, C.J.H. Porter, and W.N. Charman Drug solubilization behavior during in vitro digestion of simple triglyceride lipid solution formulations Pharm. Res. 21 2004 245 253 (Pubitemid 38221969)
24. M.P. Krafft Fluorocarbons and fluorinated amphiphiles in drug delivery and biomedical research Adv. Drug Del. Rev. 47 2001 209 228 (Pubitemid 32324115)
25. M.P. Krafft, I.A. Chittofrat, and J.G. Riess Emulsions and microemulsions with a fluorocarbon phase Curr. Opin. Colloid Interface Sci. 31 2003 S687 S697
26. M.P. Krafft, and J.G. Riess Chemical, physical chemistry, and uses of molecular fluorocarbon-hydrocarbon diblocks, triblocks, and related compounds - unique "apolar" components for self-assembled colloid and interface engineering Chem. Rev. 109 2009 1714 1792
27. M.P. Krafft, and J.G. Riess Stable highly concentrated fluorocarbon gels Angew. Chem. Int. Ed. Engl. 33 1994 1100 1101 (Pubitemid 24987551)
28. A. Larsen, R. Holm, M.L. Pedersen, and A. Müllertz Lipid-based formulations for danazol containing a digestible surfactant, labrafil M2125CS: in vivo bioavailability and In vitro lipolysis in a dynamic lipolysis model Pharm. Res. 25 2008 2769 2777
29. A. Lattes, and I. Ricolattes Microemulsions of perfluorinated and semi-fluorinated compounds. Artificial cells blood substitutes and immobilization Biotecholgy 22 1994 1007 1018 (Pubitemid 24291532)
30. T.D. Le, R.A. Arlauskas, and J.G. Weers Characterization of the lipophilicity of fluorocarbon derivatives containing halogens or hydrocarbon blocks J. Fluorine Chem. 78 1996 155 163 (Pubitemid 126164304)
31. M.L. Lind, J. Jacobsen, R. Holm, and A. Müllertz Intestinal lymphatic transport of halofantrine in rats assessed using a chylomicron flow blocking approach: the influence of polysorbate 60 and 80 Eur. J. Pharm. 35 2008 211 218
32. C.A. Lipinski, F. Lombardo, B.W. Dominy, and P.J. Feeney Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings Adv. Drug Del. Rev. 23 1997 3 25 (Pubitemid 27046991)
33. P. Lo Nostro Aggregates from semifluorinated n-alkanes: how incompatibility determines self-assembly Curr. Opion. Colloid Interface Sci. 8 2003 223 226 (Pubitemid 36980681)
34. H.U. Meier-Kriesche, R. Swinford, B.D. Kahan, P. Brannan, and R.J. Portman Reduced variability of Neoral Pharmacokinetic studies in pediatric transplantation Pediatr. Nephrol. 15 2000 2 6
35. H.U. Meier-Kriesche, R. Swinford, B.D. Kahan, P. Brannan, and R.J. Portman Reduced variability of neoral pharmacokinetic studies in pediatric renal transplantation Pediatr. Nephrol. 16 2001 309
36. F.S. Nielsen, K.B. Petersen, and A. Müllertz Bioavailability of probucol from lipid and surfactant based formulation in minipigs: influence of droplet size and dietary state Eur. J. Pharm. Biopharm. 69 2008 553 562
37. E. Nixon, S. Holland-Crimmin, B. Lupotsky, J. Chan, J. Curtis, K. Dobbs, and Z. Blaxill Applications of adaptive focused acoustics to compound management J. Biomol. Screen. 14 2009 460 467
38. G.A. Peyman, J.A. Schulman, and B. Sullivan Perfluorocarbon liquids in ophthalmology Surv. Ophthalmol. 39 1995 375 395
39. C.J.H. Porter, S.A. Charman, A.J. Humberstone, and W.N. Charman Lymphatic transport of halofantrine in the conscious rat when administered as either the free base or the hydrochloride salt: effect of lipid class and lipid vehicle dispersion J. Pharm. Sci. 85 1996 357 361 (Pubitemid 26105700)
40. J.G. Riess Fluorous micro- and nanophases with a biomedical perspective Tetrahedron 58 2002 4113 4131 (Pubitemid 34467039)
41. J.G. Riess Oxygen carriers ("blood substitutes") - Raison d'Etre, chemistry, and some physiology Chem. Rev. 101 2001 2797 2920
42. J.G. Riess, C. Cornélus, R. Follana, M.P. Krafft, A.-M. Mahé, M. Postel, and L. Zarif Novel fluorocarbon-based injectable oxygen-carrying formulations with long-term room-temperature storage stability Adv. Exp. Med. Biol. 345 1994 227 234 (Pubitemid 24145754)
43. J.G. Riess, and M.P. Krafft Flurocarbon emulsion as in vivo oxygen delivery systems: background and chemistry R.M. Winslow, Blood Substitutes 2006 Academic Press London 254 275
44. J.G. Riess, S. Pace, and L. Zarif Highly effective surfactants with low hemolytic-activity Adv. Mater. 3 1991 249 251
45. J. Sabín, J.M. Ruse, A. González-Pérez, G. Prieto, and F. Sarmiento Characterization of phospholipid + semifluorinated alkane vesicle system Colloids Surf. B 47 2006 64 70 (Pubitemid 43111606)
46. V.M. Sadtler, M.P. Krafft, and J.G. Riess Achieving stable, reverse water-in-fluorocarbon emulsions Angew. Chem. Int. Ed. Engl. 35 1996 1976 1978
47. F. Seeballuck, E. Lawless, M.B. Ashford, and C.M. O'Driscoll Stimulation of triglyceride-rich lipoprotein secretion by polysorbate 80: in vitro and in vivo correlation using Caco-2 cells and a cannulated rat intestinal lymphatic model Pharm. Res. 21 2004 2320 2326 (Pubitemid 40568446)
48. L. Sek, C.J.H. Porter, A.M. Kaukonen, and W.N. Charman Evaluation of the in-vitro digestion profiles of long and medium glycerides and the phase behaviour of their lipolutic products J. Pharm. Pharmacol. 54 2002 29 41 (Pubitemid 34116220)
49. G.J.T. Tiddy Concentration surfactant systems H.F. Eicke, Modern Trends of Colloid Science in Chemistry and Biology 1985 Birkhäuser Verlag Basel 148 183
50. H. Toguchi, Y. Ogawa, K. Iga, T. Yashiki, and T. Shimamoto Gastro-intestinal absorption of ethyl 2-chloro-3-[4-(2-methyl-phenylpropyloxy) phenyl]propionate from different dosage forms in rats and dogs Chem. Pharm. Bull. 38 1990 2792 2796 (Pubitemid 20386053)
51. H. Toguchi, Y. Ogawa, and T. Shimamoto Effect of the physiochemical properties of the emulsion formation on the bioavailability of ethyl 2-chloro-3-[4-(2-methyl-2-phenylpropyloxy)phenyl]propionate in rats Chem. Pharm. Bull. 38 1990 2797 2800 (Pubitemid 20386054)
52. W.-T. Tsai An overview of environmental hazards and exposure risk of hydrofluorocarbons (HFCs) Chemosphere 61 2005 1539 1547 (Pubitemid 41728185)
53. M.P. Turbgerg, and J.E. Brady Semifluorinated hydrocarbons - primitive surfactant molecules J. Am. Chem. Soc. 110 1988 7797 7801
54. H. Tønsberg, R. Holm, J.B. Boll, J. Jacobsen, and A. Müllertz Effects of polysorbate 80 on the in vitro precipitation and oral bioavailability of halofantrine from polyethylene glycol 400 formulations in rats J. Pharm. Pharmacol. 62 2010 63 70
55. N.H. Zangenberg, A. Müllertz, H.G. Kristensen, and L. Hovgaard A dynamic in vitro lypolysis model. I. Controlling the rate of hydrolysis by continuous addition of calcium Eur. J. Pharm. Sci. 14 2001 115 122 (Pubitemid 32737533)
56. N.H. Zangenberg, A. Müllertz, H.G. Kristensen, and L. Hovgaard A dynamic in vitro lipolysis model. II. Evaluation of the model Eur. J. Pharm. Sci. 14 2001 237 244 (Pubitemid 32884320)
57. L. Zarif, M. Postel, B. Septe, L. Trevino, J.G. Riess, A.-M. Mahé, and R. Follana Biodistribution of mixed fluorocarbon-hydrocarbon dowel molecules used as stabilizers of fluorocarbons emulsions: a quantitative study by fluorine nuclear magnetic resonance (NMR) Pharm. Res. 11 1994 122 127 (Pubitemid 24040775)