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Volumn 12, Issue 6, 2015, Pages 1980-1991

Transformation of poorly water-soluble drugs into lipophilic ionic liquids enhances oral drug exposure from lipid based formulations

Author keywords

cinnarizine; drug absorption; ionic liquid; itraconazole; lipid based formulation; poorly water soluble drug

Indexed keywords

ALCOHOL; CHLORIDE; CINNARIZINE; COUNTERION; DOCUSATE SODIUM; HALOFANTRINE; IONIC LIQUID; ITRACONAZOLE; MEDIUM CHAIN ACYLGLYCEROL;

EID: 84930676120     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp500790t     Document Type: Article
Times cited : (135)

References (38)
  • 2
    • 33847394968 scopus 로고    scopus 로고
    • Lipids and lipid-based formulations: Optimizing the oral delivery of lipophilic drugs
    • Porter, C. J. H.; Trevaskis, N. L.; Charman, W. N. Lipids and lipid-based formulations: optimizing the oral delivery of lipophilic drugs Nat. Rev. Drug Discovery 2007, 6 (3) 231-248
    • (2007) Nat. Rev. Drug Discovery , vol.6 , Issue.3 , pp. 231-248
    • Porter, C.J.H.1    Trevaskis, N.L.2    Charman, W.N.3
  • 3
    • 84890551417 scopus 로고    scopus 로고
    • Lipid-based formulations and drug supersaturation: Harnessing the unique benefits of the lipid digestion/absorption pathway
    • Williams, H. D.; Trevaskis, N. L.; Yeap, Y. Y.; Anby, M. U.; Pouton, C. W.; Porter, C. J. H. Lipid-based formulations and drug supersaturation: harnessing the unique benefits of the lipid digestion/absorption pathway Pharm. Res. 2013, 30 (12) 2976-2992
    • (2013) Pharm. Res. , vol.30 , Issue.12 , pp. 2976-2992
    • Williams, H.D.1    Trevaskis, N.L.2    Yeap, Y.Y.3    Anby, M.U.4    Pouton, C.W.5    Porter, C.J.H.6
  • 5
    • 0034583251 scopus 로고    scopus 로고
    • Ionic liquids. Green solvents for the future
    • Earle, M. J.; Seddon, K. R. Ionic liquids. Green solvents for the future Pure Appl. Chem. 2000, 72 (7) 1391-1398
    • (2000) Pure Appl. Chem. , vol.72 , Issue.7 , pp. 1391-1398
    • Earle, M.J.1    Seddon, K.R.2
  • 6
    • 0032023219 scopus 로고    scopus 로고
    • Designer solvents
    • Freemantle, M. Designer solvents Chem. Eng. News 1998, 76, 32-37
    • (1998) Chem. Eng. News , vol.76 , pp. 32-37
    • Freemantle, M.1
  • 7
    • 77950493643 scopus 로고    scopus 로고
    • Task-specific ionic liquids
    • Giernoth, R. Task-specific ionic liquids Angew. Chem., Int. Ed. 2010, 49 (16) 2834-2839
    • (2010) Angew. Chem., Int. Ed. , vol.49 , Issue.16 , pp. 2834-2839
    • Giernoth, R.1
  • 8
    • 38349047179 scopus 로고    scopus 로고
    • Applications of ionic liquids in the chemical industry
    • Plechkova, N. V.; Seddon, K. R. Applications of ionic liquids in the chemical industry Chem. Soc. Rev. 2008, 37 (1) 123-150
    • (2008) Chem. Soc. Rev. , vol.37 , Issue.1 , pp. 123-150
    • Plechkova, N.V.1    Seddon, K.R.2
  • 9
    • 84869997019 scopus 로고    scopus 로고
    • Belousov-Zhabotinsky reaction in protic ionic liquids
    • Ueki, T.; Watanabe, M.; Yoshida, R. Belousov-Zhabotinsky reaction in protic ionic liquids Angew. Chem., Int. Ed. 2012, 51 (48) 11991-11994
    • (2012) Angew. Chem., Int. Ed. , vol.51 , Issue.48 , pp. 11991-11994
    • Ueki, T.1    Watanabe, M.2    Yoshida, R.3
  • 10
    • 74049103774 scopus 로고    scopus 로고
    • Ionic liquids and catalysis: Recent progress from knowledge to applications
    • Olivier-Bourbigou, H.; Magna, L.; Morvan, D. Ionic liquids and catalysis: Recent progress from knowledge to applications Appl. Catal., A 2010, 373 (1-2) 1-56
    • (2010) Appl. Catal., A , vol.373 , Issue.12 , pp. 1-56
    • Olivier-Bourbigou, H.1    Magna, L.2    Morvan, D.3
  • 11
    • 0000034575 scopus 로고    scopus 로고
    • Ionic liquids - New 'solutions' for transition metal catalysis
    • Wasserscheid, P.; Keim, W. Ionic liquids-New 'solutions' for transition metal catalysis Angew. Chem., Int. Ed. 2000, 39 (21) 3772-3789
    • (2000) Angew. Chem., Int. Ed. , vol.39 , Issue.21 , pp. 3772-3789
    • Wasserscheid, P.1    Keim, W.2
  • 13
    • 0242441647 scopus 로고    scopus 로고
    • Ionic liquids to the rescue? Overcoming the ionic conductivity limitations of polymer electrolytes
    • Shin, J. H.; Henderson, W. A.; Passerini, S. Ionic liquids to the rescue? Overcoming the ionic conductivity limitations of polymer electrolytes Electrochem. Commun. 2003, 5 (12) 1016-1020
    • (2003) Electrochem. Commun. , vol.5 , Issue.12 , pp. 1016-1020
    • Shin, J.H.1    Henderson, W.A.2    Passerini, S.3
  • 14
    • 84858302159 scopus 로고    scopus 로고
    • An understanding of the modulation of photophysical properties of curcumin inside a micelle formed by an ionic liquid: A new possibility of tunable drug delivery system
    • Ghatak, C.; Rao, V. G.; Mandal, S.; Ghosh, S.; Sarkar, N. An understanding of the modulation of photophysical properties of curcumin inside a micelle formed by an ionic liquid: a new possibility of tunable drug delivery system J. Phys. Chem. B 2012, 116 (10) 3369-3379
    • (2012) J. Phys. Chem. B , vol.116 , Issue.10 , pp. 3369-3379
    • Ghatak, C.1    Rao, V.G.2    Mandal, S.3    Ghosh, S.4    Sarkar, N.5
  • 15
    • 78149452616 scopus 로고    scopus 로고
    • Current-stimulated release of solutes solubilized in water-immiscible room temperature ionic liquids (RTILs)
    • Jaitely, V.; Mizuuchi, H.; Florence, A. T. Current-stimulated release of solutes solubilized in water-immiscible room temperature ionic liquids (RTILs) J. Drug Target. 2010, 18 (10) 787-793
    • (2010) J. Drug Target. , vol.18 , Issue.10 , pp. 787-793
    • Jaitely, V.1    Mizuuchi, H.2    Florence, A.T.3
  • 16
    • 76949096875 scopus 로고    scopus 로고
    • Ionic liquid-assisted transdermal delivery of sparingly soluble drugs
    • Moniruzzaman, M.; Tahara, Y.; Tamura, M.; Kamiya, N.; Goto, M. Ionic liquid-assisted transdermal delivery of sparingly soluble drugs Chem. Commun. 2010, 46 (9) 1452-1454
    • (2010) Chem. Commun. , vol.46 , Issue.9 , pp. 1452-1454
    • Moniruzzaman, M.1    Tahara, Y.2    Tamura, M.3    Kamiya, N.4    Goto, M.5
  • 17
    • 75649097379 scopus 로고    scopus 로고
    • Ionogels as drug delivery system: One-step sol-gel synthesis using imidazolium ibuprofenate ionic liquid
    • Viau, L.; Tourne-Peteilh, C.; Devoisselle, J. M.; Vioux, A. Ionogels as drug delivery system: one-step sol-gel synthesis using imidazolium ibuprofenate ionic liquid Chem. Commun. 2010, 46 (2) 228-230
    • (2010) Chem. Commun. , vol.46 , Issue.2 , pp. 228-230
    • Viau, L.1    Tourne-Peteilh, C.2    Devoisselle, J.M.3    Vioux, A.4
  • 18
    • 84892844864 scopus 로고    scopus 로고
    • Ionic liquids provide unique opportunities for oral drug delivery: Structure optimization and in vivo evidence of utility
    • Williams, H. D.; Sahbaz, Y.; Ford, L.; Nguyen, T. H.; Scammells, P. J.; Porter, C. J. H. Ionic liquids provide unique opportunities for oral drug delivery: structure optimization and in vivo evidence of utility Chem. Commun. 2014, 50 (14) 1688-1690
    • (2014) Chem. Commun. , vol.50 , Issue.14 , pp. 1688-1690
    • Williams, H.D.1    Sahbaz, Y.2    Ford, L.3    Nguyen, T.H.4    Scammells, P.J.5    Porter, C.J.H.6
  • 19
    • 77149123276 scopus 로고    scopus 로고
    • In search of pure liquid salt forms of aspirin: Ionic liquid approaches with acetylsalicylic acid and salicylic acid
    • Bica, K.; Rijksen, C.; Nieuwenhuyzen, M.; Rogers, R. D. In search of pure liquid salt forms of aspirin: ionic liquid approaches with acetylsalicylic acid and salicylic acid Phys. Chem. Chem. Phys. 2010, 12 (8) 2011-2017
    • (2010) Phys. Chem. Chem. Phys. , vol.12 , Issue.8 , pp. 2011-2017
    • Bica, K.1    Rijksen, C.2    Nieuwenhuyzen, M.3    Rogers, R.D.4
  • 20
    • 84861626939 scopus 로고    scopus 로고
    • Pharmaceutically active ionic liquids with solids handling, enhanced thermal stability, and fast release
    • Bica, K.; Rodriguez, H.; Gurau, G.; Cojocaru, O. A.; Riisager, A.; Fehrmann, R.; Rogers, R. D. Pharmaceutically active ionic liquids with solids handling, enhanced thermal stability, and fast release Chem. Commun. 2012, 48 (44) 5422-5424
    • (2012) Chem. Commun. , vol.48 , Issue.44 , pp. 5422-5424
    • Bica, K.1    Rodriguez, H.2    Gurau, G.3    Cojocaru, O.A.4    Riisager, A.5    Fehrmann, R.6    Rogers, R.D.7
  • 21
    • 61749089401 scopus 로고    scopus 로고
    • Exploring an anti-crystal engineering approach to the preparation of pharmaceutically active ionic liquids
    • Dean, P. M.; Turanjanin, J.; Yoshizawa-Fujita, M.; MacFarlane, D. R.; Scott, J. L. Exploring an anti-crystal engineering approach to the preparation of pharmaceutically active ionic liquids Cryst. Growth Des. 2009, 9, 1137-1145
    • (2009) Cryst. Growth Des. , vol.9 , pp. 1137-1145
    • Dean, P.M.1    Turanjanin, J.2    Yoshizawa-Fujita, M.3    Macfarlane, D.R.4    Scott, J.L.5
  • 26
    • 84879706514 scopus 로고    scopus 로고
    • The potential for drug supersaturation during intestinal processing of lipid-based formulations may be enhanced for basic drugs
    • Yeap, Y. Y.; Trevaskis, N. L.; Porter, C. J. H. The potential for drug supersaturation during intestinal processing of lipid-based formulations may be enhanced for basic drugs Mol. Pharmaceutics 2013, 10 (7) 2601-2615
    • (2013) Mol. Pharmaceutics , vol.10 , Issue.7 , pp. 2601-2615
    • Yeap, Y.Y.1    Trevaskis, N.L.2    Porter, C.J.H.3
  • 27
    • 84872497978 scopus 로고    scopus 로고
    • The effect of administered dose of lipid-based formulations on the in Vitro and in Vivo performance of cinnarizine as a model poorly water-soluble drug
    • Lee, K. W. Y.; Porter, C. J. H.; Boyd, B. J. The effect of administered dose of lipid-based formulations on the In Vitro and In Vivo performance of cinnarizine as a model poorly water-soluble drug J. Pharm. Sci. 2013, 102 (2) 565-578
    • (2013) J. Pharm. Sci. , vol.102 , Issue.2 , pp. 565-578
    • Lee, K.W.Y.1    Porter, C.J.H.2    Boyd, B.J.3
  • 28
    • 84890554946 scopus 로고    scopus 로고
    • A Mouse model to evaluate the impact of species, sex, and lipid load on lymphatic drug transport
    • Trevaskis, N. L.; Caliph, S. M.; Nguyen, G.; Tso, P.; Charman, W. N.; Porter, C. J. H. A Mouse model to evaluate the impact of species, sex, and lipid load on lymphatic drug transport Pharm. Res. 2013, 30 (12) 3254-3270
    • (2013) Pharm. Res. , vol.30 , Issue.12 , pp. 3254-3270
    • Trevaskis, N.L.1    Caliph, S.M.2    Nguyen, G.3    Tso, P.4    Charman, W.N.5    Porter, C.J.H.6
  • 30
    • 79751484932 scopus 로고    scopus 로고
    • Liquid forms of pharmaceutical co-crystals: Exploring the boundaries of salt formation
    • Bica, K.; Shamshina, J.; Hough, W. L.; MacFarlane, D. R.; Rogers, R. D. Liquid forms of pharmaceutical co-crystals: exploring the boundaries of salt formation Chem. Commun. 2011, 47 (8) 2267-2269
    • (2011) Chem. Commun. , vol.47 , Issue.8 , pp. 2267-2269
    • Bica, K.1    Shamshina, J.2    Hough, W.L.3    Macfarlane, D.R.4    Rogers, R.D.5
  • 31
    • 84874459413 scopus 로고    scopus 로고
    • Prodrug ionic liquids: Functionalizing neutral active pharmaceutical ingredients to take advantage of the ionic liquid form
    • Cojocaru, O. A.; Bica, K.; Gurau, G.; Narita, A.; McCrary, P. D.; Shamshina, J. L.; Barber, P. S.; Rogers, R. D. Prodrug ionic liquids: functionalizing neutral active pharmaceutical ingredients to take advantage of the ionic liquid form MedChemComm 2013, 4 (3) 559-563
    • (2013) MedChemComm , vol.4 , Issue.3 , pp. 559-563
    • Cojocaru, O.A.1    Bica, K.2    Gurau, G.3    Narita, A.4    McCrary, P.D.5    Shamshina, J.L.6    Barber, P.S.7    Rogers, R.D.8
  • 32
    • 77953155195 scopus 로고    scopus 로고
    • Crystalline vs. Ionic liquid salt forms of active pharmaceutical ingredients: A position paper
    • Stoimenovski, J.; MacFarlane, D. R.; Bica, K.; Rogers, R. D. Crystalline vs. Ionic liquid salt forms of active pharmaceutical ingredients: a position paper Pharm. Res. 2010, 27 (4) 521-526
    • (2010) Pharm. Res. , vol.27 , Issue.4 , pp. 521-526
    • Stoimenovski, J.1    Macfarlane, D.R.2    Bica, K.3    Rogers, R.D.4
  • 34
    • 0029996464 scopus 로고    scopus 로고
    • A physicochemical basis for the effect of food on the absolute oral bioavailability of halofantrine
    • Humberstone, A. J.; Porter, C. J. H.; Charman, W. N. A physicochemical basis for the effect of food on the absolute oral bioavailability of halofantrine J. Pharm. Sci. 1996, 85 (5) 525-529
    • (1996) J. Pharm. Sci. , vol.85 , Issue.5 , pp. 525-529
    • Humberstone, A.J.1    Porter, C.J.H.2    Charman, W.N.3
  • 35
    • 0028920379 scopus 로고
    • Beta-cyclodextrin derivatives, Sbe4-Beta-Cd and Hp-Beta-Cd, increase the oral bioavailability of cinnarizine in beagle dogs
    • Jarvinen, T.; Jarvinen, K.; Schwarting, N.; Stella, V. J. Beta-cyclodextrin derivatives, Sbe4-Beta-Cd and Hp-Beta-Cd, increase the oral bioavailability of cinnarizine in beagle dogs J. Pharm. Sci. 1995, 84 (3) 295-299
    • (1995) J. Pharm. Sci. , vol.84 , Issue.3 , pp. 295-299
    • Jarvinen, T.1    Jarvinen, K.2    Schwarting, N.3    Stella, V.J.4
  • 36
    • 12244283119 scopus 로고    scopus 로고
    • Characterization of solid dispersions of itraconazole and hydroxypropylmethylcellulose prepared by melt extrusion - Part i
    • Verreck, G.; Six, K.; Van den Mooter, G.; Baert, L.; Peeters, J.; Brewster, M. E. Characterization of solid dispersions of itraconazole and hydroxypropylmethylcellulose prepared by melt extrusion-part I Int. J. Pharm. 2003, 251 (1-2) 165-174
    • (2003) Int. J. Pharm. , vol.251 , Issue.12 , pp. 165-174
    • Verreck, G.1    Six, K.2    Van Den Mooter, G.3    Baert, L.4    Peeters, J.5    Brewster, M.E.6
  • 37
    • 0026586447 scopus 로고
    • Self-emulsifying drug delivery systems - Formulation and biopharmaceutic evaluation of an investigational lipophilic compound
    • Charman, S. A.; Charman, W. N.; Rogge, M. C.; Wilson, T. D.; Dutko, F. J.; Pouton, C. W. Self-emulsifying drug delivery systems-formulation and biopharmaceutic evaluation of an investigational lipophilic compound Pharm. Res. 1992, 9 (1) 87-93
    • (1992) Pharm. Res. , vol.9 , Issue.1 , pp. 87-93
    • Charman, S.A.1    Charman, W.N.2    Rogge, M.C.3    Wilson, T.D.4    Dutko, F.J.5    Pouton, C.W.6
  • 38
    • 34247333334 scopus 로고    scopus 로고
    • Anion and cation effects on imidazolium salt melting points: A descriptor modelling study
    • Lopez-Martin, I.; Burello, E.; Davey, P. N.; Seddon, K. R.; Rothenberg, G. Anion and cation effects on imidazolium salt melting points: A descriptor modelling study ChemPhysChem 2007, 8 (5) 690-695
    • (2007) ChemPhysChem , vol.8 , Issue.5 , pp. 690-695
    • Lopez-Martin, I.1    Burello, E.2    Davey, P.N.3    Seddon, K.R.4    Rothenberg, G.5


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