Improvement of low bioavailability of a novel factor Xa inhibitor through formulation of cationic additives in its oral dosage form

International Journal of Pharmaceutics

Volumn 421, Issue 2, 2011, Pages 244-251

  Fujii, Yoshimine ^a   Kanamaru, Taro ^a   Kikuchi, Hiroshi ^b   Nakagami, Hiroaki ^c   Yamashita, Shinji ^d   Akashi, Mitsuru ^e   Sakuma, Shinji ^d  

^a DAIICHI SANKYO CO   (Japan)

^b EISAI CO LTD   (Japan)

^c Pharmaceutical Manufacturers' Association of Tokyo   (Japan)

^d SETSUNAN UNIVERSITY   (Japan)

^e OSAKA UNIVERSITY   (Japan)

Author keywords

Bile acid; Bioavailability; Cholestyramine; Electrostatic interaction; Factor Xa inhibitor; Nanosphere

Indexed keywords

2 [4 [(1 ACETIMIDOYL 3 PYRROLIDINYL)OXY]PHENYL] 3 (7 AMIDINO 2 NAPHTHYL)PROPIONIC ACID; BILE ACID; CHENODEOXYCHOLIC ACID; COLESTYRAMINE; DRUG ADDITIVE; NANOSPHERE; POLYSTYRENE;

ADULT; ANIMAL EXPERIMENT; ARTICLE; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG DOSAGE FORM; EXPERIMENTAL MONKEY; FEMALE; HUMAN; HUMAN EXPERIMENT; MALE; MEMBRANE PERMEABILITY; NONHUMAN; NORMAL HUMAN; PRIORITY JOURNAL; RAT; SYRUP;

ADMINISTRATION, ORAL; ADULT; ANIMALS; ANTICOAGULANTS; BILE ACIDS AND SALTS; BIOLOGICAL AVAILABILITY; CHOLESTYRAMINE RESIN; CROSS-OVER STUDIES; DOSAGE FORMS; FACTOR XA; FEMALE; HAPLORHINI; HUMANS; ION EXCHANGE RESINS; MACACA FASCICULARIS; NANOSPHERES; NAPHTHALENES; POLYMERS; PROPIONIC ACIDS; RATS; RATS, SPRAGUE-DAWLEY; YOUNG ADULT;

EID: 81755173460     PISSN: 03785173     EISSN: 18733476     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2011.09.046     Document Type: Article

References (37)

1. M. Akashi, I. Kirikihira, and N. Miyauchi Synthesis and polymerization of a styryl terminated oligovinylpyrrolidone macromonomer Angew. Macromol. Chem. 132 1985 81 89
2. M. Akashi, M. Wada, S. Yanase, and N. Miyauchi Polymer drugs and polymeric drugs. II. Synthesis of water dispersible microspheres having 5-fluorouracil and theophylline using a water soluble macromonomer J. Polym. Sci. Part C: Polym. Lett. 27 1989 377 380
3. M. Akashi, T. Niikawa, T. Serizawa, T. Hayakawa, and M. Baba Capture of HIV-1 gp120 and virions by lectin-immobilized polystyrene nanospheres Bioconjug. Chem. 9 1998 50 53
4. S.W. Altmann, H.R. Davis Jr., L.J. Zhu, X. Yao, L.M. Hoos, G. Tetzloff, S.P. Iyer, M. Maguire, A. Golovko, M. Zeng, L. Wang, N. Murgolo, and M.P. Graziano Niemann-Pick C1 Like 1 protein is critical for intestinal cholesterol absorption Science 303 2004 1201 1204
5. G.L. Amidon, H. Lennernäs, V.P. Shah, and J.R. Crison A theoretical basis for a biopharmaceutic drug classification: the correlation of in vitro drug product dissolution and in vivo bioavailability Pharm. Res. 12 1995 413 420
6. R. Ara, I. Tumur, A. Pandor, A. Duenas, R. Williams, A. Wilkinson, S. Paisley, and J. Chilcott Ezetimibe for the treatment of hypercholesterolaemia: a systematic review and economic evaluation Health Technol. Assess. 12 2008 1 212
7. M. Ast, and W.H. Frishman Bile acid sequestrants J. Clin. Pharmacol. 30 1990 99 106
8. M.-Q. Chen, A. Kishida, and M. Akashi Graft copolymers having hydrophobic backbone and hydrophilic branches. Preparation and thermosensitive properties of polystyrene microspheres having poly(N-isopropylacrylamide) branches on their surfaces J. Polym. Sci. Part A: Polym. Chem. 34 1996 2213 2220
9. S. Clarysse, J. Tack, F. Lammert, G. Duchateau, C. Reppas, and P. Augustijns Postprandial evolution in composition and characteristics of human duodenal fluids in different nutritional states J. Pharm. Sci. 98 2009 1177 1192
10. Y.-J. Fei, Y. Kanai, S. Nussberger, V. Ganapathy, F.H. Leibach, M.F. Romero, S.K. Singh, W.F. Boron, and M.A. Hediger Expression cloning of a mammalian protein-coupled oligopeptide transporter Nature 368 1994 563 566
11. Y. Fujii, M. Takahashi, H. Morita, H. Kikuchi, Y. Aramaki, and G.L. Amidon Characteristics of gastrointestinal absorption of DX-9065a, a new synthetic anticoagulant Drug Metab. Pharmcokinet. 22 2007 26 32
12. Y. Fujii, T. Kanamaru, H. Kikuchi, S. Yamashita, and S. Sakuma Enteric-coated tablets improve oral bioavailability of DX-9065, a novel anticoagulant Eur. J. Pharm. Sci. 42 2011 392 399
13. S. Futaki Membrane-permeable arginine-rich peptides and the translocation mechanisms Adv. Drug Deliv. Rev. 57 2005 547 558
14. M.J. Hediger, M.A. Coady, T.S. Ikeda, and E.M. Wright Expression cloning and cDNA sequencing of the Na+/glucose cotransporter Nature 330 1987 379 381
15. K. Hiwatari, S. Sakuma, K. Iwata, Y. Masaoka, M. Kataoka, H. Tachikawa, Y. Shoji, and S. Yamashita Poly(N-vinylacetamide) chains enhance lectin-induced biorecognition through the reduction of nonspecific interactions with non-targets Eur. J. Pharm. Biopharm. 70 2008 453 461
16. C.A. Lipinski, F. Lombardo, B.W. Dominy, and P. Feeney Experimental and computational approaches to estimate solubility and permeability in drug delivery and development setting Adv. Drug Deliv. Rev. 46 2001 3 26
17. M. Morishita, T. Goto, K. Nakamura, A.M. Lowman, K. Takayama, and N.A. Peppas Novel oral insulin delivery systems based on complexation polymer hydrogels: single and multiple administration studies in type 1 and 2 diabetic rats J. Control. Release 110 2006 587 594
18. S. Muranishi Absorption enhancers Crit. Rev. Ther. Drug Carrier Syst. 7 1990 1 34
19. N. Murayama, S. Tanaka, T. Kikuchi, M. Nakaoka, and K. Sudo Radioimmunoassay method for DX-9065a, an anticoagulant agent. Development, evaluation and application to human plasma J. Pharm. Biomed. Anal. 14 1996 1435 1445
20. T. Nagahara, Y. Yokoyama, K. Inamura, S. Katakura, S. Komoriya, H. Yamaguchi, T. Hara, and M. Iwamoto Dibasic (amidinoaryl) propanoic acid derivatives as novel blood coagulation factor Xa inhibitors J. Med. Chem. 37 1994 1200 1207
21. M. Riza, S. Tokura, A. Kishida, and M. Akashi Graft copolymers having a hydrophobic backbone and hydrophilic branches. IX. Preparation of water-dispersible microspheres having polycationic branches on their surfaces New Polym. Mater. 4 1994 189 198
22. M. Riza, S. Tokura, M. Iwasaki, E. Yashima, A. Kishida, and M. Akashi Graft copolymers having hydrophobic backbone and hydrophilic branches. X. Preparation and properties of water-dispersible polyanionic microspheres having poly (methacrylic acid) branches on their surfaces J. Polym. Sci. Polym. Chem. 33 1995 1219 1225
23. M. Saffran, G.S. Kumar, C. Savariar, J.C. Burnham, F. Williams, and D.C. Neckers A new approach to the oral administration of insulin and other peptide drugs Science 233 1986 1081 1084
24. Y. Sai, and A. Tsuji Transporter-mediated drug delivery: recent progress and experimental approach Drug Discov. Today 9 2004 712 720
25. S. Sakuma, N. Suzuki, H. Kikuchi, K. Hiwatari, K. Arikawa, A. Kishida, and M. Akashi Oral peptide delivery using nanoparticles composed of novel graft copolymers having hydrophobic backbone and hydrophilic branches Int. J. Pharm. 149 1997 93 106
26. S. Sakuma, Y. Ishida, R. Sudo, N. Suzuki, H. Kikuchi, K. Hiwatari, A. Kishida, M. Akashi, and M. Hayashi Stabilization of salmon calcitonin by polystyrene nanoparticles having surface hydrophilic polymeric chains, against enzymatic degradation Int. J. Pharm. 159 1997 181 189
27. S. Sakuma, R. Sudo, N. Suzuki, H. Kikuchi, K. Hiwatari, M. Akashi, and M. Hayashi Mucoadhesion of polystyrene nanoparticles having surface hydrophilic polymeric chains in the gastrointestinal tract Int. J. Pharm. 177 1999 161 172
28. S. Sakuma, M. Hayashi, and M. Akashi Design of nanoparticles composed of graft copolymers for oral peptide delivery Adv. Drug Deliv. Rev. 47 2001 21 37
29. S. Sakuma, R. Sudo, N. Suzuki, H. Kikuchi, M. Akashi, Y. Ishida, and M. Hayashi Behavior of mucoadhesive nanoparticles having hydrophilic polymeric chains in the intestinal membrane J. Control. Release 81 2002 282 290
30. S. Sakuma, N. Suzuki, R. Sudo, K. Hiwatari, A. Kishida, and M. Akashi Optimized chemical structure of nanoparticles as carriers for oral delivery of salmon calcitonin Int. J. Pharm. 239 2002 185 195
31. S. Sakuma, T. Matsumoto, S. Yamashita, Y. Wang, and Z.-R. Lu Conjugation of poorly absorptive drugs with mucoadhesive polymers for the improvement of oral absorption of drugs J. Control. Release 123 2007 195 202
32. S. Sakuma, T. Yano, Y. Masaoka, M. Kataoka, K. Hiwatari, H. Tachikawa, Y. Shoji, R. Kimura, H. Ma, Z. Yang, L. Tang, R.M. Hoffman, and S. Yamashita In vitro/in vivo biorecognition of lectin-immobilized fluorescent nanospheres for human colorectal cancer cells J. Control. Release 134 2009 2 10
33. S. Sakuma, T. Yano, Y. Masaoka, M. Kataoka, K. Hiwatari, H. Tachikawa, Y. Shoji, R. Kimura, H. Ma, Z. Yang, L. Tang, R.M. Hoffman, and S. Yamashita Detection of early colorectal cancer imaged with peanut agglutinin-immobilized fluorescent nanospheres having surface poly(N-vinylacetamide) chains Eur. J. Pharm. Biopharm. 74 2010 451 460
34. S. Sakuma, M. Kataoka, H. Higashino, T. Yano, Y. Masaoka, S. Yamashita, K. Hiwatari, H. Tachikawa, R. Kimura, K. Nakamura, H. Kumagai, J.C. Gore, and W. Pham A potential of peanut agglutinin-immobilized fluorescent nanospheres as a safe candidate of diagnostic drugs for colonoscopy Eur. J. Pharm. Sci. 42 2011 340 347
35. S. Sakuma, H. Higashino, H. Oshitani, Y. Masaoka, M. Kataoka, S. Yamashita, K. Hiwatari, H. Tachikawa, R. Kimura, K. Nakamura, H. Kumagai, J.C. Gore, and W. Pham Essence of affinity and specificity of peanut agglutinin-immobilized fluorescent nanospheres with surface poly(N- vinylacetamide) chains for colorectal cancer Eur. J. Pharm. Biopharm. 79 2011 537 543
36. I. Tamai, and A. Tsuji Carrier-mediated approaches for oral drug delivery Adv. Drug Deliv. Rev. 20 1996 5 32
37. T. Uchiyama, A. Kotani, H. Tatsumi, T. Kishida, A. Okamoto, and A. Yamamoto Development of novel lipophilic derivatives of DADLE (Leucine enkephalin analogue): intestinal permeability characteristics of DADLE derivatives in rats Pharm. Res. 17 2000 1461 1467