Gastrointestinal absorption of heparin by lipidization or coadministration with penetration enhancers

Current Drug Delivery

Volumn 2, Issue 3, 2005, Pages 277-287

  Ross, Benjamin P ^a   Toth, Istvan ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

Absorption enhancer; Gastrointestinal absorption; Heparin; Lipidization; Low molecular weight heparin; Oral drug delivery; Penetration enhancer; Unfractionated heparin

Indexed keywords

ANTICOAGULANT AGENT; CARBOMER; CARBOXYMETHYLCHITOSAN; CHITOSAN; DECANOIC ACID; DEOXYCHOLIC ACID; ENOXAPARIN; FATTY ACID; GELUCIRE; GELUCIRE 44/14; GLUTATHIONE; HEPARIN; LABRASOL; LIPID; LOW MOLECULAR WEIGHT HEPARIN; NANOPARTICLE; OCTANOIC ACID; OPOCRIN; PARNAPARIN; POLYCAPROLACTONE; POLYCARBOPHIL; POLYGLACTIN; POLYMER; RAZAXABAN; SAPONIN; SODIUM N [10 (2 HYDROXYBENZOYL)AMINO]DECANOATE; SODIUM N [8 (2 HYDROXYBENZOYL)AMINO]CAPRYLATE; SURFACTANT; UNCLASSIFIED DRUG; WARFARIN; XIMELAGATRAN;

ANIMAL EXPERIMENT; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG DELIVERY SYSTEM; DRUG FORMULATION; DRUG PENETRATION; GASTROINTESTINAL ABSORPTION; MOUSE; NONHUMAN; PARENTERAL DRUG ADMINISTRATION; PRIORITY JOURNAL; RAT; REVIEW;

ADMINISTRATION, ORAL; ANIMALS; ANTICOAGULANTS; DRUG INTERACTIONS; HEPARIN; INTESTINAL ABSORPTION; LIPIDS; MICE; MOLECULAR WEIGHT; RABBITS; RATS; SWINE;

EID: 21744442224     PISSN: 15672018     EISSN: None     Source Type: Journal    
DOI: 10.2174/1567201054367968     Document Type: Review

References (93)

1. Hirsh, J.; Levine, M. N. Blood, 1992, 79, 1-17.
2. Choay, J.; Petitou, M. Medical Journal of Australia, 1986, 144.
3. Hirsh, J.; Warkentin, T. E.; Shaughnessy, S. G.; Anand, S. S.; Halperin, J. L.; Raschke, R.; Granger, C.; Ohman, E. M.; Dalen, J. E. Chest, 2001, 119, 64S-94S.
4. Hoppensteadt, D.; Walenga Jeanine, M.; Farced, J.; Bick Rodger, L. Hematology/oncology clinics of North America, 2003, 17, 313-41.
5. Majerus, P. W.; Tollefsen, D. M. In Goodman & Gilman's The Pharmacological Basis of Therapeutics, Louis Sanford Goodman; Alfred Goodman Oilman; Joel G. Hardman; Lee E. Limbird, Eds.; McGraw-Hill: New York, 2001, pp. 1519-38.
6. Dal Pozzo, A.; Acquasaliente, M.; Geron, M. R.; Andriuoli, G. Thrombosis Research, 1989, 56, 119-24.
7. Mori, S.; Matsuura, A.; Prasad, Y. V. R.; Takada, K. Biological & Pharmaceutical Bulletin, 2004, 27, 418-21.
8. Atkinson, H. C.; Chambers, S. T.; McGinlay, A. M. New Zealand Medical Journal, 1989, 102, 409-11.
9. Therapeutic Guidelines Antibiotic, Therapeutic Guidelines Limited: North Melbourne, 2000.
10. Mustafa, F.; Yang, T.; Khan, M. A.; Ahsan, F. Journal of Pharmaceutical Sciences, 2004, 93, 675-83.
11. Feret, B. Formulary, 2001, 36, 831-7.
12. Petitou, M.; Duchaussoy, P.; Jaurand, G.; Gourvenec, F.; Lederman, I.; Strassel, J. M.; Barzu, T.; Crepon, B.; Herault, J. P.; Lormeau, J. C.; Bernat, A.; Herbert, J. M. Journal of Medicinal Chemistry, 1997, 40, 1600-7.
13. GlaxoSmithKline Receives Authorisation from European Commission for use of Arixtra in Medical Patients [News Release]. GlaxoSmithKline plc; 2005 [cited 2005 7 March]; Available from: URL:http://www.gsk.com/media/archive.htm
14. Heparin [Monograph]. Chromogenix Instrumentation Laboratory SpA; [cited 2004 16 May]; Available from: URL:http:// www.chromogenix.com
15. Bianchini, P.; Bergonzini, G. L.; Parma, B.; Osima, B. Haemostasis, 1995, 25, 288-98.
16. Rang, H. P.; Dale, M. M.; Ritter, J. M. Pharmacology, Churchill Livingstone: Edinburgh, 1999.
17. Erban, S. Journal of Thrombosis and Thrombolysis, 1999, 7, 145-8.
18. Hrebickova, L.; Nawarskas, J. J.; Anderson, J. R. Heart Disease, 2003, 5, 397-408.
19. Gustafsson, D.; Elg, M. Thrombosis Research, 2003, 109, S9-S15.
20. Lam, P. Y. S.; Quan, M.; He, M.; Li, R.; Clark, C. G.; Pinto, D. J. P.; Teleha, C. A.; Alexander, R. S.; Rossi, K. A.; Wright, M. R.; Bai, S. A.; He, K.; Luettgen, J. M.; Wong, P. C.; Knabb, R. M.; Wexler, R. R. Abstracts of Papers, 226th American Chemical Society National Meeting: New York, NY, United States, 2003; pp. MED1-078.
21. Davidson, B. L. Journal of Thrombosis and Thrombolysis, 2004, 16, 49-54.
22. Lee, Y.-K.; Kim, S. H.; Byun, Y. Pharmaceutical Research, 2000, 17, 1259-64.
23. Lee, Y.-k.; Nam, J. H.; Shin, H.-C.; Byun, Y. Circulation, 2001, 104, 3116-20.
24. Ubrich, N.; Hoffart, V.; Vigneron, C.; Huffman, M.; Maincent, P. S.T.P. Pharma Sciences, 2002, 12, 147-55.
25. Muranishi, S. Critical Reviews in Therapeutic Drug Carrier Systems, 1990, 7, 1-33.
26. Van Hoogdalem, E. J.; De Boer, A. G.; Breimer, D. D. Pharmacology & Therapeutics, 1989, 44, 407-43.
27. Aungst, B. J. Journal of Pharmaceutical Sciences, 2000, 89, 429-42.
28. Lindmark, T.; Soderholm, J. D.; Olaison, G.; Alvan, G.; Ocklind, G.; Artursson, P. Pharmaceutical Research, 1997, 14, 930-5.
29. Marti-Mestres, G.; Nielloud, F. Drugs and the Pharmaceutical Sciences, 2000, 105, 1-18.
30. Swenson, E. S.; Curatolo, W. J. Advanced Drug Delivery Reviews, 1992, 8, 39-92.
31. Rama Prasad, Y. V.; Minamimoto, T.; Yoshikawa, Y.; Shibata, N.; Mori, S.; Matsuura, A.; Takada, K. International Journal of Pharmaceutics, 2004, 271, 225-32.
32. Quintanar-Guerrero, D.; Allemann, E.; Fessi, H.; Doelker, E. Pharmaceutical Research, 1997, 14, 119-27.
33. Jonkman, J. H. G.; Hunt, C. A. Pharmaceutisch Weekblad, Scientific Edition, 1983, 5, 41-8.
34. Andriuoli, G.; Bossi, M.; Caramazza, I.; Zoppetti, G. Haemostasis, 1990, 20 Suppl. 1, 154-8.
35. Zoppetti, G.; Caramazza, I.; Murakami, Y.; Ohno, T. Biochimica et Biophysica Acta, 1992, 1156, 92-8.
36. Andriuoli, G.; Caramazza, I.; Galimberti, G.; Zoppetti, G.; Benedini, F.; Sala, A.; Del Soldato, P. Haemostasis, 1992, 22, 113-6.
37. Hayes, P. Y.; Ross, B. P.; Toth, I. Polycationic Lipophilic-Core Dendrons as Penetration Enhancers for the Oral Administration of Low-Molecular-Weight Heparin. In preparation.
38. Gibbons, W. A.; Hughes, R. A.; Charalambous, M.; Christodoulou, M.; Szeto, A.; Aulabaugh, A. E.; Mascagni, P.; Toth, I. Liebigs Annalen der Chemie, 1990, 1175-83.
39. Ross, B. P.; DeCruz, S. E.; Lynch, T. B.; Davis-Goff, K.; Toth, I. Journal of Medicinal Chemistry, 2004, 47, 1251-8.
40. Ross, B. P.; Braddy, A. C.; McGeary, R. P.; Blanchfield, J. T.; Prokai, L.; Toth, I. Molecular Pharmaceutics, 2004, 1, 233-45.
41. Toth, L.; Hillery, A. M.; Wood, I. P.; Magnusson, C.; Artursson, P. International Journal of Pharmaceutics, 1994, 102, 223-30.
42. Toth, I.; Hughes, R. A.; Dekany, G.; Hillery, A. M.; Ward, P. Liebigs Annalen der Chemie, 1994, 685-8.
43. Flinn, N.; Coppard, S.; Toth, I. International Journal of Pharmaceutics, 1996, 137, 33-9.
44. Capila, I.; Linhardt, R. J. Angewandte Chemie, International Edition, 2002, 41, 390-412.
45. Kasai, S.; Nagasawa, H.; Shimamura, M.; Uto, Y.; Hori, H. Bioorganic & Medicinal Chemistry Letters, 2002, 12, 951-4.
46. Sakthivel, T.; Toth, I.; Florence, A. T. Pharmaceutical Research, 1998, 15, 776-82.
47. Al-Jamal, K. T.; Sakthivel, T.; Florence, A. T. International Journal of Pharmaceutics, 2003, 254, 33-6.
48. Leone-Bay, A.; O'Shaughnessy, C.; Agarwal, R.; Rivera-Schaub, T.; Rosado-Gray, C.; Gerspach, L.; Baughman, R. A. Pharmaceutical Technology North America, 2002, 26, 38, 40, 42, 44, 46.
49. Osbourn, A. E. Phytochemistry (Elsevier), 2003, 62, 1-4.
50. Balandrin, M. F. In Advances in Experimental Medicine and Biology, 1996, 404, s1-14.
51. Morrissey, J. P.; Osbourn, A. E. Microbiology and Molecular Biology Reviews, 1999, 63, 708-24.
52. Cho, S. Y.; Sim, J.-s.; Kang, S. S.; Jeong, C.-s.; Linhardt, R. J.; Kim, Y. S. Archives of Pharmacal Research, 2003, 26, 1102-8.
53. Cho, S. Y.; Kim, J. S.; Li, H.; Shim, C.; Linhardt, R. J.; Kim, Y. S. Archives of Pharmacal Research, 2002, 25, 86-92.
54. Patel, M. M.; Smart, J. D.; Nevell, T. G.; Ewen, R. J.; Eaton, P. J.; Tsibouklis, J. Biomacromolecules, 2003, 4, 1184-90.
55. Bernkop-Schnurch, A. In Polymeric Biomaterials, 2002, pp. 147-165.
56. Woolfson, A. D.; Malcolm, R. K.; McCarron, P. A.; Jones, D. S. In Polymeric Biomaterials, 2002, pp. 1063-81.
57. Domard, A.; Domard, M. In Polymeric Biomaterials, 2002, pp. 187-212.
58. Hejazi, R.; Amiji, M. In Polymeric Biomaterials, 2002, pp. 213-37.
59. Thanou, M.; Nihot, M. T.; Jansen, M.; Verhoef, J. C.; Junginger, H. E. Journal of Pharmaceutical Sciences, 2001, 90, 38-46.
60. Thanou, M.; Verhoef, J. C.; Junginger, H. E. Advanced Drug Delivery Reviews, 2001, 52, 117-26.
61. Felt, O.; Einmahl, S.; Gurny, R.; Furrer, P.; Baeyens, V. In Polymeric Biomaterials, 2002, pp. 377-421.
62. Thanou, M.; Verhoef, J. C.; Nihot, M.-T.; Verheijden, J. H. M.; Junginger, H. E. Pharmaceutical Research, 2001, 18, 1638-41.
63. Kast, C. E.; Guggi, D.; Langoth, N.; Bernkop-Schnuerch, A. Pharmaceutical Research, 2003, 20, 931-6.
64. Clausen, A. E.; Kast, C. E.; Bernkop-Schnuerch, A. Pharmaceutical Research, 2002, 19, 602-8.
65. Bernkop-Schnurch, A.; Kast, C. E.; Guggi, D. Journal of Controlled Release, 2003, 93, 95-103.
66. Jiao, Y.; Ubrich, N.; Hoffart, V.; Marchand-Arvier, M.; Vigneron, C.; Hoffman, M.; Maincent, P. Journal of Pharmaceutical Sciences, 2002, 91, 760-8.
67. Jiao, Y.; Ubrich, N.; Marchand-Arvier, M.; Vigneron, C.; Hoffman, M.; Lecompte, T.; Maincent, P. Circulation, 2002, 105, 230-5.
68. Leone-Bay, A.; Paton, D. R.; Freeman, J.; Lercara, C.; O'Toole, D.; Gschneidner, D.; Wang, E.; Harris, E.; Rosado, C.; Rivera, T.; De Vincent, A.; Tai, M.; Mercogliano, F.; Agarwal, R.; Leipold, H.; Baughman, R. A. Journal of Medicinal Chemistry, 1998, 41, 1163-71.
69. Leone-Bay, A.; Freeman, J.; O'Toole, D.; Rosado-Gray, C.; Salo-Kostmayer, S.; Tai, M.; Mercogliano, F.; Baughman, R. A. Journal of Medicinal Chemistry, 2000, 43, 3573-6.
70. Rivera, T. M.; Leone-Bay, A.; Paton, D. R.; Leipold, H. R.; Baughman, R. A. Pharmaceutical Research, 1997, 14, 1830-1834.
71. Baughman, R. A.; Kapoor, S. C.; Agarwal, R. K.; Kisicki, J.; Catella-Lawson, F.; FitzGerald, G. A. Circulation, 1998, 98, 1610-5.
72. Berkowitz, S. D.; Marder, V. J.; Kosutic, G.; Baughman, R. A. Journal of Thrombosis and Haemostasis: JTH, 2003, 1, 1914-9.
73. Emisphere Technologies Reports Results From Phase III Oral Heparin PROTECT Trial [News Release]. Emisphere Technologies, Inc.; 2002 [cited 2004 11 March]; Available from: URL:http://www.emisphere.com/html/pr.html
74. Emisphere Technologies Presents First Analysis of PROTECT Trial at the Annual Meeting of the American Society Of Hematology [News Release]. Emisphere Technologies, Inc.; 2002 [cited 2004 11 March]; Available from: URL:http://www.emisphere. com/html/pr.html
75. Emisphere Technologies Announces Clinical Data On Solid Oral Heparin Formulations [News Release]. Emisphere Technologies, Inc.; 2002 [cited 2004 11 March]; Available from: URL:http://www.emisphere.com/html/pr.html
76. Leone-Bay, A.; Paton, D. R.; Variano, B.; Leipold, H.; Rivera, T.; Miura-Fraboni, J.; Baughman, R. A.; Santiago, N. Journal of Controlled Release, 1998, 50, 41-9.
77. Milstein, S. J.; Leipold, H.; Sarubbi, D.; Leone-Bay, A.; Mlynek, G. M.; Robinson, J. R.; Kasimova, M.; Freire, E. Journal of Controlled Release, 1998, 53, 259-67.
78. Wu, S.-J.; Robinson, J. R. Pharmaceutical Research, 1999, 16, 1266-1272.
79. Brayden, D.; Creed, E.; O'Connell, A.; Leipold, H.; Agarwal, R.; Leone-Bay, A. Pharmaceutical Research, 1997, 14, 1772-9.
80. Desamero, R. Z. B.; Cheng, H.; Cahill, S.; Girvin, M.; Deng, H.; Callender, R.; Rath, P.; Variano, B.; Smart, J. E. Biopolymers, 2002, 67, 26-40.
81. Illum, L. Journal of Controlled Release, 2003, 87, 187-98.
82. Behl, C. R.; Pimplaskar, H. K..; Sileno, A. P.; deMeireles, J.; Romeo, V. D. Advanced Drug Delivery Reviews, 1998, 29, 89-116.
83. Davis, S. S.; Illum, L. Clinical Pharmacokinetics, 2003, 42, 1107-28.
84. Illum, L. Drug Discovery Today, 2002, 7, 1184-9.
85. Arnold, J.; Ahsan, F.; Meezan, E.; Pillion, D. J. Journal of Pharmaceutical Sciences, 2002, 91, 1707-14.
86. Yang, T.; Mustafa, F.; Ahsan, F. Journal of Pharmacy and Pharmacology, 2003, 56, 53-60.
87. Yang, T.; Hussain, A.; Paulson, J.; Abbruscato, T. J.; Ahsan, F. Pharmaceutical Research, 2004, 21, 1127-36.
88. Uraizee, S. A.; McPhillips, A. M.; Sakr, A. A.; Ritschel, W. A. Pharmazeutische Industrie, 1999, 61, 259-62.
89. Zhou, X. H.; Po, A. L. W. International Journal of Pharmaceutics, 1991, 69, 29-41.
90. Hirai, S.; Yashiki, T.; Mima, H. International Journal of Pharmaceutics, 1981, 9, 173-84.
91. Chambliss, W. G. Pharmaceutical Technology, 1983, 7, 124, 126, 128, 130, 132, 138, 140.
92. Murray, L. C.; Tucker, I. G. Australian Journal of Hospital Pharmacy, 1990, 20, 235-8.
93. Samama, M.-M.; Gerotziafas, G. T. Thrombosis Research, 2003, 109, 1-11.