The development of delivery agents that facilitate the oral absorption of macromolecular drugs

Medicinal Research Reviews

Volumn 20, Issue 2, 2000, Pages 169-186

  Leone Bay, Andrea ^a   Paton, Duncan R ^a   Weidner, John J ^a  

^a Emisphere Technologies Inc   (United States)

Author keywords

Delivery agent; Drug delivery; Heparin; Human growth hormone; Oral drug delivery

Indexed keywords

BACITRACIN; BLOOD CLOTTING FACTOR 10A; CHYMOSTATIN; DRUG ADDITIVE; GAMMA INTERFERON; HEPARIN; HUMAN GROWTH HORMONE; LIPOSOME; N [8 (2 HYDROXYBENZOYL)AMINO]CAPRYLIC ACID; UNCLASSIFIED DRUG; VASOPRESSIN;

ACYLATION; ANTICOAGULATION; ARTICLE; CLINICAL TRIAL; DEEP VEIN THROMBOSIS; DOSE TIME EFFECT RELATION; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG DELIVERY SYSTEM; DRUG FORMULATION; DRUG HYDROLYSIS; HEPARINIZATION; HUMAN; LIPOPHILICITY; MACROMOLECULE; NONHUMAN; PARTIAL THROMBOPLASTIN TIME;

ADMINISTRATION, ORAL; ANIMALS; DRUG CARRIERS; HUMANS; PHARMACOKINETICS;

EID: 0034091858     PISSN: 01986325     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1098-1128(200003)20:2<169::AID-MED4>3.0.CO;2-0     Document Type: Article

References (58)

1. Wearley LL. Recent progress in protein and peptide delivery by noninvasive routes. Crit Rev Ther Drug Carrier Sys 1991;8:331-394.
2. Gombotz WR, Pettit DK. Biodegradable polymers for protein and peptide drug delivery. Bioconjug Chem 1995;6:332-351.
3. Banakar UV. Advances and opportunities in delivery of therapeutic proteins and peptides. J Biomater Appl 1997;11:377-429.
4. Tracy MA. Development and scale-up of a microsphere protein delivery system. Biotechnol Prog 1998;14:108-115.
5. Lee VHL. Enzymatic barriers to peptide and protein absorption and the use of penetration enhancers to modify absorption. In: Davis SS, Illum L, Tomlinson, E, editors. Delivery systems for peptide drugs. New York: Plenum; 1986. p 87-104.
6. Bundegaard H. Prodrugs as a means to improve the delivery of peptide drugs. Adv Drug Deliv Rev 1991;8:1-38.
7. Leone-Bay A, McInnes C, Wang NF, DeMorin F, Achan D, Lercara C, Sarubbi D, Haas S, Press J, Barantsevich E, O'Broin B, Milstein S, Paton D. Microsphere formation in a series of derivatized acids: properties, molecular modeling, and oral delivery of salmon calcitonin. J Med Chem 1995;38:4257-4262.
8. Bartus RT, Tracy MA, Emerich DF, Sale SE. Sustained delivery of proteins for novel therapeutic products. Science 1998;281:1161-1162.
9. Schreier H, Bouwstra J. Liposomes and niosomes as topical drug carriers: dermal and transdermal drug delivery. J Cont Rel 1994;30:1-15.
10. Sarciaux JM, Acar L, Sado PA. Using microemulsion formulations for oral drug delivery of therapeutic peptides. Int J Pharm 1995;120:127-136
11. Pettit DK, Gombotz WR. The development of site-specific drug delivery systems for protein and peptide biopharmaceuticals. Trends Biotech 1998;16:343-349.
12. Arap W, Pasqualini R, Ruoslahti E. Cancer treatment by targeted drug delivery to tumor vasculature in a mouse model. Science 1998;279:377-380.
13. Nimni ME. Polypeptide growth factors: targeted delivery systems. Biomater 1997;18:1201-1225.
14. Mitagotri S, Blankschtein D, Langer R. Ultrasound-mediated transdermal protein delivery. Science 1995;269:850-853.
15. Knutsen K, Krill SL, Zhang J. Solvent-mediated alterations of the stratum corneum. J Cont Rel 1990;11:93-103.
16. Artmann C, Roding J, Ghyczy M, Prazel HG. Liposomes from soya phospholipids as percutaneous drug carriers. Arzneim Forsch Drug Res 1990;40:1363-1368.
17. du Pleiss J, Egbaria K, Ramachandran C, Weiner N. Topical delivery of liposomally encapsulated gamma-interferon. Antiviral Res 1992;18:259-265.
18. Sayani AP, Chien YW. Systemic delivery of peptides and proteins across absorptive mucosae. Crit Rev Ther Drug Carrier Sys 1996;13:85-184.
19. Harris AS. Review: clinical opportunities provided by the nasal administration of peptides. J Drug Target 1993;1:101-116.
20. Silverman SL. Calcitonin. Am J Med Sci 1997;313:13-16.
21. Siminoski K, Josse RG. Calcitonin in the treatment of osteoporosis. Can Med Assoc J 1996;155:962-965.
22. Adjei A, Sundberg D, Miller J, Chun A. Bioavailability of leuprolide acetate following nasal and inhalation delivery to rats and healthy humans. Pharm Res 1992;9:244-249.
23. Igawa T, Maitani Y, Machida Y, Nagai T. Effect of absorption promoters in intranasal administration of human fibroblast Interferon as a powder dosage form in rabbits. Chem Pharm Bull 1989;37:418-421.
24. Morimoto K, Yamaguchi H, Iwakura Y, Morisaka M, Ohashi Y, Nakai Y. Effects of viscous hyaluronate sodium solutions on the nasal absorption of vasopressin and an analogue. Pharm Res 1991;8:471-474.
25. Morimoto K, Yamaguchi H, Iwakura Y, Miyazaki Y, Nakatani E, Iwamoto T, Ohashi Y, Nakai Y. Effects of proteolytic enzyme inhibitors on the nasal absorption of vasopressin and an analogue. Pharm Res 1991;8:1175-1179.
26. Ramjeesingh M, Huan LJ, Wilschanski M, Durie P, Li C, Gyomorey K, Wang Y, Kent G, Tanswell KA, Cutz E, Ackerley C, Bear CE. Assessment of the efficacy of in viva CFTR protein replacement therapy in CF mice. Hum Gene Ther 1998;9:521-528.
27. Fisher AN, Farraj NE, O'Hagan DT, Jabbal-Gill I, Johansen BR, Davis SS, Illum L. Effect of L-alpha-lysophosphatidylcholine on the nasal absorption of human growth hormone in three animal species. Int J Pharm 1991;74:147-156.
28. Yu J, Chien YW. Pulmonary drug delivery: physiologic and mechanistic aspects. Crit Rev Ther Drug Carrier Sys 1997;14:395-453.
29. Patton J. Breathing life into protein drugs. Nature Biotechnol 1998;16:141-143.
30. Kobayashi S, Kondo S, Juni K. Study on the pulmonary delivery of salmon calcitonin in rats: effects of protease inhibitors and absorption enhancers. Pharm Res 1994;11:1239-1243.
31. Adjei A, Doyle R, Pratt M, Finley R, Johnson E. Bioavailability of leuprolide following intratracheal administration to beagle dogs. Int J Pharm 1990;61:135-144.
32. Adjei A, Garren J. Pulmonary delivery of pcptide drugs: effect of particle size on bioavailability of leuprolide acetate in healthy human volunteers. Pharm Res 1992;7:565-569.
33. Smith PL, Wall DA, Gochoco CH, Wilson G. Routes of delivery: case studies. Oral absorption of peptides and proteins. Adv Drug Deliv Rev 1992;8:253-290.
34. Wang W. Oral protein drug delivery. J Drug Target 1996;4:195-232.
35. Fix JA. Oral controlled release technology for peptides: status and future prospects. Pharm Res 1996;13:1760-1764.
36. Bai JPF, Chang LL, Guo JH. Targeting of peptide and protein drugs to specific sites in the oral route. Crit Rev Ther Drug Carrier Sys 1995;12:339-371.
37. Bernkop-Schnurch A. The use of inhibitory agents to overcome the enzymatic barrier to perorally administered therapeutic peptides and proteins. J Cont Rel 1998;52:1-16.
38. Fix JA. Strategies for delivery of peptides utilizing absorption-enhancing agents. J Pharm Sci 1996;85:1282-1285.
39. Bernkop-Schnurch A, Schwarz GH, Kratzel M. Modified mucoadhesive polymers for the peroral administration of mainly elastase degradable therapeutic (poly)peptides. J Cont Rel 1997;47:113-121.
40. Bernkop-Schnurch A, Bratengeyer I, Valenta C. Development and in vitro evaluation of a drug delivery system protecting from trypsinic degradation. Int J Pharm 1997;157:17-25.
41. McConnell RM, Frizzell D, Camp A, Evans ACA, Jones W, Cagle C. New pepstatin analogues: synthesis and pepsin inhibition. J Med Chem 1991;34:2298-2300.
42. Kratzel M, Heissbock R, Bernkop-Schnurch A. Auxiliary agents for the peroral administration of peptide and protein drugs: synthesis and evaluation of novel pepstatin analogues. J Med Chem 1998;41:2339-2344.
43. Leone-Bay A, Ho KK, Agarwal R, Baughman RA, Chaudhary K, De Morin F, Genoble L, McInnes C, Lercara C, Milstein S, O'Toole D, Sarubbi D, Variano B, Paton DR. 4-[4-(2-hydroxybenzoyl)aminophenyl]-butyric acid as a novel oral delivery agent for recombinant human growth hormone. J Med Chem 1996;39:2571-2578. Portions of the accompanying text have been reprinted with permission from J Med Chem 1996;39:2571-2578. Copyright 1996 American Chemical Society.
44. Leone-Bay A, Ho KK, Agarwal R, Baughman RA, Chaudhary K, De Morin F, Genoble L, McInnes C, Lercara C, Milstein S, O'Toole D, Sarubbi D, Variano B, Paton DR. 4-[4-(2-hydroxybenzoyl)aminophenyl]-butyric acid as a novel oral delivery agent for recombinant human growth hormone. J Med Chem 1996;39:2571-2578. Portions of the accompanying text have been reprinted with permission from J Med Chem 1996;39:2571-2578. Copyright 1996 American Chemical Society.
45. Leone-Bay A, Paton DR, Freeman J, Lercara C, O'Toole D, Gschneider D, Wang E, Harris E, Rosado C, Rivera T, De Vincent A, Tai M, Mercogliano F, Agarwal R, Leipold H, Baughman RA. Synthesis and evaluation of compounds that facilitate the gastrointestinal absorption of heparin. J Med Chem 1998;41:1163-1171. Portions of the accompanying text have been reprinted with permission from J Med Chem 1998;41:1163-1171. Copyright 1998 American Chemical Society.
46. Leone-Bay A, Paton DR, Freeman J, Lercara C, O'Toole D, Gschneider D, Wang E, Harris E, Rosado C, Rivera T, De Vincent A, Tai M, Mercogliano F, Agarwal R, Leipold H, Baughman RA. Synthesis and evaluation of compounds that facilitate the gastrointestinal absorption of heparin. J Med Chem 1998;41:1163-1171. Portions of the accompanying text have been reprinted with permission from J Med Chem 1998;41:1163-1171. Copyright 1998 American Chemical Society.
47. Leone-Bay A, Leipold H, Paton DR, Milstein SJ, Baughman RA. Oral delivery of rhGH: preliminary mechanistic considerations. Drug News Perspect 1996;9:586-590.
48. Baughman RA, Kapoor SC, Agarwal RK, Kisicki J, Catella-Lawsen F, FitzGerald GA. Oral delivery of anticoagulant doses of heparin. A randomized, double-blind, controlled study in humans. Circulation 1998;98:1610-1615.
49. Neely EK, Rosenfeld RG. Use and abuse of human growth hormone. Ann Rev Med 1994;45:407-420.
50. Strobl JS, Thomas MJ. Human growth hormone. Pharm Rev 1994;46:1-34.
51. Gallus AS. Anticoagulants in the prevention of venous thrombolism. Baillieres Clin Haematol 1990;3:651-684.
52. Rivera T, Leone-Bay A, Paton D, Leipold H, Baughman RA. Oral delivery of heparin in combination with sodium N-[8-(2-hydroxybenzoyl)amino]caprylate: pharmacological considerations. Pharm Res 1997;14: 1830-1833.
53. Ho KK, Wang NF, Lercara C, O'Toole DC, Achan DM, Vuocolo EA, Leone-Bay A. Solution phase preparation of highly pure amide mixtures via in-situ chlorotrimethylsilane protection and activation. Syn Comm 1997;27:883-895.
54. White DM, Socha LA. Assignee: General Electric Company, Schenectady, NY. Method for preparing polysalicylates. US Pat. No. 4,855,483: Aug. 8, 1989.
55. Ho KK, O'Toole D, Achan DM, Lim KT, Press JB, Leone-Bay A. A Practical Synthesis of ω-aminoalkanoic acid derivatives from cycloalkanones. Syn Comm 1996;26:2641-2649.
56. Duhamel P, Kotera M, Monteil T, Marabout B. J Org Chem 1989;54:4419.
57. Griffen JP, D'Arcy PF, Speirs CJ. A manual of adverse drug interactions. John Wright.
58. Pidgeon C, Ong O, Liu H, Qiu X, Pidgeon M, Dantzig AH, Munroe J, Hornback WJ, Kasher JS, Glunz L, Szczerba T. IAM chromatography: an in vitro screen for predicting drug membrane permeability. J Med Chem 1995;38:590-594 and references cited therein.