Enabling the intestinal absorption of highly polar antiviral agents: Ion-pair facilitated membrane permeation of zanamivir heptyl ester and guanidino oseltamivir

Molecular Pharmaceutics

Volumn 7, Issue 4, 2010, Pages 1223-1234

  Miller, Jonathan M ^a   Dahan, Arik ^b   Gupta, Deepak ^a   Varghese, Sheeba ^a   Amidon, Gordon L ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

^b BEN GURION UNIVERSITY OF THE NEGEV   (Israel)

Author keywords

antiviral; Ion pair; membrane permeability; membrane transport; oral absorption

Indexed keywords

1 HYDROXY 2 NAPHTHOIC ACID; 5 ACETAMIDO 2,6 ANHYDRO 4 (2,3 BIS(TERT BUTOXYCARBONYL)GUANIDINO) 3,4,5 TRIDEOXY DEXTRO GLYCERO DEXTRO GALACTO NON 2 ENOIC ACID HEPTYL ESTER; 5 ACETAMIDO 2,6 ANHYDRO 4 (2,3 BIS(TERT BUTOXYCARBONYL)GUANIDO) 3,4,5 TRIDEOXY DEXTRO GLYCERO D GALACTO NON 2 ENOIC ACID; 5 ACETAMIDO 2,6 ANHYDRO 4 (GUANIDINO) 3,4,5 TRIDEOXY D GLYCERO DEXTRO GALACTO NON 2 ENOIC ACID HEPTYL ESTER; ANTIVIRUS AGENT; ETHYL 4 ACETAMIDO 5 (2,3 BIS(TERT BUTOXYCARBONYL)GUANIDINO) 3 (PENTAN 3 YLOXY)CYCLOHEX 1 ENE CARBOXYLATE; ETHYL 4 ACETAMIDO 5 GUANIDINO 3 (PENTAN 3 YLOXY)CYCLOHEX 1 ENECARBOXYLATE; GUANIDINO OSELTAMIVIR; METOPROLOL; UNCLASSIFIED DRUG; ZANAMIVIR HEPTYL ESTER;

ANIMAL EXPERIMENT; ARTICLE; CELL STRAIN CACO 2; DRUG PENETRATION; DRUG STRUCTURE; INTESTINE ABSORPTION; ION EXCHANGE; JEJUNUM; LIPOPHILICITY; MALE; MEMBRANE TRANSPORT; NONHUMAN; PERFUSION; PRIORITY JOURNAL; RAT;

EID: 77955235031     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp100050d     Document Type: Article

References (44)

1. Kasim, N. A.; Whitehouse, M.; Ramachandran, C.; Bermejo, M.; Lennernäs, H.; Hussain, A. S.; Junginger, H. E.; Stavchansky, S. A.; Midha, K. K.; Shah, V. P.; Amidon, G. L. Molecular Properties of WHO Essential Drugs and Provisional Biopharmaceutical Classification Mol. Pharmaceutics 2004, 1, 85-96
2. Takagi, T.; Ramachandran, C.; Bermejo, M.; Yamashita, S.; Yu, L. X.; Amidon, G. L. A Provisional Biopharmaceutical Classification of the Top 200 Oral Drug Products in the United States, Great Britain, Spain, and Japan Mol. Pharmaceutics 2006, 3, 631-643
3. Dahan, A.; Miller, J. M.; Amidon, G. L. Prediction of Solubility and Permeability Class Membership: Provisional BCS Classification of the World's Top Oral Drugs AAPS J. 2009, 11, 740-746
4. Lipinski, C. A. Drug-Like Properties and the Causes of Poor Solubility and Poor Permeability J. Pharmacol. Toxicol. Methods 2001, 44, 235-249
5. Martinez, M. N.; Amidon, G. L. A Mechanistic Approach to Understanding the Factors Affecting Drug Absorption: A Review of Fundamentals J. Clin. Pharmacol. 2002, 42, 620-643
6. Lipka, E.; Crison, J.; Amidon, G. L. Transmembrane Transport of Peptide Type Compounds: Prospects for Oral Delivery J. Controlled Release 1996, 39, 121-129
7. Walter, E.; Kissel, T.; Amidon, G. L. The Intestinal Peptide Carrier: A Potential System for Small Peptide Derived Drugs Adv. Drug Delivery Rev. 1996, 20, 33-58
8. Amidon, G. L.; Han, H.; Oh, D. M.; Walter, E.; Hilfinger, J. M. Oral Administration of Peptide and Protein Drugs Alfred Benzon Symp. 1998, 43, 146-156
9. Shin, H.; Landowski, C. P.; Sun, D.; Amidon, G. L. Transporters in the GI Tract Methods Prinb. Med. Chem. 2003, 18, 245-287
10. von Itzstein, M. The War Against Influenza: Discovery and Development of Sialidase Inhibitors Nat. Rev. Drug Discovery 2007, 6, 967-974
11. Massingale, S. Emergence of a Novel Swine-Origin Influenza A (H1N1) Virus in Humans N. Engl. J. Med. 2009, 360, 2605-2615
12. Li, W.; Escarpe, P. A.; Eisenberg, E. J.; Cundy, K. C.; Sweet, C.; Jakeman, K. J.; Merson, J.; Lew, W.; Williams, M.; Zhang, L.; Kim, C. U.; Bischofberger, N.; Chen, M. S.; Mendel, D. B. Identification of GS 4104 as an Orally Bioavailable Prodrug of the Influenza Virus Neuraminidase Inhibitor GS 4071 Antimicrob. Agents Chemother. 1998, 42, 647-653 (Pubitemid 28114822)
13. Miller, J. M.; Dahan, A.; Gupta, D.; Varghese, S.; Amidon, G. L. Quasi-Equilibrium Analysis of the Ion-Pair Mediated Membrane Transport of Low-Permeability Drugs J. Controlled Release 2009, 137, 31-37
14. Miller, J. M. The Impact of Molecular Complexation on Intestinal Membrane Permeability; Ph.D Thesis, University of Michigan: Ann Arbor, 2009.
15. Connors, K. A. Binding Constants. The Measurement of Molecular Complex Stability; John Wiley & Sons: New York, 1987.
16. Grant, D. J. W.; Higuchi, T. Ion Pairs and Solubility Behavior. In Solubility Behavior of Organic Compounds; Weissberger, A., Ed.; John Wiley & Sons: New York, 1990; pp 399 -' 433.
17. Higuchi, T. Physical Chemical Analysis of Percutaneous Absorption Process from Creams and Ointments J. Soc. Cosmet. Chem. 1960, 11, 85-97
18. Higuchi, T. Prodrug, Molecular Structure and Percutaneous Delivery. In Design of Biopharm Properties Through Prodrugs and Analogs; Roche, E. B., Ed.; American Pharmaceutical Association Academy of Pharmaceutical Sciences: Washington. DC, 1977; pp 409 -' 421.
19. Duffey, M. E.; Evans, D. F.; Cussler, E. L. Simultaneous Diffusion of Ions and Ion Pairs Across Liquid Membranes J. Membr. Sci. 1978, 3, 1-14
20. Shitara, E.; Nishimura, Y.; Nerome, K.; Hiramoto, Y.; Takeuchi, T. Synthesis of 6-Acetamido-5-Amino- and -'5-Guanidino-3, 4-Dehydro-N-(2- Ethylbutyryl)- 3-Piperidinecarboxylic Acids Related to Zanamivir and Oseltamivir, Inhibitors of Influenza Virus Neuraminidases Org. Lett. 2000, 2, 3837-40
21. Masuda, T.; Yoshida, S.; Arai, M.; Kaneko, S.; Yamashita, M.; Honda, T. Synthesis and Anti-Influenza Evaluation of Polyvalent Sialidase Inhibitors Bearing 4-Guanidino-Neu5Ac2en Derivatives Chem. Pharm. Bull. 2003, 51, 1386-1398
22. Chandler, M.; Bamford, M. J.; Conroy, R.; Lamont, B.; Patel, B.; Patel, V. K.; Steeples, I. P.; Storer, R.; Weir, N. G.; Wright, M.; Williamson, C. Synthesis of the Potent Influenza Neuraminidase Inhibitor 4-Guanidino Neu5Ac2en. X-Ray Molecular Structure of 5-Acetamido-4-Amino-2,6-Anhydro-3,4,5-Trideoxy-D- Erythro-L-Gluco-Nonionic Acid J. Chem. Soc., Perkin Trans. 1 1995, 9, 1173-1180
23. Martin, R.; Witte, K. L.; Wong, C. H. The Synthesis and Enzymatic Incorporation of Sialic Acid Derivatives for Use as Tools to Study the Structure, Activity, and Inhibition of Glycoproteins and Other Glycoconjugates Bioorg. Med. Chem. 1998, 6, 1283-1292
24. Ogura, H.; Furuhata, K.; Sato, S.; Anazawa, K.; Itoh, M.; Shitori, Y. Synthesis of 9-O-Acyl- And 4-O-Acetyl-Sialic Acids Carbohydr. Res. 1987, 167, 77-86
25. Dahan, A.; Amidon, G. L. Segmental Dependent Transport of Low Permeability Compounds Along the Small Intestine Due to P-Glycoprotein: The Role of Efflux Transport in the Oral Absorption of BCS Class III Drugs Mol. Pharmaceutics 2009, 6, 19-28
26. Kim, J. S.; Mitchell, S.; Kijek, P.; Tsume, Y.; Hilfinger, J.; Amidon, G. L. The Suitability of an In-Situ Perfusion Model for Permeability Determinations: Utility for BCS Class I Biowaiver Requests Mol. Pharmaceutics 2006, 3, 686-694
27. Dahan, A.; Sabit, H.; Amidon, G. L. Multiple Efflux Pumps are Involved in the Transepithelial Transport of Colchicine: Combined Effect of P-Glycoprotein and Multidrug Resistance-Associated Protein 2 Leads to Decreased Intestinal Absorption Throughout the Entire Small Intestine Drug Metab. Dispos. 2009, 37, 2028-2036
28. Fagerholm, U.; Johansson, M.; Lennernas, H. Comparison Between Permeability Coefficients in Rat and Human Jejunum Pharm. Res. 1996, 13, 1336-1342
29. Stahl, P. H.; Wermuth, C. G. Monographs on Acids and Bases. In Handbook of Pharmaceutical Salts Properties, Selection, and Use; Stahl, P. H.; Wermuth, C. G., Eds.; Verlag Helvetica Chimica Acta: Zürich, 2002; pp 265 -' 327.
30. Tomlinson, E. Never Mix a Cation with an Anion Pharm. Int. 1980, 8, 156-158
31. Jonkman, J. H. G.; Hunt, C. A. Ion Pair Absorption of Ionized Drugs- Fact or Fiction Pharm. Weekbl., Sci. Ed. 1983, 5, 41-48
32. Neubert, R. Ion Pair Transport Across Membranes Pharm. Res. 1989, 6, 743-747
33. Quintanar-Guerrero, D.; Allémann, E.; Fessi, F.; Doelker, E. Applications of the Ion-Pair Concept to Hydrophilic Substances with Special Emphasis on Peptides Pharm. Res. 1997, 14, 119-127
34. Meyer, J. D.; Manning, M. C. Hydrophobic Ion Pairing: Altering the Solubility Properties of Biomolecules Pharm. Res. 1998, 15, 188-193
35. Lengsfeld, C. S.; Pitera, D.; Manning, M.; Randolph, T. W. Dissolution and Partitioning Behavior of Hydrophobic Ion-Paired Compounds Pharm. Res. 2002, 19, 1572-1576
36. Irwin, G. M.; Kostenbauder, H. B.; Dittert, L. W.; Staples, R.; Misher, A.; Swintosky, J. V. Enhancement of Gastrointestinal Absorption of a Quaternary Ammonium Compound by Trichloroacetate J. Pharm. Sci. 1969, 58, 313-315
37. Gibaldi, M.; Grundhofer, B. Enhancement of Intestinal Absorption of a Quaternary Ammonium Compound by Salicylate and Trichloroacetate J. Pharm. Sci. 1973, 62, 343-344
38. Walkling, W. D.; Holmes, D. G.; Cressman, W. A.; Dix, R. K.; Piperno, E.; Mosher, A. H. Possible Ion-Pair Mediated Absorption of Mixidine II: Plasma Levels and Histology J. Pharm. Sci. 1978, 67, 948-950
39. Dal Pozzo, A.; Acquasaliente, M.; Geron, M. R. New Heparin Complexes Active By Intestinal Absorption: I-Multiple Ion Pairs With Basic Organic Compounds Thromb. Res. 1989, 56, 119-124
40. Ross, B. P.; DeCruz, S. E.; Lynch, T. B.; Davis-Goff, K.; Toth, I. Design, Synthesis, and Evaluation of a Liposaccharide Drug Delivery Agent: Application to the Gastrointestinal Absorption of Gentamicin J. Med. Chem. 2004, 47, 1251-1258
41. Mrestani, Y.; Härtl, A.; Neubert, R. H. H. Influence of Absorption Enhancers on the Pharmacokinetic Properties of Non-Oral Β-Lactam-Cefpirom Using the Rabbit (Chinchilla) in Vivo Model Int. J. Pharm. 2006, 309, 67-70
42. Lennernäs, H. Intestinal Permeability and its Relevance for Absorption and Elimination Xenobiotica 2007, 37, 1015-1051
43. Walter, E.; Janich, S.; Roessler, B. J.; Hilfinger, J. M.; Amidon, G. L. HT29-MTX/Caco-2 Co-cultures as an in Vitro Model for the Intestinal Epithelium: In Vitro-in Vivo Correlation with Permeability Data from Rats and Humans J. Pharm. Sci. 1996, 85, 1070-1076
44. Pontier, C.; Pachot, J.; Botham, R.; Lenfant, B.; Arnaud, P. HT29-MTX and Caco-2/TC7Monolayers as Predictive Models for Human Intestinal Absorption: Role of the Mucus Layer J. Pharm. Sci. 2001, 90, 1608-1619