Design of ester prodrugs to enhance oral absorption of poorly permeable compounds: Challenges to the discovery scientist

Current Drug Metabolism

Volumn 4, Issue 6, 2003, Pages 461-485

  Beaumont, Kevin ^a   Webster, Robert ^a   Gardner, Iain ^a   Dack, Kevin ^a  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ADEFOVIR DIPIVOXIL; ALCOHOL; BACAMPICILLIN; BENAZEPRIL; CANDESARTAN HEXETIL; CANDOXATRIL; CARBOXYLIC ACID; CARFECILLIN; CARINDACILLIN; CILAZAPRIL; DELAPRIL; ENALAPRIL; ESTER DERIVATIVE; FAMCICLOVIR; FOSINOPRIL; MOEXIPRIL; MOEXIPRILAT; OSELTAMIVIR; PERINDOPRIL; PIVAMPICILLIN; PRODRUG; QUINAPRIL; RAMIPRIL; SPIRAPRIL; SULTAMICILLIN; TEMOCAPRIL; TENOFOVIR DISOPROXIL; TRANDOLAPRIL; UNINDEXED DRUG; XIMELAGATRAN;

BINDING AFFINITY; CELL TRANSPORT; DRUG ABSORPTION; DRUG DEGRADATION; DRUG DELIVERY SYSTEM; DRUG DESIGN; DRUG DISTRIBUTION; DRUG HYDROLYSIS; DRUG MARKETING; DRUG PENETRATION; DRUG RESEARCH; DRUG SOLUBILITY; DRUG STABILITY; DRUG TARGETING; DRUG TRANSPORT; FOOD DRUG INTERACTION; HUMAN; HYDROGEN BOND; LIPOPHILICITY; MEDICAL LITERATURE; MEMBRANE PERMEABILITY; MOLECULAR SIZE; NONHUMAN; PH; PHYSICAL CHEMISTRY; RAT; REVIEW; STRUCTURE ACTIVITY RELATION;

ADMINISTRATION, ORAL; BILE; DRUG DESIGN; ESTERS; HYDROLYSIS; INTESTINAL ABSORPTION; LIVER; PRODRUGS;

EID: 0346958512     PISSN: 13892002     EISSN: None     Source Type: Journal    
DOI: 10.2174/1389200033489253     Document Type: Review

References (137)

1. Lipinski, C.A.; Lombardo, F.; Dominy, B. and Feeney, P.J. (1997) Advanced Drug Delivery Review 23(1-3), 3-25.
2. Ayrton, A. and Morgan, P. (2001) Xenobiotica 31(8-9), 469-497.
3. Prueksaritanont, T.; Gorham, L.M.; Hochman, J.H.; Tran, L.O. and Vyas, K.P. (1996) Drug Metab. Dispos. 24(6), 634-642.
4. Thummel, K.E.; O'Shea, D.; Paine, M.F.; Shen, D.D.; Kunze, K.L.; Perkins, J.D. and Wilkinson, G.R. (1996) Clin. Pharmacol. Ther. 59(5), 491-502.
5. Lampen, A.; Christians, U.; Guengerich, F.P.; Watkins, P.B.; Kolars, J.C.; Bader, A.; Gonschior, A.K.; Dralle, H.; Hackbarth, I. and Sewing, K.F. (1995) Drug Metab. Dispos. 23(12), 1315-1324.
6. Cappiello, M.; Giuliani, L. and Pacifici, G.M. (1991) Eur. J. Clin. Pharmacol. 41(4), 345-350.
7. Abrams, W.B.; Davies, R.O. and Gomez, H.J. (1984) J. Hypertens. Suppl. 2(2), S31-36.
8. Williams, P.E.; Brown, A.N.; Rajaguru, S.; Francis, R.J.; Walters, G.E.; McEwen, J. and Durnin, C. (1989) Br. J. Clin. Pharmacol. 27 (Suppl. 2), 181S-188S.
9. Thwaites, D.T.; Cavet, M.; Hirst, B.H. and Simmons, N.L. (1995) Br. J. Pharmacol. 114(5), 981-986.
10. Friedman, D.I. and Amidon, G.L. (1989) Pharm. Res. 6(12), 1043-1047.
11. Friedman, D.I. and Amidon, G.L. (1989) J. Pharm. Sci. 78(12), 995-998.
12. Swaan, P.W.; Stehouwer, M.C. and Tukker, J.J. (1995) Biochim. Biophys. Acta 1236(1), 31-38.
13. Kim, J.S.; Oberle, R.L.; Krummel, D.A.; Dressman, J.B. and Fleisher, D. (1994) J. Pharm. Sci. 83(9), 1350-1356.
14. Hu, M.; Zheng, L.; Chen, J.; Liu, L.; Zhu, Y.; Dantzig, A.H. and Stratford, R.E., Jr. (1995) Pharm. Res. 12(8), 1120-1125.
15. Zhu, T.; Chen, X.Z.; Steel, A.; Hediger, M.A. and Smith, D.E. (2000) Pharm. Res. 17(5), 526-532.
16. Swaan, P.W. and Tukker, J.J. (1997) J. Pharm. Sci. 86(5), 596-602.
17. Balfour, J.A. and Goa, K.L. (1991) Drugs 42(3), 511-539.
18. Oguchi, H.; Tokoo, M.; Tokunaga, S.; Higuchi, M.; Hora, K. and Furuta, S. (1995) Cardiovascular Drug Reviews 13(1), 66-85.
19. Todd, P.A. and Heel, R.C. (1986) Drugs 31(3), 198-248.
20. Tocco, D.J.; deLuna, F.A.; Duncan, A.E.; Vassil, T.C. and Ulm, E.H. (1982) Drug Metab. Dispos. 10(1), 15-19.
21. Hauptmann, J. (2002) Eur. J. Clin. Pharmacol. 57(11), 751-758.
22. Gustafsson, D.; Nystrom, J.; Carlsson, S.; Bredberg, U.; Eriksson, U.; Gyzander, E.; Elg, M.; Antonsson, T.; Hoffmann, K.; Ungell, A.; Sorensen, H.; Nagard, S.; Abrahamsson, A. and Bylund, R. (2001) Thromb. Res. 101(3), 171-181.
23. Kaye, B.; Brearley, C.J.; Cussans, N.J.; Herron, M.; Humphrey, M.J. and Mollatt, A.R. (1997) Xenobiotica 27(10), 1091-1102.
24. Tanigawara, Y.; Tamaoka, K.; Nakagawa, T. and Uno, T. (1982) Chem. Pharm. Bull. (Tokyo) 30(6), 2174-2180.
25. Li, Y.H.; Tanno, M.; Itoh, T. and Yamada, H. (1999) Int. J. Pharm. 191(2), 151-159.
26. Morrison, R.A.; Singhvi, S.M.; Peterson, A.E.; Pocetti, D.A. and Migdalof, B.H. (1990) Drug Metab. Dispos. 18(2), 253-257.
27. Friedel, H.A.; Campoli-Richards, D.M. and Goa, K.L. (1989) Drugs 37(4), 491-522.
28. Sorbera, L.A.; Castaner, R. and Castaner, J. (2000) Drugs of the Future 25(5), 474-480.
29. Perry, C.M. and Faulds, D. (1996) Drugs 52(5), 754-772.
30. Han, H.; de Vrueh, R.L.; Rhie, J.K.; Covitz, K.M.; Smith, P.L.; Lee, C.P.; Oh, D.M.; Sadee, W. and Amidon, G.L. (1998) Pharm. Res. 15(8), 1154-1159.
31. Ganapathy, M.E.; Huang, W.; Wang, H.; Ganapathy, V. and Leibach, F.H. (1998) Biochem. Biophys. Res. Commun. 246(2), 470-475.
32. Soul-Lawton, J.; Seaber, E.; On, N.; Wootton, R.; Rolan, P. and Posner, J. (1995) Antimicrob. Agents Chemother. 39(12), 2759-2764.
33. Burnette, T.C.; Harrington, J.A.; Reardon, J.E.; Merrill, B.M. and de Miranda, P. (1995) J. Biol. Chem. 270(26), 15827-15831.
34. Bullingham, R.E.; Nicholls, A.J. and Kamm, B.R. (1998) Clin. Pharmacokinet. 34(6), 429-455.
35. Ranadive, S.A.; Chen, A.X. and Serajuddin, A.T. (1992) Pharm. Res. 9(11), 1480-1486.
36. Hovgaard, L.; Brondsted, H.; Buur, A. and Bundgaard, H. (1995) Pharm. Res. 12(3), 387-392.
37. Artursson, P. (1990) J. Pharm. Sci. 79(6), 476-482.
38. Kamm, W.; Raddatz, P.; Gante, J. and Kissel, T. (1999) Pharm. Res. 16(10), 1527-1533.
39. Abel, S.; Beaumont, K.C.; Crespi, C.L.; Eve, M.D.; Fox, L.; Hyland, R.; Jones, B.C.; Muirhead, G.J.; Smith, D.A.; Venn, R.F. and Walker, D.K. (2001) Xenobiotica 31(8-9), 665-676.
40. Wetterich, U.; Spahn-Langguth, H.; Mutschler, E.; Terhaag, B.; Rosch, W. and Langguth, P. (1996) Pharm. Res. 13(4), 514-522.
41. Prueksaritanont, T.; Deluna, P.; Gorham, L.M.; Ma, B.; Cohn, D.; Pang, J.; Xu, X.; Leung, K. and Lin, J.H. (1998) Drug Metabolism and Disposition 26(6), 520-527.
42. Daehne, W.; Frederiksen, E.; Gundersen, E.; Lund, F.; Morch, P.; Petersen, H.J.; Roholt, K.; Tybring, L. and Godtfredsen, W.O. (1970) J. Med. Chem. 13(4), 607-612.
43. Ehrnebo, M.; Nilsson, S.-O. and Boreus, L.O. (1979) J. Pharmacokinet. Biopharm. 7(5), 429-451.
44. Saito, A. and Nakashima, M. (1986) Antimicrob. Agents Chemother. 29(5), 948-950.
45. Sakamoto, F.; Ikeda, S. and Tsukamoto, G. (1984) Chem. Pharm. Bull. (Tokyo) 32(6), 2241-2248.
46. Nishimura, K.; Nishizawa, S.; Yoshimi, A.; Nakamura, S.; Nishimura, M. and Kakeya, N. (1988) Chem. Pharm. Bull. (Tokyo) 36(6), 2128-2134.
47. Kasai, M.; Hatano, S.; Kitagawa, M.; Yoshimi, A.; Nishimura, K.-I.; Mori, N.; Sakai, A. and Sugihara, T. (1999) Chemical & Pharmaceutical Bulletin 47(8), 1081-1088.
48. Yoshimura, Y.; Hamaguchi, N. and Yashiki, T. (1987) International Journal of Pharmaceutics 38(1-3), 179-190.
49. Kakeya, N.; Nishimura, K.; Yoshimi, A.; Nakamura, S.; Nishizawa, S.; Tamaki, S.; Matsui, H.; Kawamura, T.; Kasai, M. and Kitao, K. (1984) Chem. Pharm. Bull. (Tokyo) 32(2), 692-698.
50. Obermeier, M.T.; Chong, S.; Dando, S.A.; Marino, A.M.; Ryono, D.E.; Starrett-Arroyo, A.; DiDonato, G.C.; Warrack, B.M., White, R.E. and Morrison, R.A. (1996) J. Pharm. Sci. 85(8), 828-833.
51. Aungst, B.J.; Blake, J.A.; Rogers, N.J.; Saitoh, H.; Hussain, M.A.; Ensinger, C.L. and Pruitt, J.R. (1995) Pharm. Res. 12(5), 763-767.
52. Kubo, K.; Kohara, Y.; Yoshimura, Y.; Inada, Y.; Shibouta, Y.; Furukawa, Y.; Kato, T.; Nishikawa, K. and Naka, T. (1993) J. Med. Chem. 36(16), 2343-2349.
53. Yoshimura, Y.; Tada, N.; Koubo, K.; Miyamoto, M.; Inada, Y.; MNishikawa, K. and Naka, T. (1994) International Journal of Pharmaceutics 103(1), 1-7.
54. Starrett, J.E., Jr.; Tortolani, D.R.; Russell, J.; Hitchcock, M.J.; Whiterock, V.; Martin, J.C. and Mansuri, M.M. (1994) J. Med. Chem. 37(12), 1857-1864.
55. Cundy, K.C.; Fishback, J.A.; Shaw, J.P.; Lee, M.L.; Soike, K.F.; Visor, G.C. and Lee, W.A. (1994) Pharm. Res. 11(6), 839-843.
56. Cundy, K.C.; Barditch-Crovo, P.; Walker, R.E.; Collier, A.C.; Ebeling, D.; Toole, J. and Jaffe, H.S. (1995) Antimicrob. Agents Chemother. 39(11), 2401-2405.
57. Annaert, P.; Gosselin, G.; Pompon, A.; Benzaria, S.; Valette, G.; Imbach, J.L.; Naesens, L.; Hatse, S.; De Clercq, E.; Van Den Mooter, G.; Kinget, R. and Augustijns, P. (1998) Pharmaceutical Research 15(2), 239-245.
58. Annaert, P.; Kinget, R.; Naesens, L.; de Clercq, E. and Augustijns, P. (1997) Pharm. Res. 14(4), 492-496.
59. Shaw, J.P.; Louie, M.S.; Krishnamurthy V.V.; Arimilli, M.N.; Jones, R.J.; Bidgood, A.M.; Lee, W.A. and Cundy, K.C. (1997) Drug Metab. Dispos. 25(3), 362-366.
60. Barditch-Crovo, P.; Toole, J.; Hendrix, C.W.; Cundy, K.C.; Ebeling, D.; Jaffe, H.S. and Lietman, P.S. (1997) J. Infect. Dis. 176(2), 406-413.
61. Naesens, L.; Bischofberger, N.; Augustijns, P.; Annaert, P.; Van den Mooter, G.; Arimilli, M.N.; Kim, C.U. and De Clercq, E. (1998) Antimicrob. Agents Chemother. 42(7), 1568-1573.
62. Shaw, J.P.; Sueoko, C.M.; Oliyai, R.; Lee, W.A.; Arimilli, M.N.; Kim, C.U. and Cundy, K.C. (1997) Pharm. Res. 14(12), 1824-1829.
63. Ingold. (1969) Structure and mechanism in organic chemistry, 2nd Ed., Cornell University Press, Ithaca, N.Y.
64. Ferres, H. (1983) Drugs of Today 19(9), 499-538.
65. Brass, E.P. (2002) Pharmacol, Rev. 54(4), 589-598.
66. Tougou, K.; Nakamura, A.; Watanabe, S.; Okuyama, Y. and Morino, A. (1998) Drug Metab. Dispos. 26(4), 355-359.
67. Biggadike, K.; Angell, R.M.; Burgess, C.M.; Farrell, R.M.; Hancock, A.P.; Harker, A.J.; Irving, W.R.; Ioannou, C.; Procopiou, P.A.; Shaw, R.E.; Solanke, Y.E.; Singh, O.M.; Snowden, M.A.; Stubbs, R.J.; Walton, S. and Weston, H.E. (2000) J. Med. Chem. 43(1), 19-21.
68. Yanagisawa, H.; Amemiya, Y.; Kanazaki, T.; Shimoji, Y.; Fujimoto, K.; Kitahara, Y.; Sada, T.; Mizuno, M.; Ikeda, M.; Miyamoto, S.; Furukawa, Y. and Koike, H. (1996) J. Med. Chem. 39(1), 323-338.
69. Nielsen, N.M. and Bundgaard, H. (1988) J. Pharm. Sci. 77(4), 285-298.
70. Mork, N. and Bundgaard, H. (1992) Pharm. Res. 9(4), 492-496.
71. Midgley, I.; Hood, A.J.; Proctor, P.; Chasseaud, L.F.; Irons, S.R.; Cheng, K.N.; Brindley, C.J. and Bonn, R. (1994) Xenobiotica 24(1), 79-92.
72. Bullingham, R.; Monroe, S.; Nicholls, A. and Hale, M. (1996) J. Clin. Pharmacol. 36(4), 315-324.
73. Kaufman, M.J. (1990) Pharm. Res. 66(1-3), 97-106.
74. Lepist, E.I.; Ostergaard, J.; Fredholt, K.; Lennernas, H. and Friis, G.J. (1999) Exp. Toxicol. Pathol. 51(4-5), 363-368.
75. Camenisch, G.P.; Wang, W.; Wang, B. and Borchardt, R.T. (1998) Pharm. Res. 15(8), 1174-1181.
76. Okudaira, N.; Tatebayashi, T.; Speirs, G.C.; Komiya, I. and Sugiyama, Y. (2000) Journal of Pharmacology and Experimental Therapeutics 294(2), 580-587.
77. Okudaira, N.; Komiya, I. and Sugiyama, Y. (2000) J. Pharmacol. Exp. Ther. 295(2), 717-723.
78. Shionoiri, H.; Takasaki, I.; Minamisawa, K.; Ishizuka, H.; Konno, K.; Naganuma, H.; Sasahara, K. and Kawahara, Y. (2001) Hypertens. Res. 24(3), 235-240.
79. Drummer, O.H.; Nicolaci, J. and Iakovidis, D. (1990) J. Pharmacol, Exp. Ther. 252(3), 1202-1206.
80. Waldmeier, F.; Kaiser, G.; Ackermann, R.; Faigle, J.W.; Wagner, J.; Barner, A. and Lasseter, K.C. (1991) Xenobiotica 21(2), 251-261.
81. Waldmeier, F.; Kaiser, G.; Ackermann, R.; Faigle, J.W.; Wagner, J.; Barner, A. and Lasseter, K.C. (1991) Xenobiotica 21(2), 251-261.
82. van Griensven, J.M.; Schoemaker, R.C.; Cohen, A.F.; Luus, H.G.; Seibert-Grafe, M. and Rothig, H.J. European Journal of Clinical Pharmacology 47(6), 513-518.
83. Jurima-Romet, M. and Huang, H.S. (1993) Biochem. Pharmacol. 46(12), 2163-2170.
84. Drummer, O.H. and Kourtis, S. (1987) Arzneimittelforschung 37(11), 1225-1228.
85. Pang, K.S.; Cherry, W.F.; Terrell, J.A. and Ulm, E.H. (1984) Drug Metab. Dispos. 12(3), 309-313.
86. de Lannoy, I.A. and Pang, K.S. (1986) Drug Metab. Dispos. 14(5), 513-520.
87. Davies, R.O.; Gomez, H.J.; Irvin, J.D. and Walker, J.F. (1984) Br. J. Clin. Pharmacol. 18(Suppl. 2), 215S-229S.
88. Hui, K.K.; Duchin, K.L.; Kripalani, K.J.; Chan, D.; Kramer, P.K. and Yanagawa, N. (1991) Clin. Pharmacol. Ther. 49(4), 457-467.
89. Singhvi, S.M.; Duchin, K.L.; Morrison, R.A.; Willard, D.A.; Everett, D.W. and Frantz, M. (1988) Br. J. Clin. Pharmacol. 25(1), 9-15.
90. Gehr, T.W.; Sica, D.A.; Grasela, D.M. and Duchin, K.L. (1993) Eur. J. Clin. Pharmacol. 45(5), 431-436.
91. Onoyama, K.; Nanishi, F.; Okuda, S.; Oh, Y.; Fujishima, M.; Tateno, M. and Omae, T. (1988) Clin. Pharmacol. Ther. 43(3), 242-249.
92. Macfadyen, R.J.; Lees, K.R. and Reid, J.L. (1990) Drugs 39(Suppl. 1), 49-63.
93. Wiseman, L.R. and McTavish, D. Drugs 48(1), 71-90.
94. Yoshigae, Y.; Imai, T.; Aso, T. and Otagiri, M. (1998) Life Sci. 62(14), 1231-1241.
95. Fix, J.A.; Alexander, J.; Cortese, M.; Engle, K.; Leppert, P. and Repta, A.J. (1990) Pharm. Res. 7(4), 384-387.
96. Srinivas, N.R.; Hubbard, J.W.; McKay, G.; Hawes, E.M. and Midha, K.K. (1991) Chirality 3(2), 99-103.
97. 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. and Mendel, D.B. (1998) Antimicrob. Agents Chemother. 42(3), 647-653.
98. Augustijns, P.; Annaert, P.; Heylen, P.; Van den Mooter, G. and Kinget, R. (1998) International Journal of Pharmaceutics 166(1), 45-53.
99. Gaviraghi, G.; Barnaby, R.J. and Pellegatti, M. (2001) in Pharmacokinetic optimisation in drug research. Biological, physicochemical and computational strategies. (Testa, B.;van de Waterbeemd, H.; Folkers, G. and Guy, R., eds.), pp. 3-14, Wiley-VCH, Zurich.
100. Obermeier, M.T.; Chong, S.; Dando, S.A.; Marino, A.M.; Ryono, D.E.; Starrett-Arroyo, A.; DiDonato, G.C.; Warrack, B.M.; White, R.E. and Morrison, R.A. Journal of Pharmaceutical Sciences 85(8), 828-833.
101. Okudaira, N.; Komiya, I. and Sugiyama, Y. (2000) Journal of Pharmacology and Experimental Therapeutics 295(2), 717-723.
102. Satoh, T. and Hosokawa, M. (1995) Toxicol. Lett. 82-83, 439-445.
103. Minagawa, T.; Kohno, Y.; Suwa, T. and Tsuji, A. (1995) Biochem. Pharmacol. 49(10), 1361-1365.
104. Breslin, E.; Posvar, E.; Neub, M.; Trenk, D. and Jahnchen, E. (1996) Journal of Clinical Pharmacology 36(5), 414-421.
105. Lees, K.R.; Green, S.T. and Reid, J.L. (1988) Clin. Pharmacol. Ther. 44(4), 418-425.
106. Hayduk, K. and Kraul, H. (1999) J. Cardiovasc. Pharmacol. 34 Suppl. (1), S19-23.
107. Hutt, V.; Pabst, G.; Dilger, C.; Poli, G. and Acerbi, D. (1994) Eur. J. Drug Metab. Pharmacokinet. 19(1), 59-69.
108. Razzetti, R. and Acerbi, D. (1995) Am. J. Cardiol. 75(18), 7F-12F.
109. Sierakowski, B.; Puchler, K.; Witte, P.U.; Renneisen, K. and Roots, I. (1997) European Journal of Clinical Pharmacology 53(3/4), 215-220.
110. Gill, K.S. and Wood, M.J. (1996) Clin. Pharmacokinet. 31(1), 1-8.
111. He, G.; Massarella, J. and Ward, P. (1999) Clin. Pharmacokinet. 37(6), 471-484.
112. Cundy, K.C. Clinical Pharmacokinetics 36(2), 127-143.
113. Gleiter, C.H. and Morike, K.E. (2002) Clin. Pharmacokinet. 41(1), 7-17.
114. van Lier, J.J.; van Heiningen, P.N. and Sunzel, M. (1997) J. Hum. Hypertens. 11 Suppl. (2), S27-28.
115. Shionoiri, H.; Naruse, M.; Minamisawa, K.; Ueda, S.; Himeno, H.; Hiroto, S. and Takasaki, I. (1997) Clin. Pharmacokinet. 32(6), 460-480.
116. Murdoch, D. and McTavish, D. (1992) Drugs 43(1), 123-140.
117. Jusko, W.J. and Lewis, G.P. (1973) J. Pharm. Sci. 62(1), 69-76.
118. Bergan, T. (1978) Antimicrob. Agents Chemother. 13(6), 971-974.
119. Hampel, B.; Lode, H.; Bruckner, G. and Koeppe, P. (1988) Drugs 35 Suppl. (7), 29-33.
120. HJ, R.; Bradbrook, I.D.; Morrison, P.J.; Spector, R.G.; Cox, D.A. and Lees, L.J. (1983) J. Antimicrob. Chemother. 11(5), 435-445.
121. Blouin, R.A. and Stoeckel, K. (1993) Clin. Pharmacokinet. 25(3), 172-188.
122. Klepser, M.E.; Marangos, M.N.; Patel, K.B.; Nicolau, D.P.; Quintiliani, R. and Nightingale, C.H. (1995) Clin. Pharmacokinet. 28(5), 361-384.
123. Tremblay, D.; Dupront, A.; Ho, C.; Coussediere, D. and Lenfant, B. (1990) J Antimicrob Chemother 26 Suppl. (E), 21-28.
124. Borin, M.T. (1991) Drugs 42 Suppl. (3), 13-21.
125. Foord, R.D. (1976) Antimicrob. Agents Chemother. 9(5), 741-747.
126. Williams, P.E. and Harding, S.M. (1984) J. Antimicrob. Chemother. 13(2), 191-196.
127. Josefsson, K.; Bergan, T.; Magni, L.; Pring, B.G. and Westerlund, D. (1982) Eur. J. Clin. Pharmacol. 23(3), 249-252.
128. Schwocho, L.R. and Masonson, H.N. (2001) Journal of Clinical Pharmacology 41(5), 515-527.
129. Warner, G.T. and Jarvis, B. (2002) Drugs 62(9), 1345-1353; discussion 1354-1346.
130. Sum, Z.M.; Sefton, A.M.; Jepson, A.P. and Williams, J.D. (1989) J. Antimicrob. Chemother. 23(6), 861-868.
131. Desager, J.P. and Horsmans, Y. (1996) Clin. Pharmacokinet. 31(5), 348-371.
132. Corsini, A.; Bellosta, S.; Baetta, R.; Fumagalli, R.; Paoletti, R. and Bernini, F. (1999) Pharmacology & Therapeutics 84(3 , 413-428.
133. Jung, D. and Dorr, A. (1999) Journal of Clinical Pharmacology 39(8), 800-804.
134. Kondo, T.; Yoshida, K.; Yoshimura, Y.; Motohashi, M. and Tanayama, S. (1996) Arzneimittelforschung 46(6), 594-600.
135. Goto, N.; Kobayashi, K. and Kishiro, K. (1994) Yakubutsu Dotai 9(6), 867-873.
136. Viread NDA submission (FDA briefing document NDA 21-356).
137. Stimpel, M.; Bonn, R.; Koch, B., and Dickstein, K. (1995) Cardiovascular Drug Reviews 13(3), 211-229.