Quantitative structure-activity relationships among macrolide antibacterial agents: In vitro and in vivo potency against Pasteurella multocida

Journal of Medicinal Chemistry

Volumn 40, Issue 9, 1997, Pages 1340-1346

  McFarland, James W ^a,b   Berger, Cynthia M ^c,d   Froshauer, Susan A ^a   Hayashi, Shigeru F ^a   Hecker, Scott J ^a,e   Jaynes, Burton H ^a   Jefson, Martin R ^a   Kamicker, Barbara J ^a   Lipinski, Christopher A ^a   Lundy, Kristin M ^a   Reese, Catherine P ^a   Vu, Chi B ^a,f  

^a PFIZER INC   (United States)

^b Reckondat Consulting   (United States)

^c PION INC   (United States)

^d Water Technology Associates Inc   (United States)

^e Microcide Pharmaceuticals Inc   (United States)

^f ARIAD PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

74211 76 0; AZITHROMYCIN; CARBOMYCIN; CLARITHROMYCIN; DESMYCAROSYLCARBOMYCIN A; DESMYCOSIN; ERYTHROMYCIN; ERYTHROMYCYLAMINE; MACROLIDE; OLEANDOMYCIN; REPROMICIN; ROSARAMICIN; TILMICOSIN; TYLOSIN; UNCLASSIFIED DRUG;

ARTICLE; BACTERICIDAL ACTIVITY; DRUG POTENCY; GRAM NEGATIVE INFECTION; NONHUMAN; PASTEURELLA MULTOCIDA; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTI-BACTERIAL AGENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HYDROGEN-ION CONCENTRATION; MACROLIDES; MICE; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; PASTEURELLA INFECTIONS; PASTEURELLA MULTOCIDA; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 15444352573     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960436i     Document Type: Article

References (31)

1. McFarland, J. W.; Hecker, S. J.; Jaynes B. H.; Jefson, M. R.; Lundy, K. M.; Vu, C. B.; Glazer, E. A.; Froshauer, S. A.; Hayashi, S. F.; Kamicker, B. J.; Reese, C. P.; Olson, J. A. Repromicin Derivatives with Potent Antibacterial Activity against Pasteurella multocida. J. Med. Chem. 1997, 40, 1041-1045.
2. Avdeef, A. pH-Metric log P. Part II: Refinement of Partition Coefficients and Ionization Constants of Multiprotic Substances. J. Pharm. Sci. 1993, 82, 183-190.
3. Avdeef, A. pH-Metric log P. Part I. Difference Plots for Determining Ion-Pair Octanol-Water Partition Coefficients of Multiprotic Substances. Quant. Struct.-Act. Relat. 1992, 11, 510-517.
4. Slater, B.; McCormack, A.; Avdeef, A.; Comer, J. E. A. pH-Metric log P. 4. Comparison of Partition Coefficients Determined by HPLC and Potentiometric Methods to Literature Values. J. Pharm. Sci. 1994, 83, 1280-1283.
5. Taylor, P. J. Hydrophobic Properties of Drugs. In Comprehensive Medicinal Chemistry; Ramsden, C. A., Ed.; Pergamon Press: Oxford, 1990; Vol. 4, pp 241-294.
6. Horváth, C.; Melander, W.; Molnár, I. Liquid Chromatography of Ionogenic Substances with Nonpolar Stationary Phases. Anal. Chem. 1977, 49, 142-154.
7. MEDCHEM, version 3.54, Daylight Chemical Information Systems, Inc., 18500 Von Karman Ave, Suite 450, Irvine, CA 92715.
8. Release 4.4.1 of RS/1, Bolt, Beranek and Newman, 150 Cambridge Park Dr, Cambridge, MA 02140.
9. Modde for Windows, User's Guide to Modde, version 2.1, Umetri AB, Box 1456, S-901 24 Umeå, Sweden, 1994.
10. Dearden, J. C. Molecular Structure and Drug Transport. In Comprehensive Medicinal Chemistry; Ramsden, C. A., Ed.; Pergamon Press: Oxford, 1990; Vol. 4, pp 375-411.
11. Kirst, H. A. Semi-synthetic Derivatives of Erythromycin. In Progress in Medicinal Chemistry; Ellis, G. P., Luscombe, D. K., Eds.; Elsevier Science Publishers B. V.: Amsterdam, 1993; Vol. 30, pp 57-88.
12. Martin, Y. C.; Jones, P. H.; Perun, T. J.; Grundy, W. E.; Bell, S.; Bower, R. R.; Shipkowitz, N. L. Chemical Modification of Erythromycin Antibiotics. 4. Structure-Activity Relationships of Erythromycin Esters. J. Med. Chem. 1972, 15, 635-638.
13. Goldman, R. C.; Zakula, D.; Flamm, R.; Beyer, J.; Capobianco, J. Tight Binding of Clarithromycin, Its 14-(R)-Hydroxy Metabolite, and Erythromycin to Helicobacter pylori Ribosomes. Antimicrob. Agents Chemother. 1994, 38, 1496-1500.
14. Selassie, C. D.; Hansch, C.; Khwaja, T. Structure-Activity Relationships of Antineoplastic Agents in Multidrug Resistance. J. Med. Chem. 1990, 33, 1914-1919.
15. Wildfeuer, A.; Lemme, J.-D. Zur Pharmakokinetik von Josamycin. (On the Pharmacokinetics of Josamycin.) Arzneim.-Forsch. 1985, 35, 639-643.
16. Ohno, M.; Ohta, K.; Morishita, M. Physicochemical properties of rokitamycin. Iyakuhin Kenkyu 1987, 18, 634-639 [cited by Muto, Y.; et al. Antimicrob. Agents Chemother. 1989, 33, 242-244, and by Kobayashi, Y.; et al. FEMS Microbiol. Lett. 1991, 81, 141-144].
17. Ohno, M.; Ohta, K.; Morishita, M. Physicochemical properties of rokitamycin. Iyakuhin Kenkyu 1987, 18, 634-639 [cited by Muto, Y.; et al. Antimicrob. Agents Chemother. 1989, 33, 242-244, and by Kobayashi, Y.; et al. FEMS Microbiol. Lett. 1991, 81, 141-144].
18. Ohno, M.; Ohta, K.; Morishita, M. Physicochemical properties of rokitamycin. Iyakuhin Kenkyu 1987, 18, 634-639 [cited by Muto, Y.; et al. Antimicrob. Agents Chemother. 1989, 33, 242-244, and by Kobayashi, Y.; et al. FEMS Microbiol. Lett. 1991, 81, 141-144].
19. Manuel, C.; Dellamonica, P.; Rosset, M. J.; Safran, C.; Pirot, D.; Audegond, L.; Pechere, J. C. Penetration of roxithromycin (ROX) into brain tissue (BT). Abstracts of the 28th Intersci. Conf. Antimicrob. Agents Chemother. 1988, 328 (No. 1224).
20. Nakagawa, Y.; Itai, S.; Yoshida, T.; Nagai, T. Physiochemical Properties and Stability in the Acidic Solution of a New Macrolide Antibiotic, Clarithromycin, in Comparison with Erythromycin. Chem. Pharm. Bull. 1992, 40, 725-728.
21. Erythromycin. In The Merck Index, Eleventh Edition; Budavari, S., Ed.; Merck & Co.: Rahway, NJ, 1989; pp 577-578 (No. 3626).
22. Goldman, R. C.; Fesik, S. W.; Doran, C. C. Role of Protonated and Neutral Forms of Macrolides in Binding to Ribosomes from Gram-Positive and Gram-Negative Bacteria. Antimicrob. Agents Chemother. 1990, 34, 426-431.
23. Gharbi-Benarous, J.; Delaforge, M.; Jankowski, C. K.; Girault, J.-P. A Comparative NMR Study between the Macrolide Antibiotic Roxithromycin and Erythromycin A with Different Biological Properties. J. Med. Chem. 1991, 34, 1117-1125.
24. Kobrehel, G.; Tamburasev, Z.; Djokic, S. Erythromycin series. IV. Thin-layer Chromatography of erythromycin, erythromycin oxime, erythromycylamine and their acyl derivatives. J. Chromatogr. 1977, 133, 415-419.
25. Delaforge, M.; Ladam, P.; Bouille, G.; Benarous, J. G.; Jaouen, M.; Girault, J. P. pH Effects on the N-Demethylation and Formation of the Cytochrome P-450 Iron II Nitrosoalkane Complex for Erythromycin Derivatives. Chem.-Biol. Interact. 1992, 85, 215-227.
26. Massey, E. H.; Kitchell, B. S.; Martin, L. D.; Gerzon, K. Antibacterial Activity of 9(S)-Erythromycylamine-Aldehyde Condensation Products. J. Med. Chem. 1974, 17, 105-107.
27. Kishi, T.; Harada, S.; Yamana, H.; Miyake, A. Studies on Juvenimicin, a New Antibiotic. II. Isolation, Chemical Characterization and Structures. J. Antibiot. 1976, 29, 1171-1181.
28. Els, H.; Celmer, W. D.; Murai, K. Oleandomycin (PA-105). II. Chemical Characterization (I). J. Am. Chem. Soc. 1958, 80, 3777-3782.
29. Shedlovsky, T.; Kay, R. L. The ionization constant of acetic acid in water-methanol mixtures at 25 °C from conductance measurements. J. Phys. Chem. 1956, 60, 151-155.
30. Shedlovsky, T. The behavior of carboxylic acids in mixed solvents. In Electolytes, Pesce, B., Ed.; Pergamon Press: New York, 1962; pp 146-151.
31. Yasuda, M. Dissociation constants of some carboxylic acids in mixed solvents. Bull. Chem. Soc. Jpn. 1959, 32, 429-432.