Pediatric erythromycins: A comparison of the properties of erythromycins A and B 2′-ethyl succinates

Journal of Medicinal Chemistry

Volumn 49, Issue 21, 2006, Pages 6334-6342

  Hassanzadeh, Abdolreza ^a   Gorry, Peter A ^a   Morris, Gareth A ^a   Barber, Jill ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BERYTHROMYCIN; ERYTHROMYCIN; ERYTHROMYCIN A 2' ETHYLSUCCINATE; ERYTHROMYCIN B 2' ETHYLSUCCINATE; ERYTHROMYCIN ETHYLSUCCINATE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; BITTER TASTE; CALCULATION; CATALYSIS; DRUG DEGRADATION; DRUG STABILITY; DRUG SYNTHESIS; ESTERIFICATION; HYDROLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; STOMACH ACID;

ANTI-BACTERIAL AGENTS; CATALYSIS; ERYTHROMYCIN; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; KINETICS; PEDIATRICS; PRODRUGS;

EID: 33750127865     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0602312     Document Type: Article

References (38)

1. Buss, A. D.; Waigh, R. D. Natural Products as Leads for New Pharmaceuticals. In Burger's Medicinal Chemistry and Drug Discovery, 5th ed.; Wolff, M. E., Ed.; John Wiley & Sons; New York, 1995; Vol. 1, pp 1009-1012.
2. McGuire, J. M.; Bunch, R. L.; Anderson, R. C.; Boaz, H. E.; Flynn, E. H.; Powell, H. M.; Smith, J. W. Ilotycin, a new antibiotic. Antibiot. Chemother. 1952, 2, 281-283.
3. Gregory, D.; Zeleznik, D.; Harnisch, J. P.; Counts, G. W. Activity of penicillin, erythromycin and cephalosporins against isolates of Corynebacterium diphtheriae from cutaneous lesions. J. Antimicrob. Chemother. 1979, 5, 479-481.
4. Mordi, M. N.; Pelta, M. D.; Boote, V.; Morris, G. A.; Barber, J. Acid-catalyzed degradation of clarithromycin and erythromycin B: a comparative study using NMR spectroscopy. J. Med. Chem. 2000, 43, 467-474.
5. Graham, E. M. Erythromycin. Obstet. Gynecoi. Clin. North Am. 1992, 19, 539-549.
6. Barber, J.; Mordi, M. N. Erythromycin B, and derivatives thereof, as antibiotic agents for the treatment of microbial infections. PCT Int. Appt. 2000, 45.
7. Jones, P. H.; Perun, T. J.; Rowley, E. K.; Baker, E. J. Chemical modification of erythromycin antibiotics. 3. Synthesis of 4″- and 11-esters of erythromycin A and B. J. Med Chem. 1972, 15, 631 -634.
8. Tsuji, K.; Goetz, J. F. Elevated column temperature for the high-performance liquid chromatographic determination of erythromycin and erythromycin ethylsuccinate. J. Chromatogr. 1978, 157, 185-196.
9. Kirst, H. A. Semi-synthetic derivatives of erythromycin. Prog. Med. Chem. 1993, 30, 57-87.
10. Sinkula, A. A. Chemical modification of erythromycin: synthesis and preliminary bioactivity of selected amides and esters. J. Pharm. Sci. 1974, 63, 842-848.
11. Tardrew, P. L.; Mao, J. C. H.; Kenney, D. Antibacterial activity of 2′-esters of erythromycin. Appl. Microbiol. 1969, 18, 159-65.
12. Steffansen, B.; Bundgaard, H. Erythromycin prodrugs: kinetics of hydrolysis of erythromycin and various erythromycin 2′-esters in aqueous solution and human plasma. Int. J. Pharm. 1989, 56, 159-168.
13. Stephens, V. C.; Conine J. W. Esters of erythromycin. III. Esters of low-molecular-weight aliphatic acids. Antibiotics Ann. 1959, 1958-1959, 346-353.
14. British Pharmacopoeia; Stationery Office: London, 2002; Vol. 1, p 676.
15. Grundy, W. E.; Alford, E. F.; Rickher, C. J.; Bower, R. R.; Rdzok, E. J.; Sylvester, J. C. A microbiological comparison of erythromycin and erythromycin B. Antibiot. Chemother. 1955, 5, 212-217.
16. Vinckier, C.; Hauchecorne, R.; Cachet, Th.; Van den Mooter, G.; Hoogmartens, J. A new mechanism for the decomposition of erythromycin A in acidic aqueous solution. Int. J. Pharm. 1989, 55, 67-76.
17. Cachet, Th.; Van den Mooter, G.; Hauchecorne, R.; Vinckier, C.; Hoogmartens, J. Decomposition kinetics of erythromycin A in acidic aqueous solutions. Int. J. Pharm. 1989, 55, 59-65.
18. Mordi, M. N.; Boote, V.; Hodgkiss, R.; Mistry, A.; Barber, J. Comparative pharmacokinetic study of erythromycin A, erythromycin B and clarithromycin using HPLC and electrospray mass spectrometry, unpublished data.
19. Bhadra, P. K.; Morris, G. A.; Barber, J. Design, synthesis and evaluation of stable and taste-free erythromycin proprodrugs. J. Med. Chem. 2005, 48, 3878-3884.
20. 13C NMR spectra. J. Chem. Soc., Perkin Trans. 2 1991, 10, 1489-1494.
21. Everett, J. R.; Hunt, E.; Tyler, J. W. Ketone-hemiacetal tautomerism in erythromycin A in nonaqueous solutions. An NMR spectroscopic study. J. Chem. Soc., Perkin Trans. 2 1991, 10, 1481-1487.
22. Moatamedolroaya Fini, M. The Design, Synthesis and Evaluation of Macrolide Pro-drugs. Ph.D. thesis, School of Pharmacy and Pharmaceutical Sciences, University of Manchester, Manchester, U.K., 2001.
23. 13C NMR spectra of anhydroerythromycin A in organic and aqueous solutions. Magn Reson. Chem. 1996, 34, 837-839.
24. 13C NMR spectra. J. Chem. Soc., Perkin Trans. 2, 1995, 1163-1167.
25. Chu, S.-H.; Mautner, H. G. Analogs of neuroeffectors. V. Neighboring-group effect in the reaction of esters. The hydrolysis and aminolysis of benzoylcholine, benzoylthiolcholine, benzoylselenolcholine, and of their dimethylamino analogs. J. Org. Chem. 1966, 31, 308-312.
26. Zaslowsky, J. A.; Fisher, E. The hydrolysis of β-diethylaminoethyl acetate, J. Phys. Chem. 1962, 67, 959-961.
27. Bruice, P. Y.; Mautner, H. G. Intramolecular catalysis and the involvement of tetrahedral intermediate partitioning in the hydrolysis of benzoylcholine, benzoylthionocholine, and their dimethylamino analogs. J. Am. Chem. Soc. 1972, 95, 1582-1586.
28. Kim, Y.-H.; Heinze, T. M.; Beger, R.; Pothuluri, J. V.; Cerniglia, C. E. A kinetic study on the degradation of erythromycin A in aqueous solution. Int. J. Pharm. 2004, 271, 63-76.
29. Barber, J. A. Preparation of antibiotic derivatives of erythromycin macrolides as antibacterial agents. PCT Int. Appl. 2004, 32.
30. Sunazuka, T.; Tsuzuki, K.; Marui, S.; Toyoda, H.; Omura, S.; Inatomi, N.; Itoh, Z. Motilides, macrolides with gastrointestinal motor stimulating activity. II. Quaternary N-substituted derivatives of 8,9-anhydroerythromycin A 6,9-hemiacetal and 9.9-dihydroerythromycin A 6,9-epoxide. Chem. Pharm. Bull. 1989, 37, 2701-2709.
31. Tsuzuki, K.; Sunazuka, T.; Marui, S.; Toyoda, H.; Omura, S.; Inatomi, N.; Itoh Z Motilides, macrolides with gastrointestinal motor stimulating activity. I. O-substituted and tertiary N-substituted derivatives of 8,9- anhydroerythromycin A 6,9-hemiacetal. Chem. Pharm. Bull. 1989, 37, 2687-2700.
32. Schiunzen, F.; Zarivach, R.; Harms, J.; Bashan, A.; Tocilj, A.; Albrecht, R.; Yonath, A.; Franceschi, F. Structural basis for the interaction of antibiotics with the peptidyl transferase centre in eubacteria. Nature 2001, 413, 814-821.
33. Taskinen, J.; Ottoila, P. Hydrolysis of 2′-esters of erythromycin. J. Antimicrob. Chem. 1988, 21, 1-8.
34. Krowicki, K.; Zamojski, A. J. Chemical modification of erythromycins. IV. 8-Hydroxyerythromycin B. J. Antibiot. 1973, 26, 587-592.
35. Clark, R. K.; Varner E. L. New esters of erythromycin. Antibiot. Chemother. 1957, 7, 487-489.
36. Bhadra, P. K. Erythromycin B: An Old Drug for the New Millennium. Ph.D. thesis, School of Pharmacy and Pharmaceutical Sciences, University of Manchester, Manchester, U.K., 2003.
37. Wiley, P. F.; Gerzon, K.; Flynn, E. H.; Sigal, M. V., Jr.; Weaver, O.; Quarck, U. C.; Chauvette, R. R.; Monahan, R. Erythromycin. X. Structure of erythromycin. J. Am. Chem. Soc. 1957, 79, 6062-6070.
38. Morris, G. A.; Barjat, H.; Home, T. J. Reference deconvolution methods. Prog. Nucl. Magn. Reson. Spectrosc. 1997, 31, 197-257.