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Chemical modification of erythromycins. I. Synthesis and antibacterial activity of 6-O-methylerythromycins A.
Open accessAbstract
The in vitro and in vivo antibacterial activities of 6-O-methylerythromycin A (TE-031, A-56268, or clarithromycin) and 6, 11-di-O-methylerythromycin A (TE-032) have been compared with those of erythromycin A (EM) and josamycin (JM). TE-031 and TE-032, having the same antibacterial spectra as EM, are active against aerobic Gram-positive bacteria, some Gram-negative bacteria, anaerobic bacteria, L-form bacteria and Mycoplasmapneumoniae. The activity of TE-031 against clinical isolates is equal to or two times more potent than that of EM, whereas TE-032 is slightly less active than EM. The activities of TE-031 and TE-032 are pH dependent (more active at pH 8 than at 5) and are increased by adding serum to medium. TE-031 and TE-032 show dose-related bactericidal activities against Haemophilus influenzae. The therapeutic efficacies of TE-031 and TE-032 against systemic and subcutaneous infections provoked by Gram-positive bacteria in mice are 4- to 35-fold superior to those of EM and JM. TE-031 and TE-032 have demonstrated higher and longer-lasting plasma levels than EM when administered orally to mice, rats or dogs.
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Citations
Cited by
Natural Products as Platforms To Overcome Antibiotic Resistance
Rossiter, S. E., Fletcher, M. H., & Wuest, W. M. (2017) · Chemical Reviews · doi:10.1021/acs.chemrev.7b00283 · Cited by 622
New Directions in Antibacterial Research
Chu, D. T. W., Plattner, J. J., & Katz, L. (1996) · Journal of Medicinal Chemistry · doi:10.1021/jm960294s · Cited by 298
Metadata
- Authors
- MORIMOTO, S., TAKAHASHI, Y., WATANABE, Y., & OMURA, S.
- Venue
- The Journal of Antibiotics
- Published
- 1984
- Volume
- 37
- Issue
- 2
- Pages
- 187-189
- ISSN
- 0021-8820 (ISSN-L)
- 1881-1469
- OpenAlex
- W2325819067
- Cited by
- 233
- References
- 0
- FWCI
- 1.19
- Type
- journal article
- Language
- en
- Open access
- bronze
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- MORIMOTO, S., TAKAHASHI, Y., WATANABE, Y., & OMURA, S. (1984). Chemical modification of erythromycins. I. Synthesis and antibacterial activity of 6-O-methylerythromycins A. The Journal of Antibiotics. https://doi.org/10.7164/antibiotics.37.187
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