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Chapter 10 : Inhibitors of Peptidoglycan Biosynthesis

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Inhibitors of Peptidoglycan Biosynthesis, Page 1 of 2

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Abstract:

The carbapenems are a subgroup of β-lactam antibiotics with a common carbapenem nucleus. Carbapenems are broad-spectrum antibiotics with activity against gram-positive and gram-negative bacteria. Like other β-lactam antibiotics, imipenem and thienamycin interfere with the biosynthesis of the peptidoglycan polymer. The discovery of the excellent activity of the imipenem-cilastatin combination against a wide variety of aerobic and anaerobic microorganisms led to extensive work on the isolation of other naturally occurring carbapenems by pharmaceutical laboratories worldwide as well as on the production of synthetic compounds. In vitro, meropenem, like imipenem, is active against most clinically important gram-positive and gram-negative aerobes and anaerobes. Both imipenem and meropenem are inactive against methicillin-resistant staphylococci, Enterococcus faecium, or Stenotrophomonas maltophilia. Ertapenem is a new β-lactam antibiotic belonging to the carbapenem subgroup. It possesses a 1-β-methyl group on the carbapenem nucleus. Unlike the penicillins, cephalosporins, and carbapenems, which are bicyclic compounds, the monobactams are monocyclic β-lactam antibiotics. The first monobactams to be discovered were naturally occurring compounds isolated from bacteria, but they exhibited poor antibacterial activity. These naturally occurring monobactams are characterized by the 2-oxoazetidine-1-sulfonic acid moiety with an acyl side chain at the 3 position with the β-orientation and, for most monobactams, a 3-α-methoxy group. The potent antibacterial activity of aztreonam is directed specifically against aerobic gram-negative bacteria. This activity varies from high against organisms such as Neisseria and Haemophilus spp. to intermediate against Pseudomonas aeruginosa to poor against Acinetobacter spp.

Citation: Mascaretti O. 2003. Inhibitors of Peptidoglycan Biosynthesis, p 153-158. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch10
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Figures

Image of Figure 10.1
Figure 10.1

Chemical structure of thienamycin.

Citation: Mascaretti O. 2003. Inhibitors of Peptidoglycan Biosynthesis, p 153-158. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch10
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Image of Figure 10.2
Figure 10.2

Chemical structures of thienamycin, imipenem (N-formimidoylthienamycin), and cilastatin. The carbapenem antibiotics are represented in the zwitterionic form. In imipenem there are two basic functionalities, a secondary amine and the imino group; for that reason, the protons are placed covering these functionalities.

Citation: Mascaretti O. 2003. Inhibitors of Peptidoglycan Biosynthesis, p 153-158. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch10
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Image of Figure 10.3
Figure 10.3

Chemical structures of meropenem and ertapenem.

Citation: Mascaretti O. 2003. Inhibitors of Peptidoglycan Biosynthesis, p 153-158. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch10
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Image of Figure 10.4
Figure 10.4

General chemical structure of naturally occurring monobactams.

Citation: Mascaretti O. 2003. Inhibitors of Peptidoglycan Biosynthesis, p 153-158. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch10
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Image of Figure 10.5
Figure 10.5

Structure-activity relationships in the different groups or functionalities of the aztreonam molecule.

Citation: Mascaretti O. 2003. Inhibitors of Peptidoglycan Biosynthesis, p 153-158. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch10
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References

/content/book/10.1128/9781555817794.chap10
1. American Medical Association. 1995. Drug Evaluation Annual 1995, p. 14881494. American Medical Association, Chicago, Ill.
2. Bush, K., 1997. Other β-lactams, p. 306327. In F. O'Grady,, H. P. Lambert,, R. G. Finch,, and D. Greenwood (ed.), Antibiotic and Chemotherapy, 7th ed. Churchill Livingstone, Inc., New York, N.Y.
3. Chambers, H. F., 2000. Other β-lactam antibiotics, p. 291293. In G. L. Mandell,, J. E. Bennet,, and R. Dolin, (ed.), Principles and Practice of Infectious Diseases, 5th ed. Churchill Livingstone, Inc., Philadelphia, Pa.
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5. Scholar, E. M.,, and W. B. Pratt. 2000. The Antimicrobial Drugs, 2nd ed. Oxford University Press, New York, N.Y.
6. Albers-Schönberg, G.,, B. H. Arison,, O. D. Hensens,, J. Hirshfield,, K. Hoogsteen,, E. A. Kaczka,, R. E. Rhodes,, J. S. Kahan,, F. M. Kahan,, R. W. Ratcliffe,, E. Walton,, L. J. Ruswinkle,, R. B. Morin,, and B. G. Christensen. 1978. Structure and absolute configuration of thienamycin. J. Am. Chem. Soc. 100: 64916499.
7. Southgate, R.,, and N. F. Osborne,. 1993. Carbapenems and penems, p. 232258. In M. Howe-Grant (ed.), Chemotherapeutics and Disease Control. John Wiley & Sons, Inc., New York, N.Y.
8. Merck & Co. 2001. Invanz. Prescribing Information. Merck & Co., Rahway, N.J.
9. Cimarusti, C. M.,, and R. B. Sykes 1984. Monocyclic β-lactam antibiotics. Med. Res. Rev. 4:124.
10. Floyd, D. M.,, A. W. Fritz,, and C. M. Cimarusti. 1982. Monobactams. Stereospecific synthesis of (S)-3-amino-2- oxoazetidine-1-sulfonic acid. J. Org. Chem. 47:176178.
11. Lindener, K. R.,, D. P. Bonner,, and W. H. Koster,. 1993. Monobactams, p. 338360. In M. Howe-Grant (ed.), Chemotherapeutics and Disease Control. John Wiley & Sons, Inc., New York, N.Y.

Tables

Generic image for table
Table 10.1

Generic and common trade names of carbapenems, the preparations available, and manufacturers in the United States

Citation: Mascaretti O. 2003. Inhibitors of Peptidoglycan Biosynthesis, p 153-158. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch10

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