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Chapter 8 : Inhibitors of Peptidoglycan Biosynthesis

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Inhibitors of Peptidoglycan Biosynthesis, Page 1 of 2

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Abstract:

This chapter provides an overview on inhibitors of peptidoglycan biosynthesis. Derivatives of penicillanic acid comprise two groups of therapeutic agents of considerable importance in medicine: the antibacterial penicillins and the β-lactamase inhibitors. Penicillin G (benzylpenicillin) and penicillin V (phenoxymethylpenicillin) are the only penicillins used in their natural forms as obtained from the fermentation of Penicillium chrysogenum. The other penicillins in clinical use are derived from 6-β-aminopenicillanic acid using standard synthetic procedures. The structural modification in the side chain of antistaphylococcal β-lactamase-resistant semisynthetic penicillins provides enough steric hindrance to make them very poor substrates for most β-lactamases. Nafcillin and the isoxazolyl penicillins also are used only for treatment of infection due to β-lactamase-producing staphylococci. The aminopenicillins include ampicillin, its ethoxycarbonyloxyethyl ester (bacampicillin), and amoxicillin. The antipseudomonal penicillins are semisynthetic derivatives of penicillanic acid and are categorized into two subgroups: the carboxypenicillins, which include carbenicillin indanyl ester (an ester for oral administration) and ticarcillin, and the ureidopenicillins, which include mezlocillin and piperacillin. Antipseudomonal penicillins retain most of the antibacterial activity of the aminopenicillins but have added activity against gram-negative bacilli. Indanyl carbenicillin (with a carboxyl side chain) is well absorbed from the gastrointestinal tract and is hydrolyzed by esterases to carbenicllin, the active drug. In the treatment of moderate to severe Pseudomonas infection, an aminoglycoside of the antipseudomonal group (gentamicin, tobramycin, or amikacin) is often administered along with an antipseudomonal penicillin (mezlocillin or piperacillin).

Citation: Mascaretti O. 2003. Inhibitors of Peptidoglycan Biosynthesis, p 129-137. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch8
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Figures

Image of Figure 8.1
Figure 8.1

Chemical structures of penicillanic acid compounds with antibiotic activity (penicillins) and a β-lactamase inhibitory activity (penicillanic acid sulfone and 6-β-bromopenicillanic acid).

Citation: Mascaretti O. 2003. Inhibitors of Peptidoglycan Biosynthesis, p 129-137. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch8
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Image of Figure 8.2
Figure 8.2

Reactions in which penicillin G inhibits a DD-transpeptidase enzyme and the β-lactam ring is opened by the action of a serine β-lactamase, yielding a penicilloic acid derivative and liberating β-lactamase, which is ready to catalyze a new reaction.

Citation: Mascaretti O. 2003. Inhibitors of Peptidoglycan Biosynthesis, p 129-137. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch8
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Image of Figure 8.3
Figure 8.3

Lack of antibiotic activity of clavulanic acid and irreversible inhibition of a serine β-lactamase through a double-hit mechanism. See the text and Fig. 11.1 for a detailed explanation of this last mechanism of reaction. The irreversibly inhibited enzyme structure formed by the so-called “suicide inhibitors” is also shown.

Citation: Mascaretti O. 2003. Inhibitors of Peptidoglycan Biosynthesis, p 129-137. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch8
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Image of Figure 8.4
Figure 8.4

Structures and some properties of natural penicillins.

Citation: Mascaretti O. 2003. Inhibitors of Peptidoglycan Biosynthesis, p 129-137. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch8
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Image of Figure 8.5
Figure 8.5

Chemical structures of procaine penicillin G and benzathine penicillin G.

Citation: Mascaretti O. 2003. Inhibitors of Peptidoglycan Biosynthesis, p 129-137. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch8
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Image of Figure 8.6
Figure 8.6

Structures and some properties of penicillinase-resistant penicillins. Abbreviations: IM, intramuscular; IV, intravenous.

Citation: Mascaretti O. 2003. Inhibitors of Peptidoglycan Biosynthesis, p 129-137. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch8
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Image of Figure 8.7
Figure 8.7

Structures and some properties of aminopenicillins. Abbreviations: IM, intramuscular; IV, intravenous.

Citation: Mascaretti O. 2003. Inhibitors of Peptidoglycan Biosynthesis, p 129-137. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch8
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Image of Figure 8.8
Figure 8.8

Products of cleavage of the double ester of bacampicillin by nonspecific esterases.

Citation: Mascaretti O. 2003. Inhibitors of Peptidoglycan Biosynthesis, p 129-137. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch8
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Image of Figure 8.9
Figure 8.9

Structures and some properties of antipseudomonal penicillins. IM, intramuscular; IV, intravenous.

Citation: Mascaretti O. 2003. Inhibitors of Peptidoglycan Biosynthesis, p 129-137. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch8
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References

/content/book/10.1128/9781555817794.chap8
1. American Medical Association. 1995. Drug Evaluations Annual, p. 13771411. American Medical Association, Chicago, Ill.
2. Chambers, H. F., 2000. Penicillins, p. 261274. In G. L. Mandell,, J. E. Bennet,, and R. Dolin (ed.), Principles and Practice of Infectious Diseases , 5th ed. Churchill Livingstone, Inc., Philadelphia, Pa.
3. Kucers, A.,, S. M. Crowe,, M. L. Grayson,, and J. F. Hoy. 1997. The Use of Antibiotics. A Clinical Review of Antibacterial, Antifungal and Antiviral Drugs , 5th ed. Butterworth- Heinemann, Oxford, United Kingdom.
4. Petri, W. A., 2001. Penicillins, cephalosporins, and other β-lactam antibiotics, p. 11891218. In J. G. Hardman, and L. E. Limbird (ed.), Goodman & Gilman's The Pharmacological Basis of Therapeutics , 10th ed. McGraw-Hill Book Co., New York, N.Y.
5. Scholar, E. M.,, and W. B. Pratt. 2000. The Antimicrobial Drugs , 2nd ed. Oxford University Press, New York, N.Y.
6. Sutherland, R., 1997. β-Lactams: penicillins, p. 256305. 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.
Parfitt, K. 1999. Parfitt, K. 1999. Martindale. The Complete Drug Reference , 32nd ed. Pharmaceutical Press, London, United Kingdom. Pages 112 through 270 cover the antibacterial agents used in the treatment and prophylaxis of bacterial infections, with particular reference to preparations BP1998, USO23, and proprietary preparations in many countries.

Tables

Generic image for table
Table 8.1

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

Citation: Mascaretti O. 2003. Inhibitors of Peptidoglycan Biosynthesis, p 129-137. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch8

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