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Chapter 2 : Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship

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Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, Page 1 of 2

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Abstract:

This chapter focuses on the classification and structural-activity relationship of antibiotics and antibacterial agents. The β-lactam family comprises four groups of molecules: penams, penems, cephems, and monocyclic β-lactams. To these should be added the β-lactamase inhibitors, some of the structures of which are featured in the four main groups. The azetidinone nucleus alone can be replaced, and monobactams, monocarbams, monophosphatams, and other heterocycles can be distinguished according to the substituents of the nitrogen atom. Based on studies by researchers, who demonstrated the transferability of resistance to certain antibiotics between and spp., other researchers were able to demonstrate that shigellae inactivated chloramphenicol. The majority of aminoglycosides have similar basic structures and are divided into four groups: streptomycin derivatives, 2-deoxystreptamine derivatives, spectinomycin derivatives, and fortimicin derivatives. The macrolides are macrocyclic antibiotics characterized by a central lactone ring containing 12 to 16 members, few double bonds, and no nitrogen atom; one or two amino sugars and/or neutral sugars are attached to the lactone or aglycone ring. More than 400 compounds constitute the family of peptide antibiotics. Dihydrofolate reductase (DHFR) inhibitors used therapeutically are the result of studies relating to the specificity of this enzyme for bacterial, parasitic, or epithelial cells. The antibacterial compounds display good antibacterial activity and a lack of inhibitory activity against epithelial cell DHFR.

Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
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References

/content/book/10.1128/9781555815929.ch02
1. Brufani M, 1977, The ansamycins, p 96212, in Sammes PG, ed, Topics in Antibiotic Chemistry, Horward Ltd.
2. Bryskier A, 1982, Les inhibiteurs de la dihydrofolate réductase. Classification et relation activité structure, p 19–36, in Modai J, ed, Triméthoprime et sulfamides, Soc Pathol Infect Langue Fr.
3. Bryskier A, 1983, Classification des céphalosporines et relation activité structure des méthoxy-imino aminothiazolyl céphalosporines, Lyon Pharm, 34, 99100.
4. Bryskier A, 1983, Classification des β-lactamines, Pathol Biol, 32, 658667.
5. Bryskier A, 1993, Recent advances in fluoroquinolones research, Curr Opin Investig Drugs, 2, 409415.
6. Bryskier A, 1993, New pyridone-β-carboxylic acid derivatives, Quinolone Bull, 10(2), 22.
7. Bryskier A, 1994, Update on fluoroquinolones, Curr Opin Investig Drugs, 3, 4149.
8. Bryskier A,, Agouridas C, 1993, Azalides: a new medicinal chemical family? Curr Opin Investig Drugs, 2, 687694.
9. Bryskier A,, Agouridas C,, Chantot J-F, 1993, Classification of macrolide antibiotics, in Bryskier A,, Butzler J-P,, Neu HC,, Tulkens PM, ed, Macrolides, Chemistry, Pharmacology and Clinical Uses, Arnette-Blackwell, Paris, p 566.
10. Bryskier A,, Agouridas C,, Chantot J-F, 1993, Relation structure activity of 14-, and 15-membered ring macrolides, Chemother J, 2, suppl 2, 211.
11. Bryskier A,, Agouridas C,, Chantot J-F, 1995, New insights into structure-activity relationships of macrolides and azalides, in Neu HC,, Acar JF,, Young LS,, Zinner S, ed, Proc 2nd Int Congr Macrolides Azalides and Streptogramins, Venice, Marcel-Dekker, New York.
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13. Bryskier A,, Chantot J-F, 1995, Fluoroquinolones, classification and structure-activity relationships, Drugs suppl—Proc Int Symp New Quinolones Singapore, 1993.
14. Bryskier A,, Labro MT, 1989, Antibiotiques: de nouveaux antipaludéens, in Bryskier A,, Labro MT, Paludisme et médicaments, Arnette, Paris, p 133169.
15. Chopra I, 1994, Tetracycline analogs whose primary target is not the bacterial ribosome, Antimicrob Agents Chemother, 38, 637640.
16. Chopra I, 1994, Glycylcyclines—third generation tetracycline analogues, Expert Opin Investig Drugs, 3, 191193.
17. Chu DTW,, Fernandes PB, 1991, Recent development in the field of quinolone antibacterial agents, Adv Drug Res, 21, 44144.
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19. Cox DA,, Richardson K,, Ross BC, 1977, Aminoglycosides, in Sammes PG, ed, Topics in Antibiotic Chemistry, Horward Ltd, p 590.
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21. Domagala JM, 1994, Structure-activity and structure-side effect relationships for the quinolone antibacterials, J Antimicrob Chemother, 33, 685706.
22. Durckheimer W,, Blumbach J,, Latrell R,, Scheunemann KH, 1985, Recent development in the field of β-lactam antibiotics, Ang Chem, 24, 180202.
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24. Nagajaran R, 1994, Structure-activity relationships of vancomycin antibiotics, p 195–218, in Nagajaran R, ed, Glycopeptide Antibiotics, Marcel Dekker, New York.
25. Price KE, 1977, Structure-activity relationships of semi-synthetic penicillins, p 1–86, in Perlman D, ed, Structure-Activity Relationships among Semi-Synthetic Antibiotics, Academic Press.
26. Price KE,, Godfrey JC,, Kawaguchi H, 1977, Effect of structural modifications on the biological properties of aminoglycoside antibiotics containing 2-deoxystreptamine, p 299–395, in Perlman D, ed, Structure-Activity Relationships among Semi-Synthetic Antibiotics, Academic Press.
27. Valcavi U, 1981, Tetracyclines: chemical aspects and some structure-activity relationships, p 502–506, in Gialdroni-Grassi G,, Sabath LD, ed, New Trends in Antibiotics: Research and Therapy, Elsevier.
28. Veyssier P,, Bryskier A, 1985, Agents antibactériens de synthèse, Enc Med Chir Thérapeutique, 5-25016 D10.

Tables

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Table 1

Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
Generic image for table
Table 2

Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
Generic image for table
Table 3

Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
Generic image for table
Table 4

Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
Generic image for table
Table 5

Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
Generic image for table
Table 6

Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2
Generic image for table
Table 7

Citation: Bryskier A. 2005. Antibiotics and Antibacterial Agents: Classifications and Structure-Activity Relationship, p 13-38. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch2

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