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Chapter 24 : Tetracyclines

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Tetracyclines, Page 1 of 2

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Abstract:

The use of tetracyclines is less widespread now than in the past due to the emergence of antibacterial resistance to these antibiotics and the discovery of more effective and selective molecules. The physicochemical properties of the tetracyclines may be modified by minimal structural variations. The antibacterial spectrum and activity of the tetracyclines include numerous gram-positive and gram-negative bacteria, anaerobes, rickettsiae, mycoplasmas, chlamydiae, Helicobacter pylori, and spirochetes. In the case of gram-negative bacteria, the first obstacle to be overcome is the bacterial outer membrane. Tetracyclines probably penetrate the periplasmic space via transmembrane proteins forming hydrophilic channels. The therapeutic use of tetracyclines is increasingly undermined by the frequent emergence of resistance. Hypersensitivity reactions to tetracyclines are rare but may include anaphylactic shock, urticaria, periorbicular edema, rashes, and morbilliform rashes. The hepatotoxicity of the tetracyclines, first described with chlortetracycline, is now known for all tetracyclines. The results of experimental studies in animals are contradictory with respect to the teratogenicity of tetracyclines: some authors have reported inhibited growth and skeletal deformities in the rat and chicken, whereas according to other authors this risk is nonexistent. Several authors have reported yellow or brown discoloration of the milk teeth in children born to mothers treated with tetracyclines (tetracycline and oxytetracycline) during the second and particularly the third trimesters of pregnancy. Majority of tetracyclines can cause a cerebral pseudotumor syndrome, characterized by a benign increase in intracranial pressure in children and adults. Tetracyclines are used in cases of nonspecific urethritis and urethral syndrome.

Citation: Bryskier A. 2005. Tetracyclines, p 642-651. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch24
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Figures

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Figure 1

Chemical structure of the tetracyclines

Citation: Bryskier A. 2005. Tetracyclines, p 642-651. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch24
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Image of Figure 2
Figure 2

Sequence of protein synthesis and site of action of the tetracyclines. (1) Binding of aminoacyl-tRNA to the A-site in the form of a complex with GTP and elongation factor Tu (EF-Tu). (2) Translocation in the presence of EF-Tu and EF-G. The tetracyclines inhibit the attachment of the aminoacyl-tRNA complex to the ribosomal site (1).

Citation: Bryskier A. 2005. Tetracyclines, p 642-651. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch24
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References

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1. Duggar BM, 1948, Aureomycin, a product of the continuing search for new antibiotics, Ann N Y Acad Sci, 51, 177181.
2. Fourtillan JB,, Lefebvre MA, 1980, Correlations structure-activité dans la famille des tetracyclines, Nouv Presse Med, 9, 6470.
3. Hlavka JJ,, Boothe JH, ed, 1985, The tetracyclines, Springer-Verlag, Berlin, Handb Exp Pharmacol, 78, 1451.
4. Igarashi K,, Kaji A, 1970, Relationship between sites 1,2 and acceptor donor sites for the binding of aminoacyl tRNA to ribosomes, Eur J Biochem, 14, 4146.
5. Neu HC, 1978, A symposium on tetracyclines, a major appraisal: introduction, Bull N Y Acad Med, 54, 141155.
6. Oliva B,, Gordon G,, McNicholas P,, Ellestad G,, Chopra I, 1992, Evidence that tetracycline analogs whose primary target is not the bacterial ribosome cause lysis of Escherichia coli, Antimicrob Agents Chemother, 36, 913919.
7. Rasmussen B,, Noller HF,, Daubresse G,, Oliva B,, Misulovin Z,, Rothstein DM,, Ellestad GA,, Gluzman Y,, Tally FP,, Chopra I, 1991, Molecular basis of tetracycline action: identification of analogs whose primary target is not the bacterial ribosome, Antimicrob Agents Chemother, 35, 23062311.
8. Siegel D, 1978, Tetracyclines, new look at old antibiotic. I. Clinical pharmacology, mechanism of action, and untoward effects, N Y State J Med, 78, 950956.
9. Siegel D, 1978, Tetracyclines, new look at old antibiotic. II. Clinical use, N Y State J Med, 78, 11151120.

Tables

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Table 1

Physicochemical properties of cyclines

Citation: Bryskier A. 2005. Tetracyclines, p 642-651. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch24
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Table 2

MICs of tetracycline, doxycycline, and minocycline for facultative aerobic and anaerobic bacteria

Citation: Bryskier A. 2005. Tetracyclines, p 642-651. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch24
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Table 3

In vitro activities of tetracycline, doxycycline, and minocycline against anaerobic bacteria and other pathogens

Citation: Bryskier A. 2005. Tetracyclines, p 642-651. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch24
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Table 4

Tetracycline resistance determinants

Citation: Bryskier A. 2005. Tetracyclines, p 642-651. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch24
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Table 5

Prevalence of tetracycline-resistant S. pneumoniae strains in Protekt studies

Citation: Bryskier A. 2005. Tetracyclines, p 642-651. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch24
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Table 6

Combined resistance of penicillin G and tetracycline within S. pneumoniae

Citation: Bryskier A. 2005. Tetracyclines, p 642-651. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch24
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Table 7

Combined resistance of penicillin G and tetracycline within S. pneumoniae in North America

Citation: Bryskier A. 2005. Tetracyclines, p 642-651. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch24
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Table 8

Prevalence of S. pneumoniae isolates resistant to tetracycline (1992–1996)

Citation: Bryskier A. 2005. Tetracyclines, p 642-651. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch24
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Table 9

Prevalence of gram-positive cocci resistant to tetracycline in North America in 1997

Citation: Bryskier A. 2005. Tetracyclines, p 642-651. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch24
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Table 10

Prevalence of tetracycline resistance in UTI

Citation: Bryskier A. 2005. Tetracyclines, p 642-651. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch24
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Table 11

Pharmacokinetic parameters of tetracyclines

Citation: Bryskier A. 2005. Tetracyclines, p 642-651. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch24

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