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Chapter 25 : Tetracyclines Under Investigation

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Abstract:

Tetracycline appears to bind directly to the S7 protein and to the region of 16S RNA from bases 892 to 1054. The hydroxyl group of tetracycline binds to the A892 base. At physiological pH, the tetracyclines exist as a mixture of two forms: (i) a low-energy, nonionized, lipophilic form and (ii) a high-energy zwitterionic form. Resistance to the action of tetracyclines is due principally to the acquisition of the Tet determinant and not to a chromosomally mediated mutation. The mechanisms of resistance of Neisseria gonorrhoeae are an exception. The tet(A) and tet(R) gene repressor and the TetA export molecule recognize the tetracyclines in the form of the chelation complex. Tet(M) and Tet(O) are 70% homologous in terms of their amino acid sequence, and likewise Otr(A), Tet(B)(P), and Tet(Q) are 45% homologous and form a third group. They appear to prevent the binding of tetracyclines to the ribosomes. The pharmacokinetics of thiacycline were determined versus those of doxycycline by Dingeldein and Ungethüm in 17 volunteers. Single doses of 100 and 200 mg of thiacycline and 200 mg of doxycycline were administered orally. The aglycone, dactylocyclinone or Sch-34164, possesses cross-resistance with the tetracyclines and is active against gram-negative bacteria. The MICs of minocycline are lower and dependent on the nature of the tet determinant. Tigecycline exhibits good in vitro activity against Streptococcus mitis, Streptococcus anginosus, Streptococcus sanguinis, Streptococcus bovis, and Streptococcus salivarius, with MICs under 0.25 µg/ml.

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Figures

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Figure 1

Structure of tetracyclines

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Figure 2

Tetracycline classification

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Figure 3

Tetracycline interaction with magnesium ion

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Figure 4

Translocation of tetracycline-Mg complex

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Figure 5

Tetracycline transport systems: tetracycline-Mg2+ complex

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Figure 6

Bactericidal tetracyclines

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Figure 7

Thiacycline (EMD-33330)

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Figure 8

Dactylocyclines

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Figure 9

8-Methoxychlortetracyclines

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Figure 10

Cyclines: 9-substituted derivatives

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Figure 11

Tigecycline

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Figure 12

8-Methoxytetracyclines

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Figure 13

PTK 0796 (Bay 73-6944)

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Figure 14

13-Alkylthio tetracycline

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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References

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Tables

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Table 1

Comparative activities of cyclines against E. coli K-12 a

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Table 2

Localization of Tet determinants a

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Table 3

Resistance mechanisms and determinants

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Table 4

Distribution of Tet resistance determinants among gram-negative bacilli a

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Table 5

Tet determinants of gram-positive bacilli a

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Table 6

Pharmacokinetics of thiacycline a

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Table 7

In vitro activities of dactylocyclines

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Table 8

In vitro activities of glycylcyclines

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Table 9

In vitro activities of glycylcyclines against Enterobacteriaceae and gram-negative bacilli

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Table 10

In vitro activities of glycylcyclines against anaerobes

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Table 11

In vitro activities of glycylcyclines against Mycoplasma spp.

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Table 12

In vitro activities of glycylcyclines against tetracycline-resistant bacteria

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Table 13

In vitro activity of tigecycline

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Table 14

Antichlamydial activity of tigecycline

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Table 15

In vitro activity of tigecycline against mycobacteria

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Table 16

In vivo activity of tigecycline in comparison with minocycline

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Table 17

Pharmacokinetics of tigecycline in healthy volunteers (ascending doses)

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Table 18

Pharmacokinetics of tigecycline according to gender

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Table 19

Pharmacokinetics of tigecycline after food intake

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Table 20

Antistaphylococcal activities of 8-methoxychlortetracyclines

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
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Table 21

In vitro activity of PTK 0796

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
Generic image for table
Table 22

In vitro activity of PTK 0796 against strains resistant to tetracycline

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
Generic image for table
Table 23

In vivo activity of PTK 0796

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25
Generic image for table
Table 24

Pharmacokinetics of PTK 0796 in animals

Citation: Bryskier A. 2005. Tetracyclines Under Investigation, p 652-667. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch25

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