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Chapter 9 : Penems

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Penems, Page 1 of 2

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Abstract:

Penems are β-lactams with an unsaturated nucleus at position 2,3 and a sulfur atom at position 1 (thiazolidine nucleus). The pharmacokinetic properties, antibacterial activity, and toxicological properties are based on the C-2 side chain. The introduction of a 6-(1-hydroxyethyl) group increases the antibacterial activity and stability against hydrolysis by β-lactamases. However, these properties are dependent on the stereochemistry. Only the 5R,6S, 8R isomer is active, whereas the other three isomers, 5R,6S,8S, 5R,6R,8R, and 5R,6R,8S, are inactive. Among the isomers, the 5R isomers are responsible for the antibacterial activity of the penems. Several series have been prepared with the aim of extending the antibacterial spectrum so as to obtain good stability against hydrolysis by renal dehydropeptidase and reduce the lipophilicity of the molecules. The activity of the penems against is inferior to that of the parenteral cephems, particularly against and . After crossing the outer membrane, the penems penetrate the periplasmic space, in which the β-lactamases are found, and finally reach their target, the penicillin-binding proteins (PBP), which are enzymes responsible for the synthesis of peptidoglycan. The penems are stable against hydrolysis by β-lactamases and may also inhibit the activity of some of them. The currently available penems are administered parenterally, principally intravenously; in the case of ritipenem, the intramuscular route appears to be possible.

Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
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Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
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Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
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Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
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Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
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Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
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Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
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Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
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Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
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Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
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Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
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Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
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Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
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Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
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Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
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Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
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References

/content/book/10.1128/9781555815929.ch09
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Tables

Generic image for table
Table 1

Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
Generic image for table
Table 2

Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
Generic image for table
Table 3

Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
Generic image for table
Table 4

Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
Generic image for table
Table 5

Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
Generic image for table
Table 6

Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
Generic image for table
Table 7

Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
Generic image for table
Table 8

Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
Generic image for table
Table 9

Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
Generic image for table
Table 10

Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
Generic image for table
Table 11

Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
Generic image for table
Table 12

Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
Generic image for table
Table 13

Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
Generic image for table
Table 14

Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
Generic image for table
Table 15

Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
Generic image for table
Table 16

Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
Generic image for table
Table 17

Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
Generic image for table
Table 18

Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
Generic image for table
Table 19

Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
Generic image for table
Table 20

Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
Generic image for table
Table 21

Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
Generic image for table
Table 23

Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
Generic image for table
Table 24

Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
Generic image for table
Table 25

Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
Generic image for table
Table 26

Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
Generic image for table
Table 27

Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9
Generic image for table
Table 28

Citation: Bryskier A. 2005. Penems, p 319-335. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch9

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