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Chapter 8 : Carbapenems

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Carbapenems, Page 1 of 2

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Abstract:

Current research into carbapenems is directed towards the synthesis of molecules that are more stable against hydrolysis by dehydropeptidase I (DHP-I), the reduction of neurologic side effects, the improvement of pharmacokinetic characteristics, oral absorption, and the absence of cross-resistance with imipenem. The structure-activity relationships of the carbapenems are complex, as they derive from an equilibrium that is difficult to achieve between antibacterial activity, chemical stability, and stability against hydrolysis by renal DHP-I. The 1-β-aminoethyl derivatives are active in vitro but are unstable at high pH, as an intramolecular rearrangement is produced. The attachment of an amino acid or a small peptide prevents this rearrangement. In this series, the chloro-L-alanine derivative possesses good in vitro and in vivo activity against and . The carbapenems exhibit good activity against and . The carbapenems possess remarkable activity against ; in particular, they are active against strains producing plasmid-mediated broad-spectrum and extended-spectrum enzymes and chromosomally mediated enzymes. There are a number of mechanisms of resistance to carbapenems. These are based on single or multiple phenomena: crossing of the bacterial wall, modification of the target penicillin-binding proteins (PBPs), and hydrolysis by β-lactamases. The imipenemases are chromosomal metalloenzymes capable of hydrolyzing the carbapenems. The major problem with the carbapenems is their chemical instability in solution. The plasma pharmacokinetics of the carbapenems are complex because of their hydrolysis by renal DHP-I to various degrees, depending on the molecule, with major interindividual variability.

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
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Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
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Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
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Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
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Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
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Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
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Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
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Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
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Tables

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Table 1

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 2

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 3

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 4

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 5

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 6

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 7

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 8

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 9

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 10

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 11

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 12

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 13

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 14

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 15

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 16

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 17

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 18

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 19

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 20

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 21

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 22

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 23

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 24

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 25

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 26

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 27

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 28

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 29

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 30

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 31

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 32

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 33

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 34

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 35

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 36

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 37

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 38

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 39

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 40

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 41

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 42

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 43

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 44

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 45

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 46

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 47

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 48

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 49

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8
Generic image for table
Table 50

Citation: Bryskier A. 2005. Carbapenems, p 269-318. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch8

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