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Inhibitors of Cell Wall SynthesisPenicillinsPMY 512 Spring 2019Harvey Berman, PhD, MPH [email protected]13A-Penicillins-2019 - January 19, 2019
β-Lactam agentsPenicillinsCephalosporinsCarbapenamMonobactamNNR223A-Penicillins-2019 - January 19, 2019
Golan, Figure 34.1 Englebert, Figure 3.133A-Penicillins-2019 - January 19, 2019
Stage I/III of bacterial cell wall synthesisUDP-N-acetylglucosamineUDP-Acetylmuramyl tripeptideUDP-Acetylmuramyl pentapeptideU=L-AlanineAlanineracemaseD-Ala-D-Ala synthetaseD-AlanineD-Alanine-D-Alanine=ULULCycloserine43A-Penicillins-2019 - January 19, 2019
CycloserineD-Alanine53A-Penicillins-2019 - January 19, 2019
Golan, Figures 34.2, 34.3 Goodman-&-Gilman, Figure 53-2Stage II and III of bacterial cell wall synthesisStage IIStage IIIJoining of the peptide side chains with the elimination of D-alanine63A-Penicillins-2019 - January 19, 2019
73A-Penicillins-2019 - January 19, 2019
Engleberg, Figure 3.383A-Penicillins-2019 - January 19, 2019
Proposed mechanism of transpeptidase inhibition by penicillinTranspeptidase (Enzyme)1. Penicillin occupies D-Ala-D-Alasubstrate site2. Reactive lactam ring is broken3. Penicillin is covalently linked to the enzymeNN93A-Penicillins-2019 - January 19, 2019
Enzymes that hydrolyze β-lactam antibioticsPenicillin6-Aminopenicillanic acidPenicilloic acidPenicillin amidasePenicillinase(β-Lactamase)β-lactamases = penicillinasesNNNNNUMEROUSENZYMEFORMSVariable specificity Broad spectrum Narrow spectrum103A-Penicillins-2019 - January 19, 2019
Classification of PenicillinsPenicillin classDrugClinically useful antimicrobial spectrumNarrow-spectrum penicillins: penicillinase-sensitivePenicillin GPenicillin VStreptococcusspecies; Neisseriaspecies, many aerobes, spirochetes, othersNarrow-spectrum penicillins: penicillinase-resistant (Antistaphylococcal penicillins)Methicillin*NafcillinOxacillinDicloxacillinStaphylococcus aureusBroad-spectrum penicillins: (Aminopenicillins)AmpicillinAmoxacillinHaemophilus influenzae, E. coli, Proteus mirabilis, Salmonella typhi, enterococci, Neisseria gonorrhoeae,Listeria monocytogenesExtended-spectrum penicillins: (Antipseudomonal penicillins)TicarcillinPiperacillinSame as broad-spectrum penicillins plus:Pseudomonas aeruginosa, Enterobacter species, Proteus(indole positive), Bacteroides fragilis, many Klebsiella,See Golan, pages 606-613113A-Penicillins-2019 - January 19, 2019
PenicillinsR=BenzylpenicillinPENICILLINGPENICILLINVPhenoxymethyl-penicillinK-salt Procaine salt Benzathine saltNarrow spectrumPenicillinase sensitiveStreptococcusNeisseriaBacillus anthracisCorynebacterium diphtheriaeClostridium perfringensTreponema pallidumTreponema pertenue123A-Penicillins-2019 - January 19, 2019

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