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Antibiotics
Dr. Wasana Kudagammana
Oct 2022
Overview
• AB Resistance
• ABs
• β-Lactams
• Penicillin & Penicillinase-stable penicillins
• Aminopenicillins (ampicillin and amoxicillin)
• Carboxypenicillins (carbenicillin and ticarcillin)
• Ureidopenicillins (mezlocillin and piperacillin)
• Cephems
• Carbapenem
• Monobactam
• Non β-Lactams
• Single-Drug Classes
Mechanisms of AB Resistance
Classification of β-Lactamases
Spectrums of activity of antibiotics -general
β-Lactams
• β-lactam antimicrobial agents all share the common, central, four-
member β-lactam ring
• Inhibition of cell wall synthesis as the primary mode of action.
• Additional ring structures or substituent groups added to the β-
lactam ring determine whether the agent is classified as a penicillin,
cephem, carbapenem, or monobactam.
Penicillin
• Penicillins are primarily active against non-β-lactamase–producing, aerobic,
gram-positive, some fastidious, aerobic, gram-negative, and some
anaerobic bacteria.
• Aminopenicillins (ampicillin and amoxicillin) are active against additional
gram-negative species, including some members of the
Enterobacteriaceae.
• Carboxypenicillins (carbenicillin and ticarcillin) and ureidopenicillins
(mezlocillin and piperacillin) are active against a considerably expanded list
of gram-negative bacteria, including many Pseudomonas and Burkholderia
spp.
• Penicillinase-stable penicillins (cloxacillin, dicloxacillin, methicillin, nafcillin,
and oxacillin) are active against predominantly gram-positive bacteria,
including penicillinase-producing staphylococci
β-Lactam/β-Lactamase Inhibitor
Combinations (BLBLIs)
• Clavulanic acid, sulbactam, and tazobactam, avibactam, vaborbactam,
relebactam.
• The results of tests of only the β-lactam portion of the combination
against β-lactamase–producing organisms are often not predictive of
susceptibility to the two-drug combination.
Cephems (Including Cephalosporins)
• Exhibit somewhat different spectrums of activity against aerobic and
anaerobic, gram-positive and gram-negative bacteria
• Cephalosporins are often referred to as “first-,” “second-,” “third-,” or
“fourth generation” cephalosporins, based on the extent of their
activity against the more antimicrobial agent– resistant, gram-
negative aerobic bacteria
• No effect on anaerobes and enterococci
Carbapenems
• Carbapenems and penems
• Differs slightly in structure from the penicillin class
• A penem is a type of β-lactam with an unsaturated five-member
heterocycle containing a sulfur atom fused to the β-lactam ring.
• Penems do not occur naturally; all are synthetic.
• Related to penems are carbapenems, which have a carbon atom in
place of the sulfur atom
• Agents in this class are much more resistant to β-lactamase
hydrolysis, which provides them with broad-spectrum activity against
many gram-positive and gram-negative bacteria
Monobactams
• Monobactam antimicrobial agents are monocyclic β-lactams
• Has activity only against aerobic, gram-negative bacteria
• Aztreonam- only monobactam antimicrobial agent approved for use
in the United States by the FDA
Non-β-lactams
• Aminoglycosides
• Folate Pathway Inhibitors
• Glycopeptides
• Lipopeptides
• Macrolides
• Nitroimidazoles
• Oxazolidinones
• Quinolones
• Streptogramins
• Tetracyclines
• Single-Drug Classes
Aminoglycosides
• Aminoglycosides are structurally related antimicrobial agents that
inhibit bacterial protein synthesis at the ribosomal level
• This class includes agents variously affected by aminoglycoside-
inactivating enzymes
• Aminoglycosides are used primarily to treat aerobic, gram-negative
rod infections or in synergistic combinations with cell wall– active
antimicrobial agents (eg, penicillin, ampicillin, vancomycin) against
some resistant, gram-positive bacteria, such as enterococci
Folate Pathway Inhibitors
• Sulfamethoxazole is usually tested in combination with trimethoprim,
because these two antimicrobial agents inhibit sequential steps in the
folate pathway of some gram-positive and gram-negative bacteria
Glycopeptides
• Glycopeptide antimicrobial agents
• which include vancomycin and teicoplanin
• share a complex chemical structure and a principal mode of action of
inhibition of cell wall synthesis at a different site than that of the β-lactams
• The activity of this group is directed primarily at
aerobic, gram-positive bacteria
• Vancomycin is an accepted agent for treatment of
• Gram-positive bacterial infection eg, MRSA and some enterococci)
• in the penicillin-allergic patient
Lipopeptides
• Lipopeptides are antimicrobial agents- the principal target is the cell membrane
• The polymyxin subclass
• Has activity against gram-negative organisms.
• polymyxin B and colistin
• Daptomycin is a cyclic lipopeptide
• Has activity against gram-positive organisms
• Lipopeptide activity is strongly influenced by the presence of divalent cations
• The presence of excess calcium cations inhibits the activity of the polymyxins,
• Whereas the presence of physiological levels (50 mg/L) of calcium ions is essential for the
proper activity of daptomycin
Macrolides
• Macrolides are structurally related antimicrobial agents that inhibit
bacterial protein synthesis at the ribosomal level
• against fastidious, gram-negative bacterial isolates and gram-positive
organisms
• The macrolide group of antimicrobial agents consists of several
subgroups
• azithromycin, clarithromycin, dirithromycin, the ketolide telithromycin, and
the fluoroketolide solithromycin.
Nitroimidazoles
• Nitroimidazoles- metronidazole and tinidazole are bactericidal agents
that are converted intracellularly in susceptible organisms to
metabolites that disrupt the host deoxyribonucleic acid (DNA)
• active only against strictly anaerobic bacteria
Oxazolidinones
• The oxazolidinone class is a class of antimicrobial agents with a
unique mechanism of action that inhibits protein synthesis
• The first agent approved in this class was linezolid which has activity
against only gram positive organisms
Quinolones
• Quinolones (quinolones and fluoroquinolones) are structurally related
antimicrobial agents that function primarily by inhibiting the DNA-
gyrase or topoisomerase activity of many gram-positive and gram-
negative bacteria
• Some differences in spectrum may require separate testing of the
individual agents.
• N acid, ciprofloxacin, levoflox, moxi and few more
Streptogramins
• Streptogramins, which include quinupristin-dalfopristin and
linopristin-flopristin, are combinations of two cyclic peptides
produced by Streptomyces spp.
• They work synergistically to inhibit protein synthesis, mainly in gram-
positive organisms, although they do have limited activity against
some gram-negative and anaerobic organisms.
Tetracyclines
• Tetracyclines are structurally related antimicrobial agents that inhibit
protein synthesis at the ribosomal level of certain gram-positive and
gram-negative bacteria.
• Organisms that are susceptible to tetracycline are also considered
susceptible to doxycycline and minocycline
• Tigecycline, a glycylcycline, is a derivative of minocycline that has
activity against organisms that may be resistant to other tetracyclines
Single-Drug Classes
The following antimicrobial agents (antimicrobial classes) are currently the only members of their respective
classes used in humans
• Chloramphenicol (phenicols) inhibit protein synthesis
• Clindamycin (lincosamides) inhibit protein synthesis
• fusidic acid (steroidal) inhibit protein synthesis
• mupirocin (pseudomonic acid) inhibit protein synthesis
• spectinomycin (aminocyclitols) inhibit protein synthesis;
• rifampin (ansamycins)
• Rifamycin (rifaximin) inhibits protein synthesis: poor absorption when given orally; hepatic ncephalopathy
• fidaxomicin (macrocyclics), which are ribonucleic acid (RNA) synthesis inhibitors
• Nitrofurantoin (nitrofurans), which is used only in the therapy of urinary tract infections, acts by inhibiting
several protein synthesis-and-assembly steps at the ribosomal level
• Fosfomycin (fosfomycins), approved by the FDA for urinary tract infections only, inhibits enzymes involved in
cell wall synthesis
•Thank you!

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Antibiotics use.pdf

  • 2. Overview • AB Resistance • ABs • β-Lactams • Penicillin & Penicillinase-stable penicillins • Aminopenicillins (ampicillin and amoxicillin) • Carboxypenicillins (carbenicillin and ticarcillin) • Ureidopenicillins (mezlocillin and piperacillin) • Cephems • Carbapenem • Monobactam • Non β-Lactams • Single-Drug Classes
  • 3. Mechanisms of AB Resistance
  • 5. Spectrums of activity of antibiotics -general
  • 6.
  • 7. β-Lactams • β-lactam antimicrobial agents all share the common, central, four- member β-lactam ring • Inhibition of cell wall synthesis as the primary mode of action. • Additional ring structures or substituent groups added to the β- lactam ring determine whether the agent is classified as a penicillin, cephem, carbapenem, or monobactam.
  • 8. Penicillin • Penicillins are primarily active against non-β-lactamase–producing, aerobic, gram-positive, some fastidious, aerobic, gram-negative, and some anaerobic bacteria. • Aminopenicillins (ampicillin and amoxicillin) are active against additional gram-negative species, including some members of the Enterobacteriaceae. • Carboxypenicillins (carbenicillin and ticarcillin) and ureidopenicillins (mezlocillin and piperacillin) are active against a considerably expanded list of gram-negative bacteria, including many Pseudomonas and Burkholderia spp. • Penicillinase-stable penicillins (cloxacillin, dicloxacillin, methicillin, nafcillin, and oxacillin) are active against predominantly gram-positive bacteria, including penicillinase-producing staphylococci
  • 9. β-Lactam/β-Lactamase Inhibitor Combinations (BLBLIs) • Clavulanic acid, sulbactam, and tazobactam, avibactam, vaborbactam, relebactam. • The results of tests of only the β-lactam portion of the combination against β-lactamase–producing organisms are often not predictive of susceptibility to the two-drug combination.
  • 10. Cephems (Including Cephalosporins) • Exhibit somewhat different spectrums of activity against aerobic and anaerobic, gram-positive and gram-negative bacteria • Cephalosporins are often referred to as “first-,” “second-,” “third-,” or “fourth generation” cephalosporins, based on the extent of their activity against the more antimicrobial agent– resistant, gram- negative aerobic bacteria • No effect on anaerobes and enterococci
  • 11. Carbapenems • Carbapenems and penems • Differs slightly in structure from the penicillin class • A penem is a type of β-lactam with an unsaturated five-member heterocycle containing a sulfur atom fused to the β-lactam ring. • Penems do not occur naturally; all are synthetic. • Related to penems are carbapenems, which have a carbon atom in place of the sulfur atom • Agents in this class are much more resistant to β-lactamase hydrolysis, which provides them with broad-spectrum activity against many gram-positive and gram-negative bacteria
  • 12. Monobactams • Monobactam antimicrobial agents are monocyclic β-lactams • Has activity only against aerobic, gram-negative bacteria • Aztreonam- only monobactam antimicrobial agent approved for use in the United States by the FDA
  • 13. Non-β-lactams • Aminoglycosides • Folate Pathway Inhibitors • Glycopeptides • Lipopeptides • Macrolides • Nitroimidazoles • Oxazolidinones • Quinolones • Streptogramins • Tetracyclines • Single-Drug Classes
  • 14. Aminoglycosides • Aminoglycosides are structurally related antimicrobial agents that inhibit bacterial protein synthesis at the ribosomal level • This class includes agents variously affected by aminoglycoside- inactivating enzymes • Aminoglycosides are used primarily to treat aerobic, gram-negative rod infections or in synergistic combinations with cell wall– active antimicrobial agents (eg, penicillin, ampicillin, vancomycin) against some resistant, gram-positive bacteria, such as enterococci
  • 15. Folate Pathway Inhibitors • Sulfamethoxazole is usually tested in combination with trimethoprim, because these two antimicrobial agents inhibit sequential steps in the folate pathway of some gram-positive and gram-negative bacteria
  • 16. Glycopeptides • Glycopeptide antimicrobial agents • which include vancomycin and teicoplanin • share a complex chemical structure and a principal mode of action of inhibition of cell wall synthesis at a different site than that of the β-lactams • The activity of this group is directed primarily at aerobic, gram-positive bacteria • Vancomycin is an accepted agent for treatment of • Gram-positive bacterial infection eg, MRSA and some enterococci) • in the penicillin-allergic patient
  • 17. Lipopeptides • Lipopeptides are antimicrobial agents- the principal target is the cell membrane • The polymyxin subclass • Has activity against gram-negative organisms. • polymyxin B and colistin • Daptomycin is a cyclic lipopeptide • Has activity against gram-positive organisms • Lipopeptide activity is strongly influenced by the presence of divalent cations • The presence of excess calcium cations inhibits the activity of the polymyxins, • Whereas the presence of physiological levels (50 mg/L) of calcium ions is essential for the proper activity of daptomycin
  • 18. Macrolides • Macrolides are structurally related antimicrobial agents that inhibit bacterial protein synthesis at the ribosomal level • against fastidious, gram-negative bacterial isolates and gram-positive organisms • The macrolide group of antimicrobial agents consists of several subgroups • azithromycin, clarithromycin, dirithromycin, the ketolide telithromycin, and the fluoroketolide solithromycin.
  • 19. Nitroimidazoles • Nitroimidazoles- metronidazole and tinidazole are bactericidal agents that are converted intracellularly in susceptible organisms to metabolites that disrupt the host deoxyribonucleic acid (DNA) • active only against strictly anaerobic bacteria
  • 20. Oxazolidinones • The oxazolidinone class is a class of antimicrobial agents with a unique mechanism of action that inhibits protein synthesis • The first agent approved in this class was linezolid which has activity against only gram positive organisms
  • 21. Quinolones • Quinolones (quinolones and fluoroquinolones) are structurally related antimicrobial agents that function primarily by inhibiting the DNA- gyrase or topoisomerase activity of many gram-positive and gram- negative bacteria • Some differences in spectrum may require separate testing of the individual agents. • N acid, ciprofloxacin, levoflox, moxi and few more
  • 22. Streptogramins • Streptogramins, which include quinupristin-dalfopristin and linopristin-flopristin, are combinations of two cyclic peptides produced by Streptomyces spp. • They work synergistically to inhibit protein synthesis, mainly in gram- positive organisms, although they do have limited activity against some gram-negative and anaerobic organisms.
  • 23. Tetracyclines • Tetracyclines are structurally related antimicrobial agents that inhibit protein synthesis at the ribosomal level of certain gram-positive and gram-negative bacteria. • Organisms that are susceptible to tetracycline are also considered susceptible to doxycycline and minocycline • Tigecycline, a glycylcycline, is a derivative of minocycline that has activity against organisms that may be resistant to other tetracyclines
  • 24. Single-Drug Classes The following antimicrobial agents (antimicrobial classes) are currently the only members of their respective classes used in humans • Chloramphenicol (phenicols) inhibit protein synthesis • Clindamycin (lincosamides) inhibit protein synthesis • fusidic acid (steroidal) inhibit protein synthesis • mupirocin (pseudomonic acid) inhibit protein synthesis • spectinomycin (aminocyclitols) inhibit protein synthesis; • rifampin (ansamycins) • Rifamycin (rifaximin) inhibits protein synthesis: poor absorption when given orally; hepatic ncephalopathy • fidaxomicin (macrocyclics), which are ribonucleic acid (RNA) synthesis inhibitors • Nitrofurantoin (nitrofurans), which is used only in the therapy of urinary tract infections, acts by inhibiting several protein synthesis-and-assembly steps at the ribosomal level • Fosfomycin (fosfomycins), approved by the FDA for urinary tract infections only, inhibits enzymes involved in cell wall synthesis