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Nafcillin, Oxacillin, Methicillin & Dicloxacillin

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Pharmacology

Summary

Anti-staphylococcal penicillins--- which include nafcillin, oxacillin, cloxacillin, and dicloxacillin--- play a pivotal role in targeting beta-lactamase-producing staphylococci. By covalently binding to penicillin-binding proteins (PBPs), they inhibit the transpeptidation reaction and impede peptidoglycan synthesis at the cell wall, which effectively kills the bacterial cell. These antibiotics have bulky R-groups that prevent beta-lactamase from binding to them, making them resistant and effective against penicillin-resistant strains of staphlococci.

Due to their narrow spectrum of activity, anti-staphylococcal penicillins are often the drug of choice for treating methicillin-sensitive staph infections. They're commonly used empirically to treat skin and soft tissue infections and can also treat more serious systemic staphlococcal infections like staph endocarditis and staph osteomyelitis. However, these agents are ineffective against methicillin-resistant Staph aureus (MRSA), which produces altered PBPs, thereby reducing drug affinity and thus their bactericidal activity.

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FAQs

What are the unique characteristics of anti-staph penicillins like nafcillin and oxacillin?

Anti-staph penicillins, including nafcillin and oxacillin, are beta-lactam antibiotics that contain a beta-lactam ring. These antibiotics are noted for their activity against penicillin-resistant gram-positive staphylococci such as methicillin-sensitive Staph aureus. Unique to these anti-staph penicillins are their bulky R-groups, which prevent beta-lactamase binding and make them resistant to beta-lactamases (enzymes that often confer resistance to pencillin-resistant bacteria).

How does the mechanism of action of anti-staph penicillins work?

Anti-staph penicillins work by interacting with the peptidoglycan cell wall in bacteria. The penicillins bind to a protein called penicillin-binding protein (PBP), which plays a crucial role in the synthesis of this cell wall by forming peptidoglycan cross-links. The binding of the antibiotic disrupts this process, leading to a weakening of the cell wall and eventually bacterial cell death.

What types of infections can be treated with anti-staph penicillins?

Anti-staph penicillins such as nafcillin and oxacillin can be used as empiric treatment for a variety of infections caused by methicillin-sensitive Staph aureus (MSSA). These include skin and soft tissue infections like folliculitis and abscesses, as well as more serious conditions like staphylococcal endocarditis and staphylococcal osteomyelitis.

How does methicillin-resistant Staph aureus (MRSA) show resistance to beta-lactam antibiotics like anti-staph penicillins?

Methicillin-resistant Staph aureus (MRSA) can produce altered forms of penicillin-binding proteins (PBPs) that are resistant to the actions of beta-lactam antibiotics. This means that the antibiotics are unable to bind effectively to the PBPs and disrupt the synthesis of the bacterial cell wall, allowing the MRSA to survive.

What is the role of dicloxacillin in the treatment of staphylococcal infections?

Like nafcillin and oxacillin, dicloxacillin is an anti-staph penicillin that works by interfering with the synthesis of the bacterial cell wall, and it is effective against a range of gram-positive bacteria, including staphylococci. Dicloxacillin is also resistant to beta-lactamases, making it more effective against resistant strains compared to other types of penicillin.