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The β-lactam core structures. (A) A penam.(B) A carbapenam.(C) An oxapenam.(D) A penem.(E) A carbapenem.(F) A monobactam.(G) A cephem.(H) A carbacephem.(I) An oxacephem. This is a list of common β-lactam antibiotics—both administered drugs and those not in clinical use—organized by structural class.
Skeletal formulae of the basic structures of penicillin (1) and cephalosporin (2) antibiotics, highlighting the beta-lactam ring (red). Created using ACD/ChemSketch 10.0 and Inkscape . Legend
β-Lactam antibiotics are indicated for the prevention and treatment of bacterial infections caused by susceptible organisms. At first, β-lactam antibiotics were mainly active only against gram-positive bacteria, yet the recent development of broad-spectrum β-lactam antibiotics active against various gram-negative organisms has increased their usefulness.
A lactam is a cyclic amide, and beta-lactams are named so because the nitrogen atom is attached to the β-carbon atom relative to the carbonyl. The simplest β-lactam possible is 2-azetidinone. β-lactams are significant structural units of medicines as manifested in many β-lactam antibiotics. [2]
Dicloxacillin is a narrow-spectrum β-lactam antibiotic of the penicillin class. [1] It is used to treat infections caused by susceptible (non-resistant) Gram-positive bacteria . [ 1 ] It is active against beta-lactamase -producing organisms such as Staphylococcus aureus , which would otherwise be resistant to most penicillins .
Since the discovery of the beta-lactam antibiotic penicillin, the rates of antimicrobial resistance have increased. [38] Over time, methods for testing the sensitivity of bacteria to antibiotics have developed and changed. [25] Alexander Fleming in the 1920s developed the first method of susceptibility testing.
The β-lactam ring is not fused to another ring, in contrast to most other β-lactams. [ 1 ] Monobactams are narrow-spectrum antibiotics [ 2 ] effective only against (strictly or facultatively [ 3 ] ) aerobic Gram-negative bacilli , [ 4 ] [ 5 ] [ 3 ] exhibiting a high level of resistance to beta-lactamases of these organisms. [ 3 ]
It is not recommended in people who have previously had a penicillin allergy. [1] Use during pregnancy appears to be relatively safe. [1] Cloxacillin is in the penicillin family of medications. [2] Cloxacillin was patented in 1960 and approved for medical use in 1965. [3] It is on the World Health Organization's List of Essential Medicines. [4]