Beta-lactam antibiotics
Drug class | |
Class identifiers | |
Use | Bacterial infection |
ATC code | J01C |
Biological target | Penicillin binding protein |
External links | |
MeSH | D047090 |
Legal status | |
In Wikidata |
Bacteria often develop resistance to
Medical use
[edit]In uninflamed (normal) brain meninges, the penetration of beta-lactam antibiotics is low, at 0.15 of
Adverse effects
[edit]Adverse drug reactions
[edit]Common adverse drug reactions for the
Infrequent adverse effects include fever, vomiting, erythema, dermatitis, angioedema, pseudomembranous colitis.[8]
Pain and inflammation at the injection site is also common for parenterally administered
Allergy/hypersensitivity
[edit]Immunologically mediated adverse reactions to any
Nevertheless, the risk of cross-reactivity is sufficient to warrant the contraindication of all
A Jarisch–Herxheimer reaction may occur after initial treatment of a spirochetal infection such as syphilis with a
Mechanism of action
[edit]Inhibition of cell wall synthesis
[edit]Under normal circumstances, peptidoglycan precursors signal a reorganisation of the bacterial cell wall and, as a consequence, trigger the activation of autolytic cell wall hydrolases. Inhibition of cross-linkage by
Guanine oxidation
[edit]Another possibility that has been proposed to account for much of the cytotoxicity of beta lactams focuses on the oxidation of the guanine nucleotide in the bacterial nucleotide pool.[15] The incorporation of oxidized guanine nucleotide into DNA could cause cytotoxicity. Bacterial cytotoxicity could arise from incomplete repair of closely spaced 8-oxo-2'-deoxyguanosine lesions in the DNA resulting in double-strand breaks.[15]
Potency
[edit]Two structural features of
Modes of resistance
[edit]By definition, all
Enzymatic hydrolysis of the β -lactam ring
[edit]If the bacterium produces the enzyme
The production of a
Other
However, in all cases where infection with
In the context of medical pharmacology, penicillins, cephalosporins, and carbapenems, while all have the
Possession of altered penicillin-binding proteins
[edit]As a response to the use of
Nomenclature
[edit]β -lactams fused to saturated five-membered rings:β -lactams containing thiazolidine rings are named penams.β -lactams containing pyrrolidine rings are named carbapenams.β -lactams fused to oxazolidine rings are named oxapenams or clavams.
β -lactams fused to unsaturated five-membered rings:β -lactams containing 2,3-dihydrothiazole rings are named penems.β -lactams containing 2,3-dihydro-1H-pyrrole rings are named carbapenems.
β -lactams fused to unsaturated six-membered rings:β -lactams containing 3,6-dihydro-2H-1,3-thiazine rings are named cephems.β -lactams containing 1,2,3,4-tetrahydropyridine rings are named carbacephems.β -lactams containing 3,6-dihydro-2H-1,3-oxazine rings are named oxacephems.
β -lactams not fused to any other ring are named monobactams.
By convention, the bicyclic
The numbering of monobactams follows that of the IUPAC; the nitrogen atom is position 1, the carbonyl carbon is 2, the
Biosynthesis
[edit]To date, two distinct methods of biosynthesizing the
The biosynthesis of cephems branch off at isopenicillin N by an oxidative ring expansion to the cephem core. As with the penams, the variety of cephalosporins and cephamycins come from different transamidations, as is the case for the penicillins.[citation needed]
While the ring closure in penams and cephems is between positions 1 and 4 of the
The biosynthesis of the
See also
[edit]- List of
β -lactam antibiotics - ATC code J01C Beta-lactam antibacterials, penicillins
- ATC code J01D Other beta-lactam antibacterials
- Bacteria
- Cell wall
- Discovery and development of cephalosporins
- History of penicillin
- Nitrocefin
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