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Cefotaxime
Systematic (IUPAC) name
(6R,7R,Z)-3-(acetoxymethyl)-7-(2-(2-aminothiazol-4-yl)-
2-(methoxyimino)acetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]
oct-2-ene-2-carboxylic acid
Identifiers
CAS number 63527-52-6
ATC code J01DD01
PubChem 5479527
DrugBank APRD00854
ChemSpider 4586392
Chemical data
Formula C 16H17N5O7S2  
Mol. mass 455.47 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability n/a
Metabolism Hepatic
Half life 0.8–1.4 hours
Excretion 50–85% renal
Therapeutic considerations
Pregnancy cat. B1(AU) B(US)
Legal status Prescription Only (S4) (AU)
Routes Intravenous
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Cefotaxime (INN) (pronounced /ˌsɛfɵˈtæksiːm/) is a third-generation cephalosporin antibiotic. Like other third-generation cephalosporins, it has broad spectrum activity against Gram positive and Gram negative bacteria. In most cases, it is considered to be equivalent to ceftriaxone in terms of safety and efficacy. Cefotaxime sodium is marketed under various trade names including Claforan (Roussel-Uclaf)& Taxim (Alkem Laboratories)

Contents

Mechanism of action

Inhibits bacterial cell wall synthesis by binding to one or more of the penicillin-binding proteins (PBPs) which in turn inhibits the final transpeptidation step of peptidoglycan synthesis in bacterial cell walls, thus inhibiting cell wall biosynthesis. Bacteria eventually lyse due to ongoing activity of cell wall autolytic enzymes (autolysins and murein hydrolases) while cell wall assembly is arrested.[1]

Cefotaxime, like other β-lactam antibiotics does not only block the division of bacteria, including cyanobacteria, but also the division of cyanelles, the photosynthetic organelles of the Glaucophytes, and the division of chloroplasts of bryophytes. In contrast, it has no effect on the plastids of the highly developed vascular plants. This is supporting the endosymbiotic theory and indicates an evolution of plastid division in land plants [2].

Clinical use

Cefotaxime is used for infections of the respiratory tract, skin, bones, joints, urogenital system, meningitis, and septicemia. It generally has good coverage against most Gram-negative bacteria, with the notable exception of Pseudomonas. It is also effective against most Gram-positive cocci except for Enterococcus.[1] It is active against penicillin-resistant strains of Streptococcus pneumoniae. It has modest activity against the anaerobic Bacteroides fragilis.

Chemistry

The syn-configuration of the methoxyimino moiety confers stability to β-lactamase enzymes produced by many Gram-negative bacteria. Such stability to β-lactamases increases the activity of cefotaxime against otherwise resistant Gram-negative organisms.

References

  1. ^ a b Cefotaxime drug information
  2. ^ Britta Kasten und Ralf Reski (1997): β-lactam antibiotics inhibit chloroplast division in a moss (Physcomitrella patens) but not in tomato (Lycopersicon esculentum). Journal of Plant Physiology 150, 137-140. [1]
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