Cefotaxime

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
Clinical data
Trade names	Claforan
AHFS/Drugs.com	monograph
MedlinePlus	a682765
Pregnancy cat.	B1(AU) B(US)
Legal status	Prescription Only (S4) (AU)
Routes	Intravenous
Pharmacokinetic data
Bioavailability	n/a
Metabolism	Hepatic
Half-life	0.8–1.4 hours
Excretion	50–85% renal
Identifiers
CAS number	63527-52-6
ATC code	J01DD01
PubChem	CID 5479527
DrugBank	APRD00854
ChemSpider	4586392 Y
UNII	N2GI8B1GK7 Y
KEGG	D07647 Y
ChEMBL	CHEMBL102 Y
Chemical data
Formula	C16H17N5O7S2
Mol. mass	455.47 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C16H17N5O7S2/c1-6(22)28-3-7-4-29-14-10(13(24)21(14)11(7)15(25)26)19-12(23)9(20-27-2)8-5-30-16(17)18-8/h5,10,14H,3-4H2,1-2H3,(H2,17,18)(H,19,23)(H,25,26)/b20-9+/t10-,14-/m1/s1 Y Key:GPRBEKHLDVQUJE-VINNURBNSA-N Y
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Cefotaxime (INN) ( /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.

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]