| content | ||||||||||||||||||||||||||||||||||||||||||||
 |
|
|
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 | |
| ATC code | J01 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C16H17N5O7S2 |
| Mol. mass | 455.47 g/mol |
| Pharmacokinetic data | |
| Bioavailability | n/a |
| Metabolism | Hepatic |
| Half life | 0.8–1.4 hours |
| Excretion | 50–85% renal |
| Therapeutic considerations | |
| Pregnancy cat. | |
| Legal status | |
| Routes | Intravenous |
Cefotaxime (INN) (pronounced /sɛfəˈtæksiːm/, /kɛfə-/) 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 (Sanofi-Aventis).
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]
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
