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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
Identifiers
CAS number 63527-52-6
ATC code J01DD01
PubChem 456256
DrugBank APRD00854
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.

B1(AU) B(US)

Legal status

Prescription Only (S4)(AU)

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).

Additional recommended knowledge

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

Treatment of susceptible infection in respiratory tract, skin and skin structure, bone and joint, urinary tract, gynecologic as well as septicemia, and documented or suspected meningitis. Active against most gram-negative bacilli (not Pseudomonas) and gram-positive cocci (not enterococcus). Active against many penicillin-resistant pneumococci[1] (See also cephalosporin).

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
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Cefotaxime". A list of authors is available in Wikipedia.
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