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Cefotaxime was synthesized by Hoechst and Roussel-Uclaf in 1977. It was the first derivative of cephalosporin to introduce the methoxyimino and aminothiazole groups at the 7 position of the cephem nucleus. Although it shows unexpectedly low oral absorption, its excellent activity against a wide range of gram-positive and gram-negative organisms, including Serratia, Enterobacter, Citrobacter, and anaerobes, guided research and development of the newer synthetic cephems, the so-called thirdgeneration cephalosporins.

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White to pale yellow crystalline powder

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Cefotaxime sodium salt acts as a beta-lactamase resistant antibiotic. It is used as an effective antibacterial against gram-negative bacteria, with the notable exception of pseudomonas and penicillin-resistant strains of streptococcus pneumoniae. It is used to treat infections of the bones, joints, skin, respiratory tract and blood stream.

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ChEBI: A cephalosporin organic sodium salt having acetoxymethyl and [2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino side-groups.

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Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards

Clinical Use

Cefotaxime (Claforan) was the first third-generationcephalosporin to be introduced. It possesses excellentbroad-spectrum activity against Gram-positive and Gramnegativeaerobic and anaerobic bacteria. It is more activethan moxalactam against Gram-positive organisms. Manyβ-lactamase–producing bacterial strains are sensitive to cefotaxime,including N. gonorrhoeae, Klebsiella spp., H. influenzae,S. aureus, and E. cloacae. Some, but not all,Pseudomonas strains are sensitive. Enterococci and Listeriamonocytogenes are resistant.
The syn-isomer of cefotaxime is significantly more activethan the anti-isomer against β-lactamase–producing bacteria.This potency difference is, in part, because of greaterresistance of the syn-isomer to the action of β-lactamases.The higher affinity of the syn-isomer for PBPs, however,may also be a factor.
Cefotaxime is metabolized in part to the less active desacetylmetabolite. Approximately 20% of the metaboliteand 25% of the parent drug are excreted in the urine. Theparent drug reaches the cerebrospinal fluid in sufficient concentrationto be effective in the treatment of meningitis.Solutions of cefotaxime sodium should be used within 24hours. If stored, they should be refrigerated. Refrigerated solutionsmaintain potency up to 10 days.

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