Cefoxitin Sodium

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Cat Number

API33564306

CAS Number

33564-30-6

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CAS Number

33564-30-6

EINECS

251-574-6

Storage

2-8℃

Synonyms

Cefoxitin sodium salt

Molecular Formula

C16H16N3NaO7S2

Molecular Weight

449.4

Smiles

CO[C@@]1([C@@H]2N(C1=O)C(=C(CS2)COC(=O)N)C(=O)[O-])NC(=O)CC3=CC=CS3.[Na+]

Appearance

White solid

Melting Point

>160℃

Boiling Point

843℃

General Description

Cefoxitin Sodium is the sodium salt of cefoxitin, a semi-synthetic cephamycin antibiotic derived from cephamycin C produced by Streptomyces lactamdurans. Unlike true cephalosporins, it contains a methoxy group at the 7α position of the beta-lactam ring, conferring enhanced resistance to many beta-lactamases.

Mechanism of Action

Cefoxitin Sodium inhibits bacterial cell wall synthesis by binding to penicillin-binding proteins (PBPs), particularly PBP2, blocking peptidoglycan cross-linking via transpeptidation. The 7α-methoxy group provides steric protection against hydrolysis by many beta-lactamases, including those produced by Bacteroides fragilis.

Application

Indicated for the treatment of intra-abdominal infections, including those caused by anaerobic bacteria such as Bacteroides fragilis. Cefoxitin Sodium is a cephamycin antibiotic with a 7alpha-methoxy group conferring enhanced resistance to beta-lactamases, distinguishing it from conventional cephalosporins.

Cefoxitin sodium was incorporated into hyaluronic acid thin films using electrospraying technology for wound dressing applications. Scanning electron microscopy revealed that hyaluronic acid-containing thin films were composed of numerous nanoparticles with irregular surfaces connected by nanofibers. Cefoxitin-loaded films contained fewer but larger particles with smooth surfaces. Fourier transform infrared and X-ray diffraction analyses confirmed that cefoxitin remained unmodified during incorporation and retained antibacterial activity against Klebsiella pneumoniae, Staphylococcus aureus, and Listeria monocytogenes. These nanofiber scaffolds of hyaluronic acid containing cefoxitin may be used in dressings to control postoperative infections.

Fig. 2 AFM images and roughness graphs of hyaluronic acid thin film (HAF). (Ahire J J, Dicks L M T. 2016)

References

Ahire J J, Dicks L M T. Antimicrobial hyaluronic acid–cefoxitin sodium thin films produced by electrospraying. Current microbiology, 2016, 73(2): 236-241.

What differentiates Cefoxitin Sodium from conventional cephalosporins?

The unique 7alpha-methoxy group provides steric protection against a broader range of beta-lactamases compared to cephalosporins, making it effective against beta-lactamase-producing anaerobes.