Cefmetazole Sodium

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Cat Number

API56796395

CAS Number

56796-39-5

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CAS Number

56796-39-5

EINECS

627-393-7

Storage

Store at 2-8°C

Synonyms

Zefazone; CEFMETAZOLE SODIUM SALT; CMZ sodium; CS 1170 sodium; SKF 83088 sodium; DTXSID5045590

Molecular Formula

C15H16N7NaO5S3

Molecular Weight

493.5

Smiles

CN1C(=NN=N1)SCC2=C(N3[C@@H]([C@@](C3=O)(NC(=O)CSCC#N)OC)SC2)C(=O)[O-].[Na+]

Appearance

White to off-white powder

Melting Point

163-165°C

Relative Density

1.8±0.1

General Description

Cefmetazole sodium is a semisynthetic second‑generation cephamycin antibiotic, distinguished by a 7‑alpha‑methoxy group that confers stability against a wide range of beta‑lactamases. The molecule contains a methyltetrazolethiol (MTT) side chain at the 3‑position, which is characteristic of certain cephalosporins and cephamycins.

Mechanism of Action

Cefmetazole inhibits bacterial cell wall synthesis by binding to penicillin‑binding proteins, particularly those involved in septal peptidoglycan formation. The 7‑alpha‑methoxy group prevents hydrolysis by most beta‑lactamases, including the plasmid‑mediated enzymes commonly found in E. coli and Klebsiella. The drug also demonstrates activity against anaerobes such as Bacteroides fragilis due to its high stability and penetration. The MTT side chain can be cleaved, releasing methyltetrazolethiol, which inhibits vitamin K‑dependent carboxylation.

Application

Cefmetazole is indicated for the treatment of respiratory tract infections, urinary tract infections, intra‑abdominal infections, pelvic infections, and septicemia caused by susceptible gram‑positive and gram‑negative aerobes and anaerobes. It is also used for surgical prophylaxis in colorectal and gynecologic procedures.

A retrospective study of 69 patients with ESBL‑producing Enterobacteriaceae bacteremia compared definitive therapy with cefmetazole versus carbapenems. The carbapenem group had higher baseline Pittsburgh Bacteremia scores (more severe illness), but mortality did not differ significantly between groups (5/43 vs. 1/26, P=0.24). Over time, infectious disease physicians increasingly preferred cefmetazole. The authors conclude that cefmetazole can be safely used as definitive therapy in relatively stable patients with ESBL bacteremia.

Fig. 1 Enrollment of the patients. (Fukuchi T, et al., 2016)

References

Fukuchi T, et al. Cefmetazole for bacteremia caused by ESBL-producing enterobacteriaceae comparing with carbapenems. BMC Infect Dis. 2016;16(1):427.

Twenty‑one nanomaterials were screened against Neisseria gonorrhoeae. Silver nanoparticles (120 nm) were most potent (MIC 12.5 µg/mL) and showed low cytotoxicity to human fibroblasts and epithelial cells. Electron microscopy revealed compromised bacterial membrane integrity. Combined treatment with 120 nm Ag NPs and cefmetazole produced additive effects against multidrug‑resistant clinical isolates. These nanoparticles could serve as adjuvants to antibiotics for topical use or biomaterial coatings to prevent or treat multidrug‑resistant N. gonorrhoeae infections.

Fig. 2 Ag NPs form a complex with cefmetazole (CMZ). (Li LH, et al., 2013)

References

Li LH, et al. Non-cytotoxic nanomaterials enhance antimicrobial activities of cefmetazole against multidrug-resistant Neisseria gonorrhoeae. PLoS One. 2013;8(5):e64794.

Does Cefmetazole Sodium require refrigerated storage as a cephamycin antibiotic?

Yes, it must be stored at 2-8°C. At room temperature, hydrolysis of the beta-lactam ring and decarbamoylation occur rapidly, reducing antibacterial activity.

Is Cefmetazole Sodium sensitive to light and moisture?

Yes, it is both photosensitive and hygroscopic. Store in original, tightly sealed, light-resistant containers with desiccant under refrigeration.

What is the stability of Cefmetazole Sodium after reconstitution for injection?

Reconstituted solutions have limited stability (typically 24-48 hours under refrigeration).

How is the impurity cefmetazole Δ3-isomer (the inactive isomer) monitored?

This degradation product is specifically quantified using a stability-indicating HPLC method, ensuring it remains within pharmacopoeial limits.