Cefuroxime sodium
[CAS# 56238-63-2]

Identification

• Classification: API >> Antibiotics >> Cephalosporin
• Name: Cefuroxime sodium
• Synonyms: Sodium [6R-[6a,7b(Z)]]-3-[[(aminocarbonyl)oxy]methyl]-7-[2-furyl(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• Molecular Formula: C₁₆H₁₅N₄NaO₈S
• Molecular Weight: 446.37
• CAS Registry Number: 56238-63-2
• EC Number: 260-073-1
• SMILES: CO/N=C(/C1=CC=CO1)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)N)C(=O)[O-].[Na+]

Properties

• Solubility: DMSO: 19mg/mL (Expl.)

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Risk Statements: H317-H334
• Safety Statements: P233-P260-P261-P271-P272-P280-P284-P302+P352-P304+P340-P321-P333+P317-P342+P316-P362+P364-P403-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Respiratory sensitization	Resp. Sens.	1	H334
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

Cefuroxime sodium is the sodium salt form of cefuroxime, a second-generation cephalosporin antibiotic widely used in clinical practice. Chemically, cefuroxime sodium is a β-lactam compound with the molecular formula C₁₆H₁₆N₄NaO₈S₂, reflecting its complex structure that includes a β-lactam ring fused to a dihydrothiazine ring, as well as various functional groups contributing to its antibacterial activity.

The core structure of cefuroxime consists of the cephem nucleus, characteristic of cephalosporins, which contains a four-membered β-lactam ring essential for its mechanism of action. The sodium salt enhances the compound’s water solubility, facilitating parenteral administration and absorption in oral formulations.

Cefuroxime sodium was developed to address bacterial resistance and broaden the spectrum of antimicrobial activity compared to first-generation cephalosporins. It exhibits bactericidal activity by inhibiting bacterial cell wall synthesis. This is achieved through binding to penicillin-binding proteins (PBPs), enzymes involved in the final stages of peptidoglycan cross-linking, leading to cell lysis and death.

The antibiotic is effective against a wide range of gram-positive and gram-negative bacteria, including *Staphylococcus aureus*, *Streptococcus pneumoniae*, *Haemophilus influenzae*, and *Escherichia coli*. Its enhanced stability against certain β-lactamases, enzymes produced by bacteria that degrade β-lactam antibiotics, contributes to its clinical utility.

Cefuroxime sodium is synthesized through semi-synthetic processes involving the fermentation-derived 7-aminocephalosporanic acid (7-ACA) as a core intermediate. Chemical modification introduces specific side chains at the 7-position of the cephem nucleus, including the methoxyiminoacetyl group, which imparts resistance to β-lactamase degradation and influences spectrum and pharmacokinetics.

Pharmacokinetically, cefuroxime sodium is well absorbed orally and widely distributed in body tissues and fluids. It is primarily excreted unchanged by the kidneys via glomerular filtration and tubular secretion, necessitating dose adjustment in patients with renal impairment. The drug has a half-life of approximately 1 to 2 hours and is typically administered two to three times daily.

Clinically, cefuroxime sodium is used to treat respiratory tract infections, urinary tract infections, skin and soft tissue infections, and Lyme disease, among others. It is available in various dosage forms, including oral tablets, injectable solutions, and suspensions, allowing for versatile therapeutic applications.

Adverse effects are generally mild but may include gastrointestinal disturbances, hypersensitivity reactions, and, rarely, nephrotoxicity or hematologic abnormalities. Caution is advised in patients with penicillin allergies due to potential cross-reactivity.

In summary, cefuroxime sodium is a second-generation cephalosporin antibiotic with broad-spectrum bactericidal activity. Its chemical structure, enhanced β-lactamase stability, and pharmacokinetic properties contribute to its widespread clinical use in treating bacterial infections.

References

1994. Cefuroxime axetil in the treatment of sinusitis. A review. Archives of Family Medicine, 3(2).
DOI: 10.1001/archfami.3.2.165

2001. Kinetics of Cefuroxime Sodium Salt Decay in Solid Phase. Reaction Kinetics, Mechanisms and Catalysis, 73(2).
DOI: 10.1023/a:1014175710690

2024. Evolution of mutations in the ftsI gene leading to amino acid substitutions in PBP3 in Haemophilus influenzae strains under the selective pressure of ampicillin and cefuroxime. International Journal of Medical Microbiology, 314.
DOI: 10.1016/j.ijmm.2024.151626