cefuroxime

cefuroxime
IUPAC name	(6R,7R)-3-[(carbamoyloxy)methyl]-7-image = Cefuroxime structure.svg | tradename = Zinacef, Ceftin, others | CAS_number = 55268-75-2 | DrugBank = DB01112 | PubChem = 5479529 | ChemSpiderID = 4586394 | UNII = O1R9FJ93ED | ChEMBL = 501 | ATC_prefix = J01 | ATC_suffix = DC02

cefuroxime is a second-generation cephalosporin antibiotic used to treat and prevent a variety of bacterial infections. It is effective against many Gram-positive bacteria and Gram-negative bacteria, including strains producing beta-lactamase. The drug is available for administration via intravenous injection, intramuscular injection, and in oral formulations.

Medical uses

Cefuroxime is indicated for the treatment of infections caused by susceptible organisms, including lower respiratory tract infections such as bronchitis and pneumonia. It is also used for urinary tract infections, skin and skin structure infections, and Lyme disease in its early stages. In surgical settings, it is a common agent for surgical prophylaxis, particularly in procedures like cardiac surgery and orthopedic surgery to prevent surgical site infection. The World Health Organization includes it on its List of Essential Medicines.

Adverse effects

Common adverse effects are generally mild and include gastrointestinal disturbances such as diarrhea, nausea, and vomiting. As with other beta-lactam antibiotics, there is a risk of hypersensitivity reactions ranging from skin rash to severe anaphylaxis. Prolonged use may lead to Clostridioides difficile infection, causing antibiotic-associated colitis. Rare but serious effects include hepatotoxicity, neutropenia, and a positive Coombs test.

Pharmacology

Cefuroxime exerts its bactericidal effect by inhibiting bacterial cell wall synthesis through binding to essential penicillin-binding proteins. It exhibits stability against many beta-lactamase enzymes produced by bacteria such as Staphylococcus aureus and Haemophilus influenzae. Pharmacokinetically, it is poorly absorbed from the gastrointestinal tract, necessitating the oral prodrug cefuroxime axetil; it distributes well into tissues and fluids, including cerebrospinal fluid in inflamed meninges. Excretion is primarily via the kidney through glomerular filtration.

Chemistry

Cefuroxime is a semisynthetic antibiotic derived from the cephalosporin C nucleus. Its chemical structure includes a beta-lactam ring fused to a dihydrothiazine ring, characteristic of cephalosporins. A key feature is the methoxyimino group at the 7-position side chain, which confers stability against beta-lactamase degradation. The carbamoyloxymethyl group at the 3-position influences its pharmacokinetic properties. It is typically formulated as a sodium salt for injection.

History

Cefuroxime was developed in the 1970s by the British pharmaceutical company Glaxo (now GlaxoSmithKline) as part of efforts to create beta-lactamase-stable cephalosporins. Its development followed the introduction of first-generation agents like cephalothin and aimed to broaden the spectrum of activity. The Food and Drug Administration approved cefuroxime axetil in the late 1980s, expanding its use to oral outpatient therapy. Its introduction was significant in the history of penicillin and antibiotic development.

Society and culture

Cefuroxime is marketed under various brand names globally, including Zinacef and Ceftin. It is included in the treatment guidelines of major health bodies like the Infectious Diseases Society of America. The drug has been the subject of patent litigation, notably involving companies like GlaxoSmithKline and generic manufacturers. Its role in antimicrobial stewardship programs is emphasized to combat antimicrobial resistance, a major concern highlighted by the World Health Organization and the Centers for Disease Control and Prevention.

Category:World Health Organization essential medicines Category:Cephalosporin antibiotics Category:GlaxoSmithKline