Cefuroxime

Cefuroxime, sold under the brand name Zinacef among others, is a second-generation cephalosporin antibiotic used to treat and prevent a number of bacterial infections. These include pneumonia, meningitis, otitis media, sepsis, urinary tract infections, and Lyme disease. It is used by mouth or by injection into a vein or muscle.

Cefuroxime
Clinical data
Trade namesZinacef, Ceftin, Furacia, others
AHFS/Drugs.comMonograph
MedlinePlusa601206
License data
Pregnancy
category
  • B
Routes of
administration		Intramuscular, intravenous, by mouth
Drug classSecond-generation cephalosporin
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • US: WARNING
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability37% on an empty stomach, up to 52% if taken after food
Elimination half-life80 minutes
ExcretionUrine 66–100% unchanged
Identifiers
  • (6R,7R)-3-{[(Aminocarbonyl)oxy]methyl}-7-{[(2Z)-2-(2-furyl)-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.054.127
Chemical and physical data
FormulaC16H16N4O8S
Molar mass424.38 g·mol−1
3D model (JSmol)
  • O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)C(=N\OC)\c3occc3)COC(=O)N)C(=O)O
  • InChI=1S/C16H16N4O8S/c1-26-19-9(8-3-2-4-27-8)12(21)18-10-13(22)20-11(15(23)24)7(5-28-16(17)25)6-29-14(10)20/h2-4,10,14H,5-6H2,1H3,(H2,17,25)(H,18,21)(H,23,24)/b19-9+/t10-,14-/m1/s1 Y
  • Key:JFPVXVDWJQMJEE-SWWZKJRFSA-N Y
  (verify)

Common side effects include nausea, diarrhea, allergic reactions, and pain at the site of injection. Serious side effects may include Clostridium difficile infection, anaphylaxis, and Stevens–Johnson syndrome. Use in pregnancy and breastfeeding is believed to be safe. It is a second-generation cephalosporin and works by interfering with a bacteria's ability to make a cell wall resulting in its death.

Cefuroxime was patented in 1971, and approved for medical use in 1977. It is on the World Health Organization's List of Essential Medicines. In 2020, it was the 325th most commonly prescribed medication in the United States, with more than 800 thousand prescriptions.

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