Cefuroxime

Cefuroxime
Clinical data
Trade namesZinacef, others
AHFS/Drugs.comMonograph
MedlinePlusa601206
License data
Routes of
administration		Intramuscular, intravenous, by mouth
Drug classSecond-generation cephalosporin
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only[1]
  • 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
IUPAC name
  • (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)
SMILES
  • O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)C(=N\OC)\c3occc3)COC(=O)N)C(=O)O
InChI
  • 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)

Cefuroxime, sold under the brand name Zinacef among others, is a second-generation cephalosporin[2] antibiotic used to treat and prevent a number of bacterial infections.[3] These include pneumonia, meningitis, otitis media, sepsis, urinary tract infections, and Lyme disease.[4] It is used by mouth or by injection into a vein or muscle.[4]

Common side effects include nausea, diarrhea, allergic reactions, and pain at the site of injection.[4] Serious side effects may include Clostridioides difficile infection, anaphylaxis, and Stevens–Johnson syndrome.[4] Use in pregnancy and breastfeeding is believed to be safe.[5] It is a second-generation cephalosporin and works by interfering with a bacteria's ability to make a cell wall resulting in its death.[4]

Cefuroxime was patented in 1971 and approved for medical use in 1977.[6] It is on the World Health Organization's List of Essential Medicines.[7] In 2022, it was the 283rd most commonly prescribed medication in the United States, with more than 600,000 prescriptions.[8][9]

  1. ^ "Product monograph brand safety updates". Health Canada. 7 July 2016. Retrieved 13 July 2024.
  2. ^ Katzung B (2018). Basic & Clinical Pharmacology. McGraw Hill. p. 803.
  3. ^ British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 518. ISBN 9780857113382.
  4. ^ a b c d e "Cefuroxime Sodium Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 22 March 2019.
  5. ^ "Cefuroxime Use During Pregnancy". Drugs.com. Retrieved 3 March 2019.
  6. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 493. ISBN 9783527607495.
  7. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  8. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  9. ^ "Cefuroxime Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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