Cefuroxime

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Cefuroxime
Skeletal formula of cefuroxime
Ball-and-stick model of the cefuroxime molecule
Clinical data
Trade names Zinacef, Ceftin
MedlinePlus a601206
Pregnancy
category
  • B
Routes of
administration
intramuscular, intravenous
ATC code J01DC02 (WHO) S01AA27 (WHO) QJ51DC02 (WHO)
Legal status
Legal status
  • ℞ (Prescription only)
Pharmacokinetic data
Bioavailability 37% on an empty stomach, up to 52% if taken after food
Biological half-life 80 minutes
Excretion Urine 66–100% unchanged
Identifiers
CAS Number 55268-75-2 YesY
PubChem (CID) 5361202
DrugBank DB01112 YesY
ChemSpider 4514699 YesY
UNII O1R9FJ93ED YesY
KEGG D00262 YesY
ChEMBL CHEMBL466 YesY
Chemical and physical data
Formula C16H16N4O8S
Molar mass 424.386 g/mol
3D model (Jmol) Interactive image
  (verify)

Cefuroxime is an enteral second-generation cephalosporin antibiotic. It was discovered by the Glaxo, now GlaxoSmithKline and first marketed in 1978 as Zinacef. It received approval from the U.S. Food and Drug Administration in October 1983.[1]

Cefuroxime axetil is an acetoxyetyl-ester-prodrug of cefuroxime which is effective orally.[2]

Medical uses[edit]

As with the other cephalosporins, although as a second-generation variety, it is less susceptible to beta-lactamase. Hence, it may have greater activity against Haemophilus influenzae, Neisseria gonorrhoeae, and Lyme disease. Unlike most other second-generation cephalosporins, cefuroxime can cross the blood-brain barrier.

Side effects[edit]

Cefuroxime is generally well-tolerated and its side effects are usually transient. If ingested after food, this antibiotic is both better absorbed and less likely to cause its most common side effects of diarrhea, nausea, vomiting, headaches/migraines, dizziness, and abdominal pain compared to most antibiotics in its class.[citation needed]

Although a widely stated cross-allergic risk of about 10% exists between cephalosporins and penicillin, recent assessments have shown no increased risk for a cross-allergic reaction for cefuroxime and several other second-generation or later cephalosporins.[3]

Trade names[edit]

In US it is available as Zinacef by Covis Pharmaceuticals as the company acquired the US rights of the product from GSK.[4] In Bangladesh it is available as Xorimax by Sandoz. In India it is available as Supacef by GSK.[5] In Poland it is available as Zamur by Mepha, subsidiary of Teva Pharmaceutical Industries.[6]

See also[edit]

References[edit]

  1. ^ "Cefuroxime medical facts from". Drugs.com. 
  2. ^ Walter Sneader. "Drug Discovery: History". 
  3. ^ Pichichero ME (2006). "Cephalosporins can be prescribed safely for penicillin-allergic patients" (PDF). The Journal of family practice. 55 (2): 106–12. PMID 16451776. 
  4. ^ http://www.covispharma.ch/assets/pdf/covis-pharma-acquires-portfolio-of-drugs-from-glaxosmithkline.pdf
  5. ^ "GlaxoSmithKline Pharmaceuticals Limited – Prescription Medicines – Anti-Infective". Gsk-india.com. 26 March 2013. 
  6. ^ "Charakterystyka produktu lecznicznego" (PDF). Urząd Rejestracji Produktów Leczniczych, Wyrobów Medycznych i Produktów Biobójczych. 12 November 2015.