Cefuroxime

Cefuroxime

Systematic (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
Clinical data
Trade names	Ceftin, Zinacef
AHFS/Drugs.com	monograph
MedlinePlus	a601206
Pregnancy cat.	Not known to be harmful (BNF)
Legal status	Prescription Only Medicine(UK/USA)
Routes	oral, intramuscular, intravenous
Pharmacokinetic data
Bioavailability	37% on empty stomach, up to 52% if taken after food
Metabolism	axetil moiety is metabolized to acetaldehyde and acetic acid
Half-life	80 minutes
Excretion	Urine 66-100% Unchanged
Identifiers
CAS number	55268-75-2 Y
ATC code	J01DC02 QJ51DA06
PubChem	CID 5361202
DrugBank	APRD00285
ChemSpider	4514699 Y
UNII	O1R9FJ93ED Y
KEGG	D00262 Y
ChEMBL	CHEMBL466 Y
Chemical data
Formula	C16H16N4O8S
Mol. mass	424.386 g/mol
SMILES	eMolecules & PubChem
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
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Cefuroxime is a second-generation cephalosporin antibiotic that has been widely available in the USA as Ceftin since 1977. GlaxoSmithKline sells the antibiotic in the United Kingdom (and other countries, such as Australia, Turkey, Israel, Bangladesh, Thailand, Hungary and Poland) under the name Zinnat.^[1]

Indications

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

Side effects

Cefuroxime is generally well tolerated and side effects are usually transient. Cefuroxime, if ingested with food, is both better absorbed and less likely to cause its most common side effects of diarrhea, nausea, vomiting, headaches/migraines, dizziness and abdominal pain.

Although there is a widely quoted cross-allergy risk of 10% between cephalosporins and penicillin, recent assessments have shown no increased risk for cross-allergy for cefuroxime and several other 2nd generation or later cephalosporins.^[2]

References

1. ^ Zinnat entry on the Glaxo Smith Kline website.
2. ^ Pichichero ME (2006). "Cephalosporins can be prescribed safely for penicillin-allergic patients" (PDF). The Journal of family practice 55 (2): 106–12. PMID 16451776. http://www.jfponline.com/pdf%2F5502%2F5502JFP_AppliedEvidence1.pdf.