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	Zinacef
MedlinePlus	a601206
Pregnancy cat.	Not known to be harmful (BNF)
Legal status	Prescription Only Medicine
Routes	intramuscular, intravenous
Pharmacokinetic data
Bioavailability	37% on empty stomach, up to 52% if taken after food
Half-life	80 minutes
Excretion	Urine 66–100% Unchanged
Identifiers
CAS number	55268-75-2 Y
ATC code	J01DC02 S01AA27 QJ51DC02
PubChem	CID 5361202
DrugBank	DB01112
ChemSpider	4514699 Y
UNII	O1R9FJ93ED Y
KEGG	D00262 Y
ChEMBL	CHEMBL466 Y
Chemical data
Formula	C16H16N4O8S
Mol. mass	424.386 g/mol
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
Y (what is this?)  (verify)

Cefuroxime is a parenteral second generation cephalosporin antibiotic. It was discovered by Glaxo now GlaxoSmithKline and introduced in 1978 as Zinacef. It was approved by FDA on 19 Oct 1983. In US it is available as Zinacef by Covis Pharmaceuticals as the company acquired the US rights of the product from GSK. In India it is available as Supacef by GSK. Cefuroxime axetil is an acetoxyetyl ester prodrug of cefuroxime which is effective orally.

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 after 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 compared to most antibiotics in its class.^{[citation needed]}

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 second generation or later cephalosporins.