Cefuroxime

Cefuroxime

Skeletal formula of cefuroxime
Ball-and-stick model of the cefuroxime molecule
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, Ceftin
MedlinePlus	a601206
Pregnancy category	B
Legal status	℞ (Prescription only)
Routes of administration	intramuscular, intravenous
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 Y
ATC code	J01DC02 (WHO) S01AA27 QJ51DC02 (WHO)
PubChem	CID: 5361202
DrugBank	DB01112 Y
ChemSpider	4514699 Y
UNII	O1R9FJ93ED Y
KEGG	D00262 Y
ChEMBL	CHEMBL466 Y
Chemical data
Formula	C16H16N4O8S
Molecular 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
(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 of 1983.

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

Medical uses

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

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.

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.

Trade names

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

See also

• Cefuroxime axetil