Cefuroxime

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Cefuroxime
Cefuroxime.svg
Cefuroxime ball-and-stick.png
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 namesZinacef,TURBOCEF
MedlinePlusa601206
Pregnancy cat.B
Legal statusRX only
Routesintramuscular, intravenous, oral
Pharmacokinetic data
Bioavailability37 percent on empty stomach, up to 52 percent if taken after food
Half-life80 minutes
ExcretionUrine 66–100 percent unchanged
Identifiers
CAS number55268-75-2 YesY
ATC codeJ01DC02 S01AA27 QJ51DC02
PubChemCID 5361202
DrugBankDB01112
ChemSpider4514699 YesY
UNIIO1R9FJ93ED YesY
KEGGD00262 YesY
ChEMBLCHEMBL466 YesY
Chemical data
FormulaC16H16N4O8S 
Mol. mass424.386 g/mol
 YesY (what is this?)  (verify)
 
  (Redirected from Ceftin)
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Cefuroxime
Cefuroxime.svg
Cefuroxime ball-and-stick.png
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 namesZinacef,TURBOCEF
MedlinePlusa601206
Pregnancy cat.B
Legal statusRX only
Routesintramuscular, intravenous, oral
Pharmacokinetic data
Bioavailability37 percent on empty stomach, up to 52 percent if taken after food
Half-life80 minutes
ExcretionUrine 66–100 percent unchanged
Identifiers
CAS number55268-75-2 YesY
ATC codeJ01DC02 S01AA27 QJ51DC02
PubChemCID 5361202
DrugBankDB01112
ChemSpider4514699 YesY
UNIIO1R9FJ93ED YesY
KEGGD00262 YesY
ChEMBLCHEMBL466 YesY
Chemical data
FormulaC16H16N4O8S 
Mol. mass424.386 g/mol
 YesY (what is this?)  (verify)

Cefuroxime is a parenteral or oral second-generation cephalosporin antibiotic. This antibiotic was discovered by the Glaxo company, now GlaxoSmithKline, and it was first marketed in 1978 as Zinacef. Zinacef was approved by the U.S. Food and Drug Administration on Oct 19, 1983.[1] The generic form of cefuroxime is also called "Ceftin". The 17-year patent for this antibiotic has now expired in the United States, hence the patent "rights" to produce this medication are now irrelevant.

In the United States this antibiotic is also sold as "Zinacef" by Covis Pharmaceuticals.[2] In India, this antibiotic is sold as Supacef by GSK.[3]

Cefuroxime axetil is an acetoxyetyl-ester-prodrug of cefuroxime which is effective orally.[4] In Bangladesh, this drug is available as Xorimax by Sandoz, Turbocef by Beximco Pharmaceuticals Limited.

Indications[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 there is a widely-stated crossallergic risk of about 10 percent between cephalosporins and penicillin, recent assessments have shown no increased risk for a crossallergic reaction for cefuroxime and several other second-generation or later cephalosporins.[5]

References[edit]