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
  • B
Legal status
  • RX only
Routesintramuscular, intravenous, oral
Pharmacokinetic data
Bioavailability37% on an empty stomach, up to 52% if taken after food
Half-life80 minutes
ExcretionUrine 66–100% 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 
Molecular 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
  • B
Legal status
  • RX only
Routesintramuscular, intravenous, oral
Pharmacokinetic data
Bioavailability37% on an empty stomach, up to 52% if taken after food
Half-life80 minutes
ExcretionUrine 66–100% 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 
Molecular mass424.386 g/mol
 YesY (what is this?)  (verify)

Cefuroxime or "Ceftin" is a parenteral or oral second-generation cephalosporin antibiotic. Discovered by the Glaxo company (now GlaxoSmithKline), it was first marketed in 1978 as Zinacef and received approval from the U.S. Food and Drug Administration in October of 1983.[1]

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

Trade names[edit]

The U.S. patent for Cefuroxime has expired. It is sold generically there as Ceftin, and remains available as Zinacef by Covis Pharmaceuticals.[3] It is sold as Supacef by GSK in India,[4] and as Xorimax by Sandoz, Roxibac by RAK Pharmaceuticals Pvt. ltd., Turbocef by Beximco Pharmaceuticals and Furocef (ফিউরোসেফ) by Renata, Kilmax (কিলম্যাক্স)by SK+F Limited, Axet by Orion Pharma Ltd in Bangladesh.

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 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.[5]

Syntheses[edit]

Another simpler way of the synthesis of cefuroxime is by direct acylation of 7-amino-3-aminocarbonyloxymethyl-3-cefem-4-carboxylic acid.

References[edit]