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Cefuroxime
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| 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 QJ51DC02 |
| 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
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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
- ^ Zinnat entry on the Glaxo Smith Kline website.
- ^ 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.
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Antibacterials: cell envelope antibiotics (J01C-J01D)
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| Intracellular |
inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin) • DADAL/AR inhibitors (Cycloserine) • bactoprenol inhibitors (Bacitracin)
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| Glycopeptide |
inhibit PG chain elongation: Vancomycin# (Oritavancin, Telavancin) • Teicoplanin (Dalbavancin) • Ramoplanin
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β-lactams/
(inhibit PBP
cross-links) |
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Penicillins
(penams)
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Extended sp.
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aminopenicillins: Amoxicillin# • Ampicillin# (Pivampicillin, Hetacillin, Bacampicillin, Metampicillin, Talampicillin) • Epicillin
carboxypenicillins: Carbenicillin (Carindacillin) • Ticarcillin • Temocillin
ureidopenicillins: Azlocillin • Piperacillin • Mezlocillin
other: Mecillinam (Pivmecillinam) • Sulbenicillin
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Narrow sp.
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β-lactamase sensitive
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Benzylpenicillin (G)#: Clometocillin • Benzathine benzylpenicillin# • Procaine benzylpenicillin# • Azidocillin • Penamecillin
Phenoxymethylpenicillin (V) #: Propicillin • Benzathine phenoxymethylpenicillin • Pheneticillin
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β-lactamase resistant
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Cloxacillin# (Dicloxacillin, Flucloxacillin) • Oxacillin • Meticillin • Nafcillin
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Penems
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Faropenem
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Carbapenems
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Biapenem • Ertapenem • antipseudomonal (Doripenem • Imipenem • Meropenem) • Panipenem
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Cephalosporins/Cephamycins
(cephems)
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1st (PEcK)
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Cefazolin# • Cefacetrile • Cefadroxil • Cefalexin • Cefaloglycin • Cefalonium • Cefaloridine • Cefalotin • Cefapirin • Cefatrizine • Cefazedone • Cefazaflur • Cefradine • Cefroxadine • Ceftezole
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2nd (HEN)
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Cefaclor • Cefamandole • Cefminox • Cefonicid • Ceforanide • Cefotiam • Cefprozil • Cefbuperazone • Cefuroxime • Cefuzonam • cephamycin (Cefoxitin, Cefotetan, Cefmetazole) • carbacephem (Loracarbef)
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3rd
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Cefixime# • Ceftriaxone# • antipseudomonal (Ceftazidime# • Cefoperazone) • Cefcapene • Cefdaloxime • Cefdinir • Cefditoren • Cefetamet • Cefmenoxime • Cefodizime • Cefotaxime • Cefpimizole • Cefpiramide • Cefpodoxime • Cefsulodin • Cefteram • Ceftibuten • Ceftiolene • Ceftizoxime • oxacephem (Flomoxef, Latamoxef ‡)
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4th (antips-)
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Cefepime • Cefozopran • Cefpirome • Cefquinome
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5th
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Ceftobiprole • Ceftaroline fosamil
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Veterinary
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Ceftiofur • Cefquinome • Cefovecin
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Monobactams
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Aztreonam • Tigemonam • Carumonam • Nocardicin A
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β-lactamase inh.
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penam (Sulbactam, Tazobactam) • clavam (Clavulanic acid)
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Combinations
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Amoxicillin/clavulanic acid# • Imipenem/cilastatin# • Ampicillin/flucloxacillin • Ampicillin/sulbactam (Sultamicillin) • Piperacillin/tazobactam
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| Other |
polymyxins/detergent (Colistin, Polymyxin B) • depolarizing (Daptomycin) • hydrolyze NAM-NAG (Lysozyme) • Gramicidin
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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gr+f/gr+a(t)/gr-p(c)/gr-o
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