Cefuroxime

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Product Details:

  • CAS No: 55268-75-2
  • AHFC code: 08:12.06.08
  • Synonyms: (6R,7R)-7-(2-(2-Furyl)glyoxylamido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid 7(sup 2)-(Z)-(O-methyloxime) carbamate (ester), 640/359, Biofuroksym, BRN 5783190, Cefuril, Cefuroxim, Cefuroxime, Cefuroximo, Cefuroximo [INN-Spanish], Cefuroximum, Cefuroximum [INN-Latin], Cephuroxime, EINECS 259-560-1, Sharox, UNII-O1R9FJ93ED, Zinacef Danmark
  • ATC Code: J01DC02 S01AA27
  • Chemical Formula: C16-H16-N4-O8-S
  • Molecular Weight: 424.3884
  • Assay/Purity: Typically NLT 98%
  • DrugBank: DB01112
  • SMILES: N12[C,,H]([C,,H](NC(C(c3ccco3)=N/OC)=O)C2=O)SCC(=C1C(O)=O)COC(N)=O
  • InChl: 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
  • PubChem:
  • IUPAC: 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-(((aminocarbonyl)oxy)methyl)-7-((2-furanyl(methoxyimino)acetyl)amino)-8-oxo-, (6R-(6alpha,7beta(Z)))- Cefuroxime

Additional Details

Indication:
For the treatment of many different types of bacterial infections such as bronchitis, sinusitis, tonsillitis, ear infections, skin infections, gonorrhea, and urinary tract infections.
Pharmacodynamics:
Cefuroxime is a β-lactam type antibiotic. More specifically, it is a second-generation cephalosporin. Cephalosporins work the same way as penicillins: they interfere with the peptidoglycan synthesis of the bacterial wall by inhibiting the final transpeptidation needed for the cross-links. This effect is bactericidal. Cefuroxime is effective against the following organisms: Aerobic Gram-positive Microorganisms: Staphylococcus aureus, Streptococcus pneumoniae, Streptococcus pyogenes. Aerobic Gram-negative Microorganisms: Escherichia coli, Haemophilus influenzae (including beta-lactamase-producing strains), Haemophilus parainfluenzae, Klebsiella pneumoniae, Moraxella catarrhalis (including beta-lactamase-producing strains), Neisseria gonorrhoeae (including beta-lactamase-producing strains). Spirochetes: Borrelia burgdorferi. Cefuroxime axetil is the prodrug
Mode of Action:
Cefuroxime, like the penicillins, is a beta-lactam antibiotic. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefuroxime interferes with an autolysin inhibitor.
Metabolism:
The axetil moiety is metabolized to acetaldehyde and acetic acid.
Toxicity:
Allergic reactions might be expected, including rash, nasal congestion, cough, dry throat, eye irritation, or anaphylactic shock. Overdosage of cephalosporins can cause cerebral irritation leading to convulsions.
General Reference:
Perry CM, Brogden RN: Cefuroxime axetil. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1996 Jul;52(1):125-58. Pubmed
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