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Cefuroxime axetil information


Cefuroxime axetil
Clinical data
Trade namesZinnat, Ceftin, Ceftum
Other namesCefuroxime 1-acetoxyethyl ester
AHFS/Drugs.comMonograph
MedlinePlusa601206
Routes of
administration
By mouth, intravenous, intramuscular
ATC code
  • None
Legal status
Legal status
  • AU: S4 (Prescription only)[1]
  • US: ℞-only
Pharmacokinetic data
Bioavailabilitywell absorbed
MetabolismCefuroxime is not metabolized and excreted as it is in urine, axetil is metabolized to acetaldehyde and acetic acid[medical citation needed]
ExcretionUrine
Identifiers
IUPAC name
  • 1-Acetoxyethyl (6R,7R)-3-[(carbamoyloxy)methyl]-7-{[(2Z)-2-(2-furyl)-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
CAS Number
  • 64544-07-6
PubChem CID
  • 6321416
DrugBank
  • DBSALT001355
ChemSpider
  • 4882027
UNII
  • Z49QDT0J8Z
KEGG
  • D00914
ChEBI
  • CHEBI:3516
ChEMBL
  • ChEMBL1095930
CompTox Dashboard (EPA)
  • DTXSID0022775 Edit this at Wikidata
ECHA InfoCard100.166.374 Edit this at Wikidata
Chemical and physical data
FormulaC20H22N4O10S
Molar mass510.47 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)C(=N\OC)/c3occc3)COC(=O)N)C(=O)OC(OC(=O)C)C
InChI
  • InChI=1S/C20H22N4O10S/c1-9(25)33-10(2)34-19(28)15-11(7-32-20(21)29)8-35-18-14(17(27)24(15)18)22-16(26)13(23-30-3)12-5-4-6-31-12/h4-6,10,14,18H,7-8H2,1-3H3,(H2,21,29)(H,22,26)/b23-13-/t10?,14-,18-/m1/s1
  • Key:KEJCWVGMRLCZQQ-YJBYXUATSA-N

Cefuroxime axetil, sold under the brand name Ceftin among others, is a second generation oral cephalosporin antibiotic.

It is an acetoxyethyl ester prodrug of cefuroxime which is effective orally.[2] The activity depends on in vivo hydrolysis and release of cefuroxime tablets.[citation needed]

It was patented in 1976 and approved for medical use in 1987.[3]

  1. ^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
  2. ^ Sneader W (23 June 2005). Drug Discovery: A History. John Wiley, Chichester, UK. ISBN 0-471-89979-8.
  3. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 494. ISBN 9783527607495.

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