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Cefuroxime axetil

Chemical compound

Summary

Chemical compound

FieldValue
imageCefuroxime axetil.svg
image_classskin-invert-image
tradenameZinnat, Ceftin, Ceftum
Drugs.com
MedlinePlusa601206
pregnancy_AU
routes_of_administrationBy mouth, intravenous, intramuscular
ATC_prefixNone
legal_AUS4
legal_AU_comment
legal_CA
legal_UK
legal_USRx-only
bioavailabilitywell absorbed
metabolismCefuroxime is not metabolized and excreted as it is in urine, axetil is metabolized to acetaldehyde and acetic acid
excretionUrine
CAS_number64544-07-6
PubChem6321416
DrugBankDBSALT001355
ChemSpiderID4882027
ChEBI3516
ChEMBL1095930
UNIIZ49QDT0J8Z
KEGGD00914
synonymsCefuroxime 1-acetoxyethyl ester
IUPAC_name1-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
C20H=22N=4O=10S=1
smilesO=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
StdInChI1S/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
StdInChIKeyKEJCWVGMRLCZQQ-YJBYXUATSA-N

| Drugs.com =

| elimination_half-life =

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

It is an ester prodrug of cefuroxime which is effective orally. The activity depends on in vivo hydrolysis and release of cefuroxime tablets.

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

Medical uses

Second generation cephalosporins are more effective in treating Gram-negative bacilli compared to first generation cephalosporins, which have a greater coverage for Gram-positive cocci. Also, it has been reported that cefuroxime is resistant to hydrolysis by β-lactamases produced by Gram-negative bacteria.

Some medical uses are:

  • Upper respiratory tract infections
  • Lower respiratory tract infections
  • Urinary tract infections
  • Skin and soft tissue infections
  • Gonorrhoea
  • Early Lyme disease

Bacterial susceptibility

Cefuroxime axetil treats infections against methicillin-, oxacillin- and penicillin-sensitive bacterial strains. Cefuroxime axetil does not work against enterococci.

Gram-positive aerobic microorganisms

  • Staphylococcus aureus (Methicillin-sensitive only)
  • Staphylococcus epidermidis
  • Streptococcus pneumoniae (Penicillin-sensitive only)

Gram-negative aerobic microorganisms

  • Haemophilus influenzae
  • Moraxella catarrhalis
  • Neisseria gonorrhoeae
  • Escherichia coli
  • Proteus mirabilis
  • Klebsiella pneumoniae (variable activity)

Mechanism of action

Cefuroxime axetil is a second generation cephalosporin that, like penicillins antibiotics, contains a β-lactam ring structure. Cephalosporins work as bactericidal antibiotics; that by binding to penicillin-binding proteins (PBPs), inhibit the last step of the bacterial cell wall synthesis. Once the β-lactam ring binds to PBPs, cross-linking between peptidoglycan units is inhibited.

Pharmacokinetics

Absorption: Once consumed, cefuroxime axetil is converted to the active compound cefuroxime by esterases of mucosal cells in the gastrointestinal tract. Cefuroxime is then released for systematic circulation. If cefuroxime axetil is given with food, absorption values can increase from 37% in fasting patients to 52% in fed patients.

Distribution: It has been reported that after cefuroxime axetil administration, it can be found in tonsil tissue, sinus tissue, bronchial tissue and middle ear effusion.

Elimination: After cefuroxime production, the body is unable to metabolize the drug, and is eliminated unchanged in the urine.

History

It was discovered by Glaxo (now GlaxoSmithKline) and introduced in 1987. It was approved by FDA on December 28, 1987. It is available by GSK as Ceftin in the US and Ceftum in India.

References

References

  1. (21 June 2022). "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017".
  2. (2005-06-23). "Drug Discovery: A History". John Wiley, Chichester, UK.
  3. (2006). "Analogue-based Drug Discovery". John Wiley & Sons.
  4. (2020). "StatPearls". StatPearls Publishing.
  5. (July 1996). "Cefuroxime axetil. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy". Drugs.
  6. (2015). "Ceftin (cefuroxime axetil).". U.S. Food and Drug Administration.
  7. "Zinnat SUMMARY OF PRODUCT CHARACTERISTICS - GSKPro for Healthcare Professionals".
  8. "Our history - About GSK". GlaxoSmithKline.
  9. "Cefuroxime Axetil Monograph for Professionals". Drugs.com.
  10. (2018-03-22). "Brands". Gsksource.com.
  11. "Our products". GlaxoSmithKline.
Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

cephalosporin-antibiotics prodrugs acetate-esters carbamates
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