Ceftibuten

Ceftibuten is a third-generation cephalosporin antibiotic.[1][2] It is an orally administered agent, with two dosage forms, capsule or oral suspension. It is marketed by Pernix Therapeutics under the trade name Cedax.

Ceftibuten
Clinical data
Trade namesCedax
AHFS/Drugs.comMonograph
MedlinePlusa698023
ATC code
Identifiers
IUPAC name
  • (6R,7R)-7-([(Z)-2-(2-Amino-1,3-thiazol-4-yl)-5-hydroxy-5-oxopent-2-enoyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.238.211
Chemical and physical data
FormulaC15H14N4O6S2
Molar mass410.42 g·mol−1
3D model (JSmol)
SMILES
  • O=C2N1/C(=C\CS[C@@H]1[C@@H]2NC(=O)C(=C/CC(=O)O)\c3nc(sc3)N)C(=O)O
InChI
  • InChI=1S/C15H14N4O6S2/c16-15-17-7(5-27-15)6(1-2-9(20)21)11(22)18-10-12(23)19-8(14(24)25)3-4-26-13(10)19/h1,3,5,10,13H,2,4H2,(H2,16,17)(H,18,22)(H,20,21)(H,24,25)/b6-1-/t10-,13-/m1/s1 Y
  • Key:UNJFKXSSGBWRBZ-BJCIPQKHSA-N Y
  (verify)

Medical uses
Main article: Cephalosporin

Ceftibuten is used to treat acute bacterial exacerbations of chronic bronchitis (ABECB), acute bacterial otitis media, pharyngitis, and tonsilitis. It is also indicated for pneumonia, infections of the urinary tract, enteritis, and gastroenteritis.

Adverse effects

In 3,000 patients, ceftibuten was well tolerated. The most frequent reactions were gastrointestinal and nausea.

Susceptibility

Ceftibuten is active against Haemophilus influenzae, Moraxella catarrhalis, Escherichia coli, Klebsiella pneumoniae, K. oxytoca, Proteus vulgaris, P. mirabilis, P. providence, Salmonella sp., Shigella sp., Enterobacter sp., and Streptococcus sp.

The following represents minimum inhibitory concentration (MIC) susceptibility data for a few clinically significant microorganisms:

  • Haemophilus influenzae: 0.015–1.0 μg/ml
  • Moraxella catarrhalis: 0.5–4.0  μg/ml
  • Streptococcus pneumoniae: 0.5–256 μg/ml [3]

References
  1. Owens RC, Nightingale CH, Nicolau DP (1997). "Ceftibuten: an overview". Pharmacotherapy. 17 (4): 707–20. PMID 9250548.
  2. Guay DR (September 1997). "Ceftibuten: a new expanded-spectrum oral cephalosporin". The Annals of Pharmacotherapy. 31 (9): 1022–33. doi:10.1177/106002809703100913. PMID 9296244.
  3. "Ceftibuten Susceptibility and Minimum Inhibitory Concentration Range (MIC) Data" (PDF). TOKU-E. June 2020.
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