Ceftibuten

Ceftibuten
Clinical data
Trade names	Cedax
AHFS/Drugs.com	Monograph
MedlinePlus	a698023
ATC code	J01DD14 (WHO) ;
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	97519-39-6 ;
PubChem CID	5282242;
DrugBank	DB01415 ;
ChemSpider	4445419 ;
UNII	IW71N46B4Y;
KEGG	D00922 ;
ChEBI	CHEBI:3510 ;
ChEMBL	ChEMBL1605 ;
CompTox Dashboard (EPA)	DTXSID4045925 ;
ECHA InfoCard	100.238.211
Chemical and physical data
Formula	C15H14N4O6S2
Molar mass	410.42 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:UNJFKXSSGBWRBZ-BJCIPQKHSA-N ;
	(verify)

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.

Medical uses

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.^{[citation needed]}

Adverse effects

In 3,000 patients, ceftibuten was well tolerated. The most frequent reactions were gastrointestinal and nausea.^{[citation needed]}

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.^{[citation needed]}

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

^ Owens RC, Nightingale CH, Nicolau DP (1997). "Ceftibuten: an overview". Pharmacotherapy. 17 (4): 707–20. doi:10.1002/j.1875-9114.1997.tb03746.x. PMID 9250548. S2CID 32735943.
^ 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. S2CID 39852306.
^ "Ceftibuten Susceptibility and Minimum Inhibitory Concentration Range (MIC) Data" (PDF). TOKU-E. June 2020.

External links

[Owens_1997-1] Owens RC, Nightingale CH, Nicolau DP (1997). "Ceftibuten: an overview". Pharmacotherapy. 17 (4): 707–20. doi:10.1002/j.1875-9114.1997.tb03746.x. PMID 9250548. S2CID 32735943.

[Guay_1997-2] 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. S2CID 39852306.

[3] "Ceftibuten Susceptibility and Minimum Inhibitory Concentration Range (MIC) Data" (PDF). TOKU-E. June 2020.

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