Ceftibuten

Ceftibuten
Names
Trade names	Cedax
Other names	Cephtibuten
	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;
Clinical data
Drug class	3rd-generation cephalosporin
Main uses	Middle ear infection, strep throat, pneumonia, urinary tract infection
Side effects	Nausea, diarrhea, headache, abdominal pain
WHO AWaRe
Typical dose	400 mg OD
External links
AHFS/Drugs.com	Monograph
MedlinePlus	a698023
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 ;

Ceftibuten, sold under the brand name Cedax among others, is an antibiotic used to treat middle ear infection, strep throat, pneumonia, and urinary tract infection.^[2] Use is not generally recommended for sinusitis.^[2] It is taken by mouth.^[2]

Common side effects include nausea, diarrhea, headache, and abdominal pain.^[2] Other side effects may include anaphylaxis, Stevens-Johnson syndrome, and Clostridioides difficile infection.^[2] While there is no evidence of harm in pregnancy, such use has not been well studied.^[3] It is a third-generation cephalosporin and works by interfering with the bacterial cell wall.^[1]

Ceftibuten was approved for medical use in the United States in 1995.^[2] It has been discontinued in the United States as of 2021.^[4]

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]}

The typical dose is 400 mg per day.^[2]

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:

The most frequent reactions were gastrointestinal and nausea.

It was marketed by Pernix Therapeutics.

↑ ^1.0 ^1.1 Beauduy, Camille E.; Winston, Lisa G. (2020). "43. Beta-lactam and other cell wall - & membrane - active antibiotics". In Katzung, Bertram G.; Trevor, Anthony J. (eds.). Basic and Clinical Pharmacology (15th ed.). New York: McGraw-Hill. p. 832. ISBN 978-1-260-45231-0. Archived from the original on 2021-10-10. Retrieved 2021-11-30.
↑ ^2.0 ^2.1 ^2.2 ^2.3 ^2.4 ^2.5 ^2.6 ^2.7 ^2.8 ^2.9 "Ceftibuten Monograph for Professionals". Drugs.com. Archived from the original on 2 August 2019. Retrieved 2 January 2022.
↑ "Ceftibuten (Cedax) Use During Pregnancy". Drugs.com. Archived from the original on 4 December 2020. Retrieved 2 January 2022.
↑ "Drugs@FDA: FDA-Approved Drugs". www.accessdata.fda.gov. Archived from the original on 22 March 2021. Retrieved 2 January 2022.
↑ "Ceftibuten Susceptibility and Minimum Inhibitory Concentration Range (MIC) Data" (PDF). TOKU-E. June 2020. Archived (PDF) from the original on 2019-08-02. Retrieved 2021-06-21.