Ceftibuten

Chemical to treat chronic bronchitis

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^Y

PubChem CID

5282242

DrugBank

DB01415^Y

ChemSpider

4445419^Y

UNII

IW71N46B4Y

KEGG

D00922^Y

ChEBI

CHEBI:3510^Y

ChEMBL

ChEMBL1605^Y

CompTox Dashboard (EPA)

DTXSID4045925

ECHA InfoCard100.238.211

Chemical and physical dataFormulaC₁₅H₁₄N₄O₆S₂Molar mass410.42 g·mol⁻¹3D 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^Y
Key:UNJFKXSSGBWRBZ-BJCIPQKHSA-N^Y

(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

Manufacturer's website
Drug information from RxList

Antibacterials active on the cell wall and envelope (J01C-J01D)

Beta-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)

Penicillins (Penams)

Narrow
spectrum

β-lactamase sensitive (1st generation)	Benzylpenicillin (G)^# Benzathine benzylpenicillin^# Procaine benzylpenicillin^# Phenoxymethylpenicillin (V)^# Propicillin^‡ Pheneticillin^‡ Azidocillin^‡ Clometocillin^‡ Penamecillin^‡
β-lactamase resistant (2nd generation)	Cloxacillin^# (Dicloxacillin Flucloxacillin) Oxacillin Nafcillin Methicillin^‡

Extended
spectrum

Aminopenicillins (3rd generation)	Amoxicillin^# Ampicillin^# (Pivampicillin Hetacillin^‡ Bacampicillin^‡ Lenampicillin Metampicillin^‡ Talampicillin^‡) Epicillin^‡
Carboxypenicillins (4th generation)	Ticarcillin Carbenicillin^‡ / Carindacillin^‡ Temocillin^‡
Ureidopenicillins (4th generation)	Piperacillin Azlocillin^‡ Mezlocillin^‡
Other	Mecillinam (Pivmecillinam) Sulbenicillin^‡

Carbapenems / Penems

Cephems
Cephalosporins
Cephamycins
Carbacephems

1st generation	Cefazolin^# Cefalexin ^# Cefadroxil Cefapirin Cefazedone^‡ Cefazaflur^‡ Cefradine^‡ Cefroxadine^‡ Ceftezole^‡ Cefaloglycin^‡ Cefacetrile^‡ Cefalonium^‡ Cefaloridine^‡ Cefalotin Cefatrizine^‡
2nd generation	Cefaclor Cefprozil Cefuroxime Cefuroxime axetil Cefamandole^‡ Cefonicid^‡ Ceforanide^‡ Cefuzonam^‡ Cephamycin (Cefoxitin Cefotetan Cefminox^‡ Cefbuperazone^‡ Cefmetazole^‡) Carbacephem (Loracarbef^‡)
3rd generation	Cefixime^# Ceftriaxone^# Cefotaxime^# Antipseudomonal (Ceftazidime^# Cefoperazone) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefotiam^‡ Cefetamet^‡ Cefodizime^‡ Cefpimizole^‡ Cefsulodin^‡ Cefteram^‡ Ceftiolene^‡ Oxacephem (Flomoxef Latamoxef^‡)
4th generation	Cefepime Cefozopran^‡ Cefpirome Cefquinome^‡
5th generation	Ceftaroline fosamil Ceftolozane Ceftobiprole
Siderophore	Cefiderocol^#
Veterinary	Ceftiofur Cefquinome Cefovecin

Monobactams

β-lactamase inhibitors

Combinations

Polypeptides

Glycopeptides Lipoglycopeptides	Inhibit PG chain elongation: Vancomycin^# (Oritavancin Telavancin) Teicoplanin (Dalbavancin) Ristocetin^‡ Avoparcin Inhibit autolysin: Corbomycin (not approved)
Lipopeptides	Insert into bacterial cell wall causing perforation and depolarization: Daptomycin Surfactin
Polymyxins	Bind to LPS in the outer bacterial membrane, acting in detergent-like fashion: Colistin Polymyxin B
Other	Inhibits PG elongation and crosslinking: Ramoplanin^§