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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H14N4O6S2
Molecular Weight 410.425
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CEFTIBUTEN

SMILES

[H][C@]12SCC=C(N1C(=O)[C@H]2NC(=O)C(=C/CC(O)=O)\C3=CSC(N)=N3)C(O)=O

InChI

InChIKey=UNJFKXSSGBWRBZ-BJCIPQKHSA-N
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

HIDE SMILES / InChI

Description

Ceftibuten is a 3rd generation cephalosporin that is FDA approved for the treatment of acute bacterial exacerbations of chronic bronchitis, acute bacterial otitis media, pharyngitis and tonsillitis. Ceftibuten exerts its bactericidal action by binding to essential target proteins of the bacterial cell wall. This binding leads to inhibition of cell-wall synthesis. Common adverse reactions include diarrhea, nausea, vomiting and headache. The effect of increased gastric pH on the bioavailability of ceftibuten was evaluated in 18 healthy adult volunteers. Each volunteer was administered one 400-mg ceftibuten capsule. A single dose of liquid antacid did not affect the Cmax or AUC of ceftibuten; however, 150 mg of ranitidine q12h for 3 days increased the ceftibuten Cmax by 23% and ceftibuten AUC by 16%.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
CEDAX
Curative
CEDAX
Curative
CEDAX
Curative
CEDAX

Cmax

ValueDoseCo-administeredAnalytePopulation
14.98 μg/mL
400 mg single, oral
CEFTIBUTEN plasma
Homo sapiens
17.85 μg/mL
400 mg 1 times / day steady-state, oral
CEFTIBUTEN plasma
Homo sapiens
18.7 μg/mL
400 mg 1 times / day steady-state, oral
CEFTIBUTEN plasma
Homo sapiens
15 μg/mL
400 mg single, oral
CEFTIBUTEN plasma
Homo sapiens
23.3 μg/mL
800 mg single, oral
CEFTIBUTEN plasma
Homo sapiens
9.85 μg/mL
200 mg single, oral
CEFTIBUTEN plasma
Homo sapiens
17 μg/mL
400 mg single, oral
CEFTIBUTEN plasma
Homo sapiens
13.4 μg/mL
9 mg/kg bw single, oral
CEFTIBUTEN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
73.74 μg × h/mL
400 mg single, oral
CEFTIBUTEN plasma
Homo sapiens
80.22 μg × h/mL
400 mg 1 times / day steady-state, oral
CEFTIBUTEN plasma
Homo sapiens
82.53 μg × h/mL
400 mg 1 times / day steady-state, oral
CEFTIBUTEN plasma
Homo sapiens
73.7 μg × h/mL
400 mg single, oral
CEFTIBUTEN plasma
Homo sapiens
118 μg × h/mL
800 mg single, oral
CEFTIBUTEN plasma
Homo sapiens
42.1 μg × h/mL
200 mg single, oral
CEFTIBUTEN plasma
Homo sapiens
79.2 μg × h/mL
400 mg single, oral
CEFTIBUTEN plasma
Homo sapiens
56 μg × h/mL
9 mg/kg bw single, oral
CEFTIBUTEN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2.45 h
400 mg single, oral
CEFTIBUTEN plasma
Homo sapiens
2.35 h
400 mg 1 times / day steady-state, oral
CEFTIBUTEN plasma
Homo sapiens
2.37 h
400 mg 1 times / day steady-state, oral
CEFTIBUTEN plasma
Homo sapiens
2.4 h
400 mg single, oral
CEFTIBUTEN plasma
Homo sapiens
2.25 h
800 mg single, oral
CEFTIBUTEN plasma
Homo sapiens
2.01 h
200 mg single, oral
CEFTIBUTEN plasma
Homo sapiens
2.29 h
400 mg single, oral
CEFTIBUTEN plasma
Homo sapiens
2 h
9 mg/kg bw single, oral
CEFTIBUTEN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
35%
400 mg single, oral
CEFTIBUTEN plasma
Homo sapiens
35%
9 mg/kg bw single, oral
CEFTIBUTEN plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Ceftibuten must be administered at least 2 hours before or 1 hour after a meal. maximum daily dose is 400 mg (during 10 days).
Route of Administration: Oral
In Vitro Use Guide
Ceftibuten displayed high activity against Haemophilus influenzae and Branhamella catarrhalis. There was reduced activity against Streptococcus pneumoniae (MIC90 16 mg/l).