U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C15H14N4O6S2.2H2O
Molecular Weight 446.455
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CEFTIBUTEN DIHYDRATE

SMILES

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

InChI

InChIKey=SSWTVBYDDFPFAF-DKOGRLLHSA-N
InChI=1S/C15H14N4O6S2.2H2O/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);2*1H2/b6-1-;;/t10-,13-;;/m1../s1

HIDE SMILES / InChI

Molecular Formula C15H14N4O6S2
Molecular Weight 410.425
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/mtm/ceftibuten.html http://www.rxlist.com/cedax-drug.htm http://www.wikidoc.org/index.php/Ceftibuten

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%.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P0AD68
Gene ID: 944799.0
Gene Symbol: ftsI
Target Organism: Escherichia coli (strain K12)
Target ID: P02918
Gene ID: 947907.0
Gene Symbol: mrcA
Target Organism: Escherichia coli (strain K12)
Target ID: P02919
Gene ID: 944843.0
Gene Symbol: mrcB
Target Organism: Escherichia coli (strain K12)
Target ID: P0AD65
Gene ID: 945240.0
Gene Symbol: mrdA
Target Organism: Escherichia coli (strain K12)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
CEDAX

Approved Use

Ceftibuten is indicated for the treatment of individuals with mild-to-moderate infections caused by susceptible strains of the designated microorganisms in the specific conditions listed below (see DOSAGE AND ADMINISTRATION and CLINICAL STUDIES sections). Acute Bacterial Exacerbations of Chronic Bronchitis due to Haemophilus influenzae (including β-lactamase-producing strains), Moraxella catarrhalis (including β-lactamase-producing strains), or Streptococcus pneumoniae (penicillin-susceptible strains only). NOTE: In acute bacterial exacerbations of chronic bronchitis clinical trials where Moraxella catarrhalis was isolated from infected sputum at baseline, ceftibuten clinical efficacy was 22% less than control. Acute Bacterial Otitis Media due to Haemophilus influenzae (including β-lactamase-producing strains), Moraxella catarrhalis (including β-lactamase-producing strains), or Streptococcus pyogenes. NOTE: Although ceftibuten used empirically was equivalent to comparators in the treatment of clinically and/or microbiologically documented acute otitis media, the efficacy against Streptococcus pneumoniae was 23% less than control. Therefore, ceftibuten should be given empirically only when adequate antimicrobial coverage against Streptococcus pneumoniae has been previously administered. Pharyngitis and Tonsillitis due to Streptococcus pyogenes. NOTE: Only penicillin by the intramuscular route of administration has been shown to be effective in the prophylaxis of rheumatic fever. Ceftibuten is generally effective in the eradication of Streptococcus pyogenes from the oropharynx; however, data establishing the efficacy of the Ceftibuten product for the prophylaxis of subsequent rheumatic fever are not available.

Launch Date

1995
Curative
CEDAX

Approved Use

Ceftibuten is indicated for the treatment of individuals with mild-to-moderate infections caused by susceptible strains of the designated microorganisms in the specific conditions listed below (see DOSAGE AND ADMINISTRATION and CLINICAL STUDIES sections). Acute Bacterial Exacerbations of Chronic Bronchitis due to Haemophilus influenzae (including β-lactamase-producing strains), Moraxella catarrhalis (including β-lactamase-producing strains), or Streptococcus pneumoniae (penicillin-susceptible strains only). NOTE: In acute bacterial exacerbations of chronic bronchitis clinical trials where Moraxella catarrhalis was isolated from infected sputum at baseline, ceftibuten clinical efficacy was 22% less than control. Acute Bacterial Otitis Media due to Haemophilus influenzae (including β-lactamase-producing strains), Moraxella catarrhalis (including β-lactamase-producing strains), or Streptococcus pyogenes. NOTE: Although ceftibuten used empirically was equivalent to comparators in the treatment of clinically and/or microbiologically documented acute otitis media, the efficacy against Streptococcus pneumoniae was 23% less than control. Therefore, ceftibuten should be given empirically only when adequate antimicrobial coverage against Streptococcus pneumoniae has been previously administered. Pharyngitis and Tonsillitis due to Streptococcus pyogenes. NOTE: Only penicillin by the intramuscular route of administration has been shown to be effective in the prophylaxis of rheumatic fever. Ceftibuten is generally effective in the eradication of Streptococcus pyogenes from the oropharynx; however, data establishing the efficacy of the Ceftibuten product for the prophylaxis of subsequent rheumatic fever are not available.

Launch Date

1995
Curative
CEDAX

Approved Use

Ceftibuten is indicated for the treatment of individuals with mild-to-moderate infections caused by susceptible strains of the designated microorganisms in the specific conditions listed below (see DOSAGE AND ADMINISTRATION and CLINICAL STUDIES sections). Acute Bacterial Exacerbations of Chronic Bronchitis due to Haemophilus influenzae (including β-lactamase-producing strains), Moraxella catarrhalis (including β-lactamase-producing strains), or Streptococcus pneumoniae (penicillin-susceptible strains only). NOTE: In acute bacterial exacerbations of chronic bronchitis clinical trials where Moraxella catarrhalis was isolated from infected sputum at baseline, ceftibuten clinical efficacy was 22% less than control. Acute Bacterial Otitis Media due to Haemophilus influenzae (including β-lactamase-producing strains), Moraxella catarrhalis (including β-lactamase-producing strains), or Streptococcus pyogenes. NOTE: Although ceftibuten used empirically was equivalent to comparators in the treatment of clinically and/or microbiologically documented acute otitis media, the efficacy against Streptococcus pneumoniae was 23% less than control. Therefore, ceftibuten should be given empirically only when adequate antimicrobial coverage against Streptococcus pneumoniae has been previously administered. Pharyngitis and Tonsillitis due to Streptococcus pyogenes. NOTE: Only penicillin by the intramuscular route of administration has been shown to be effective in the prophylaxis of rheumatic fever. Ceftibuten is generally effective in the eradication of Streptococcus pyogenes from the oropharynx; however, data establishing the efficacy of the Ceftibuten product for the prophylaxis of subsequent rheumatic fever are not available.

Launch Date

1995
Curative
CEDAX

Approved Use

Ceftibuten is indicated for the treatment of individuals with mild-to-moderate infections caused by susceptible strains of the designated microorganisms in the specific conditions listed below (see DOSAGE AND ADMINISTRATION and CLINICAL STUDIES sections). Acute Bacterial Exacerbations of Chronic Bronchitis due to Haemophilus influenzae (including β-lactamase-producing strains), Moraxella catarrhalis (including β-lactamase-producing strains), or Streptococcus pneumoniae (penicillin-susceptible strains only). NOTE: In acute bacterial exacerbations of chronic bronchitis clinical trials where Moraxella catarrhalis was isolated from infected sputum at baseline, ceftibuten clinical efficacy was 22% less than control. Acute Bacterial Otitis Media due to Haemophilus influenzae (including β-lactamase-producing strains), Moraxella catarrhalis (including β-lactamase-producing strains), or Streptococcus pyogenes. NOTE: Although ceftibuten used empirically was equivalent to comparators in the treatment of clinically and/or microbiologically documented acute otitis media, the efficacy against Streptococcus pneumoniae was 23% less than control. Therefore, ceftibuten should be given empirically only when adequate antimicrobial coverage against Streptococcus pneumoniae has been previously administered. Pharyngitis and Tonsillitis due to Streptococcus pyogenes. NOTE: Only penicillin by the intramuscular route of administration has been shown to be effective in the prophylaxis of rheumatic fever. Ceftibuten is generally effective in the eradication of Streptococcus pyogenes from the oropharynx; however, data establishing the efficacy of the Ceftibuten product for the prophylaxis of subsequent rheumatic fever are not available.

Launch Date

1995
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
14.98 μg/mL
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CEFTIBUTEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
17.85 μg/mL
400 mg 1 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CEFTIBUTEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
18.7 μg/mL
400 mg 1 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CEFTIBUTEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
15 μg/mL
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CEFTIBUTEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
23.3 μg/mL
800 mg single, oral
dose: 800 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CEFTIBUTEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
9.85 μg/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CEFTIBUTEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
17 μg/mL
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CEFTIBUTEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
13.4 μg/mL
9 mg/kg bw single, oral
dose: 9 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
CEFTIBUTEN plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
73.74 μg × h/mL
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CEFTIBUTEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
80.22 μg × h/mL
400 mg 1 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CEFTIBUTEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
82.53 μg × h/mL
400 mg 1 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CEFTIBUTEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
73.7 μg × h/mL
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CEFTIBUTEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
118 μg × h/mL
800 mg single, oral
dose: 800 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CEFTIBUTEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
42.1 μg × h/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CEFTIBUTEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
79.2 μg × h/mL
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CEFTIBUTEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
56 μg × h/mL
9 mg/kg bw single, oral
dose: 9 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
CEFTIBUTEN plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.45 h
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CEFTIBUTEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2.35 h
400 mg 1 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CEFTIBUTEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2.37 h
400 mg 1 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CEFTIBUTEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2.4 h
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CEFTIBUTEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
2.25 h
800 mg single, oral
dose: 800 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CEFTIBUTEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2.01 h
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CEFTIBUTEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2.29 h
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CEFTIBUTEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2 h
9 mg/kg bw single, oral
dose: 9 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
CEFTIBUTEN plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
35%
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CEFTIBUTEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
35%
9 mg/kg bw single, oral
dose: 9 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
CEFTIBUTEN plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
400 mg 1 times / day steady, oral
Recommended
Dose: 400 mg, 1 times / day
Route: oral
Route: steady
Dose: 400 mg, 1 times / day
Sources:
healthy, 18 - 26 years
n = 12
Health Status: healthy
Age Group: 18 - 26 years
Sex: M
Population Size: 12
Sources:
800 mg single, oral
Highest studied dose
Dose: 800 mg
Route: oral
Route: single
Dose: 800 mg
Sources:
healthy, 19 - 38 years
n = 18
Health Status: healthy
Age Group: 19 - 38 years
Sex: M
Population Size: 18
Sources:
9 mg/kg 1 times / day steady, oral
Recommended
Dose: 9 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 9 mg/kg, 1 times / day
Sources:
unhealthy, mean 4.9 years
n = 1152
Health Status: unhealthy
Condition: Infectious Disease
Age Group: mean 4.9 years
Sex: M+F
Population Size: 1152
Sources:
Disc. AE: Gastrointestinal disorders...
Other AEs: Gastrointestinal disorders...
AEs leading to
discontinuation/dose reduction:
Gastrointestinal disorders (0.9%)
Other AEs:
Gastrointestinal disorders (160 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Gastrointestinal disorders 0.9%
Disc. AE
9 mg/kg 1 times / day steady, oral
Recommended
Dose: 9 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 9 mg/kg, 1 times / day
Sources:
unhealthy, mean 4.9 years
n = 1152
Health Status: unhealthy
Condition: Infectious Disease
Age Group: mean 4.9 years
Sex: M+F
Population Size: 1152
Sources:
Gastrointestinal disorders 160 patients
9 mg/kg 1 times / day steady, oral
Recommended
Dose: 9 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 9 mg/kg, 1 times / day
Sources:
unhealthy, mean 4.9 years
n = 1152
Health Status: unhealthy
Condition: Infectious Disease
Age Group: mean 4.9 years
Sex: M+F
Population Size: 1152
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim

Drug as victim

PubMed

PubMed

TitleDatePubMed
Inhibitory effect of zinc on PEPT1-mediated transport of glycylsarcosine and beta-lactam antibiotics in human intestinal cell line Caco-2.
2003 Sep
Human organic anion transporter hOAT3 is a potent transporter of cephalosporin antibiotics, in comparison with hOAT1.
2005 Oct 1
Patents

Sample Use Guides

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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:59:29 GMT 2023
Edited
by admin
on Fri Dec 15 15:59:29 GMT 2023
Record UNII
62F4443RWP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEFTIBUTEN DIHYDRATE
MI   ORANGE BOOK   VANDF   WHO-DD  
Common Name English
CEFTIBUTEN DIHYDRATE [MI]
Common Name English
CEFTIBUTEN HYDRATE [JAN]
Common Name English
CEFTIBUTEN DIHYDRATE [ORANGE BOOK]
Common Name English
Ceftibuten dihydrate [WHO-DD]
Common Name English
CEFTIBUTEN DIHYDRATE [VANDF]
Common Name English
CEDAX
Brand Name English
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-((2-(2-AMINO-4-THIAZOLYL)-4-CARBOXY-1-OXO-2-BUTENYL)AMINO)-8-OXO-, DIHYDRATE, (6R-(6.ALPHA.,7.BETA.(Z)))-
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C357
Created by admin on Fri Dec 15 15:59:29 GMT 2023 , Edited by admin on Fri Dec 15 15:59:29 GMT 2023
Code System Code Type Description
SMS_ID
100000128353
Created by admin on Fri Dec 15 15:59:29 GMT 2023 , Edited by admin on Fri Dec 15 15:59:29 GMT 2023
PRIMARY
NCI_THESAURUS
C61667
Created by admin on Fri Dec 15 15:59:29 GMT 2023 , Edited by admin on Fri Dec 15 15:59:29 GMT 2023
PRIMARY
PUBCHEM
5282241
Created by admin on Fri Dec 15 15:59:29 GMT 2023 , Edited by admin on Fri Dec 15 15:59:29 GMT 2023
PRIMARY
DRUG BANK
DBSALT001212
Created by admin on Fri Dec 15 15:59:29 GMT 2023 , Edited by admin on Fri Dec 15 15:59:29 GMT 2023
PRIMARY
DAILYMED
62F4443RWP
Created by admin on Fri Dec 15 15:59:29 GMT 2023 , Edited by admin on Fri Dec 15 15:59:29 GMT 2023
PRIMARY
CAS
118081-34-8
Created by admin on Fri Dec 15 15:59:29 GMT 2023 , Edited by admin on Fri Dec 15 15:59:29 GMT 2023
PRIMARY
EVMPD
SUB35311
Created by admin on Fri Dec 15 15:59:29 GMT 2023 , Edited by admin on Fri Dec 15 15:59:29 GMT 2023
PRIMARY
MERCK INDEX
m3220
Created by admin on Fri Dec 15 15:59:29 GMT 2023 , Edited by admin on Fri Dec 15 15:59:29 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
Ceftibuten dihydrate
Created by admin on Fri Dec 15 15:59:29 GMT 2023 , Edited by admin on Fri Dec 15 15:59:29 GMT 2023
PRIMARY
FDA UNII
62F4443RWP
Created by admin on Fri Dec 15 15:59:29 GMT 2023 , Edited by admin on Fri Dec 15 15:59:29 GMT 2023
PRIMARY
RXCUI
1297879
Created by admin on Fri Dec 15 15:59:29 GMT 2023 , Edited by admin on Fri Dec 15 15:59:29 GMT 2023
PRIMARY RxNorm
CHEBI
34618
Created by admin on Fri Dec 15 15:59:29 GMT 2023 , Edited by admin on Fri Dec 15 15:59:29 GMT 2023
PRIMARY
ChEMBL
CHEMBL1605
Created by admin on Fri Dec 15 15:59:29 GMT 2023 , Edited by admin on Fri Dec 15 15:59:29 GMT 2023
PRIMARY
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