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
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
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 |
DescriptionCurator'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
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%.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P0AD68 Gene ID: 944799.0 Gene Symbol: ftsI Target Organism: Escherichia coli (strain K12) Sources: https://www.ncbi.nlm.nih.gov/pubmed/2120175 |
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Target ID: P02918 Gene ID: 947907.0 Gene Symbol: mrcA Target Organism: Escherichia coli (strain K12) Sources: https://www.ncbi.nlm.nih.gov/pubmed/2120175 |
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Target ID: P02919 Gene ID: 944843.0 Gene Symbol: mrcB Target Organism: Escherichia coli (strain K12) Sources: https://www.ncbi.nlm.nih.gov/pubmed/2120175 |
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Target ID: P0AD65 Gene ID: 945240.0 Gene Symbol: mrdA Target Organism: Escherichia coli (strain K12) Sources: https://www.ncbi.nlm.nih.gov/pubmed/2120175 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | CEDAX Approved UseCeftibuten 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 Date1995 |
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Curative | CEDAX Approved UseCeftibuten 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 Date1995 |
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Curative | CEDAX Approved UseCeftibuten 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 Date1995 |
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Curative | CEDAX Approved UseCeftibuten 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 Date1995 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
14.98 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7726497/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7726497/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7726497/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7726498/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7726498/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7726498/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
73.74 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7726497/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7726497/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7726497/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7726498/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7726498/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7726498/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.45 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7726497/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7726497/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7726497/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7726498/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7726498/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7726498/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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 |
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
AE | Significance | Dose | Population |
---|---|---|---|
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: |
PubMed
Title | Date | PubMed |
---|---|---|
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2120175
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
Edited
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on
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Record UNII |
IW71N46B4Y
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Validated (UNII)
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5282242
Created by
admin on Fri Dec 15 15:39:54 GMT 2023 , Edited by admin on Fri Dec 15 15:39:54 GMT 2023
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PRIMARY |
Related Record | Type | Details | ||
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SOLVATE->ANHYDROUS |
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BINDER->LIGAND |
BINDING
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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