Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C19H18N6O5S3 |
| Molecular Weight | 506.578 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 2 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12SCC(\C=C/C3=C(C)N=CS3)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C4=CSC(N)=N4)C(O)=O
InChI
InChIKey=KMIPKYQIOVAHOP-YLGJWRNMSA-N
InChI=1S/C19H18N6O5S3/c1-8-11(33-7-21-8)4-3-9-5-31-17-13(16(27)25(17)14(9)18(28)29)23-15(26)12(24-30-2)10-6-32-19(20)22-10/h3-4,6-7,13,17H,5H2,1-2H3,(H2,20,22)(H,23,26)(H,28,29)/b4-3-,24-12-/t13-,17-/m1/s1
DescriptionCurator's Comment: description was created based on several sources, including:
https://www.drugs.com/dosage/cefditoren.html
http://www.rxlist.com/spectracef-drug.htm
http://www.wikidoc.org/index.php/Cefditoren
Curator's Comment: description was created based on several sources, including:
https://www.drugs.com/dosage/cefditoren.html
http://www.rxlist.com/spectracef-drug.htm
http://www.wikidoc.org/index.php/Cefditoren
Cefditoren pivoxil is a semi-synthetic cephalosporin antibiotic for oral administration. It is a 3rd generation cephalosporin that is FDA approved for the treatment of acute bacterial exacerbation of chronic bronchitis, community acquired pneumonia, infection of skin and/or subcutaneous tissue, and pharyngitis/tonsillitis. Cefditoren is a cephalosporin with antibacterial activity against gram-positive and gram-negative pathogens. The bactericidal activity of cefditoren results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs). Common adverse reactions include diarrhea, nausea and candida vaginitis. Co-administration of a single dose of an antacid which contained both magnesium (800 mg) and aluminum (900 mg) hydroxides or co-administration of a single dose of intravenously administered famotidine (20 mg) reduced the oral absorption of a single 400 mg dose of cefditoren pivoxil administered following a meal. Co-administration of probenecid with cefditoren pivoxil resulted in an increase in the plasma exposure of cefditoren.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P0A3M6 Gene ID: 933948.0 Gene Symbol: penA Target Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6) |
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Target ID: Q8XJ01 Gene ID: 990276.0 Gene Symbol: pbpA Target Organism: Clostridium perfringens (strain 13 / Type A) |
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Target ID: P59676 Gene ID: 934744.0 Gene Symbol: pbpX Target Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | SPECTRACEF Approved UseSPECTRACEF® (cefditoren pivoxil) is indicated for the treatment of mild to moderate infections in adults and adolescents (12 years of age or older) which are caused by susceptible strains of the designated microorganisms in the conditions listed below. Acute Bacterial Exacerbation of Chronic Bronchitis caused by Haemophilus influenzae (including ß-lactamase-producing strains), Haemophilus parainfluenzae (including ß-lactamase producing strains), Streptococcus pneumoniae (penicillin susceptible strains only), or Moraxella catarrhalis (including ß-lactamase-producing strains). Community-Acquired Pneumonia caused by Haemophilus influenzae (including ß-lactamase-producing strains), Haemophilus parainfluenzae (including ß-lactamase-producing strains), Streptococcus pneumoniae (penicillin-susceptible strains only), or Moraxella catarrhalis (including ß-lactamase producing strains). Pharyngitis/Tonsillitis caused by Streptococcus pyogenes. NOTE: SPECTRACEF® is effective in the eradication of Streptococcus pyogenes from the oropharynx. SPECTRACEF® has not been studied for the prevention of rheumatic fever following Streptococcus pyogenes pharyngitis/tonsillitis. Only intramuscular penicillin has been demonstrated to be effective for the prevention of rheumatic fever. Uncomplicated Skin and Skin-Structure Infections caused by Staphylococcus aureus (including ß-lactamase-producing strains) or Streptococcus pyogenes. To reduce the development of drug-resistant bacteria and maintain the effectiveness of SPECTRACEF® and other antibacterial drugs, SPECTRACEF® should be used only to treat infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Launch Date2001 |
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| Curative | SPECTRACEF Approved UseSPECTRACEF® (cefditoren pivoxil) is indicated for the treatment of mild to moderate infections in adults and adolescents (12 years of age or older) which are caused by susceptible strains of the designated microorganisms in the conditions listed below. Acute Bacterial Exacerbation of Chronic Bronchitis caused by Haemophilus influenzae (including ß-lactamase-producing strains), Haemophilus parainfluenzae (including ß-lactamase producing strains), Streptococcus pneumoniae (penicillin susceptible strains only), or Moraxella catarrhalis (including ß-lactamase-producing strains). Community-Acquired Pneumonia caused by Haemophilus influenzae (including ß-lactamase-producing strains), Haemophilus parainfluenzae (including ß-lactamase-producing strains), Streptococcus pneumoniae (penicillin-susceptible strains only), or Moraxella catarrhalis (including ß-lactamase producing strains). Pharyngitis/Tonsillitis caused by Streptococcus pyogenes. NOTE: SPECTRACEF® is effective in the eradication of Streptococcus pyogenes from the oropharynx. SPECTRACEF® has not been studied for the prevention of rheumatic fever following Streptococcus pyogenes pharyngitis/tonsillitis. Only intramuscular penicillin has been demonstrated to be effective for the prevention of rheumatic fever. Uncomplicated Skin and Skin-Structure Infections caused by Staphylococcus aureus (including ß-lactamase-producing strains) or Streptococcus pyogenes. To reduce the development of drug-resistant bacteria and maintain the effectiveness of SPECTRACEF® and other antibacterial drugs, SPECTRACEF® should be used only to treat infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Launch Date2001 |
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| Curative | SPECTRACEF Approved UseSPECTRACEF® (cefditoren pivoxil) is indicated for the treatment of mild to moderate infections in adults and adolescents (12 years of age or older) which are caused by susceptible strains of the designated microorganisms in the conditions listed below. Acute Bacterial Exacerbation of Chronic Bronchitis caused by Haemophilus influenzae (including ß-lactamase-producing strains), Haemophilus parainfluenzae (including ß-lactamase producing strains), Streptococcus pneumoniae (penicillin susceptible strains only), or Moraxella catarrhalis (including ß-lactamase-producing strains). Community-Acquired Pneumonia caused by Haemophilus influenzae (including ß-lactamase-producing strains), Haemophilus parainfluenzae (including ß-lactamase-producing strains), Streptococcus pneumoniae (penicillin-susceptible strains only), or Moraxella catarrhalis (including ß-lactamase producing strains). Pharyngitis/Tonsillitis caused by Streptococcus pyogenes. NOTE: SPECTRACEF® is effective in the eradication of Streptococcus pyogenes from the oropharynx. SPECTRACEF® has not been studied for the prevention of rheumatic fever following Streptococcus pyogenes pharyngitis/tonsillitis. Only intramuscular penicillin has been demonstrated to be effective for the prevention of rheumatic fever. Uncomplicated Skin and Skin-Structure Infections caused by Staphylococcus aureus (including ß-lactamase-producing strains) or Streptococcus pyogenes. To reduce the development of drug-resistant bacteria and maintain the effectiveness of SPECTRACEF® and other antibacterial drugs, SPECTRACEF® should be used only to treat infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Launch Date2001 |
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| Curative | SPECTRACEF Approved UseSPECTRACEF® (cefditoren pivoxil) is indicated for the treatment of mild to moderate infections in adults and adolescents (12 years of age or older) which are caused by susceptible strains of the designated microorganisms in the conditions listed below. Acute Bacterial Exacerbation of Chronic Bronchitis caused by Haemophilus influenzae (including ß-lactamase-producing strains), Haemophilus parainfluenzae (including ß-lactamase producing strains), Streptococcus pneumoniae (penicillin susceptible strains only), or Moraxella catarrhalis (including ß-lactamase-producing strains). Community-Acquired Pneumonia caused by Haemophilus influenzae (including ß-lactamase-producing strains), Haemophilus parainfluenzae (including ß-lactamase-producing strains), Streptococcus pneumoniae (penicillin-susceptible strains only), or Moraxella catarrhalis (including ß-lactamase producing strains). Pharyngitis/Tonsillitis caused by Streptococcus pyogenes. NOTE: SPECTRACEF® is effective in the eradication of Streptococcus pyogenes from the oropharynx. SPECTRACEF® has not been studied for the prevention of rheumatic fever following Streptococcus pyogenes pharyngitis/tonsillitis. Only intramuscular penicillin has been demonstrated to be effective for the prevention of rheumatic fever. Uncomplicated Skin and Skin-Structure Infections caused by Staphylococcus aureus (including ß-lactamase-producing strains) or Streptococcus pyogenes. To reduce the development of drug-resistant bacteria and maintain the effectiveness of SPECTRACEF® and other antibacterial drugs, SPECTRACEF® should be used only to treat infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Launch Date2001 |
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| Curative | SPECTRACEF Approved UseSPECTRACEF® (cefditoren pivoxil) is indicated for the treatment of mild to moderate infections in adults and adolescents (12 years of age or older) which are caused by susceptible strains of the designated microorganisms in the conditions listed below. Acute Bacterial Exacerbation of Chronic Bronchitis caused by Haemophilus influenzae (including ß-lactamase-producing strains), Haemophilus parainfluenzae (including ß-lactamase producing strains), Streptococcus pneumoniae (penicillin susceptible strains only), or Moraxella catarrhalis (including ß-lactamase-producing strains). Community-Acquired Pneumonia caused by Haemophilus influenzae (including ß-lactamase-producing strains), Haemophilus parainfluenzae (including ß-lactamase-producing strains), Streptococcus pneumoniae (penicillin-susceptible strains only), or Moraxella catarrhalis (including ß-lactamase producing strains). Pharyngitis/Tonsillitis caused by Streptococcus pyogenes. NOTE: SPECTRACEF® is effective in the eradication of Streptococcus pyogenes from the oropharynx. SPECTRACEF® has not been studied for the prevention of rheumatic fever following Streptococcus pyogenes pharyngitis/tonsillitis. Only intramuscular penicillin has been demonstrated to be effective for the prevention of rheumatic fever. Uncomplicated Skin and Skin-Structure Infections caused by Staphylococcus aureus (including ß-lactamase-producing strains) or Streptococcus pyogenes. To reduce the development of drug-resistant bacteria and maintain the effectiveness of SPECTRACEF® and other antibacterial drugs, SPECTRACEF® should be used only to treat infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Launch Date2001 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.8 μg/mL |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
CEFDITOREN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.6 h |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
CEFDITOREN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
12% |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
CEFDITOREN plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
400 mg 3 times / day steady, oral Studied dose Dose: 400 mg, 3 times / day Route: oral Route: steady Dose: 400 mg, 3 times / day Sources: |
healthy, 18-30 years n = 8 Health Status: healthy Age Group: 18-30 years Sex: M Population Size: 8 Sources: |
Disc. AE: Gastrointestinal disturbance... AEs leading to discontinuation/dose reduction: Gastrointestinal disturbance (1 patient) Sources: |
200 mg 2 times / day steady, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: steady Dose: 200 mg, 2 times / day Sources: |
unhealthy, adult n = 2150 Health Status: unhealthy Condition: chronic bronchitis Age Group: adult Sex: unknown Population Size: 2150 Sources: |
Disc. AE: Gastrointestinal disturbance, Diarrhoea... AEs leading to discontinuation/dose reduction: Gastrointestinal disturbance (2%) Sources: Diarrhoea (0.7%) |
400 mg 2 times / day steady, oral Recommended Dose: 400 mg, 2 times / day Route: oral Route: steady Dose: 400 mg, 2 times / day Sources: |
unhealthy, adult n = 2149 Health Status: unhealthy Condition: chronic bronchitis Age Group: adult Sex: unknown Population Size: 2149 Sources: |
Disc. AE: Gastrointestinal disturbance, Diarrhoea... AEs leading to discontinuation/dose reduction: Gastrointestinal disturbance (3%) Sources: Diarrhoea (1.4%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Gastrointestinal disturbance | 1 patient Disc. AE |
400 mg 3 times / day steady, oral Studied dose Dose: 400 mg, 3 times / day Route: oral Route: steady Dose: 400 mg, 3 times / day Sources: |
healthy, 18-30 years n = 8 Health Status: healthy Age Group: 18-30 years Sex: M Population Size: 8 Sources: |
| Diarrhoea | 0.7% Disc. AE |
200 mg 2 times / day steady, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: steady Dose: 200 mg, 2 times / day Sources: |
unhealthy, adult n = 2150 Health Status: unhealthy Condition: chronic bronchitis Age Group: adult Sex: unknown Population Size: 2150 Sources: |
| Gastrointestinal disturbance | 2% Disc. AE |
200 mg 2 times / day steady, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: steady Dose: 200 mg, 2 times / day Sources: |
unhealthy, adult n = 2150 Health Status: unhealthy Condition: chronic bronchitis Age Group: adult Sex: unknown Population Size: 2150 Sources: |
| Diarrhoea | 1.4% Disc. AE |
400 mg 2 times / day steady, oral Recommended Dose: 400 mg, 2 times / day Route: oral Route: steady Dose: 400 mg, 2 times / day Sources: |
unhealthy, adult n = 2149 Health Status: unhealthy Condition: chronic bronchitis Age Group: adult Sex: unknown Population Size: 2149 Sources: |
| Gastrointestinal disturbance | 3% Disc. AE |
400 mg 2 times / day steady, oral Recommended Dose: 400 mg, 2 times / day Route: oral Route: steady Dose: 400 mg, 2 times / day Sources: |
unhealthy, adult n = 2149 Health Status: unhealthy Condition: chronic bronchitis Age Group: adult Sex: unknown Population Size: 2149 Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes | ||||
| yes |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes [Km 122.7 uM] | ||||
| yes [Km 189.7 uM] | ||||
| yes | ||||
| yes | ||||
| yes |
Sample Use Guides
Acute bacterial exacerbation of chronic bronchitis: 400 mg twice a day for 10 days.
Community-acquired pneumonia: 400 mg twice a day for 14 days
Tonsillitis/Pharyngitis and Uncomplicated Skin or Soft Tissue Infection: 200 mg twice a day for 10 days
Route of Administration:
Oral
The level of cefditoren activity against S. pneumoniae (MIC(90,) 0.5 microg/mL) was superior to all marketed oral cephalosporins and at least equal to amoxicillin +/- clavulanate. H. influenzae (MIC(90,) 0.016-0.03 microg/mL) and M. catarrhalis (MIC(90,) 0.06-0.5 microg/mL) were also very susceptible to cefditoren. cefditoren was active against oxacillin-susceptible staphylococci (MIC(90,) < or = 1 microg/mL) at a level comparable to cefuroxime axetil, cefaclor or cefprozil.
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NCI_THESAURUS |
C357
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NDF-RT |
N0000011161
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LIVERTOX |
162
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NDF-RT |
N0000011161
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N0000011161
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NDF-RT |
N0000011161
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WHO-ATC |
J01DD16
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NDF-RT |
N0000011161
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NDF-RT |
N0000011161
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NDF-RT |
N0000011161
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WHO-VATC |
QJ01DD16
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NDF-RT |
N0000011161
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NDF-RT |
N0000011161
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NDF-RT |
N0000011161
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NDF-RT |
N0000011161
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NDF-RT |
N0000011161
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NDF-RT |
N0000175488
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100000081797
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SUB07387MIG
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6919
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DTXSID501328012
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59343
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81QS09V3YW
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81QS09V3YW
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CHEMBL454446
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Cefditoren
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m3192
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CEFDITOREN
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83682
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DB01066
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104145-95-1
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C073460
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C72625
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ACTIVE MOIETY
PRODRUG (METABOLITE ACTIVE)
SALT/SOLVATE (PARENT)
