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

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H17N6O5S3.Na
Molecular Weight 528.56
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of CEFDITOREN SODIUM

SMILES

[Na+].[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=VFUMWBZIKOREOO-WSWQWPGSSA-M
InChI=1S/C19H18N6O5S3.Na/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);/q;+1/p-1/b4-3-,24-12-;/t13-,17-;/m1./s1

HIDE SMILES / InChI

Description
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

2001
194
Targets

Targets

Primary TargetPharmacologyConditionPotency
Penicillin-binding protein 2B
10
Target ID: P0A3M6
Gene ID: 933948.0
Gene Symbol: penA
Target Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Inhibitor
8297
Penicillin-binding protein 1A
45
Target ID: Q8XJ01
Gene ID: 990276.0
Gene Symbol: pbpA
Target Organism: Clostridium perfringens (strain 13 / Type A)
Inhibitor
8297
Penicillin-binding protein 2X
5
Target ID: P59676
Gene ID: 934744.0
Gene Symbol: pbpX
Target Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
SPECTRACEF

Approved Use

SPECTRACEF® (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 Date

2001
Curative
Approved
8429
SPECTRACEF

Approved Use

SPECTRACEF® (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 Date

2001
Curative
Approved
8429
SPECTRACEF

Approved Use

SPECTRACEF® (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 Date

2001
Curative
Approved
8429
SPECTRACEF

Approved Use

SPECTRACEF® (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 Date

2001
Curative
Approved
8429
SPECTRACEF

Approved Use

SPECTRACEF® (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 Date

2001
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.8 μg/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021222s013s016lbl.pdf
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

T1/2

ValueDoseCo-administeredAnalytePopulation
1.6 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021222s013s016lbl.pdf
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

Funbound

ValueDoseCo-administeredAnalytePopulation
12%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021222s013s016lbl.pdf
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

Doses

DosePopulationAdverse 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:
https://pubmed.ncbi.nlm.nih.gov/17530036/
healthy, 18-30 years
n = 8
Health Status: healthy
Age Group: 18-30 years
Sex: M
Population Size: 8
Sources:
https://pubmed.ncbi.nlm.nih.gov/17530036/
Disc. AE: Gastrointestinal disturbance...
AEs leading to
discontinuation/dose reduction:
Gastrointestinal disturbance (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/17530036/
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:
https://pubmed.ncbi.nlm.nih.gov/11817976/
unhealthy, adult
n = 2150
Health Status: unhealthy
Condition: chronic bronchitis
Age Group: adult
Sex: unknown
Population Size: 2150
Sources:
https://pubmed.ncbi.nlm.nih.gov/11817976/
Disc. AE: Gastrointestinal disturbance, Diarrhoea...
AEs leading to
discontinuation/dose reduction:
Gastrointestinal disturbance (2%)
Diarrhoea (0.7%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/11817976/
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:
https://pubmed.ncbi.nlm.nih.gov/11817976/
unhealthy, adult
n = 2149
Health Status: unhealthy
Condition: chronic bronchitis
Age Group: adult
Sex: unknown
Population Size: 2149
Sources:
https://pubmed.ncbi.nlm.nih.gov/11817976/
Disc. AE: Gastrointestinal disturbance, Diarrhoea...
AEs leading to
discontinuation/dose reduction:
Gastrointestinal disturbance (3%)
Diarrhoea (1.4%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/11817976/
AEs

AEs

AESignificanceDosePopulation
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:
https://pubmed.ncbi.nlm.nih.gov/17530036/
healthy, 18-30 years
n = 8
Health Status: healthy
Age Group: 18-30 years
Sex: M
Population Size: 8
Sources:
https://pubmed.ncbi.nlm.nih.gov/17530036/
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:
https://pubmed.ncbi.nlm.nih.gov/11817976/
unhealthy, adult
n = 2150
Health Status: unhealthy
Condition: chronic bronchitis
Age Group: adult
Sex: unknown
Population Size: 2150
Sources:
https://pubmed.ncbi.nlm.nih.gov/11817976/
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:
https://pubmed.ncbi.nlm.nih.gov/11817976/
unhealthy, adult
n = 2150
Health Status: unhealthy
Condition: chronic bronchitis
Age Group: adult
Sex: unknown
Population Size: 2150
Sources:
https://pubmed.ncbi.nlm.nih.gov/11817976/
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:
https://pubmed.ncbi.nlm.nih.gov/11817976/
unhealthy, adult
n = 2149
Health Status: unhealthy
Condition: chronic bronchitis
Age Group: adult
Sex: unknown
Population Size: 2149
Sources:
https://pubmed.ncbi.nlm.nih.gov/11817976/
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:
https://pubmed.ncbi.nlm.nih.gov/11817976/
unhealthy, adult
n = 2149
Health Status: unhealthy
Condition: chronic bronchitis
Age Group: adult
Sex: unknown
Population Size: 2149
Sources:
https://pubmed.ncbi.nlm.nih.gov/11817976/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP
270

UGT
192

OATP1B1
406

OATP2B1
104

BCRP
561
BCRP
75
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
BCRP
773
 yes
P-gp
1650
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
OATP2B1
104
 yes [Km 122.7 uM]
OATP1B1
406
 yes [Km 189.7 uM]
BCRP
561
 yes
CYP
270
 yes
UGT
192
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:59343
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:59343
ChemicalBook
CB2874737
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2874737
ZINC
ZINC000004215234
http://zinc15.docking.org/substances/ZINC000004215234
PubMed

PubMed

TitleDatePubMed
Antibiotic susceptibility of respiratory pathogens recently isolated in Italy: focus on cefditoren.
2010 Jun
Patents

Patents

EP 175610
3
US4839350 A
3

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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.
Name Type Language
CEFDITOREN SODIUM
Common Name English
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-(((2Z)-2-(2-AMINO-4-THIAZOLYL)-2-(METHOXYIMINO)ACETYL)AMINO)-3-((1Z)-2-(4-METHYL-5-THIAZOLYL)ETHENYL)-8-OXO-, SODIUM SALT (1:1), (6R,7R)-
Systematic Name English
ME-1206
Code English
Code System Code Type Description
CAS
104146-53-4
Created by admin on Sat Dec 16 10:51:26 GMT 2023 , Edited by admin on Sat Dec 16 10:51:26 GMT 2023
PRIMARY
FDA UNII
C634TP4VZ5
Created by admin on Sat Dec 16 10:51:26 GMT 2023 , Edited by admin on Sat Dec 16 10:51:26 GMT 2023
PRIMARY
PUBCHEM
23673042
Created by admin on Sat Dec 16 10:51:26 GMT 2023 , Edited by admin on Sat Dec 16 10:51:26 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of CEFDITOREN
SUBSTANCE RECORD
Structure of CEFDITOREN SODIUM
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966