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

Details

Stereochemistry ABSOLUTE
Molecular Formula C25H28N6O7S3
Molecular Weight 620.721
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of CEFDITOREN PIVOXIL

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)OCOC(=O)C(C)(C)C

InChI

InChIKey=AFZFFLVORLEPPO-UVYJNCLZSA-N
InChI=1S/C25H28N6O7S3/c1-12-15(41-10-27-12)7-6-13-8-39-21-17(29-19(32)16(30-36-5)14-9-40-24(26)28-14)20(33)31(21)18(13)22(34)37-11-38-23(35)25(2,3)4/h6-7,9-10,17,21H,8,11H2,1-5H3,(H2,26,28)(H,29,32)/b7-6-,30-16-/t17-,21-/m1/s1

HIDE SMILES / InChI

Molecular Formula C25H28N6O7S3
Molecular Weight 620.721
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 2
Optical Activity UNSPECIFIED

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P0A3M6
Gene ID: 933948.0
Gene Symbol: penA
Target Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Target ID: Q8XJ01
Gene ID: 990276.0
Gene Symbol: pbpA
Target Organism: Clostridium perfringens (strain 13 / Type A)
Target ID: P59676
Gene ID: 934744.0
Gene Symbol: pbpX
Target Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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

9.9904317E11
Curative
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

9.9904317E11
Curative
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

9.9904317E11
Curative
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

9.9904317E11
Curative
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

9.9904317E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

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:
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%)
Diarrhoea (0.7%)
Sources:
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%)
Diarrhoea (1.4%)
Sources:
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:
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:
PubMed

PubMed

TitleDatePubMed
Patents

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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:57:03 UTC 2023
Edited
by admin
on Fri Dec 15 15:57:03 UTC 2023
Record UNII
78THA212DH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEFDITOREN PIVOXIL
MART.   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
CEFDITOREN PIVOXIL [USAN]
Common Name English
CEFDITOREN PIVOXIL [JAN]
Common Name English
MEIACT
Brand Name English
CEFDITOREN PIVALOYLOXYMETHYL ESTER
MI  
Common Name English
SPECTRACEF
Brand Name English
ME1207
Code English
CEFDITOREN PIVALOYLOXYMETHYL ESTER [MI]
Common Name English
CEFDITOREN PIVOXIL [MART.]
Common Name English
(+)-(6R,7R)-7-(2-(2-AMINO-4-THIAZOLYL)GLYOXYLAMIDO)-3-((Z)-2-(4-METHYL-5-THIAZOLYL)VINYL)-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLATE PIVALOYLOXY METHYL ESTER, 7(SUP 2)-(Z)-(O-METHYLOXIME)
Common Name English
Cefditoren pivoxil [WHO-DD]
Common Name English
ME-1207
Code English
NSC-759098
Code English
CEFDITOREN PIVOXIL [VANDF]
Common Name English
CDTR-PI
Code English
CEFDITOREN PIVOXIL [ORANGE BOOK]
Common Name English
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7(((2Z)-(2-AMINO-4-THIAZOLYL)(METHOXYIMINO)ACETYL)AMINO)-3-((1Z)-2-(4-METHYL-5-THIAZOLYL)ETHENYL)-8-OXO-, (2,2-DIMETHYL-1-OXOPROPOXY)METHYL ESTER, (6R,7R)-
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C357
Created by admin on Fri Dec 15 15:57:03 UTC 2023 , Edited by admin on Fri Dec 15 15:57:03 UTC 2023
Code System Code Type Description
FDA UNII
78THA212DH
Created by admin on Fri Dec 15 15:57:03 UTC 2023 , Edited by admin on Fri Dec 15 15:57:03 UTC 2023
PRIMARY
CAS
117467-28-4
Created by admin on Fri Dec 15 15:57:03 UTC 2023 , Edited by admin on Fri Dec 15 15:57:03 UTC 2023
PRIMARY
DRUG CENTRAL
534
Created by admin on Fri Dec 15 15:57:03 UTC 2023 , Edited by admin on Fri Dec 15 15:57:03 UTC 2023
PRIMARY
ChEMBL
CHEMBL454446
Created by admin on Fri Dec 15 15:57:03 UTC 2023 , Edited by admin on Fri Dec 15 15:57:03 UTC 2023
PRIMARY
MERCK INDEX
m3192
Created by admin on Fri Dec 15 15:57:03 UTC 2023 , Edited by admin on Fri Dec 15 15:57:03 UTC 2023
PRIMARY Merck Index
DAILYMED
78THA212DH
Created by admin on Fri Dec 15 15:57:03 UTC 2023 , Edited by admin on Fri Dec 15 15:57:03 UTC 2023
PRIMARY
DRUG BANK
DB01066
Created by admin on Fri Dec 15 15:57:03 UTC 2023 , Edited by admin on Fri Dec 15 15:57:03 UTC 2023
PRIMARY
MESH
C057710
Created by admin on Fri Dec 15 15:57:03 UTC 2023 , Edited by admin on Fri Dec 15 15:57:03 UTC 2023
PRIMARY
SMS_ID
100000091310
Created by admin on Fri Dec 15 15:57:03 UTC 2023 , Edited by admin on Fri Dec 15 15:57:03 UTC 2023
PRIMARY
EVMPD
SUB01112MIG
Created by admin on Fri Dec 15 15:57:03 UTC 2023 , Edited by admin on Fri Dec 15 15:57:03 UTC 2023
PRIMARY
NSC
759098
Created by admin on Fri Dec 15 15:57:03 UTC 2023 , Edited by admin on Fri Dec 15 15:57:03 UTC 2023
PRIMARY
USAN
LL-103
Created by admin on Fri Dec 15 15:57:03 UTC 2023 , Edited by admin on Fri Dec 15 15:57:03 UTC 2023
PRIMARY
RXCUI
72611
Created by admin on Fri Dec 15 15:57:03 UTC 2023 , Edited by admin on Fri Dec 15 15:57:03 UTC 2023
PRIMARY RxNorm
CHEBI
560555
Created by admin on Fri Dec 15 15:57:03 UTC 2023 , Edited by admin on Fri Dec 15 15:57:03 UTC 2023
PRIMARY
EPA CompTox
DTXSID2048743
Created by admin on Fri Dec 15 15:57:03 UTC 2023 , Edited by admin on Fri Dec 15 15:57:03 UTC 2023
PRIMARY
NCI_THESAURUS
C47434
Created by admin on Fri Dec 15 15:57:03 UTC 2023 , Edited by admin on Fri Dec 15 15:57:03 UTC 2023
PRIMARY
PUBCHEM
6437877
Created by admin on Fri Dec 15 15:57:03 UTC 2023 , Edited by admin on Fri Dec 15 15:57:03 UTC 2023
PRIMARY
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
METABOLITE -> PARENT
Does not undergo extensive metabolism. Excretion in urine. Can lead to depletion of carnitine.
Related Record Type Details
ACTIVE MOIETY