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

CO\N=C(/C(=O)N[C@H]1[C@H]2SCC(\C=C/C3=C(C)N=CS3)=C(N2C1=O)C(=O)OCOC(=O)C(C)(C)C)C4=CSC(N)=N4

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

Description

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

PubMed

PubMed

TitleDatePubMed
Patents

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 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
CEFDITOREN PIVOXIL [WHO-DD]
Common Name English
CEFDITOREN PIVOXIL [USP-RS]
Common 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
ME-1207
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 Tue Oct 22 00:13:15 UTC 2019 , Edited by admin on Tue Oct 22 00:13:15 UTC 2019
Code System Code Type Description
CAS
117467-28-4
Created by admin on Tue Oct 22 00:13:15 UTC 2019 , Edited by admin on Tue Oct 22 00:13:15 UTC 2019
PRIMARY
ChEMBL
CHEMBL454446
Created by admin on Tue Oct 22 00:13:15 UTC 2019 , Edited by admin on Tue Oct 22 00:13:15 UTC 2019
PRIMARY
MERCK INDEX
M3192
Created by admin on Tue Oct 22 00:13:15 UTC 2019 , Edited by admin on Tue Oct 22 00:13:15 UTC 2019
PRIMARY Merck Index
DRUG BANK
DB01066
Created by admin on Tue Oct 22 00:13:15 UTC 2019 , Edited by admin on Tue Oct 22 00:13:15 UTC 2019
PRIMARY
MESH
C057710
Created by admin on Tue Oct 22 00:13:15 UTC 2019 , Edited by admin on Tue Oct 22 00:13:15 UTC 2019
PRIMARY
EVMPD
SUB01112MIG
Created by admin on Tue Oct 22 00:13:15 UTC 2019 , Edited by admin on Tue Oct 22 00:13:15 UTC 2019
PRIMARY
RXCUI
72611
Created by admin on Tue Oct 22 00:13:15 UTC 2019 , Edited by admin on Tue Oct 22 00:13:15 UTC 2019
PRIMARY RxNorm
EPA CompTox
117467-28-4
Created by admin on Tue Oct 22 00:13:15 UTC 2019 , Edited by admin on Tue Oct 22 00:13:15 UTC 2019
PRIMARY
NCI_THESAURUS
C47434
Created by admin on Tue Oct 22 00:13:15 UTC 2019 , Edited by admin on Tue Oct 22 00:13:15 UTC 2019
PRIMARY
PUBCHEM
6437877
Created by admin on Tue Oct 22 00:13:15 UTC 2019 , Edited by admin on Tue Oct 22 00:13:15 UTC 2019
PRIMARY