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

Details

Stereochemistry ABSOLUTE
Molecular Formula C15H17N5O6S2
Molecular Weight 427.455
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CEFPODOXIME

SMILES

COCC1=C(N2[C@H](SC1)[C@H](NC(=O)C(=N/OC)\C3=CSC(N)=N3)C2=O)C(O)=O

InChI

InChIKey=WYUSVOMTXWRGEK-HBWVYFAYSA-N
InChI=1S/C15H17N5O6S2/c1-25-3-6-4-27-13-9(12(22)20(13)10(6)14(23)24)18-11(21)8(19-26-2)7-5-28-15(16)17-7/h5,9,13H,3-4H2,1-2H3,(H2,16,17)(H,18,21)(H,23,24)/b19-8-/t9-,13-/m1/s1

HIDE SMILES / InChI

Description

Cefpodoxime is an orally administered, extended spectrum, semi-synthetic antibiotic of the cephalosporin class. Cefpodoxime is a bactericidal agent that acts by inhibition of bacterial cell wall synthesis. Cefpodoxime has activity in the presence of some beta-lactamases, both penicillinases and cephalosporinases, of Gram-negative and Gram-positive bacteria. Cefpodoxime is indicated for the treatment of patients with mild to moderate infections caused by susceptible strains of the designated microorganisms in the conditions: acute otitis media; pharyngitis and/or tonsillitis; community-acquired pneumonia; acute bacterial exacerbation of chronic bronchitis; gonorrhea; uncomplicated skin and skin structure infections; acute maxillary sinusitis and uncomplicated urinary tract infections (cystitis). Common adverse reactions include diarrhea, nausea, vaginal fungal infections, vulvovaginal infections, abdominal pain, headache. Concomitant administration of high doses of antacids (sodium bicarbonate and aluminum hydroxide) or H2 blockers reduces peak plasma levels by 24% to 42% and the extent of absorption by 27% to 32%, respectively. Oral anti-cholinergics (e.g., propantheline) delay peak plasma levels (47% increase in Tmax), but do not affect the extent of absorption (AUC). Probenecid: As with other beta-lactam antibiotics, renal excretion of cefpodoxime was inhibited by probenecid and resulted in an approximately 31% increase in AUC and 20% increase in peak cefpodoxime plasma levels.

CNS Activity

Originator

Approval Year

PMID

PMID

TitleDatePMID
Comparing the disk-diffusion and agar dilution tests for <i>Neisseria gonorrhoeae</i> antimicrobial susceptibility testing.
2016
Investigation of molecular interaction between cefpodoxime acid and human mixtard insulin by ultrasonic and spectral methods.
2016 Sep 10
In vitro transfer of methicillin resistance determinants mecA from methicillin resistant Staphylococcus aureus (MRSA) to methicillin susceptible Staphylococcus aureus (MSSA).
2017 Apr 4
Characterization of ESBL-producing Escherichia coli recovered from companion dogs in Tai'an, China.
2017 Mar 31
Validated HPLC method for the pharmacokinetic study of oral extended-release cefpodoxime proxetil chitosan-alginate beads in rabbits.
2017 May
Patent

Sample Use Guides

In Vivo Use Guide
The recommended dosages, durations of treatment, and applicable patient population are: Pharyngitis and/or tonsillitis 100 mg Q 12 hours (5 to 10 days) Acute community-acquired pneumonia 200 mg Q 12 hours (14 days) Acute bacterial exacerbations of chronic bronchitis 200 mg Q 12 hours (10 day) Uncomplicated gonorrhea (men and women) and rectal gonococcal infections (women) 200 mg single dose Skin and skin structure 400 mg Q 12 hours (7 to 14 days) Acute maxillary sinusitis 200 mg Q 12 hours (10 days) Uncomplicated urinary tract infection 100 mg Q 12 hours (7 days).
Route of Administration: Oral
In Vitro Use Guide
The in-vitro activity of cefpodoxime was studied in 529 clinical isolates and compared with the activity of other oral beta-lactams. Amongst the Enterobacteriaceae cefpodoxime was very active (MIC90 less than or equal to 1 mg/l--other than genera commonly possessing chromosomal beta-lactamases). Against these strains cefpodoxime was comparable in activity to cefixime and about eight-fold more active than cefuroxime and 8-16-fold more active than cefaclor and cephalexin. Staphylococcus aureus strains were moderately susceptible (MIC90 4 mg/l) to cefpodoxime.
Name Type Language
CEFPODOXIME
INN   MI   WHO-DD  
INN  
Official Name English
CEFPODOXIME [MI]
Common Name English
(+)-(6R,7R)-7-(2-(2-AMINO-4-THIAZOLYL)-2-((Z)-METHOXYIMINO)ACETAMIDO)-3-(METHOXYMETHYL)-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID
Systematic Name English
EPOXIM
Brand Name English
(+)-(6R,7R)-7-(2-(2-AMINO-4-THIAZOLYL)GLYOXYLAMIDO)-3-(METHOXYMETHYL)-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7(SUP 2)-(Z)-(O-METHYLOXIME)
Common Name English
CEFPODOXIME [INN]
Common Name English
CEFPODOXIME [JAN]
Common Name English
CEFPODOXIME [WHO-DD]
Common Name English
Classification Tree Code System Code
NDF-RT N0000011161
Created by admin on Tue Mar 06 10:27:00 UTC 2018 , Edited by admin on Tue Mar 06 10:27:00 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 10:27:00 UTC 2018 , Edited by admin on Tue Mar 06 10:27:00 UTC 2018
WHO-ATC J01DD13
Created by admin on Tue Mar 06 10:27:00 UTC 2018 , Edited by admin on Tue Mar 06 10:27:00 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 10:27:00 UTC 2018 , Edited by admin on Tue Mar 06 10:27:00 UTC 2018
NDF-RT N0000175488
Created by admin on Tue Mar 06 10:27:00 UTC 2018 , Edited by admin on Tue Mar 06 10:27:00 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 10:27:00 UTC 2018 , Edited by admin on Tue Mar 06 10:27:00 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 10:27:00 UTC 2018 , Edited by admin on Tue Mar 06 10:27:00 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 10:27:00 UTC 2018 , Edited by admin on Tue Mar 06 10:27:00 UTC 2018
WHO-VATC QJ01DD13
Created by admin on Tue Mar 06 10:27:00 UTC 2018 , Edited by admin on Tue Mar 06 10:27:00 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 10:27:00 UTC 2018 , Edited by admin on Tue Mar 06 10:27:00 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 10:27:00 UTC 2018 , Edited by admin on Tue Mar 06 10:27:00 UTC 2018
LIVERTOX 168
Created by admin on Tue Mar 06 10:27:00 UTC 2018 , Edited by admin on Tue Mar 06 10:27:00 UTC 2018
CFR 21 CFR 520.370
Created by admin on Tue Mar 06 10:27:00 UTC 2018 , Edited by admin on Tue Mar 06 10:27:00 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 10:27:00 UTC 2018 , Edited by admin on Tue Mar 06 10:27:00 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 10:27:00 UTC 2018 , Edited by admin on Tue Mar 06 10:27:00 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 10:27:00 UTC 2018 , Edited by admin on Tue Mar 06 10:27:00 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 10:27:00 UTC 2018 , Edited by admin on Tue Mar 06 10:27:00 UTC 2018
Code System Code Type Description
EPA CompTox
80210-62-4
Created by admin on Tue Mar 06 10:27:00 UTC 2018 , Edited by admin on Tue Mar 06 10:27:00 UTC 2018
PRIMARY
WIKIPEDIA
CEFPODOXIME
Created by admin on Tue Mar 06 10:27:00 UTC 2018 , Edited by admin on Tue Mar 06 10:27:00 UTC 2018
PRIMARY
RXCUI
20489
Created by admin on Tue Mar 06 10:27:00 UTC 2018 , Edited by admin on Tue Mar 06 10:27:00 UTC 2018
PRIMARY RxNorm
ChEMBL
CHEMBL1201016
Created by admin on Tue Mar 06 10:27:00 UTC 2018 , Edited by admin on Tue Mar 06 10:27:00 UTC 2018
PRIMARY
PUBCHEM
6335986
Created by admin on Tue Mar 06 10:27:00 UTC 2018 , Edited by admin on Tue Mar 06 10:27:00 UTC 2018
PRIMARY SWITZERF
EVMPD
SUB07414MIG
Created by admin on Tue Mar 06 10:27:00 UTC 2018 , Edited by admin on Tue Mar 06 10:27:00 UTC 2018
PRIMARY
INN
6123
Created by admin on Tue Mar 06 10:27:00 UTC 2018 , Edited by admin on Tue Mar 06 10:27:00 UTC 2018
PRIMARY
NCI_THESAURUS
C65305
Created by admin on Tue Mar 06 10:27:00 UTC 2018 , Edited by admin on Tue Mar 06 10:27:00 UTC 2018
PRIMARY
MESH
C053268
Created by admin on Tue Mar 06 10:27:00 UTC 2018 , Edited by admin on Tue Mar 06 10:27:00 UTC 2018
PRIMARY
CAS
80210-62-4
Created by admin on Tue Mar 06 10:27:00 UTC 2018 , Edited by admin on Tue Mar 06 10:27:00 UTC 2018
PRIMARY
MERCK INDEX
M3212
Created by admin on Tue Mar 06 10:27:00 UTC 2018 , Edited by admin on Tue Mar 06 10:27:00 UTC 2018
PRIMARY Merck Index