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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

[H][C@]12SCC(COC)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C3=CSC(N)=N3)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

Molecular Formula C15H17N5O6S2
Molecular Weight 427.455
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
133.0 µM [IC50]
133.0 µM [IC50]
133.0 µM [IC50]
81.7 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
CEFPODOXIME PROXETIL
Curative
CEFPODOXIME PROXETIL
Curative
CEFPODOXIME PROXETIL
Curative
CEFPODOXIME PROXETIL
Curative
CEFPODOXIME PROXETIL
Curative
CEFPODOXIME PROXETIL
Curative
CEFPODOXIME PROXETIL
Curative
CEFPODOXIME PROXETIL
Curative
CEFPODOXIME PROXETIL
Curative
CEFPODOXIME PROXETIL

Cmax

ValueDoseCo-administeredAnalytePopulation
2.18 μg/mL
200 mg single, oral
CEFPODOXIME plasma
Homo sapiens
2.33 μg/mL
200 mg 2 times / day steady-state, oral
CEFPODOXIME plasma
Homo sapiens
4.16 μg/mL
400 mg single, oral
CEFPODOXIME plasma
Homo sapiens
4.2 μg/mL
400 mg 2 times / day steady-state, oral
CEFPODOXIME plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
11.8 μg × h/mL
200 mg single, oral
CEFPODOXIME plasma
Homo sapiens
11.8 μg × h/mL
200 mg 2 times / day steady-state, oral
CEFPODOXIME plasma
Homo sapiens
25 μg × h/mL
400 mg single, oral
CEFPODOXIME plasma
Homo sapiens
24 μg × h/mL
400 mg 2 times / day steady-state, oral
CEFPODOXIME plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2.7 h
200 mg single, oral
CEFPODOXIME plasma
Homo sapiens
2.6 h
200 mg 2 times / day steady-state, oral
CEFPODOXIME plasma
Homo sapiens
2.6 h
400 mg single, oral
CEFPODOXIME plasma
Homo sapiens
2.7 h
400 mg 2 times / day steady-state, oral
CEFPODOXIME plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

PubMed

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.
Substance Class Chemical
Record UNII
7R4F94TVGY
Record Status Validated (UNII)
Record Version