Chemistry:Cefpodoxime

Short description: Antibiotic

Cefpodoxime

Clinical data
Trade names	Vantin, others
Other names	Cefpodoxime proxetil
AHFS/Drugs.com	Monograph
MedlinePlus	a698024
Pregnancy category	AU: B1
Routes of administration	By mouth
ATC code	J01DD13 (WHO)
Legal status
Legal status	CA: ℞-only US: ℞-only
Pharmacokinetic data
Bioavailability	50%
Protein binding	21% to 29%
Metabolism	Negligible. Cefpodoxime proxetil is metabolized to cefpodoxime by the liver
Elimination half-life	2 hours
Excretion	Kidney, unchanged
Identifiers
IUPAC name (6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyimino-acetyl]amino}-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS Number	80210-62-4 N
PubChem CID	6335986
DrugBank	DB01416 N
ChemSpider	4891496 Y
UNII	7R4F94TVGY
KEGG	D07650 Y
ChEBI	CHEBI:3504 N
ChEMBL	ChEMBL1672 Y
Chemical and physical data
Formula	C15H17N5O6S2
Molar mass	427.45 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)C(=N\OC)/c3nc(sc3)N)COC)C(=O)O
InChI 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 Y Key:WYUSVOMTXWRGEK-HBWVYFAYSA-N Y
NY (what is this?)  (verify)

Cefpodoxime is an oral, third-generation cephalosporin antibiotic available in various generic preparations. It is active against both Gram-positive and Gram-negative organisms with notable exceptions including Pseudomonas aeruginosa, Enterococcus, and Bacteroides fragilis. It is typically used to treat acute otitis media, pharyngitis, sinusitis, and gonorrhea. It also finds use as oral continuation therapy when intravenous cephalosporins (such as ceftriaxone) are no longer necessary for continued treatment.

Cefpodoxime inhibits peptidoglycan synthesis in bacterial cell walls. It has an oral bioavailability of approximately 50%, which is increased when taken with food. It has an elimination half-life of 2-3 hours in adults, which is prolonged in renal failure. Approved indications include community acquired pneumonia, uncomplicated skin and skin structure infections, and uncomplicated urinary tract infections.

It was patented in 1980 and approved for medical use in 1989.

Spectrum of bacterial susceptibility and resistance

Cefpodoxime has been used to treat gonorrhoea, tonsillitis, pneumonia, and bronchitis. The following minimum inhibitory concentrations have been reported:

• Haemophilus influenzae: ≤0.03 – 1 μg/ml
• Neisseria gonorrhoeae: 0.004 – 0.06 μg/ml
• Streptococcus pyogenes: ≤0.004 – 2 μg/ml

Brand names

Zoetis markets cefpodoxime proxetil under the trade name Simplicef for veterinary use, Finecure, India markets the products under trade name Cefpo.

Vantin (by Pfizer) in suspension or tablet form.

Toraxim (by Delta Pharma Ltd. Bangladesh)

Trucef (by Renata Limited, Bangladesh)

Tricef (by Alkaloid Skopje, North Macedonia)

Orelox (by Sanofi-Aventis)

MAPDOX-CV: Cefpodoxime and Clavulanic acid combination

MONOTAX O (Cefpodoxime)/ MONOTAX CV (Cefpodoxime and Clavulanic acid combination) (by Zydus Healthcare Ltd.)

ACXIME 200/CV (by Allencia Biosciences, India)

POSTPOD-50 (Cefpodoxime 50mg/5ml) (by Laafon Galaxy Pharmaceuticals)

External links

• CID 6526396 from PubChem – cefpodoxime proxetil
• Vantin Tablets and Oral Suspension Torpod (Torrent) Full U.S. Prescribing Information (from manufacturer's website)
• Simplicef (from manufacturer's website)
• Intas Pharmaceuticals Ltd. » Animal Health :: Intas - a leading global pharmaceutical formulation development, manufacturing and marketing company