Cefpodoxime

Antibiotic

AU: B1

Routes of
administrationBy mouthATC code

J01DD13 (WHO)

CA: ℞-only
US: ℞-only

Pharmacokinetic dataBioavailability50%Protein binding21% to 29%MetabolismNegligible. Cefpodoxime proxetil is metabolized to cefpodoxime by the liverElimination half-life2 hoursExcretionKidney, unchangedIdentifiers

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

CompTox Dashboard (EPA)

DTXSID6022765

ECHA InfoCard100.210.871

Chemical and physical dataFormulaC₁₅H₁₇N₅O₆S₂Molar mass427.45 g·mol⁻¹3D 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.^[1]

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:^[2]

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,^[3] India markets the products under trade name Cefpo.^[4]

Vantin (by Pfizer)^[5] 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)^[6]

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)^[7]

References

^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 495. ISBN 9783527607495.
^ "Cefpodoxime, Free Acid Susceptibility and Minimum Inhibitory Concentration (MIC) Data" (PDF).
^ "Pharmaceuticals Manufacturer, Marketer, Pharmaceutical Manufacturing Company India". www.finecurepharma.com. Retrieved 2019-05-26.
^ "Anti Biotics and Anti Bacterial". Finecurepharmaceuticalsltd. Archived from the original on 2012-03-06. Retrieved 2012-03-27.
^ "Vantin – Drugs.com". www.drugs.com. Retrieved 2019-05-02.
^ "Orelox – Drugs.com". www.drugs.com. Retrieved 2015-11-28.
^ "Postpod dry syrup". Laafon Galaxy Pharmaceuticals Company in Karnal. Retrieved 2020-09-16.

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

Antibacterials active on the cell wall and envelope (J01C-J01D)

Beta-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)

Penicillins (Penams)

Narrow
spectrum

β-lactamase sensitive (1st generation)	Benzylpenicillin (G)^# Benzathine benzylpenicillin^# Procaine benzylpenicillin^# Phenoxymethylpenicillin (V)^# Propicillin^‡ Pheneticillin^‡ Azidocillin^‡ Clometocillin^‡ Penamecillin^‡
β-lactamase resistant (2nd generation)	Cloxacillin^# (Dicloxacillin Flucloxacillin) Oxacillin Nafcillin Methicillin^‡

Extended
spectrum

Aminopenicillins (3rd generation)	Amoxicillin^# Ampicillin^# (Pivampicillin Hetacillin^‡ Bacampicillin^‡ Lenampicillin Metampicillin^‡ Talampicillin^‡) Epicillin^‡
Carboxypenicillins (4th generation)	Ticarcillin Carbenicillin^‡ / Carindacillin^‡ Temocillin^‡
Ureidopenicillins (4th generation)	Piperacillin Azlocillin^‡ Mezlocillin^‡
Other	Mecillinam (Pivmecillinam) Sulbenicillin^‡

Carbapenems / Penems

Cephems
Cephalosporins
Cephamycins
Carbacephems

1st generation	Cefazolin^# Cefalexin ^# Cefadroxil Cefapirin Cefazedone^‡ Cefazaflur^‡ Cefradine^‡ Cefroxadine^‡ Ceftezole^‡ Cefaloglycin^‡ Cefacetrile^‡ Cefalonium^‡ Cefaloridine^‡ Cefalotin Cefatrizine^‡
2nd generation	Cefaclor Cefprozil Cefuroxime Cefuroxime axetil Cefamandole^‡ Cefonicid^‡ Ceforanide^‡ Cefuzonam^‡ Cephamycin (Cefoxitin Cefotetan Cefminox^‡ Cefbuperazone^‡ Cefmetazole^‡) Carbacephem (Loracarbef^‡)
3rd generation	Cefixime^# Ceftriaxone^# Cefotaxime^# Antipseudomonal (Ceftazidime^# Cefoperazone) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefotiam^‡ Cefetamet^‡ Cefodizime^‡ Cefpimizole^‡ Cefsulodin^‡ Cefteram^‡ Ceftiolene^‡ Oxacephem (Flomoxef Latamoxef^‡)
4th generation	Cefepime Cefozopran^‡ Cefpirome Cefquinome^‡
5th generation	Ceftaroline fosamil Ceftolozane Ceftobiprole
Siderophore	Cefiderocol^#
Veterinary	Ceftiofur Cefquinome Cefovecin

Monobactams

β-lactamase inhibitors

Combinations

Polypeptides

Glycopeptides Lipoglycopeptides	Inhibit PG chain elongation: Vancomycin^# (Oritavancin Telavancin) Teicoplanin (Dalbavancin) Ristocetin^‡ Avoparcin Inhibit autolysin: Corbomycin (not approved)
Lipopeptides	Insert into bacterial cell wall causing perforation and depolarization: Daptomycin Surfactin
Polymyxins	Bind to LPS in the outer bacterial membrane, acting in detergent-like fashion: Colistin Polymyxin B
Other	Inhibits PG elongation and crosslinking: Ramoplanin^§