Cefpodoxime
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| Systematic (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 |
| Clinical data |
| Trade names |
Vantin |
| AHFS/Drugs.com |
monograph |
| MedlinePlus |
a698024 |
| Pregnancy cat. |
B1(AU) B(US) |
| Legal status |
℞-only (US) |
| Routes |
Oral |
| Pharmacokinetic data |
| Bioavailability |
50% |
| Protein binding |
21% to 29% |
| Metabolism |
Negligible. Cefpodoxime proxetil is metabolized to cefpodoxime by the liver |
| Half-life |
2 hours |
| Excretion |
Renal, unchanged |
| Identifiers |
| CAS number |
82619-04-3  Y |
| ATC code |
J01DD13 |
| PubChem |
CID 6335986 |
| DrugBank |
DB01416 |
| ChemSpider |
4891496 Y |
| UNII |
7R4F94TVGY  N |
| KEGG |
D07650 Y |
| ChEBI |
CHEBI:3504 N |
| ChEMBL |
CHEMBL1672 Y |
| Chemical data |
| Formula |
C15H17N5O6S2 |
| Mol. mass |
427.458 g/mol |
| SMILES |
eMolecules & PubChem |
InChI
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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
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 N(what is this?) (verify)
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Cefpodoxime is an oral third generation cephalosporin antibiotic. It is marketed as the prodrug cefpodoxime proxetil by Pharmacia & Upjohn under the trade name Vantin. It is active against most Gram positive and Gram negative organisms. Notable exceptions include Pseudomonas aeruginosa, Enterococcus, and Bacteroides fragilis. It is commonly used to treat acute otitis media, pharyngitis, and sinusitis. It also finds use as oral continuation therapy when intravenous cephalosporins (such as ceftriaxone) are no longer necessary for continued treatment.
Pfizer, the parent company of Pharmacia & Upjohn, markets cefpodoxime proxetil under the trade name Simplicef for veterinary use. The dose range in dogs is 5–10 mg/kg body weight, administered orally, once a day.
Structural formula of cefpodoxime
proxetil
External links
- PubChem 6526396 - cefpodoxime proxetil
- Vantin Tablets and Oral Suspension Torpod (Torrent)Full U.S. Prescribing Information (from manufacturer's website)
- Simplicef (from manufacturer's website)
- http://www.intaspharma.com/index.php?option=com_djcatalog2&view=itemstable&cid=3&Itemid=77
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Antibacterials: cell envelope antibiotics (J01C-J01D)
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| Intracellular |
inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin) • DADAL/AR inhibitors (Cycloserine) • bactoprenol inhibitors (Bacitracin)
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| Glycopeptide |
inhibit PG chain elongation: Vancomycin# (Oritavancin, Telavancin) • Teicoplanin (Dalbavancin) • Ramoplanin
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β-lactams/
(inhibit PBP
cross-links) |
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Penicillins
(penams)
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Extended sp.
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aminopenicillins: Amoxicillin# • Ampicillin# (Pivampicillin, Hetacillin, Bacampicillin, Metampicillin, Talampicillin) • Epicillin
carboxypenicillins: Carbenicillin (Carindacillin) • Ticarcillin • Temocillin
ureidopenicillins: Azlocillin • Piperacillin • Mezlocillin
other: Mecillinam (Pivmecillinam) • Sulbenicillin
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Narrow sp.
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β-lactamase sensitive
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Benzylpenicillin (G)#: Clometocillin • Benzathine benzylpenicillin# • Procaine benzylpenicillin# • Azidocillin • Penamecillin
Phenoxymethylpenicillin (V) #: Propicillin • Benzathine phenoxymethylpenicillin • Pheneticillin
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β-lactamase resistant
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Cloxacillin# (Dicloxacillin, Flucloxacillin) • Oxacillin • Meticillin • Nafcillin
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Penems
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Faropenem
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Carbapenems
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Biapenem • Ertapenem • antipseudomonal (Doripenem • Imipenem • Meropenem) • Panipenem
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Cephalosporins/Cephamycins
(cephems)
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1st (PEcK)
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Cefazolin# • Cefacetrile • Cefadroxil • Cefalexin • Cefaloglycin • Cefalonium • Cefaloridine • Cefalotin • Cefapirin • Cefatrizine • Cefazedone • Cefazaflur • Cefradine • Cefroxadine • Ceftezole
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2nd (HEN)
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Cefaclor • Cefamandole • Cefminox • Cefonicid • Ceforanide • Cefotiam • Cefprozil • Cefbuperazone • Cefuroxime • Cefuzonam • cephamycin (Cefoxitin, Cefotetan, Cefmetazole) • carbacephem (Loracarbef)
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3rd
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Cefixime# • Ceftriaxone# • antipseudomonal (Ceftazidime# • Cefoperazone) • Cefcapene • Cefdaloxime • Cefdinir • Cefditoren • Cefetamet • Cefmenoxime • Cefodizime • Cefotaxime • Cefpimizole • Cefpiramide • Cefpodoxime • Cefsulodin • Cefteram • Ceftibuten • Ceftiolene • Ceftizoxime • oxacephem (Flomoxef, Latamoxef ‡)
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4th (antips-)
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Cefepime • Cefozopran • Cefpirome • Cefquinome
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5th
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Ceftobiprole • Ceftaroline fosamil
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Veterinary
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Ceftiofur • Cefquinome • Cefovecin
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Monobactams
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Aztreonam • Tigemonam • Carumonam • Nocardicin A
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β-lactamase inh.
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penam (Sulbactam, Tazobactam) • clavam (Clavulanic acid)
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Combinations
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Amoxicillin/clavulanic acid# • Imipenem/cilastatin# • Ampicillin/flucloxacillin • Ampicillin/sulbactam (Sultamicillin) • Piperacillin/tazobactam
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| Other |
polymyxins/detergent (Colistin, Polymyxin B) • depolarizing (Daptomycin) • hydrolyze NAM-NAG (Lysozyme) • Gramicidin
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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gr+f/gr+a(t)/gr-p(c)/gr-o
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