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Identification
NameCefpodoxime
Accession NumberDB01416
TypeSmall Molecule
GroupsApproved, Vet Approved
DescriptionCefpodoxime is an oral third generation cephalosporin antibiotic. It is active against most Gram positive and Gram negative bacteria. It is commonly used to treat acute otitis media, pharyngitis, and sinusitis. Cefpodoxime proxetil is a prodrug which is absorbed and de-esterified by the intestinal mucosa to Cefpodoxime.
Structure
Thumb
Synonyms
Cefpodoxima
Cefpodoximum
External Identifiers
  • RU 51807
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Oreloxtablet100 mgoralSanofi Aventis Canada IncNot applicableNot applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cefpodoxime Proxetilgranule, for suspension100 mg/5mLoralNorth Star Rx Llc2007-06-08Not applicableUs
Cefpodoxime Proxetiltablet, film coated100 mg/1oralSandoz Inc2008-05-28Not applicableUs
Cefpodoxime Proxetilgranule, for suspension50 mg/5mLoralAurobindo Pharma Limited2007-06-08Not applicableUs
Cefpodoxime Proxetiltablet, film coated200 mg/1oralGen Source Rx2007-06-11Not applicableUs
Cefpodoxime Proxetiltablet, film coated100 mg/1oralNorth Star Rx Llc2007-06-11Not applicableUs
Cefpodoxime Proxetiltablet, film coated100 mg/1oralPutney Inc2008-05-28Not applicableUs
Cefpodoxime Proxetilgranule, for suspension100 mg/5mLoralAurobindo Pharma Limited2007-06-08Not applicableUs
Cefpodoxime Proxetiltablet, film coated200 mg/1oralSandoz Inc2008-05-28Not applicableUs
Cefpodoxime Proxetiltablet, film coated200 mg/1oralPd Rx Pharmaceuticals, Inc.2007-06-11Not applicableUs
Cefpodoxime Proxetiltablet, film coated200 mg/1oralNorth Star Rx Llc2007-06-11Not applicableUs
Cefpodoxime Proxetiltablet, film coated200 mg/1oralPutney Inc2008-05-28Not applicableUs
Cefpodoxime Proxetiltablet, film coated100 mg/1oralCronus Pharma LLC2007-06-11Not applicableUs
Cefpodoxime Proxetilgranule, for suspension50 mg/5mLoralSandoz Inc2009-06-25Not applicableUs
Cefpodoxime Proxetiltablet, film coated100 mg/1oralAurobindo Pharma Limited2007-06-11Not applicableUs
Cefpodoxime Proxetilgranule, for suspension50 mg/5mLoralNorth Star Rx Llc2007-06-08Not applicableUs
Cefpodoxime Proxetiltablet, film coated100 mg/1oralGen Source Rx2007-06-11Not applicableUs
Cefpodoxime Proxetiltablet, film coated200 mg/1oralCronus Pharma LLC2007-06-11Not applicableUs
Cefpodoxime Proxetilgranule, for suspension100 mg/5mLoralSandoz Inc2009-06-25Not applicableUs
Cefpodoxime Proxetiltablet, film coated200 mg/1oralAurobindo Pharma Limited2007-06-11Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
BananNot Available
DoxefNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Cefpodoxime proxetil
87239-81-4
Thumb
  • InChI Key: LTINZAODLRIQIX-FBXRGJNPSA-N
  • Monoisotopic Mass: 557.125019817
  • Average Mass: 557.59
DBSALT001354
Cefpodoxime sodium
82619-04-3
Thumb
  • InChI Key: JNMXSNGAMPXCDR-XYNKDNFRSA-M
  • Monoisotopic Mass: 449.04396988
  • Average Mass: 449.43
DBSALT001810
Categories
UNII7R4F94TVGY
CAS number80210-62-4
WeightAverage: 427.455
Monoisotopic: 427.062024681
Chemical FormulaC15H17N5O6S2
InChI KeyInChIKey=WYUSVOMTXWRGEK-HBWVYFAYSA-N
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
IUPAC Name
(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
[H][C@]12SCC(COC)=C(N1C(=O)[[email protected]]2NC(=O)C(=N/OC)\C1=CSC(N)=N1)C(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentCephalosporins
Alternative Parents
Substituents
  • Cephalosporin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • 2,4-disubstituted 1,3-thiazole
  • Primary aromatic amine
  • Meta-thiazine
  • Heteroaromatic compound
  • Thiazole
  • Tertiary carboxylic acid amide
  • Azole
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Oxime ether
  • Carboxamide group
  • Azetidine
  • Azacycle
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Monocarboxylic acid or derivatives
  • Ether
  • Enamine
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of patients with mild to moderate infections caused by susceptible strains of the designated microorganisms.
PharmacodynamicsCefpodoxime is an oral third generation cephalosporin antibiotic. It is active against most Gram positive and Gram negative bacteria. Notable exceptions include Pseudomonas aeruginosa, Enterococcus, and Bacteroides fragilis.
Mechanism of actionCefpodoxime is active against a wide spectrum of Gram-positive and Gram-negative bacteria. Cefpodoxime is stable in the presence of beta-lactamase enzymes. As a result, many organisms resistant to penicillins and cephalosporins, due to their production of beta-lactamase, may be susceptible to cefpodoxime. Cefpodoxime is inactivated by certain extended spectrum beta-lactamases. The bactericidal activity of cefpodoxime results from its inhibition of cell wall synthesis. The active metabolite of cefpodoxime binds preferentially to penicillin binding protein 3, which inhibits production of peptidoglycan, the primary constituent of bacterial cell walls.
Related Articles
AbsorptionCefpodoxime proxetil is a prodrug that is absorbed from the gastrointestinal tract and de-esterified to its active metabolite, cefpodoxime. Following oral administration of 100 mg of cefpodoxime proxetil to fasting subjects, approximately 50% of the administered cefpodoxime dose was absorbed systemically.
Volume of distributionNot Available
Protein binding22 to 33% in serum and from 21 to 29% in plasma.
MetabolismNot Available
Route of eliminationOver the recommended dosing range (100 to 400 mg), approximately 29 to 33% of the administered cefpodoxime dose was excreted unchanged in the urine in 12 hours.
Half life2.09 to 2.84 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Enteric bacteria and other eubacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5556
Blood Brain Barrier-0.984
Caco-2 permeable-0.7549
P-glycoprotein substrateSubstrate0.7587
P-glycoprotein inhibitor INon-inhibitor0.8753
P-glycoprotein inhibitor IIInhibitor0.6389
Renal organic cation transporterNon-inhibitor0.8645
CYP450 2C9 substrateNon-substrate0.8729
CYP450 2D6 substrateNon-substrate0.8183
CYP450 3A4 substrateSubstrate0.535
CYP450 1A2 substrateNon-inhibitor0.7905
CYP450 2C9 inhibitorNon-inhibitor0.8017
CYP450 2D6 inhibitorNon-inhibitor0.8895
CYP450 2C19 inhibitorNon-inhibitor0.7558
CYP450 3A4 inhibitorNon-inhibitor0.7875
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9144
Ames testNon AMES toxic0.8249
CarcinogenicityNon-carcinogens0.8656
BiodegradationNot ready biodegradable0.9863
Rat acute toxicity1.9732 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9764
hERG inhibition (predictor II)Non-inhibitor0.8162
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Granule, for suspensionoral100 mg/5mL
Granule, for suspensionoral50 mg/5mL
Tablet, film coatedoral100 mg/1
Tablet, film coatedoral200 mg/1
Tabletoral100 mg
Prices
Unit descriptionCostUnit
Vantin 20 200 mg tablet Bottle194.37USD bottle
Vantin 20 100 mg tablet Bottle137.26USD bottle
Vantin 100 mg/5ml Suspension 100ml Bottle133.84USD bottle
Vantin 50 mg/5ml Suspension 100ml Bottle70.34USD bottle
Vantin 50 mg/5ml Suspension 50ml Bottle36.95USD bottle
Vantin 200 mg tablet9.67USD tablet
Cefpodoxime Proxetil 200 mg tablet7.02USD tablet
Cefpodoxime 200 mg tablet6.41USD tablet
Vantin 100 mg tablet6.33USD tablet
Cefpodoxime 100 mg tablet5.11USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.185 mg/mLALOGPS
logP0.05ALOGPS
logP-1.2ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)3.22ChemAxon
pKa (Strongest Basic)4.16ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area156.44 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity100.71 m3·mol-1ChemAxon
Polarizability39.9 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

Yatendra Kumar, Neera Tewari, Ram Aryan, Bishwa Rai, Hashim Nizar, “Process for the preparation of cefpodoxime acid.” U.S. Patent US20050020561, issued January 27, 2005.

US20050020561
General ReferencesNot Available
External Links
ATC CodesJ01DD13
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (369 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
Aluminum hydroxideThe serum concentration of Cefpodoxime can be decreased when it is combined with Aluminum hydroxide.
Aluminum phosphateThe serum concentration of Cefpodoxime can be decreased when it is combined with Aluminum phosphate.
AsenapineAsenapine can cause a decrease in the absorption of Cefpodoxime resulting in a reduced serum concentration and potentially a decrease in efficacy.
Bismuth SubcitrateThe serum concentration of Cefpodoxime can be decreased when it is combined with Bismuth Subcitrate.
Calcium carbonateThe serum concentration of Cefpodoxime can be decreased when it is combined with Calcium carbonate.
CimetidineCimetidine can cause a decrease in the absorption of Cefpodoxime resulting in a reduced serum concentration and potentially a decrease in efficacy.
DoxepinDoxepin can cause a decrease in the absorption of Cefpodoxime resulting in a reduced serum concentration and potentially a decrease in efficacy.
EpinastineEpinastine can cause a decrease in the absorption of Cefpodoxime resulting in a reduced serum concentration and potentially a decrease in efficacy.
FamotidineFamotidine can cause a decrease in the absorption of Cefpodoxime resulting in a reduced serum concentration and potentially a decrease in efficacy.
MagaldrateThe serum concentration of Cefpodoxime can be decreased when it is combined with Magaldrate.
Magnesium carbonateThe serum concentration of Cefpodoxime can be decreased when it is combined with Magnesium carbonate.
Magnesium hydroxideThe serum concentration of Cefpodoxime can be decreased when it is combined with Magnesium hydroxide.
Magnesium oxideThe serum concentration of Cefpodoxime can be decreased when it is combined with Magnesium oxide.
Magnesium TrisilicateThe serum concentration of Cefpodoxime can be decreased when it is combined with Magnesium Trisilicate.
MethanthelineMethantheline can cause a decrease in the absorption of Cefpodoxime resulting in a reduced serum concentration and potentially a decrease in efficacy.
MetiamideMetiamide can cause a decrease in the absorption of Cefpodoxime resulting in a reduced serum concentration and potentially a decrease in efficacy.
NizatidineNizatidine can cause a decrease in the absorption of Cefpodoxime resulting in a reduced serum concentration and potentially a decrease in efficacy.
OlanzapineOlanzapine can cause a decrease in the absorption of Cefpodoxime resulting in a reduced serum concentration and potentially a decrease in efficacy.
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Cefpodoxime.
RanitidineRanitidine can cause a decrease in the absorption of Cefpodoxime resulting in a reduced serum concentration and potentially a decrease in efficacy.
Roxatidine acetateRoxatidine acetate can cause a decrease in the absorption of Cefpodoxime resulting in a reduced serum concentration and potentially a decrease in efficacy.
Food Interactions
  • Take on empty stomach: 1 hour before or 2 hours after meals.

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Peptidoglycan glycosyltransferase activity
Specific Function:
Essential cell division protein that is required for the synthesis of peptidoglycan at the division septum (PubMed:1103132, PubMed:9614966). Catalyzes the synthesis of cross-linked peptidoglycan from the lipid-linked precursors (PubMed:7030331). Required for localization of FtsN (PubMed:9282742).
Gene Name:
ftsI
Uniprot ID:
P0AD68
Molecular Weight:
63876.925 Da
References
  1. Boaretti M, Lleo MM, Canepari P: In vitro activity, beta-lactamase stability and PBP affinity of RU 51,746-2, the active metabolite of the new orally absorbed cephalosporin ester, RU 51807. J Chemother. 1991 Jan;3 Suppl 1:57-61. [PubMed:12041787 ]
Comments
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Drug created on July 23, 2007 07:09 / Updated on August 17, 2016 12:23