Cefpodoxime

Identification

Summary

Cefpodoxime is a third-generation cephalosporin antibiotic used in the treatment of various bacterial infections, including gonorrhea, community acquired pneumonia, and sinusitis.

Generic Name
Cefpodoxime
DrugBank Accession Number
DB01416
Background

Cefpodoxime is an oral third generation cephalosporin antibiotic with effectiveness against most Gram positive and Gram negative bacteria. 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.

Type
Small Molecule
Groups
Approved, Vet approved
Structure
Thumb
Weight
Average: 427.455
Monoisotopic: 427.062024681
Chemical Formula
C15H17N5O6S2
Synonyms
  • Cefpodoxima
  • Cefpodoxime
  • Cefpodoximum
External IDs
  • RU 51807

Pharmacology

Indication

Indicated for the treatment of patients with mild to moderate infections caused by susceptible strains of the designated microorganisms.

Pharmacology
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:
Machine Learning
Data Science
Drug Discovery
Accelerate your drug discovery research with our fully connected ADMET dataset
Learn more
Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
Contraindications & Blackbox Warnings
With our commercial data, access important information on dangerous risks, contraindications, and adverse effects.
Learn more
Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects
Learn more
Pharmacodynamics

Cefpodoxime is shown to be effective against most Gram positive and Gram negative bacteria, except Pseudomonas aeruginosa, Enterococcus, and Bacteroides fragilis.

Mechanism of action

Cefpodoxime 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.

TargetActionsOrganism
APeptidoglycan synthase FtsI
inhibitor
Escherichia coli (strain K12)
Absorption

Cefpodoxime 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 distribution

Not Available

Protein binding

22 to 33% in serum and from 21 to 29% in plasma.

Metabolism
Not Available
Route of elimination

Over 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-life

2.09 to 2.84 hours

Clearance

Not Available

Adverse Effects
Medicalerrors
Reduce medical errors
and improve treatment outcomes with our comprehensive & structured data on drug adverse effects.
Learn more
Reduce medical errors & improve treatment outcomes with our adverse effects data
Learn more
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirCefpodoxime may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbciximabThe therapeutic efficacy of Abciximab can be decreased when used in combination with Cefpodoxime.
AceclofenacCefpodoxime may decrease the excretion rate of Aceclofenac which could result in a higher serum level.
AcemetacinThe risk or severity of nephrotoxicity can be increased when Cefpodoxime is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding can be increased when Cefpodoxime is combined with Acenocoumarol.
AcetaminophenCefpodoxime may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
Acetylsalicylic acidThe risk or severity of nephrotoxicity can be increased when Acetylsalicylic acid is combined with Cefpodoxime.
AclidiniumCefpodoxime may decrease the excretion rate of Aclidinium which could result in a higher serum level.
AcrivastineCefpodoxime may decrease the excretion rate of Acrivastine which could result in a higher serum level.
AcyclovirCefpodoxime may decrease the excretion rate of Acyclovir which could result in a higher serum level.
Interactions
Improve patient outcomes
Build effective decision support tools with the industry’s most comprehensive drug-drug interaction checker.
Learn more
Food Interactions
  • Take on an empty stomach. Take at least 1 hour before or 2 hours after meals.

Products

Products
Comprehensive & structured drug product info
From application numbers to product codes, connect different identifiers through our commercial datasets.
Learn more
Easily connect various identifiers back to our datasets
Learn more
Product Ingredients
IngredientUNIICASInChI Key
Cefpodoxime proxetil2TB00A1Z7N87239-81-4LTINZAODLRIQIX-FBXRGJNPSA-N
Cefpodoxime sodium3ULP5169B382619-04-3JNMXSNGAMPXCDR-XYNKDNFRSA-M
Product Images
International/Other Brands
Banan / Doxef
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
OreloxTabletOralSanofi AventisNot applicableNot applicableCanada flag
VantinGranule, for suspension50 mg/5mLOralPharmacia and Upjohn Company LLC1991-08-292007-10-29US flag
VantinTablet, film coated100 mg/1OralPharmacia and Upjohn Company LLC1991-08-292008-12-31US flag
VantinTablet, film coated200 mg/1OralPd Rx Pharmaceuticals, Inc.1991-08-292015-05-12US flag
VantinGranule, for suspension100 mg/5mLOralPharmacia and Upjohn Company LLC1991-08-292007-10-29US flag
VantinTablet, film coated200 mg/1OralPharmacia and Upjohn Company LLC1991-08-292010-03-31US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Cefpodoxime ProxetilGranule, for suspension100 mg/5mLOralRising Pharmaceuticals, Inc.2007-06-08Not applicableUS flag
Cefpodoxime ProxetilTablet, film coated200 mg/1OralSandoz Inc2008-05-28Not applicableUS flag
Cefpodoxime ProxetilGranule, for suspension50 mg/5mLOralAurobindo Pharma Limited2007-06-08Not applicableUS flag
Cefpodoxime ProxetilGranule, for suspension50 mg/5mLOralNorthStar Rx LLC2007-06-08Not applicableUS flag
Cefpodoxime ProxetilTablet, film coated200 mg/1OralNorthStar Rx LLC2007-06-11Not applicableUS flag
Cefpodoxime ProxetilGranule, for suspension100 mg/5mLOralSandoz Inc2009-06-252019-07-31US flag
Cefpodoxime ProxetilTablet, film coated200 mg/1OralPD-Rx Pharmaceuticals, Inc.2007-06-11Not applicableUS flag
Cefpodoxime ProxetilTablet, film coated200 mg/1OralNorth Star Rx Llc2009-08-122011-11-30US flag
Cefpodoxime ProxetilTablet, film coated100 mg/1OralAurobindo Pharma Limited2007-06-11Not applicableUS flag
Cefpodoxime ProxetilTablet, film coated100 mg/1OralSandoz Inc2008-05-28Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
INFEX PLUS 100/62.5 MG/5 ML ORAL SUSPANSIYON HAZIRLAMAK ICIN KURU TOZ, 100 MLCefpodoxime (100 mg) + Clavulanic acid (62.5 mg)PowderOralCELTİS İLAÇ SAN. VE TİC. A.Ş.2020-08-142018-07-09Turkey flag
INFEX PLUS 40/62.5 MG/5 ML ORAL SUSPANSIYON HAZIRLAMAK ICIN KURU TOZ, 100 MLCefpodoxime (40 mg) + Clavulanic acid (62.5 mg)PowderOralCELTİS İLAÇ SAN. VE TİC. A.Ş.2020-08-142018-07-09Turkey flag
INFEX PLUS 50/62.5 MG/5 ML ORAL SUSPANSIYON HAZIRLAMAK ICIN KURU TOZ, 100 MLCefpodoxime (50 mg) + Clavulanic acid (62.5 mg)PowderOralCELTİS İLAÇ SAN. VE TİC. A.Ş.2020-08-142018-07-09Turkey flag
TEXEF PLUS 100/62.5 MG FİLM KAPLI TABLET, 20 ADETCefpodoxime (100 mg) + Clavulanic acid (62.5 mg)Tablet, film coatedOralNEUTEC İLAÇ SAN. TİC. A.Ş.2020-08-14Not applicableTurkey flag
TEXEF PLUS 100/62.5 MG GRANUL ICEREN SASE, 20 ADETCefpodoxime (100 mg) + Clavulanic acid (62.5 mg)GranuleOralNEUTEC İLAÇ SAN. TİC. A.Ş.2020-08-14Not applicableTurkey flag
TEXEF PLUS 200/125 MG FILM KAPLI TABLET, 20 ADETCefpodoxime (200 mg) + Clavulanic acid (125 mg)Tablet, coatedOralNEUTEC İLAÇ SAN. TİC. A.Ş.2020-08-14Not applicableTurkey flag
TEXEF PLUS 40 MG/62.5 MG GRANÜL İÇEREN SAŞE, 20 ADETCefpodoxime (40 mg) + Clavulanic acid (62.5 mg)GranuleOralNEUTEC İLAÇ SAN. TİC. A.Ş.2020-08-14Not applicableTurkey flag
TEXEF PLUS 50 MG/62.5 MG GRANÜL İÇEREN SAŞE, 20 ADETCefpodoxime (50 mg) + Clavulanic acid (62.5 mg)GranuleOralNEUTEC İLAÇ SAN. TİC. A.Ş.2020-08-14Not applicableTurkey flag

Categories

ATC Codes
J01DD13 — Cefpodoxime
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Lactams
Sub Class
Beta lactams
Direct Parent
Cephalosporins
Alternative Parents
N-acyl-alpha amino acids and derivatives / 2,4-disubstituted thiazoles / 1,3-thiazines / 2-amino-1,3-thiazoles / Tertiary carboxylic acid amides / Heteroaromatic compounds / Secondary carboxylic acid amides / Amino acids / Azetidines / Dialkylthioethers
show 10 more
Substituents
1,3-thiazol-2-amine / 2,4-disubstituted 1,3-thiazole / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azetidine / Azole
show 25 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
cephalosporin, carboxylic acid (CHEBI:3504)
Affected organisms
  • Enteric bacteria and other eubacteria

Chemical Identifiers

UNII
7R4F94TVGY
CAS number
80210-62-4
InChI Key
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)[C@H]2NC(=O)C(=N/OC)\C1=CSC(N)=N1)C(O)=O

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 References
Not Available
Human Metabolome Database
HMDB0015486
KEGG Drug
D07650
KEGG Compound
C08114
PubChem Compound
6335986
PubChem Substance
46504897
ChemSpider
4891496
BindingDB
50292251
RxNav
20489
ChEBI
3504
ChEMBL
CHEMBL1672
ZINC
ZINC000003830453
Therapeutic Targets Database
DAP000457
PharmGKB
PA164746385
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Cefpodoxime
AHFS Codes
  • 08:12.06.12 — Third Generation Cephalosporins
FDA label
Download (369 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentOtitis Media With Effusion1
3RecruitingTreatmentRhinosinusitis / Rhinosinusitis Acute / Sinus infection / Sinusitis / Sinusitis, Acute1
1CompletedTreatmentDiarrhea / Neoplasms1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentNeuroblastomas1
1CompletedTreatmentTumors, Solid2
0TerminatedTreatmentOsteomyelitis1
Not AvailableActive Not RecruitingOtherAnti-Bacterial Agents / Microbiota1
Not AvailableCompletedTreatmentUrinary Tract Infection1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Aurobindo Pharma Ltd.
  • Dispensing Solutions
  • Murfreesboro Pharmaceutical Nursing Supply
  • Northstar Rx LLC
  • Nucare Pharmaceuticals Inc.
  • Orchid Healthcare
  • PD-Rx Pharmaceuticals Inc.
  • Pfizer Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmacia Inc.
  • Public Health Department Seattle and King County
  • Putney Inc.
  • Ranbaxy Laboratories
  • Redpharm Drug
  • Sandoz
Dosage Forms
FormRouteStrength
Tablet, film coatedOral
Granule, for suspensionOral
Powder, for suspensionOral
PowderParenteral
Granule, for suspensionOral100 mg/5mL
Granule, for suspensionOral50 mg/5mL
Tablet, film coatedOral100 mg/1
Tablet, film coatedOral200 mg/1
Tablet, coatedOral
SuspensionOral
GranuleOral
PowderOral
TabletOral
Tablet, film coatedOral
GranuleOral
Tablet, coatedOral
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
Accelerate your drug discovery research
with our fully connected ADMET & drug target dataset.
Learn more
Accelerate your drug discovery research with our ADMET & drug target dataset
Learn more
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 fr...
Gene Name
ftsI
Uniprot ID
P0AD68
Uniprot Name
Peptidoglycan synthase FtsI
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]

Drug created on July 23, 2007 13:09 / Updated on May 06, 2021 06:19