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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
Structure for Cefpodoxime (DB01416)
- 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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Acute bacterial exacerbation of chronic bronchitis •••••••••••• Used in combination to treat Acute bronchitis Combination Product in combination with: Clavulanic acid (DB00766) •••••••••••• •••••••• ••••••• •••••• Used in combination to treat Acute otitis media Combination Product in combination with: Clavulanic acid (DB00766) •••••••••••• •••••••• •••••••• •••••• Used in combination to treat Acute sinusitis Combination Product in combination with: Clavulanic acid (DB00766) •••••••••••• •••••••• •••••• Treatment of Acute maxillary sinusitis •••••••••••• - Contraindications & Blackbox Warnings
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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.
Target Actions Organism APeptidoglycan synthase FtsI inhibitorEscherichia 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
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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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Cefpodoxime may decrease the excretion rate of Abacavir which could result in a higher serum level. Abciximab The therapeutic efficacy of Abciximab can be decreased when used in combination with Cefpodoxime. Aceclofenac The risk or severity of nephrotoxicity can be increased when Cefpodoxime is combined with Aceclofenac. Acemetacin The risk or severity of nephrotoxicity can be increased when Cefpodoxime is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding can be increased when Cefpodoxime is combined with Acenocoumarol. - Food Interactions
- Take on an empty stomach. Take at least 1 hour before or 2 hours after meals.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Cefpodoxime proxetil 2TB00A1Z7N 87239-81-4 LTINZAODLRIQIX-FBXRGJNPSA-N Cefpodoxime sodium 3ULP5169B3 82619-04-3 JNMXSNGAMPXCDR-XYNKDNFRSA-M - Product Images
- International/Other Brands
- Banan / Doxef
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Orelox Tablet 100 mg Oral Sanofi Aventis Deutschland Gmb H Not applicable Not applicable Canada 
Vantin Tablet, film coated 100 mg/1 Oral Pharmacia & Upjohn Company LLC 1991-08-29 2008-12-31 US 
Vantin Granule, for suspension 50 mg/5mL Oral Pharmacia & Upjohn Company LLC 1991-08-29 2007-10-29 US Vantin Tablet, film coated 200 mg/1 Oral PD-Rx Pharmaceuticals, Inc. 1991-08-29 2015-05-12 US Vantin Tablet, film coated 200 mg/1 Oral Pharmacia & Upjohn Company LLC 1991-08-29 2010-03-31 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cefpodoxime Proxetil Tablet, film coated 100 mg/1 Oral Acetris Health, Llc 2007-06-11 2019-05-31 US Cefpodoxime Proxetil Tablet, film coated 200 mg/1 Oral Aurobindo Pharma (Italia) S.R.L. 2007-06-11 Not applicable US Cefpodoxime Proxetil Granule, for suspension 100 mg/5mL Oral NorthStar Rx LLC 2007-06-08 Not applicable US Cefpodoxime Proxetil Granule, for suspension 50 mg/5mL Oral Aurobindo Pharma (Italia) S.R.L. 2007-06-08 Not applicable US Cefpodoxime Proxetil Tablet, film coated 200 mg/1 Oral Nucare Pharmaceuticals,inc. 2023-02-13 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image INFEX PLUS 100/62.5 MG/5 ML ORAL SUSPANSIYON HAZIRLAMAK ICIN KURU TOZ, 100 ML Cefpodoxime (100 mg) + Clavulanic acid (62.5 mg) Powder Oral CELTİS İLAÇ SAN. VE TİC. A.Ş. 2011-02-15 Not applicable Turkey 
INFEX PLUS 40/62.5 MG/5 ML ORAL SUSPANSIYON HAZIRLAMAK ICIN KURU TOZ, 100 ML Cefpodoxime (40 mg) + Clavulanic acid (62.5 mg) Powder Oral CELTİS İLAÇ SAN. VE TİC. A.Ş. 2011-02-15 Not applicable Turkey INFEX PLUS 50/62.5 MG/5 ML ORAL SUSPANSIYON HAZIRLAMAK ICIN KURU TOZ, 100 ML Cefpodoxime (50 mg) + Clavulanic acid (62.5 mg) Powder Oral CELTİS İLAÇ SAN. VE TİC. A.Ş. 2011-02-15 Not applicable Turkey TEXEF PLUS 100/62.5 MG FİLM KAPLI TABLET, 20 ADET Cefpodoxime (100 mg) + Clavulanic acid (62.5 mg) Tablet, film coated Oral NEUTEC İLAÇ SAN. TİC. A.Ş. 2015-07-15 Not applicable Turkey TEXEF PLUS 100/62.5 MG GRANUL ICEREN SASE, 20 ADET Cefpodoxime (100 mg) + Clavulanic acid (62.5 mg) Granule Oral NEUTEC İLAÇ SAN. TİC. A.Ş. 2010-12-20 Not applicable Turkey
Categories
- ATC Codes
- J01DD13 — Cefpodoxime
- Drug Categories
- Amides
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- beta Lactam Antibiotics
- beta-Lactams
- Cefpodoxime
- Cephalosporins
- Heterocyclic Compounds, Fused-Ring
- Lactams
- Nephrotoxic agents
- Prodrugs
- Sulfur Compounds
- Thiazines
- Third-Generation Cephalosporins
- 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
- External Links
- Human Metabolome Database
- HMDB0015486
- KEGG Drug
- D07650
- KEGG Compound
- C08114
- PubChem Compound
- 6335986
- PubChem Substance
- 46504897
- ChemSpider
- 4891496
- BindingDB
- 50292251
- 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
- FDA label
- Download (369 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Other Antibacterial therapy / Microbiota 1 somestatus stop reason just information to hide Not Available Completed Treatment Urinary Tract Infection 1 somestatus stop reason just information to hide 4 Completed Treatment Otitis Media With Effusion (OME) 1 somestatus stop reason just information to hide 4 Enrolling by Invitation Treatment Bone and Joint Infections / Endovascular Infection / Gastrointestinal Tract Infections / Genitourinary tract infection / Pulmonary Infections / Skin and Soft Tissue Infections (SSTIs) 1 somestatus stop reason just information to hide 3 Recruiting Treatment Acute rhino-sinusitis / Acute Sinusitis / Rhino Sinusitis / Sinus infection / Sinusitis 1 somestatus stop reason just information to hide
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
Form Route Strength Granule, for suspension Oral Granule, for suspension Oral 0.8 % Tablet Oral 200 MG Tablet, film coated Oral 100 MG Tablet, film coated Oral 200 MG Powder Parenteral 40 MG/5ML Powder, for suspension Oral 40 MG/5ML Granule, for suspension Oral 100 mg/5mL Granule, for suspension Oral 50 mg/5mL Tablet, film coated Oral 100 mg/1 Tablet, film coated Oral 200 mg/1 Tablet, coated Oral 100 mg Tablet, coated Oral 10000000 mg Powder, for suspension Oral 800 mg Powder, for suspension Oral 80000000 mg Suspension Oral 20 mg/ml Suspension Oral 50 mg/5ml Suspension Oral 40 mg/5ml Granule Oral Tablet, film coated Oral 400 mg Powder Oral Granule, for suspension Oral 40 mg/5ml Suspension Oral 800.000 mg Tablet Oral 100 mg Tablet Oral 260.90 mg Granule Oral 40 mg/5ml Tablet, film coated Oral Tablet, film coated Oral Granule Oral Tablet, coated Oral - Prices
Unit description Cost Unit Vantin 20 200 mg tablet Bottle 194.37USD bottle Vantin 20 100 mg tablet Bottle 137.26USD bottle Vantin 100 mg/5ml Suspension 100ml Bottle 133.84USD bottle Vantin 50 mg/5ml Suspension 100ml Bottle 70.34USD bottle Vantin 50 mg/5ml Suspension 50ml Bottle 36.95USD bottle Vantin 200 mg tablet 9.67USD tablet Cefpodoxime Proxetil 200 mg tablet 7.02USD tablet Cefpodoxime 200 mg tablet 6.41USD tablet Vantin 100 mg tablet 6.33USD tablet Cefpodoxime 100 mg tablet 5.11USD 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
Property Value Source Water Solubility 0.185 mg/mL ALOGPS logP 0.05 ALOGPS logP -1.3 Chemaxon logS -3.4 ALOGPS pKa (Strongest Acidic) 2.75 Chemaxon pKa (Strongest Basic) 3.61 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 9 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 156.44 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 100.71 m3·mol-1 Chemaxon Polarizability 39.9 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.5556 Blood Brain Barrier - 0.984 Caco-2 permeable - 0.7549 P-glycoprotein substrate Substrate 0.7587 P-glycoprotein inhibitor I Non-inhibitor 0.8753 P-glycoprotein inhibitor II Inhibitor 0.6389 Renal organic cation transporter Non-inhibitor 0.8645 CYP450 2C9 substrate Non-substrate 0.8729 CYP450 2D6 substrate Non-substrate 0.8183 CYP450 3A4 substrate Substrate 0.535 CYP450 1A2 substrate Non-inhibitor 0.7905 CYP450 2C9 inhibitor Non-inhibitor 0.8017 CYP450 2D6 inhibitor Non-inhibitor 0.8895 CYP450 2C19 inhibitor Non-inhibitor 0.7558 CYP450 3A4 inhibitor Non-inhibitor 0.7875 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9144 Ames test Non AMES toxic 0.8249 Carcinogenicity Non-carcinogens 0.8656 Biodegradation Not ready biodegradable 0.9863 Rat acute toxicity 1.9732 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9764 hERG inhibition (predictor II) Non-inhibitor 0.8162
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0a4j-4947100000-7fb35c48f19f043ffd92 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-004m-0345900000-e9356eee92c31e9ce597 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-002k-1190100000-14c111998cfa63ac5790 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0ue9-0679300000-9d96f8c4ec5f6cbacf17 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4s-5966100000-3cd15731f48dd27e6e9f Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-016v-0948100000-363d03f4f2a3adb819af Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-00fr-2902000000-76bced9bb9dfdcae8fce Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 210.6237773 predictedDarkChem Lite v0.1.0 [M-H]- 196.0408773 predictedDarkChem Lite v0.1.0 [M-H]- 194.09866 predictedDeepCCS 1.0 (2019) [M+H]+ 210.7452773 predictedDarkChem Lite v0.1.0 [M+H]+ 196.6608773 predictedDarkChem Lite v0.1.0 [M+H]+ 196.45667 predictedDeepCCS 1.0 (2019) [M+Na]+ 211.8171773 predictedDarkChem Lite v0.1.0 [M+Na]+ 196.9886773 predictedDarkChem Lite v0.1.0 [M+Na]+ 202.58571 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Essential cell division protein that catalyzes cross-linking of the peptidoglycan cell wall at the division septum (PubMed:1103132, PubMed:3531167, PubMed:6450748, PubMed:7030331, PubMed:9614966). Required for localization of FtsN (PubMed:9282742).
- Specific Function
- penicillin binding
- Gene Name
- ftsI
- Uniprot ID
- P0AD68
- Uniprot Name
- Peptidoglycan synthase FtsI
- Molecular Weight
- 63876.925 Da
References
- 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. [Article]
Drug created at July 23, 2007 13:09 / Updated at October 13, 2024 00:21