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Cefpodoxime

July 24, 2017
Common Name

Cefpodoxime Description

Cefpodoxime 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

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source CefpodoximaChEBI CefpodoximumChEBI Cefpodoxime proxetilHMDB CPDX-PRHMDB RU 51807HMDB

Chemical Formlia

C15H17N5O6S2 Average Molecliar Weight

427.455 Monoisotopic Molecliar Weight

427.062024681 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 Traditional Name

cefpodoxime CAS Registry Number

82619-04-3 SMILES

[H][C@]12SCC(COC)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)C1=CSC(N)=N1)C(O)=O

InChI Identifier

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

InChI Key

WYUSVOMTXWRGEK-HBWVYFAYSA-N Chemical Taxonomy 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
  • Dialkyl ethers
  • Carboxylic acids
  • Azacyclic compounds
  • Thiohemiaminal derivatives
  • Monocarboxylic acids and derivatives
  • Organopnictogen compounds
  • Carbonyl compounds
  • Primary amines
  • Hydrocarbon derivatives
  • Organic oxides

    • Substituents

  • Cephalosporin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • 2,4-disubstituted 1,3-thiazole
  • Meta-thiazine
  • 1,3-thiazol-2-amine
  • Heteroaromatic compound
  • Azole
  • Thiazole
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Amino acid
  • Azetidine
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Thioether
  • Hemithioaminal
  • Carboxylic acid derivative
  • Dialkylthioether
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Azacycle
  • Carboxylic acid
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • cephalosporin (CHEBI:3504 )
  • carboxylic acid (CHEBI:3504 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anti-Bacterial Agents
  • Antibacterial Agents
  • Cephalosporins

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility1.85e-01 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.18 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 Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01416

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01416

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01416 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    4891496 KEGG Compound ID

    C08114 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Cefpodoxime NuGOwiki Link

    HMDB15486 Metagene Link

    HMDB15486 METLIN ID

    Not Available PubChem Compound

    6335986 PDB ID

    Not Available ChEBI ID

    3504

    Product: Maribavir

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Fukutsu N, Sakamaki Y, Kawasaki T, Saito K, Nakazawa H: Verification of cefmetazole and cefpodoxime proxetil contamination to other pharmaceuticals by liquid chromatography-tandem mass spectrometry. Chem Pharm Bull (Tokyo). 2006 Oct;54(10):1469-72. [PubMed:17015995 ]
    2. Fukutsu N, Sakamaki Y, Kawasaki T, Saito K, Nakazawa H: LC/MS/MS method for the determination of trace amounts of cefmetazole and cefpodoxime proxetil contaminants in pharmaceutical manufacturing environments. J Pharm Biomed Anal. 2006 Jun 16;41(4):1243-50. Epub 2006 May 15. [PubMed:16704914 ]

    PMID: 25788259

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