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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2020-02-26 21:41:42 UTC
HMDB IDHMDB0015486
Secondary Accession Numbers
  • HMDB15486
Metabolite Identification
Common NameCefpodoxime
DescriptionCefpodoxime, also known as CPDX or epoxim, belongs to the class of organic compounds known as morpholines. These are organic compounds containing a morpholine moiety, which consists of a six-member aliphatic saturated ring with the formula C4H9NO, where the oxygen and nitrogen atoms lie at positions 1 and 4, respectively. The bactericidal activity of cefpodoxime results from its inhibition of cell wall synthesis. Commonly used to treat acute otitis media, pharyngitis, and sinusitis, Cefpodoxime is a prodrug which is absorbed and de-esterified by the intestinal mucosa to Cefpodoxime. Cefpodoxime is shown to be effective against most Gram positive and Gram negative bacteria, except Pseudomonas aeruginosa, Enterococcus, and Bacteroides fragilis. Cefpodoxime is a strong basic compound (based on its pKa). Cefpodoxime is stable in the presence of beta-lactamase enzymes. Cefpodoxime is inactivated by certain extended spectrum beta-lactamases. 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.
Structure
Data?1582753302
Synonyms
ValueSource
(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 acidChEBI
CefpodoximaChEBI
CefpodoximumChEBI
CPDXKegg
EpoximKegg
(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-carboxylateGenerator
Cefpodoxime proxetilHMDB
CPDX-PRHMDB
RU 51807HMDB
Chemical FormulaC15H17N5O6S2
Average Molecular Weight427.455
Monoisotopic Molecular Weight427.062024681
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 Namecefpodoxime
CAS Registry Number82619-04-3
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 KeyWYUSVOMTXWRGEK-HBWVYFAYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as morpholines. These are organic compounds containing a morpholine moiety, which consists of a six-member aliphatic saturated ring with the formula C4H9NO, where the oxygen and nitrogen atoms lie at positions 1 and 4, respectively.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassOxazinanes
Sub ClassMorpholines
Direct ParentMorpholines
Alternative Parents
Substituents
  • Morpholine
  • Piperidine
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Heteroaromatic compound
  • Tertiary alcohol
  • Thiophene
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxirane
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Azacycle
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Aromatic alcohol
  • Organic salt
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.18 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity100.71 m³·mol⁻¹ChemAxon
Polarizability39.9 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4j-4947100000-7fb35c48f19f043ffd92Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-6921700000-58a4337e22cba20cc0efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000f-3985400000-0154e7f09d2f653a943aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-6962000000-f322fc3d8142ba0bf8bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052k-9410000000-6ec94e250ee3855436d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0394200000-f82d810f5962c73616b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0985000000-8838e20245454c8e1d49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9300000000-f94d3d2cfe84b8759f73Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01416 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01416 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01416
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4891496
KEGG Compound IDC08114
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCefpodoxime
METLIN IDNot Available
PubChem Compound6335986
PDB IDNot Available
ChEBI ID3504
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot 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 ]