Cefpodoxime proxetil (CHEM016618)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:38:36 UTC
Update Date2016-11-09 01:15:26 UTC
Accession NumberCHEM016618
Identification
Common NameCefpodoxime proxetil
ClassSmall Molecule
DescriptionThe 1-ethyl (proxetil) ester prodrug of cefpodoxime. After swallowing, hydrolysis of the ester group occurs in the intestinal epithelium, to release active cefpodoxime in the bloodstream. It is used to treat acute otitis media, pharyngitis, and sinusitis.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(RS)-1-((Isopropoxycarbonyl)oxy)ethyl (+)-(6R,7R)-7-(2-(2-amino-4-thiazolyl)-2-((Z)-methoxyimino)acetamido)-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylateChEBI
Cefpodoxime 1-(isopropyloxycarbonyloxy)ethyl esterChEBI
CPDX-PRKegg
VantinKegg
(RS)-1-((Isopropoxycarbonyl)oxy)ethyl (+)-(6R,7R)-7-(2-(2-amino-4-thiazolyl)-2-((Z)-methoxyimino)acetamido)-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidGenerator
1-Propan-2-yloxycarbonyloxyethyl (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidGenerator
1-(Isopropoxycarbonyloxy)ethyl-7-(2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetamido)-3-methoxymethyl-8-oxo-5-thia-1-azabicyclo(4,2,0)-oct-2-ene-2-carboxylateMeSH
DoxefMeSH
Cefpodoxime proxetilMeSH
Cephalosporin 807MeSH
Chemical FormulaC21H27N5O9S2
Average Molecular Mass557.590 g/mol
Monoisotopic Mass557.125 g/mol
CAS Registry Number87239-81-4
IUPAC Name(2Z)-2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)-2-(methoxyimino)-N-[(6R,7R)-3-(methoxymethyl)-8-oxo-2-[(1-{[(propan-2-yloxy)carbonyl]oxy}ethoxy)carbonyl]-5-thia-1-azabicyclo[4.2.0]oct-2-en-7-yl]ethanimidic acid
Traditional Namesimplicef
SMILES[H]C(C)(OC(=O)OC(C)C)OC(=O)C1=C(COC)CS[C@@]2([H])N1C(=O)[C@@]2([H])N=C(O)C(=N/OC)\C1=CSC(=N)N1
InChI IdentifierInChI=1S/C21H27N5O9S2/c1-9(2)33-21(30)35-10(3)34-19(29)15-11(6-31-4)7-36-18-14(17(28)26(15)18)24-16(27)13(25-32-5)12-8-37-20(22)23-12/h8-10,14,18H,6-7H2,1-5H3,(H2,22,23)(H,24,27)/b25-13-/t10?,14-,18-/m1/s1
InChI KeyLTINZAODLRIQIX-FBXRGJNPSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cephalosporins. Cephalosporins 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
  • Meta-thiazine
  • Carbonic acid diester
  • 1,3-thiazol-2-amine
  • Azole
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Thiazole
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Amino acid or derivatives
  • Azetidine
  • Carboxamide group
  • Carboxylic acid ester
  • Carbonic acid derivative
  • Secondary carboxylic acid amide
  • Hemithioaminal
  • Acetal
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Thioether
  • Dialkylthioether
  • Carboxylic acid derivative
  • Azacycle
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxide
  • Organic nitrogen compound
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP1.7ALOGPS
logP2.17ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)3.73ChemAxon
pKa (Strongest Basic)0.72ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area181.43 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity144.67 m³·mol⁻¹ChemAxon
Polarizability55.21 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-3964730000-4e8ad0fd8f67da24074bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bta-9343200000-8483a91d8746ea61095aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06r2-9121000000-1fb85b89298bd5010a21Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052r-1490310000-60fd46d5bad5c738d801Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9770210000-d111259b323589c04a12Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9400000000-9b94fc90c16f14088a99Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDBSALT001354
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCefpodoxime
Chemspider IDNot Available
ChEBI ID3505
PubChem Compound ID6526396
Kegg Compound IDC08115
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available