Cefroxadine (CHEM016619)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:38:37 UTC
Update Date2016-11-09 01:15:26 UTC
Accession NumberCHEM016619
Identification
Common NameCefroxadine
ClassSmall Molecule
DescriptionA first-generation cephalosporin antibiotic having methoxy and amino side groups located at positions 3 and 7 respectively.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(6R,7R)-7-{[(2R)-2-amino-2-(cyclohexa-1,4-dien-1-yl)acetyl]amino}-3-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidChEBI
CefroxadinoChEBI
CefroxadinumChEBI
CXDChEBI
Cefthan-DSKegg
(6R,7R)-7-{[(2R)-2-amino-2-(cyclohexa-1,4-dien-1-yl)acetyl]amino}-3-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateGenerator
(6R,7R)-7-[[(2R)-2-amino-2-Cyclohexa-1,4-dien-1-ylacetyl]amino]-3-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateGenerator
7-(D-2-amino-2-(1,4-Cyclohexadienyl)acetamido)-3-methoxy-3-cephem-4-carboxylic acidMeSH
CefroxadineMeSH
CefroxadinMeSH
Chemical FormulaC16H19N3O5S
Average Molecular Mass365.400 g/mol
Monoisotopic Mass365.105 g/mol
CAS Registry Number51762-05-1
IUPAC Name(6R,7R)-7-[(2R)-2-amino-2-(cyclohexa-1,4-dien-1-yl)acetamido]-3-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Traditional Namecefroxadine
SMILES[H][C@]12SCC(OC)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CCC=CC1)C(O)=O
InChI IdentifierInChI=1S/C16H19N3O5S/c1-24-9-7-25-15-11(14(21)19(15)12(9)16(22)23)18-13(20)10(17)8-5-3-2-4-6-8/h2-3,6,10-11,15H,4-5,7,17H2,1H3,(H,18,20)(H,22,23)/t10-,11-,15-/m1/s1
InChI KeyRDMOROXKXONCAL-UEKVPHQBSA-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 amide
  • Alpha-amino acid or derivatives
  • Meta-thiazine
  • Vinylogous ester
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Amino acid
  • Azetidine
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Thioether
  • Hemithioaminal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkylthioether
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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 Solubility0.99 g/LALOGPS
logP0.65ALOGPS
logP-3.4ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.28ChemAxon
pKa (Strongest Basic)7.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area121.96 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity94.51 m³·mol⁻¹ChemAxon
Polarizability36.5 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-1912000000-e1afd0c4411f50f2ceddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-2921000000-505c1269f073bda7925aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9810000000-9ffec131700c425effb7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0925000000-0bf242f3c4c7445f493fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0609-1593000000-fcf7827fa94163577f71Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-bc90ca862f2b0ac89cd8Spectrum
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 IDDB11367
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 LinkCefroxadine
Chemspider IDNot Available
ChEBI ID31379
PubChem Compound IDNot Available
Kegg Compound IDC12979
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=2258253
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=29017833
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=6752462
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=7334594