Cefoxitin (CHEM016617)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:38:35 UTC
Update Date2016-11-09 01:15:26 UTC
Accession NumberCHEM016617
Identification
Common NameCefoxitin
ClassSmall Molecule
DescriptionA semisynthetic cephamycin antibiotic which, in addition to the methoxy group at the 7alpha position, has 2-thienylacetamido and carbamoyloxymethyl side-groups. It is resistant to beta-lactamase.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(6R,7S)-3-[(Carbamoyloxy)methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidChEBI
CefoxitinaChEBI
CefoxitineChEBI
CefoxitinumChEBI
CeftoxitinChEBI
CephoxitinChEBI
CFXChEBI
RephoxitinChEBI
(6R,7S)-3-[(Carbamoyloxy)methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateGenerator
MSD Brand OF cefoxitin sodiumHMDB
Sodium, cefoxitinHMDB
Merck brand OF cefoxitin sodiumHMDB
Cefoxitin sodiumHMDB
MefoxitinHMDB
MefoxinHMDB
Merck frosst brand OF cefoxitin sodiumHMDB
Merck sharp and dohme brand OF cefoxitin sodiumHMDB
MéfoxinHMDB
Chemical FormulaC16H17N3O7S2
Average Molecular Mass427.452 g/mol
Monoisotopic Mass427.051 g/mol
CAS Registry Number35607-66-0
IUPAC Name(6R,7S)-3-[(carbamoyloxy)methyl]-7-methoxy-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Traditional Namecefoxitin
SMILES[H][C@]12SCC(COC(N)=O)=C(N1C(=O)[C@]2(NC(=O)CC1=CC=CS1)OC)C(O)=O
InChI IdentifierInChI=1S/C16H17N3O7S2/c1-25-16(18-10(20)5-9-3-2-4-27-9)13(23)19-11(12(21)22)8(6-26-15(17)24)7-28-14(16)19/h2-4,14H,5-7H2,1H3,(H2,17,24)(H,18,20)(H,21,22)/t14-,16+/m1/s1
InChI KeyWZOZEZRFJCJXNZ-ZBFHGGJFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentSteroid esters
Alternative Parents
Substituents
  • Steroid ester
  • Androstane-skeleton
  • N-methylpiperazine
  • N-alkylpiperazine
  • 1,4-diazinane
  • Dicarboxylic acid or derivatives
  • Piperazine
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Carbonyl group
  • Organic nitrogen compound
  • Organic salt
  • Organic cation
  • 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 Solubility0.2 g/LALOGPS
logP0.22ALOGPS
logP0.29ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)3.59ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area148.26 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity98.76 m³·mol⁻¹ChemAxon
Polarizability39.46 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-9324000000-05cb1df27c44fb10d1f0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006w-9111500000-bf31bd6d1e9af793d957Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0152900000-dcfff8fc4fd3f312364aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0096-0920000000-12829e022c644e05c20dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-4930000000-b840384f3eb09ebca7c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9132100000-8247f1786ca63286b408Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9111000000-3136ee10c61ca55fabbcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9510000000-6fe60420b7da0fc35ee7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-016r-0009800000-0aab03e94594dab686d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0171-1059200000-d98c8e6245c4548a77acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000j-9277000000-b3dc1748967d8be6f876Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fb9-0015900000-11bd6d703d43a001e23eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-2092200000-0fab277122b825145b75Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-9220000000-b8f3a5c616f492419695Spectrum
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 IDDB01331
HMDB IDHMDB0015426
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDCFX
Wikipedia LinkCefoxitin
Chemspider ID389981
ChEBI ID209807
PubChem Compound ID441199
Kegg Compound IDC06887
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12569987
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17043131
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17178800
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=17220412
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=17353248
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=17387156
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=17923492
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=18056283
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=18070972
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=2083978
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=29017833
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=8360877