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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2018-05-20 20:18:42 UTC
HMDB IDHMDB0015426
Secondary Accession Numbers
  • HMDB15426
Metabolite Identification
Common NameCefoxitin
DescriptionCefoxitin is only found in individuals that have used or taken this drug. It is a semi-synthetic, broad-spectrum cepha antibiotic for intravenous administration. It is derived from cephamycin C, which is produced by Streptomyces lactamdurans.The bactericidal action of cefoxitin results from inhibition of cell wall synthesis.
Structure
Thumb
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 sodiumMeSH
Sodium, cefoxitinMeSH
Merck brand OF cefoxitin sodiumMeSH
Cefoxitin sodiumMeSH
MefoxitinMeSH
MefoxinMeSH
Merck frosst brand OF cefoxitin sodiumMeSH
Merck sharp and dohme brand OF cefoxitin sodiumMeSH
MéfoxinMeSH
Chemical FormulaC16H17N3O7S2
Average Molecular Weight427.452
Monoisotopic Molecular Weight427.050791293
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
CAS Registry Number35607-66-0
SMILES
[H][C@]12SCC(COC(N)=O)=C(N1C(=O)[C@]2(NC(=O)CC1=CC=CS1)OC)C(O)=O
InChI Identifier
InChI=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
DescriptionThis compound belongs to the class of organic compounds known as cephalosporin 3'-carbamates. These are cephalosporins that are substituted at the 3'-position by a carbamate group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentCephalosporin 3'-carbamates
Alternative Parents
Substituents
  • Cephalosporin 3'-carbamate
  • Cephamycin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Meta-thiazine
  • Heteroaromatic compound
  • Carbamic acid ester
  • Thiophene
  • Tertiary carboxylic acid amide
  • Azetidine
  • Carboxamide group
  • Carbonic acid derivative
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point149.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.2 g/LNot Available
LogP-0.02SANGSTER (1993)
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-9324000000-05cb1df27c44fb10d1f0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006w-9111500000-bf31bd6d1e9af793d957View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0152900000-dcfff8fc4fd3f312364aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0096-0920000000-12829e022c644e05c20dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-4930000000-b840384f3eb09ebca7c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9132100000-8247f1786ca63286b408View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9111000000-3136ee10c61ca55fabbcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9510000000-6fe60420b7da0fc35ee7View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01331 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01331 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01331
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID389981
KEGG Compound IDC06887
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCefoxitin
METLIN IDNot Available
PubChem Compound441199
PDB IDCFX
ChEBI ID209807
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available