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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2020-02-26 21:41:36 UTC
HMDB IDHMDB0015426
Secondary Accession Numbers
  • HMDB15426
Metabolite Identification
Common NameCefoxitin
DescriptionCefoxitin, also known as CFX or cephoxitin, 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. Cefoxitin is only found in individuals that have used or taken this drug. Cefoxitin is a drug which is used for the treatment of serious infections caused by susceptible strains microorganisms. It is derived from cephamycin C, which is produced by Streptomyces lactamdurans. Cefoxitin is a cephamycin antibiotic often grouped with the second-generation cephalosporins. Cefoxitin is an extremely weak basic (essentially neutral) compound (based on its pKa). The acute intravenous LD50 in the adult female mouse and rabbit was about 8.0 g/kg and greater than 1.0 g/kg, respectively. The methoxy group in the 7a position provides cefoxitin with a high degree of stability in the presence of beta-lactamases, both penicillinases and cephalosporinases, of gram-negative bacteria. Minimal (approximately 85 percent of cefoxitin is excreted unchanged by the kidneys over a 6-hour period).
Structure
Data?1582753296
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 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
Description 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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 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
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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available