Cefoxitin (CED0002102)

Record Information
Version1.0
Creation Date2016-05-22 03:38:35 UTC
Update Date2026-08-19 15:41:58 UTC
Accession NumberCHEM016617
Identification
Common NameCefoxitin
ClassSmall Molecule
Description
Cefoxitin is an organic compound with the chemical formula C16H17N3O7S2 and an average molecular weight of 427.45 g/mol. Cefoxitin belongs to the beta lactams, a subclass of lactams within the organic compounds. It is categorized under the superclass of organoheterocyclic compounds. The substance is found in or released from eight recorded sources. These include healthcare, pharmaceuticals, and veterinary products, specifically antibiotics and beta-lactam antibacterials. It is also associated with electrical and electronic equipment, such as television systems, video games, and emergency protective devices. Other sources include food, food processing, and cookware, specifically the processing of meats, as well as household cleaning and consumer products, including other smoking requisites and non-electric simulated smoking devices. Recorded exposure routes for the compound include oral, intravenous, intramuscular, and inhalation. In terms of biological activity, cefoxitin has twelve recorded protein targets. It acts as an inhibitor of several proteins, including penicillin-binding protein 1A (mrcA), penicillin-binding protein 1B (mrcB), peptidoglycan D,D-transpeptidase FtsI (ftsI), and D-alanyl-D-alanine carboxypeptidase DacA (dacA), along with eight other proteins.
Contaminant TypeNot Available
Chemical Structure
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
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0005-9324000000-05cb1df27c44fb10d1f0Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-006w-9111500000-bf31bd6d1e9af793d957Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01t9-0152900000-dcfff8fc4fd3f312364aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0096-0920000000-12829e022c644e05c20dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kf-4930000000-b840384f3eb09ebca7c7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9132100000-8247f1786ca63286b408Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9111000000-3136ee10c61ca55fabbcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9510000000-6fe60420b7da0fc35ee7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-016r-0009800000-0aab03e94594dab686d7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0171-1059200000-d98c8e6245c4548a77acNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000j-9277000000-b3dc1748967d8be6f876Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fb9-0015900000-11bd6d703d43a001e23eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-016r-2092200000-0fab277122b825145b75Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0005-9220000000-b8f3a5c616f492419695Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
6409.0Log mg/kg[3600:11000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
341Beta-lactam antibacterialsHealthcare, pharmaceuticals & veterinary productsNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
552Processing MeatsFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureBeta-lactamaseB2ZTR6Acinetobacter baumanniiPredicted (SEA)0.0778492
Click to view 3D structureADC-11D6NSM8Acinetobacter baumanniiPredicted (SEA)0.0778492
Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1 structureClick to view 3D structureCarboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1Q9GZU7HumansPredicted (SEA)7.62922
Click to view 3D structureSolute carrier family 22 member 6Q4U2R8HumansPredicted (SEA)1.47914
Click to view 3D structureOrganic anion transporter 3Q8TCC7HumansPredicted (SEA)2.64687
Solute carrier family 22 member 11 structureClick to view 3D structureSolute carrier family 22 member 11Q9NSA0HumansPredicted (SEA)0.856341
Click to view 3D structurePER-2 beta-lactamaseA2RP81Citrobacter freundiiPredicted (SEA)0.0778492
DNA (cytosine-5)-methyltransferase 1 structureClick to view 3D structureDNA (cytosine-5)-methyltransferase 1P26358HumansPredicted (SEA)45.6975
Estrogen receptor beta structureClick to view 3D structureEstrogen receptor betaQ92731HumansPredicted (SEA)144.644
Induced myeloid leukemia cell differentiation protein Mcl-1 structureClick to view 3D structureInduced myeloid leukemia cell differentiation protein Mcl-1Q07820HumansPredicted (SEA)391.971
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)764.713
Speckle-type POZ protein structureClick to view 3D structureSpeckle-type POZ proteinO43791HumansPredicted (SEA)4.9045
Neutrophil elastase structureClick to view 3D structureNeutrophil elastaseP08246HumansPredicted (SEA)271.46
Tyrosine-protein phosphatase non-receptor type 7 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 7P35236HumansPredicted (SEA)368.305
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)1271.82
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)1529.58
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)799.823
Click to view 3D structureCarbonic anhydrase 5A, mitochondrialP35218HumansPredicted (SEA)583.48
Click to view 3D structureCarbonic anhydrase 5B, mitochondrialQ9Y2D0HumansPredicted (SEA)433.075
Cathepsin G structureClick to view 3D structureCathepsin GP08311HumansPredicted (SEA)447.166
Prothrombin structureClick to view 3D structureProthrombinP00734HumansPredicted (SEA)2355.33
Dual specificity protein kinase CLK4 structureClick to view 3D structureDual specificity protein kinase CLK4Q9HAZ1HumansPredicted (SEA)4814.66
Fibroblast growth factor receptor 1 structureClick to view 3D structureFibroblast growth factor receptor 1P11362HumansPredicted (SEA)5396.59
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)5952.04
Click to view 3D structureAtaxin-2O70305Mus musculusPredicted (SEA)402.87
Concentrations
Not Available
External Links
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