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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:41:14 UTC
HMDB IDHMDB0015244
Secondary Accession Numbers
  • HMDB15244
Metabolite Identification
Common NameCefuroxime
DescriptionCefuroxime is only found in individuals that have used or taken this drug. It is a broad-spectrum cephalosporin antibiotic resistant to beta-lactamase. It has been proposed for infections with gram-negative and gram-positive organisms, gonorrhea, and haemophilus. [PubChem]Cefuroxime, like the penicillins, is a beta-lactam antibiotic. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefuroxime interferes with an autolysin inhibitor.
Structure
Data?1582753274
Synonyms
ValueSource
(6R,7R)-3-[(Carbamoyloxy)methyl]-7-{[(2Z)-2-furan-2-yl-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidChEBI
CefuroximChEBI
CefuroximoChEBI
CefuroximumChEBI
CephuroximeChEBI
SharoxChEBI
Zinacef danmarkChEBI
CXMKegg
(6R,7R)-3-[(Carbamoyloxy)methyl]-7-{[(2Z)-2-furan-2-yl-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateGenerator
KetocefHMDB
ZinacefHMDB
Chemical FormulaC16H16N4O8S
Average Molecular Weight424.385
Monoisotopic Molecular Weight424.068884198
IUPAC Name(6R,7R)-3-[(carbamoyloxy)methyl]-7-[(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Traditional Namesharox
CAS Registry Number55268-75-2
SMILES
[H][C@]12SCC(COC(N)=O)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C1=CC=CO1)C(O)=O
InChI Identifier
InChI=1S/C16H16N4O8S/c1-26-19-9(8-3-2-4-27-8)12(21)18-10-13(22)20-11(15(23)24)7(5-28-16(17)25)6-29-14(10)20/h2-4,10,14H,5-6H2,1H3,(H2,17,25)(H,18,21)(H,23,24)/b19-9-/t10-,14-/m1/s1
InChI KeyJFPVXVDWJQMJEE-IZRZKJBUSA-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
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Meta-thiazine
  • Furan
  • Heteroaromatic compound
  • Carbamic acid ester
  • Tertiary carboxylic acid amide
  • Azetidine
  • Carboxamide group
  • Carbonic acid derivative
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Azacycle
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point218 - 225 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.28 g/LNot Available
LogP-0.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.28 g/LALOGPS
logP-0.24ALOGPS
logP-0.9ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)3.15ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area173.76 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity97.17 m³·mol⁻¹ChemAxon
Polarizability38.75 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-3926000000-2148cf05d31b3658ebcfSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9320300000-45c45b3354d001c25453Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ar0-2192200000-206265fb15a436edf6acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0avi-4293000000-c8a2cea122e40dacb6e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aou-9561000000-9cb40ec2c90933d73f88Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052f-9262100000-c572c9da887b9e4fe33cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9210000000-469bbe70e6e9b2ae098dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-6a9d50ea1c4e799bc865Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01112 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01112 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01112
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4586393
KEGG Compound IDC06894
BioCyc IDCPD0-2069
BiGG IDNot Available
Wikipedia LinkCefuroxime
METLIN IDNot Available
PubChem Compound5479529
PDB IDKOV
ChEBI ID3515
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Perry CM, Brogden RN: Cefuroxime axetil. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1996 Jul;52(1):125-58. [PubMed:8799689 ]

Transporters

General function:
Involved in transporter activity
Specific function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular weight:
78805.3
References
  1. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297 ]
General function:
Involved in transporter activity
Specific function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides
Gene Name:
SLC15A2
Uniprot ID:
Q16348
Molecular weight:
81782.8
References
  1. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297 ]