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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 IDHMDB0015427
Secondary Accession Numbers
  • HMDB15427
Metabolite Identification
Common NameCeftizoxime
DescriptionCeftizoxime, also known as CEFIZOX or SK and F 88373-2, belongs to the class of organic compounds known as cephalosporins. Cephalosporins are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof. Ceftizoxime is a drug which is used for the treatment of infections due to susceptible strains of microorganisms. Ceftizoxime is a strong basic compound (based on its pKa). Ceftizoxime is highly resistant to a broad spectrum of beta-lactamases and is active against a wide range of both aerobic and anaerobic gram-positive and gram-negative organisms. 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. Ceftizoxime, like the penicillins, is a beta-lactam antibiotic. Ceftizoxime is an aminothiazolyl cephalosporin with an extended spectrum of activity against many gram-negative, nosocomially acquired pathogens. It has excellent beta-lactamase stability, with good in vitro activity against Haemophilus influenzae, Neisseria gonorrhoeae and Klebsiella pneumoniae.
Structure
Data?1582753296
Synonyms
ValueSource
7-[2-(2-Amino-thiazol-4-yl)-2-methoxyimino-acetylamino]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acidChEBI
CEFIZOXChEBI
CeftizoximaChEBI
CeftizoximumChEBI
Syn-7-(2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido)-3-cephem-4-carboxylic acidChEBI
CZXKegg
7-[2-(2-Amino-thiazol-4-yl)-2-methoxyimino-acetylamino]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylateGenerator
Syn-7-(2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido)-3-cephem-4-carboxylateGenerator
Ceftizoxime monosodium saltHMDB
Salt, ceftizoxime monosodiumHMDB
Sodium, ceftizoximeHMDB
Yamanouchi brand OF ceftizoxime sodiumHMDB
SK And F 88373-2HMDB
GlaxoSmithKline brand OF cetizoxime sodiumHMDB
SK And F 88373 2HMDB
SK And F 883732HMDB
Fujiwasa brand OF cetizoxime sodiumHMDB
Monosodium salt, ceftizoximeHMDB
Ceftizoxime sodiumHMDB
Chemical FormulaC13H13N5O5S2
Average Molecular Weight383.403
Monoisotopic Molecular Weight383.035809931
IUPAC Name(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Traditional Nameceftizoxime
CAS Registry Number68401-81-0
SMILES
[H][C@]12SCC=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C1=CSC(N)=N1)C(O)=O
InChI Identifier
InChI=1S/C13H13N5O5S2/c1-23-17-7(5-4-25-13(14)15-5)9(19)16-8-10(20)18-6(12(21)22)2-3-24-11(8)18/h2,4,8,11H,3H2,1H3,(H2,14,15)(H,16,19)(H,21,22)/b17-7-/t8-,11-/m1/s1
InChI KeyNNULBSISHYWZJU-LLKWHZGFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cephalosporins. Cephalosporins are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentCephalosporins
Alternative Parents
Substituents
  • Cephalosporin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • 2,4-disubstituted 1,3-thiazole
  • Meta-thiazine
  • 1,3-thiazol-2-amine
  • Azole
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Thiazole
  • Amino acid or derivatives
  • Amino acid
  • Carboxamide group
  • Azetidine
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Azacycle
  • Dialkylthioether
  • Thioether
  • Hemithioaminal
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Organopnictogen 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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.23 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.23 g/LALOGPS
logP0.4ALOGPS
logP-0.85ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)3.13ChemAxon
pKa (Strongest Basic)4.16ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area147.21 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity89.9 m³·mol⁻¹ChemAxon
Polarizability35.38 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-4913000000-42786f9c3320ba883cd4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9411200000-8cd3c9d0af48f25309c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-2945000000-60f610871e0522e1596cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0007-4911000000-93791c9670a6f9a8b1dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052e-9400000000-fd43a1760b518b7e5161Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0019-0194000000-34ce0f3a6b62f87e9c6aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-3974000000-975fd06347e2ec56d533Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-a53dfd2b405bbb20fad4Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01332 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01332 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01332
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5018818
KEGG Compound IDC06890
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCeftizoxime
METLIN IDNot Available
PubChem Compound6533629
PDB IDNot Available
ChEBI ID553473
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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. Tsuji A: Transporter-mediated Drug Interactions. Drug Metab Pharmacokinet. 2002;17(4):253-74. [PubMed:15618677 ]