Ceftizoxime (CED0006291)

Record Information
Version1.0
Creation Date2016-05-25 18:26:49 UTC
Update Date2026-08-18 23:28:57 UTC
Accession NumberCHEM022285
Identification
Common NameCeftizoxime
ClassSmall Molecule
Description
Ceftizoxime is an organic compound with the formula C13H13N5O5S2 and an average molecular weight of 383.40 g/mol. Ceftizoxime belongs to the beta lactams, a subclass of lactams within the organic compounds. It is further categorized as an organoheterocyclic compound. The compound is found in or released from four recorded sources: healthcare, pharmaceuticals & veterinary products (specifically antibiotics and beta-lactam antibacterials), electrical & electronic equipment (video games), and household cleaning & consumer products (other smoking requisites). Recorded exposure routes for this substance include oral, intravenous, intramuscular, and inhalation. At the molecular level, ceftizoxime interacts with three recorded protein targets. It acts as a binder or inhibitor of penicillin-binding protein 1A (mrcA) and penicillin-binding protein 1B (mrcB). Additionally, it targets D-alanyl-D-alanine carboxypeptidase DacC (dacC).
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
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
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
CZXHMDB
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 Mass383.403 g/mol
Monoisotopic Mass383.036 g/mol
CAS Registry Number68401-81-0
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
SMILES[H][C@]12SCC=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C1=CSC(N)=N1)C(O)=O
InChI IdentifierInChI=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
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 Solubility0.23 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
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0a4i-4913000000-42786f9c3320ba883cd4Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00di-9411200000-8cd3c9d0af48f25309c1Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-2945000000-60f610871e0522e1596cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0007-4911000000-93791c9670a6f9a8b1dcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052e-9400000000-fd43a1760b518b7e5161Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0019-0194000000-34ce0f3a6b62f87e9c6aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4r-3974000000-975fd06347e2ec56d533Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9300000000-a53dfd2b405bbb20fad4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0009000000-27490ef7fb8de924c4bfNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0978000000-1e0d0fb020ca219956a4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-056r-0911000000-8ef6255a616142dc0922Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052r-0059000000-7d77f00807f9810ba6f9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-059l-4739000000-3738018dc53842f64ddbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0abd-9602000000-6f9d979ca6b7e73128aaNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot 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
6394.0Log 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
539Video GamesElectrical & Electronic EquipmentNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
Pathways
1 pathway
Ceftizoxime Drug Metabolism Action Pathway
Ceftizoxime Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureBeta-lactamaseB2ZTR6Acinetobacter baumanniiPredicted (SEA)0.0778492
Click to view 3D structureADC-11D6NSM8Acinetobacter baumanniiPredicted (SEA)0.0778492
Click to view 3D structureAmpCQ83TT7Escherichia coliPredicted (SEA)0.155698
Click to view 3D structureSolute carrier family 22 member 6Q4U2R8HumansPredicted (SEA)0.467095
Click to view 3D structureOrganic anion transporter 3Q8TCC7HumansPredicted (SEA)0.311397
Penicillin-binding protein 1A structureClick to view 3D structurePenicillin-binding protein 1AQ07806Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)Predicted (SEA)0.233548
Solute carrier family 22 member 11 structureClick to view 3D structureSolute carrier family 22 member 11Q9NSA0HumansPredicted (SEA)0.311397
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)16.1926
Click to view 3D structureSHV-5 extended spectrum beta-lactamaseQ6REX6Escherichia coliPredicted (SEA)0.233548
Peptidoglycan D,D-transpeptidase FtsI structureClick to view 3D structurePeptidoglycan D,D-transpeptidase FtsIQ51504Pseudomonas aeruginosaPredicted (SEA)0.311397
72 kDa type IV collagenase structureClick to view 3D structure72 kDa type IV collagenaseP08253HumansPredicted (SEA)168.933
Click to view 3D structureBeta-lactamase ACC-4A4ZYU9Escherichia coliPredicted (SEA)0.155698
Apoptotic protease-activating factor 1 structureClick to view 3D structureApoptotic protease-activating factor 1O14727HumansPredicted (SEA)7.94062
26S proteasome non-ATPase regulatory subunit 14 structureClick to view 3D structure26S proteasome non-ATPase regulatory subunit 14O00487HumansPredicted (SEA)5.2159
Speckle-type POZ protein structureClick to view 3D structureSpeckle-type POZ proteinO43791HumansPredicted (SEA)2.49118
Click to view 3D structureEfflux transporterQ3S5C3Salmonella newportPredicted (SEA)0.544945
Click to view 3D structureClass C beta-lactamase CMY-36Q48435Klebsiella pneumoniaePredicted (SEA)0.544945
Click to view 3D structureProbable nicotinate-nucleotide adenylyltransferaseP65502Staphylococcus aureus (strain N315)Predicted (SEA)167.999
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)565.886
Small ubiquitin-related modifier 1 structureClick to view 3D structureSmall ubiquitin-related modifier 1P63165HumansPredicted (SEA)446.387
Click to view 3D structurePER-2 beta-lactamaseA2RP81Citrobacter freundiiPredicted (SEA)0.622794
D-amino-acid oxidase structureClick to view 3D structureD-amino-acid oxidaseP14920HumansPredicted (SEA)166.208
Excitatory amino acid transporter 2 structureClick to view 3D structureExcitatory amino acid transporter 2P43004HumansPredicted (SEA)240.788
Click to view 3D structureReceptor (TNFRSF)-interacting serine-threonine kinase 1 (Predicted)D3ZYL0Rattus norvegicusPredicted (SEA)210.426
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1 structureClick to view 3D structure1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1P19174HumansPredicted (SEA)19.1509
Concentrations
Not Available
External Links
DrugBank IDDB01332
HMDB IDHMDB0015427
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCeftizoxime
Chemspider ID5018818
ChEBI ID553473
PubChem Compound ID6533629
Kegg Compound IDC06890
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11452157
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11711261
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=1384868
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=15716453
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22726927
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23394621
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=29017833