Cefatrizine (CHEM016612)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:38:28 UTC
Update Date2016-11-09 01:15:26 UTC
Accession NumberCHEM016612
Identification
Common NameCefatrizine
ClassSmall Molecule
DescriptionA cephalosporin compound having (1H-1,2,3-triazol-4-ylsulfanyl)methyl and acetamido side-groups. An antibacterial drug first prepared in the 1970s, it has more recently been found to be an inhibitor of eukaryotic elongation factor-2 kinase (eEF2K), which is known to regulate apoptosis, autophagy and ER stress in many types of human cancers.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(7R)-7-(alpha-D-4-Hydroxyphenylglycylamino)-3-(1H-1,2,3-triazol-4-ylthiomethyl)-3-cephem-4-carboxylic acidChEBI
Antibiotic BL-S 640ChEBI
BL-S 640ChEBI
BL-S640ChEBI
BLS 640ChEBI
CefatrizinaChEBI
CefatrizinumChEBI
SKF 60771ChEBI
CFTKegg
(7R)-7-(a-D-4-Hydroxyphenylglycylamino)-3-(1H-1,2,3-triazol-4-ylthiomethyl)-3-cephem-4-carboxylateGenerator
(7R)-7-(a-D-4-Hydroxyphenylglycylamino)-3-(1H-1,2,3-triazol-4-ylthiomethyl)-3-cephem-4-carboxylic acidGenerator
(7R)-7-(alpha-D-4-Hydroxyphenylglycylamino)-3-(1H-1,2,3-triazol-4-ylthiomethyl)-3-cephem-4-carboxylateGenerator
(7R)-7-(Α-D-4-hydroxyphenylglycylamino)-3-(1H-1,2,3-triazol-4-ylthiomethyl)-3-cephem-4-carboxylateGenerator
(7R)-7-(Α-D-4-hydroxyphenylglycylamino)-3-(1H-1,2,3-triazol-4-ylthiomethyl)-3-cephem-4-carboxylic acidGenerator
BL S 640MeSH
SK And F 60771MeSH
SK And F60771MeSH
S 640 PMeSH
S 640-PMeSH
SK And F-60771MeSH
BL S640MeSH
Chemical FormulaC18H18N6O5S2
Average Molecular Mass462.500 g/mol
Monoisotopic Mass462.078 g/mol
CAS Registry Number51627-14-6
IUPAC Name(6R,7R)-7-{[(2R)-2-amino-1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}-8-oxo-3-[(1H-1,2,3-triazol-5-ylsulfanyl)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Traditional Namecefatrizine
SMILES[H][C@](N)(C(O)=N[C@]1([H])C(=O)N2C(C(O)=O)=C(CSC3=CN=NN3)CS[C@]12[H])C1=CC=C(O)C=C1
InChI IdentifierInChI=1S/C18H18N6O5S2/c19-12(8-1-3-10(25)4-2-8)15(26)21-13-16(27)24-14(18(28)29)9(7-31-17(13)24)6-30-11-5-20-23-22-11/h1-5,12-13,17,25H,6-7,19H2,(H,21,26)(H,28,29)(H,20,22,23)/t12-,13-,17-/m1/s1
InChI KeyUOCJDOLVGGIYIQ-PBFPGSCMSA-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 amide
  • Phenylacetamide
  • Alpha-amino acid or derivatives
  • Aryl thioether
  • Phenol
  • Alkylarylthioether
  • Aralkylamine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Meta-thiazine
  • Benzenoid
  • Monocyclic benzene moiety
  • Tertiary carboxylic acid amide
  • 1,2,3-triazole
  • Heteroaromatic compound
  • Azole
  • Amino acid or derivatives
  • Azetidine
  • Amino acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Sulfenyl compound
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organosulfur compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Amine
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxide
  • Organic oxygen compound
  • Primary amine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
logP-1.2ALOGPS
logP-2.1ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)2.52ChemAxon
pKa (Strongest Basic)8.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area178.02 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity115.15 m³·mol⁻¹ChemAxon
Polarizability43.98 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0c00-3695300000-2fad81ebc0404b46f2efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-5973000000-8761b3117f4a78f134adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-9610000000-5944da30b554869a353aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4j-4191400000-12c3eec7a256baaee5b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9120000000-fe991412555685d1fe0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-f2d655e43a38609e5468Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB13266
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCefatrizine
Chemspider IDNot Available
ChEBI ID131730
PubChem Compound ID6410758
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1137381
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=2329468
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23894823
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=239917
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=26776155
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=29017833
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=3915469
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=6660858
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=813573