Cefotaxime (CHEM022120)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:20:47 UTC
Update Date2016-11-09 01:17:25 UTC
Accession NumberCHEM022120
Identification
Common NameCefotaxime
ClassSmall Molecule
DescriptionCefotaxime is a third-generation cephalosporin antibiotic. Like other third-generation cephalosporins, it has broad spectrum activity against Gram positive and Gram negative bacteria. In most cases, it is considered to be equivalent to ceftriaxone in terms of safety and efficacy. Cefotaxime is marketed under various trade names including Cefotaxime (Sanofi-Aventis).
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(6R,7R)-3-(Acetoxymethyl)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidChEBI
(6R,7R)-3-Acetoxymethyl-7-{2-(2-amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acidChEBI
(6R,7R,Z)-3-(Acetoxymethyl)-7-(2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acidChEBI
CefotaximaChEBI
CefotaximumChEBI
CephotaximeChEBI
CTXKegg
Cefotaxim hikmaKegg
(6R,7R)-3-(Acetoxymethyl)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateGenerator
(6R,7R)-3-Acetoxymethyl-7-{2-(2-amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylateGenerator
(6R,7R,Z)-3-(Acetoxymethyl)-7-(2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylateGenerator
Aventis brand OF cefotaxime sodiumHMDB
Aventis pharma brand OF cefotaxime sodiumHMDB
BiosintHMDB
Cefotaxime sodiumHMDB
ClaforanHMDB
TaporinHMDB
FotexinaHMDB
Hoechst brand OF cefotaxime sodiumHMDB
KendrickHMDB
KlaforanHMDB
BenaximaHMDB
CefotaximHMDB
CefradilHMDB
Fustery brand OF cefotaxime sodiumHMDB
Galen brand OF cefotaxime sodiumHMDB
Pisa brand OF cefotaxime sodiumHMDB
PrimafenHMDB
Viken brand OF cefotaxime sodiumHMDB
CephotaximHMDB
Liomont brand OF cefotaxime sodiumHMDB
Merck brand OF cefotaxime sodiumHMDB
Sodium, cefotaximeHMDB
Chemical FormulaC16H17N5O7S2
Average Molecular Mass455.465 g/mol
Monoisotopic Mass455.057 g/mol
CAS Registry Number63527-52-6
IUPAC Name(6R,7R)-3-[(acetyloxy)methyl]-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 Namecefotaxime
SMILES[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C1=CSC(N)=N1)C(O)=O
InChI IdentifierInChI=1S/C16H17N5O7S2/c1-6(22)28-3-7-4-29-14-10(13(24)21(14)11(7)15(25)26)19-12(23)9(20-27-2)8-5-30-16(17)18-8/h5,10,14H,3-4H2,1-2H3,(H2,17,18)(H,19,23)(H,25,26)/b20-9-/t10-,14-/m1/s1
InChI KeyGPRBEKHLDVQUJE-QSWIMTSFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cephalosporin 3'-esters. These are cephalosporins that are esterified at the 3'-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentCephalosporin 3'-esters
Alternative Parents
Substituents
  • Cephalosporin 3'-ester
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • 2,4-disubstituted 1,3-thiazole
  • Meta-thiazine
  • Dicarboxylic acid or derivatives
  • 1,3-thiazol-2-amine
  • Azole
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Thiazole
  • Carboxylic acid ester
  • Amino acid or derivatives
  • Amino acid
  • Carboxamide group
  • Azetidine
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Carboxylic acid
  • 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
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 Solubility0.15 g/LALOGPS
logP0.14ALOGPS
logP-1.4ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)3.18ChemAxon
pKa (Strongest Basic)4.15ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area173.51 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity105.11 m³·mol⁻¹ChemAxon
Polarizability41.78 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-7964500000-c5ecb2b4177742d5f8d7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9323210000-9dff7305ebaab7563b89Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066u-2092400000-67d979a25d99bc3d7b4eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ba-5192000000-c1ad5f753b47daae1c57Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-9220000000-31a4e9ed04066cb738d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-2291300000-8ba55e49221ca1189086Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-4792100000-245e52ddda85c4ce73a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9300000000-ebc2c7d988b6101ba548Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4j-0026900000-c96be99e67d8b754f5e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053v-0597500000-3eeaecfaf09f7f0896a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-0954000000-1744d3e612e159fb9e7aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0013900000-4a069d614d1936cd1f50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0229-4893300000-bdb4980e88ed2f7afb83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9501000000-155425232683bfeabe12Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
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 IDDB00493
HMDB IDHMDB0014636
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCefotaxime
Chemspider ID4674877
ChEBI ID204928
PubChem Compound ID5742673
Kegg Compound IDC06885
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10866367
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11034276
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11061623
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=11677129
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=12833570
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=1384868
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=14512220
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=1502708
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=15164972
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=15361989
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=15969234
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=1635063
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=17006042
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=17386217
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=18611527
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=19741292
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=21425867
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=24038683
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=24211456
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=29017833
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=9131470