Cefotaxime (CED0001529)

Record Information
Version1.0
Creation Date2016-05-25 18:20:47 UTC
Update Date2026-08-19 15:43:27 UTC
Accession NumberCHEM022120
Identification
Common NameCefotaxime
ClassSmall Molecule
Description
Cefotaxime is an organic compound with the formula C16H17N5O7S2 and an average molecular weight of 455.46 g/mol. Cefotaxime belongs to the beta lactams, a subclass of lactams within the organic compounds. It is further classified as an organoheterocyclic compound. The compound is found in or released from two recorded sources: pharmaceuticals and veterinary products, specifically within the categories of antibiotics and beta-lactam antibacterials. Recorded exposure routes for this substance include oral, intravenous, intramuscular, and inhalation. In terms of biological activity, Cefotaxime interacts with 13 recorded protein targets. It acts as a binder or inhibitor of Penicillin-binding protein 1A (pbpA), Penicillin-binding protein 1b (pbp1b), Penicillin-binding protein 2a (pbp2a), and Penicillin-binding protein 3 (pbpC), as well as 9 other proteins.
Contaminant TypeNot Available
Chemical Structure
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
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 Solubility0.15 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0a4l-7964500000-c5ecb2b4177742d5f8d7Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-006x-9323210000-9dff7305ebaab7563b89Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-066u-2092400000-67d979a25d99bc3d7b4eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01ba-5192000000-c1ad5f753b47daae1c57Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052b-9220000000-31a4e9ed04066cb738d0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-2291300000-8ba55e49221ca1189086Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-4792100000-245e52ddda85c4ce73a2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052f-9300000000-ebc2c7d988b6101ba548Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4j-0026900000-c96be99e67d8b754f5e1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-053v-0597500000-3eeaecfaf09f7f0896a0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-056r-0954000000-1744d3e612e159fb9e7aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0013900000-4a069d614d1936cd1f50Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0229-4893300000-bdb4980e88ed2f7afb83Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0abc-9501000000-155425232683bfeabe12Not 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
5468.0Log mg/kg[3100:9700]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
341Beta-lactam antibacterialsHealthcare, pharmaceuticals & veterinary productsNot Available
Pathways
1 pathway
Cefotaxime Drug Metabolism Action Pathway
Cefotaxime Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureSolute carrier family 22 member 6Q4U2R8HumansPredicted (SEA)0.0778492
Click to view 3D structureOrganic anion transporter 3Q8TCC7HumansPredicted (SEA)0.0778492
Click to view 3D structureBeta-lactamaseB2ZTR6Acinetobacter baumanniiPredicted (SEA)0.0778492
Click to view 3D structureADC-11D6NSM8Acinetobacter baumanniiPredicted (SEA)0.0778492
Solute carrier family 22 member 11 structureClick to view 3D structureSolute carrier family 22 member 11Q9NSA0HumansPredicted (SEA)0.0778492
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)8.87481
Click to view 3D structureAmpCQ83TT7Escherichia coliPredicted (SEA)0.233548
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
Peptidoglycan D,D-transpeptidase FtsI structureClick to view 3D structurePeptidoglycan D,D-transpeptidase FtsIQ51504Pseudomonas aeruginosaPredicted (SEA)0.311397
Click to view 3D structureSHV-5 extended spectrum beta-lactamaseQ6REX6Escherichia coliPredicted (SEA)0.233548
Apoptotic protease-activating factor 1 structureClick to view 3D structureApoptotic protease-activating factor 1O14727HumansPredicted (SEA)3.89246
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)16.0369
Speckle-type POZ protein structureClick to view 3D structureSpeckle-type POZ proteinO43791HumansPredicted (SEA)0.467095
72 kDa type IV collagenase structureClick to view 3D structure72 kDa type IV collagenaseP08253HumansPredicted (SEA)264.22
Click to view 3D structureBeta-lactamase ACC-4A4ZYU9Escherichia coliPredicted (SEA)0.233548
26S proteasome non-ATPase regulatory subunit 14 structureClick to view 3D structure26S proteasome non-ATPase regulatory subunit 14O00487HumansPredicted (SEA)7.86277
DNA (cytosine-5)-methyltransferase 1 structureClick to view 3D structureDNA (cytosine-5)-methyltransferase 1P26358HumansPredicted (SEA)80.8075
Click to view 3D structurePER-2 beta-lactamaseA2RP81Citrobacter freundiiPredicted (SEA)0.233548
Click to view 3D structureProbable nicotinate-nucleotide adenylyltransferaseP65502Staphylococcus aureus (strain N315)Predicted (SEA)126.739
Excitatory amino acid transporter 2 structureClick to view 3D structureExcitatory amino acid transporter 2P43004HumansPredicted (SEA)42.8171
Click to view 3D structureEfflux transporterQ3S5C3Salmonella newportPredicted (SEA)0.778492
Click to view 3D structureClass C beta-lactamase CMY-36Q48435Klebsiella pneumoniaePredicted (SEA)0.778492
Small ubiquitin-related modifier 1 structureClick to view 3D structureSmall ubiquitin-related modifier 1P63165HumansPredicted (SEA)334.907
D-amino-acid oxidase structureClick to view 3D structureD-amino-acid oxidaseP14920HumansPredicted (SEA)78.0049
Alpha-synuclein structureClick to view 3D structureAlpha-synucleinP37840HumansPredicted (SEA)76.9929
Concentrations
Not Available
External Links
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