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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1436
CHEMBL1436
Compound Name CEFUROXIME
ChEMBL Synonyms 640/359 | Cefuroximine | Zinacef | BRITACEF | ZINACEF | CEFUROXIME | Kefurox | KEFUROX | CEFUROXIME SODIUM
Max Phase 4 (Approved)
Trade Names BRITACEF | ZINACEF | CEFUROXIME SODIUM | KEFUROX
Molecular Formula C16H16N4O8S

Additional synonyms for CHEMBL1436 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CO\N=C(/C(=O)N[C@H]1[C@H]2SCC(=C(N2C1=O)C(=O)O)COC(=O)N)\c3o ...
Download SMILES
Standard InChI InChI=1S/C16H16N4O8S/c1-26-19-9(8-3-2-4-27-8)12(21)18-10-13( ...
Download InChI
Standard InChI Key JFPVXVDWJQMJEE-IZRZKJBUSA-N

Sources

  • British National Formulary
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL1436

Molecule Features

CHEMBL1436 compound icon
Drug Type:Natural Product-derived Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:N Parenteral:Y Topical:N Black Box:N Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Bacterial penicillin-binding protein inhibitor Bacterial penicillin-binding protein PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
OsteomyelitisD010019EFO:0003102osteomyelitis0ClinicalTrials
ClinicalTrials
InfectionD007239EFO:0000544infection2ClinicalTrials
PneumoniaD011014EFO:0003106pneumonia3ClinicalTrials

Clinical Data

ClinicalTrials.gov CEFUROXIME
The Cochrane Collaboration CEFUROXIME

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL1436. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL2725 Beta-lactamase Enterobacter cloacae 1.000
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.999
CHEMBL2219 Protein-tyrosine phosphatase LC-PTP Homo sapiens 0.996
CHEMBL2608 Lysosomal alpha-glucosidase Homo sapiens 0.950
CHEMBL1293299 Histone-lysine N-methyltransferase MLL Homo sapiens 0.948
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.496
CHEMBL4159 Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens 0.210
CHEMBL1963 Thyroid stimulating hormone receptor Homo sapiens 0.210



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL2725 Beta-lactamase Enterobacter cloacae 1.000
CHEMBL5619 DNA-(apurinic or apyrimidinic site) lyase Homo sapiens 1.000
CHEMBL6110 Thioredoxin glutathione reductase Schistosoma mansoni 0.972
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.830
CHEMBL4159 Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens 0.638
CHEMBL3577 Aldehyde dehydrogenase 1A1 Homo sapiens 0.566
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.487

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
424.4 424.0689 -0.54 7 173.76 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
9 3 0 12 4 1


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
2.59 - .26 -3.48 1 29 0.3

Structural Alerts

There are 12 structural alerts for CHEMBL1436. To view alerts please click here.

Compound Cross References

ATC S - SENSORY ORGANS
S01 - OPHTHALMOLOGICALS
S01A - ANTIINFECTIVES
S01AA - Antibiotics
S01AA27 - cefuroxime

J - ANTIINFECTIVES FOR SYSTEMIC USE
J01 - ANTIBACTERIALS FOR SYSTEMIC USE
J01D - OTHER BETA-LACTAM ANTIBACTERIALS
J01DC - Second-generation cephalosporins
J01DC02 - cefuroxime

ChemSpider ChemSpider:JFPVXVDWJQMJEE-IZRZKJBUSA-N
DailyMed cefuroxime cefuroxime sodium

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1436



ACToR 153012-39-6
BindingDB 50422689
ChEBI 3515
ChemicalBook CB7707485
DrugBank DB01112
DrugCentral 565
eMolecules 29538669
FDA SRS O1R9FJ93ED
Human Metabolome Database HMDB0015244
KEGG Ligand C06894
LINCS LSM-44947
MolPort MolPort-005-938-003
Nikkaji J13.093A
PDBe KOV
PubChem 5479529
PubChem: Drugs of the Future 12015285
PubChem: Thomson Pharma 14758434 16838488
SureChEMBL SCHEMBL1821942
ZINC ZINC000003871978

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/JFPVXVDWJQMJEE-IZRZKJBUSA-N spacer
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