ChEMBL logo

ChEMBL

spacer
ChEMBL Statistics
  Loading Statistics...
spacer

Compound Report Card

Compound Name and Classification

Compound ID CHEMBL768
CHEMBL768
Compound Name ESMOLOL
ChEMBL Synonyms ESMOLOL | BREVIBLOC | ASL-8052 | ESMOLOL HYDROCHLORIDE
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names BREVIBLOC | ESMOLOL HYDROCHLORIDE
Molecular Formula C16H25NO4

Additional synonyms for CHEMBL768 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES COC(=O)CCc1ccc(OCC(O)CNC(C)C)cc1
Standard InChI InChI=1S/C16H25NO4/c1-12(2)17-10-14(18)11-21-15-7-4-13(5-8-1 ...
Download InChI
Standard InChI Key AQNDDEOPVVGCPG-UHFFFAOYSA-N

Sources

  • British National Formulary
  • DrugMatrix
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification
  • Withdrawn Drugs

Alternate Forms of Compound in ChEMBL


CHEMBL768

Molecule Features

CHEMBL768 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Racemic Mixture Prodrug:N Oral:N Parenteral:Y Topical:N Black Box:Y Availability Type:Prescription-only

Withdrawal Information

Year 2007
Country United States
Reason Increased risk of medication errors resulting in serious adverse events, including deaths
Class

Mechanism of Action

Mechanism of Action ChEMBL Target References
Beta-1 adrenergic receptor antagonist Beta-1 adrenergic receptor DailyMed
Beta-2 adrenergic receptor antagonist Beta-2 adrenergic receptor DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Ovarian CystsD0100481ClinicalTrials
ClinicalTrials
Shock, SepticD012772EFO:0006834septic shock2ClinicalTrials
Diabetic FootD017719EFO:1001459diabetic foot1ClinicalTrials
Brain NeoplasmsD001932EFO:0003833brain neoplasm1ClinicalTrials
Atrial FibrillationD001281EFO:0000275atrial fibrillation2ClinicalTrials
Coronary Artery DiseaseD003324EFO:0000378coronary artery disease3ClinicalTrials
Cardiovascular DiseasesD002318EFO:0000319cardiovascular disease4ATC

Clinical Data

ClinicalTrials.gov ESMOLOL
The Cochrane Collaboration ESMOLOL

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 CHEMBL768. 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
CHEMBL213 Beta-1 adrenergic receptor Homo sapiens 1.000
CHEMBL210 Beta-2 adrenergic receptor Homo sapiens 1.000
CHEMBL246 Beta-3 adrenergic receptor Homo sapiens 1.000
CHEMBL4302 P-glycoprotein 1 Homo sapiens 1.000
CHEMBL1878 Calcium sensing receptor Homo sapiens 1.000
CHEMBL3892 Sphingosine 1-phosphate receptor Edg-3 Homo sapiens 1.000
CHEMBL3373 Beta-2 adrenergic receptor Bos taurus 0.999
CHEMBL5414 Beta-2 adrenergic receptor Cavia porcellus 0.999
CHEMBL3252 Beta-1 adrenergic receptor Rattus norvegicus 0.995
CHEMBL4333 Sphingosine 1-phosphate receptor Edg-1 Homo sapiens 0.992
CHEMBL3815 Squalene synthetase Rattus norvegicus 0.638
CHEMBL3318 Tyrosinase Agaricus bisporus 0.631
CHEMBL3399910 Probable G-protein coupled receptor 88 Homo sapiens 0.449
CHEMBL1987 Prostanoid FP receptor Homo sapiens 0.411
CHEMBL283 Matrix metalloproteinase 3 Homo sapiens 0.374
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.358



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL213 Beta-1 adrenergic receptor Homo sapiens 1.000
CHEMBL246 Beta-3 adrenergic receptor Homo sapiens 1.000
CHEMBL210 Beta-2 adrenergic receptor Homo sapiens 1.000
CHEMBL3373 Beta-2 adrenergic receptor Bos taurus 1.000
CHEMBL3252 Beta-1 adrenergic receptor Rattus norvegicus 1.000
CHEMBL4302 P-glycoprotein 1 Homo sapiens 1.000
CHEMBL1878 Calcium sensing receptor Homo sapiens 1.000
CHEMBL5414 Beta-2 adrenergic receptor Cavia porcellus 0.998
CHEMBL3892 Sphingosine 1-phosphate receptor Edg-3 Homo sapiens 0.997
CHEMBL3815 Squalene synthetase Rattus norvegicus 0.995
CHEMBL4333 Sphingosine 1-phosphate receptor Edg-1 Homo sapiens 0.988
CHEMBL2289 Beta-2 adrenergic receptor Canis lupus familiaris 0.915
CHEMBL1987 Prostanoid FP receptor Homo sapiens 0.750
CHEMBL283 Matrix metalloproteinase 3 Homo sapiens 0.330
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.321

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
295.4 295.1784 1.53 9 67.79 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
5 2 0 5 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
13.88 9.43 1.92 -.18 1 21 0.68

Structural Alerts

There are 2 structural alerts for CHEMBL768. To view alerts please click here.

Compound Cross References

ATC C - CARDIOVASCULAR SYSTEM
C07 - BETA BLOCKING AGENTS
C07A - BETA BLOCKING AGENTS
C07AB - Beta blocking agents, selective
C07AB09 - esmolol

ChemSpider ChemSpider:AQNDDEOPVVGCPG-UHFFFAOYSA-N
DailyMed esmolol hydrochloride
Wikipedia Esmolol

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL768



ACToR 103598-03-4 81147-92-4
BindingDB 50404796
ChEBI 88206
DrugBank DB00187
DrugCentral 1054
eMolecules 901849
EPA CompTox Dashboard DTXSID4022995
Guide to Pharmacology 7178
Human Metabolome Database HMDB0014333
IBM Patent System 355AEF97732963A985F844487DEB576E
KEGG Ligand C06980
LINCS LSM-4957
Nikkaji J32.840E
PharmGKB PA449500
PubChem 59768
PubChem: Thomson Pharma 14825011
SureChEMBL SCHEMBL3605

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