ChEMBL logo

ChEMBL

spacer
ChEMBL Statistics
  Loading Statistics...
spacer

Compound Report Card

Compound Name and Classification

Compound ID CHEMBL13
CHEMBL13
Compound Name METOPROLOL
ChEMBL Synonyms LOPRESOR SR | H 93/26 SUCCINATE | TENSOMEX | METOPROLOL TARTRATE | LOPRESOR | METOPROLOL FUMARATE | Metoprolol | Toprol | MEPRANIX 50 | LOPRESSOR | METOROS LS | METOROS | Toprol XL | TOPROL XL | BELOC COR | H-93/26 | BETALOC S.A. | BETALOC | ARBRALENE | CGP 2175C | TOPROL-XL | Lopressidone | MEPRANIX 100 | METOPROLOL SUCCINATE | CGP-2175E | Toprol-XL
Max Phase 4 (Approved)
Trade Names LOPRESOR SR | METOPROLOL SUCCINATE | MEPRANIX 100 | TOPROL-XL | ARBRALENE | BETALOC | BETALOC S.A. | BELOC COR | TOPROL XL | LOPRESSOR | METOROS | METOROS LS | Toprol XL | Toprol | MEPRANIX 50 | LOPRESOR | METOPROLOL TARTRATE | TENSOMEX
Molecular Formula C15H25NO3

Additional synonyms for CHEMBL13 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES COCCc1ccc(OCC(O)CNC(C)C)cc1
Standard InChI InChI=1S/C15H25NO3/c1-12(2)16-10-14(17)11-19-15-6-4-13(5-7-1 ...
Download InChI
Standard InChI Key IUBSYMUCCVWXPE-UHFFFAOYSA-N

Sources

  • British National Formulary
  • Curated Drug Metabolism Pathways
  • DrugMatrix
  • Gene Expression Atlas Compounds
  • 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


CHEMBL13

Molecule Features

CHEMBL13 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Racemic Mixture Prodrug:N Oral:Y Parenteral:Y Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

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

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Hypotension, OrthostaticD007024EFO:0005252orthostatic hypotension2ClinicalTrials
Ventricular FibrillationD014693EFO:0004287ventricular fibrillation2ClinicalTrials
Cardiovascular DiseasesD002318EFO:0000319cardiovascular disease4ATC
ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma3ClinicalTrials
Death, Sudden, CardiacD016757EFO:0004278sudden cardiac arrest2ClinicalTrials
Diabetic RetinopathyD003930EFO:0003770diabetic retinopathy1ClinicalTrials
Heart DiseasesD006331EFO:0003777heart disease2ClinicalTrials
Angina PectorisD000787EFO:0003913angina pectoris4DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
Diabetes Mellitus, Type 2D003924EFO:0001360type II diabetes mellitus2ClinicalTrials
HypertensionD006973EFO:0000537hypertension4DailyMed
DailyMed
DailyMed
DailyMed
DailyMed
ClinicalTrials
Myocardial InfarctionD009203EFO:0000612myocardial infarction4DailyMed
ClinicalTrials
Heart FailureD006333EFO:0003144heart failure3ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm1ClinicalTrials
Tachycardia, VentricularD017180EFO:0005306ventricular tachycardia2ClinicalTrials
Angina, StableD060050EFO:0003913angina pectoris0ClinicalTrials
MalariaD008288EFO:0001068malaria1ClinicalTrials
Vascular DiseasesD014652EFO:0004264vascular disease2ClinicalTrials
Arrhythmias, CardiacD0011452ClinicalTrials
Atrial FibrillationD001281EFO:0000275atrial fibrillation3ClinicalTrials
ObesityD009765EFO:0001073obesity2ClinicalTrials
Dermatitis, AtopicD003876EFO:0000274atopic eczema1ClinicalTrials
Prader-Willi SyndromeD011218Orphanet:739Prader-Willi syndrome2ClinicalTrials
PsoriasisD011565EFO:0000676psoriasis1ClinicalTrials
beta-ThalassemiaD017086Orphanet:848Beta-thalassemia2ClinicalTrials
Heart FailureD006333EFO:0000373congestive heart failure4DailyMed
DailyMed
DailyMed
DailyMed
DailyMed

Clinical Data

ClinicalTrials.gov METOPROLOL
The Cochrane Collaboration METOPROLOL

Metabolites for CHEMBL13

Open in full screen

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 CHEMBL13. 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
CHEMBL3892 Sphingosine 1-phosphate receptor Edg-3 Homo sapiens 1.000
CHEMBL3373 Beta-2 adrenergic receptor Bos taurus 1.000
CHEMBL1878 Calcium sensing receptor Homo sapiens 1.000
CHEMBL4333 Sphingosine 1-phosphate receptor Edg-1 Homo sapiens 0.999
CHEMBL5414 Beta-2 adrenergic receptor Cavia porcellus 0.999
CHEMBL3252 Beta-1 adrenergic receptor Rattus norvegicus 0.990
CHEMBL4302 P-glycoprotein 1 Homo sapiens 0.891
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.594
CHEMBL283 Matrix metalloproteinase 3 Homo sapiens 0.586
CHEMBL333 Matrix metalloproteinase-2 Homo sapiens 0.325
CHEMBL2274 Sphingosine 1-phosphate receptor Edg-8 Homo sapiens 0.205



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
CHEMBL1878 Calcium sensing receptor Homo sapiens 1.000
CHEMBL3892 Sphingosine 1-phosphate receptor Edg-3 Homo sapiens 1.000
CHEMBL3252 Beta-1 adrenergic receptor Rattus norvegicus 1.000
CHEMBL2289 Beta-2 adrenergic receptor Canis lupus familiaris 0.999
CHEMBL5414 Beta-2 adrenergic receptor Cavia porcellus 0.999
CHEMBL4333 Sphingosine 1-phosphate receptor Edg-1 Homo sapiens 0.999
CHEMBL5471 Beta-1 adrenergic receptor Cavia porcellus 0.999
CHEMBL4302 P-glycoprotein 1 Homo sapiens 0.988
CHEMBL283 Matrix metalloproteinase 3 Homo sapiens 0.798
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.656
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.586
CHEMBL332 Matrix metalloproteinase-1 Homo sapiens 0.562
CHEMBL3815 Squalene synthetase Rattus norvegicus 0.432
CHEMBL333 Matrix metalloproteinase-2 Homo sapiens 0.267

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
267.4 267.1834 1.61 9 50.72 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
4 2 0 4 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
13.89 9.43 1.63 -.47 1 19 0.71

Structural Alerts

There are 1 structural alerts for CHEMBL13. 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
C07AB02 - metoprolol

ChemSpider ChemSpider:IUBSYMUCCVWXPE-UHFFFAOYSA-N
DailyMed metoprolol succinate metoprolol tartrate
PubChem SID: 251919670
Wikipedia Metoprolol

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL13



ACToR 51384-51-1 37350-58-6
Atlas metoprolol
BindingDB 25756
Brenda 114656 151880
ChEBI 6904
DrugBank DB00264
DrugCentral 1786
eMolecules 902124
EPA CompTox Dashboard DTXSID2023309
Guide to Pharmacology 553
Human Metabolome Database HMDB0001932
IBM Patent System 69D97A6F838A6700A62199A24FDAFCC4
KEGG Ligand C07202
LINCS LSM-1259
Mcule MCULE-7999715986
MolPort MolPort-005-938-039
Nikkaji J31.137E
PharmGKB PA450480
PubChem 4171
PubChem: Thomson Pharma 14799183
SureChEMBL SCHEMBL4093

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