METOPROLOL

Search structure
Synonyms:
Status: Approved (1978)
Entry Type: Small molecule
Molecule Category: Parent
ATC: C07AB02
UNII: GEB06NHM23

Structure
InChI Key IUBSYMUCCVWXPE-UHFFFAOYSA-N
Smile COCCc1ccc(OCC(O)CNC(C)C)cc1
InChI
InChI=1S/C15H25NO3/c1-12(2)16-10-14(17)11-19-15-6-4-13(5-7-15)8-9-18-3/h4-7,12,14,16-17H,8-11H2,1-3H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C15H25NO3
Molecular Weight 267.37
AlogP 1.61
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 9.0
Polar Surface Area 50.72
Molecular species BASE
Aromatic Rings 1.0
Heavy Atoms 19.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) 1.88 - EXP
Henry's Law Constant 1.40E-13 atm-m3/mole EST
Atmospheric OH Rate Constant 1.47E-10 cm3/molecule-sec EST
Water Solubility 1.69E+04 mg/L EXP
Vapor Pressure 2.88E-07 mm Hg EST

Pharmacology

Primary Target
β1-adrenoceptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D6
- 24000 - - -
Enzyme
- 24000 - - -
Ion channel Voltage-gated ion channel Voltage-gated sodium channel
- - - - 14-47
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Adrenergic receptor
- 190-320 15-724 398-5012 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Serotonin receptor
- - - 10000 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 20
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 32

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Cardiovascular Diseases 4 D002318 ClinicalTrials
Heart Failure 3 D006333 ClinicalTrials
Diabetes Mellitus, Type 2 3 D003924 ClinicalTrials
Myocardial Infarction 3 D009203 ClinicalTrials
Non-ST Elevated Myocardial Infarction 3 D000072658 ClinicalTrials
Atherosclerosis 3 D050197 ClinicalTrials
Hypercholesterolemia 3 D006937 ClinicalTrials
ST Elevation Myocardial Infarction 3 D000072657 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Heart Failure 3 D006333 ClinicalTrials
Coronary Disease 3 D003327 ClinicalTrials
Atrial Fibrillation 3 D001281 ClinicalTrials
Hypertension 3 D006973 ClinicalTrials
Ventricular Fibrillation 2 D014693 ClinicalTrials
Hypotension, Orthostatic 2 D007024 ClinicalTrials
Obesity 2 D009765 ClinicalTrials
Heart Diseases 2 D006331 ClinicalTrials
Death, Sudden, Cardiac 2 D016757 ClinicalTrials
beta-Thalassemia 2 D017086 ClinicalTrials
Tachycardia, Ventricular 2 D017180 ClinicalTrials
Prader-Willi Syndrome 2 D011218 ClinicalTrials
Premature Birth 2 D047928 ClinicalTrials
Arrhythmias, Cardiac 2 D001145 ClinicalTrials
HIV Infections 1 D015658 ClinicalTrials
Malaria 1 D008288 ClinicalTrials
Psoriasis 1 D011565 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
Dermatitis, Atopic 1 D003876 ClinicalTrials

Related Entries

MCS

Salt
Salt

Cross References

Resources Reference
CAS NUMBER 51384-51-1
ChEBI 6904
ChEMBL CHEMBL13
DrugBank DB00264
DrugCentral 1786
EPA CompTox DTXSID2023309
FDA SRS GEB06NHM23
Human Metabolome Database HMDB0001932
Guide to Pharmacology 553
KEGG C07202
PharmGKB PA450480
PubChem 4171
SureChEMBL SCHEMBL4093
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