METOPROLOL

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Synonyms
Status
Molecule Category Free-form
ATC C07AB02
UNII GEB06NHM23
EPA CompTox DTXSID2023309

Structure

InChI Key IUBSYMUCCVWXPE-UHFFFAOYSA-N
Smiles 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
Assay Description Organism Bioactivity Reference
In vitro inhibitory activity against beta-1 adrenergic receptor measured by inhibition of positive chronotropic effect of isoproterenolin in isolated guinea pig atria Cavia porcellus 14.79 nM
Antagonist activity was determined against beta-1 adrenergic receptor in spontaneously beating rat atria None 22.91 nM
Cardioselectivity for the beta-1 adrenergic receptor was determined against isoprenaline (antagonism) in isolated rat atria None 22.91 nM
Beta-2 adrenergic receptor antagonistic activity on guinea pig tracheal chains Cavia porcellus 162.18 nM
In vitro beta-2 adrenergic receptor activity was determined by measuring inhibition of the isoproterenol induced relaxation in isolated guinea pig tracheal chains contracted with PGF2-alpha Cavia porcellus 162.18 nM
In vitro inhibitory activity against beta-2 adrenergic receptor was measured by the inhibition of isoproterenol-induced relaxation of PGF2-alpha contracted guinea pig trachea Cavia porcellus 162.18 nM
Cardioselectivity for the beta-1 adrenergic receptor was determined against isoprenaline (antagonism) in isolated guinea pig trachea Cavia porcellus 724.44 nM
Compound was tested for its Beta-1 adrenergic receptor antagonistic activity on guinea pig arteria Cavia porcellus 14.79 nM
In vitro beta-1 adrenergic receptor activity was determined via inhibition of the positive chronotropic actions of isoproterenol in isolated guinea pig atrial preparations Cavia porcellus 14.79 nM
Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on voltage dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex at 10 uM Cavia porcellus 14.0 %
Inhibition of binding of Batrachotoxinin [3H]BTX-B to high-affinity sites on voltage-dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex at 100 uM Cavia porcellus 47.3 %
The compound was tested for its ability to inhibit (-)-[3H]dihydroalprenolol binding to beta-adrenergic receptor sites in rat cortex None 500.0 nM
Tested for beta-1-adrenergic blocking effect by measuring the ability to inhibit the positive inotropic effect of isoproterenol on the isolated right atrium of guinea pigs Cavia porcellus 190.0 nM
Tested for beta-2-adrenergic blocking effect by measuring the ability to inhibit the relaxing effect of epinephrine on the isolated tracheal muscle of guinea pigs Cavia porcellus 320.0 nM
Antagonist activity at rat wild type beta-1 adrenergic receptor expressed in CHO cells Rattus norvegicus 398.11 nM
Antagonist activity at rat beta-1 adrenergic receptor W134A mutant expressed in CHO cells Rattus norvegicus 630.96 nM
Displacement of [125I]dihydroalprenolol from beta adrenergic receptor None 45.0 nM
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens 32.4 %
DRUGMATRIX: Adrenergic beta1 radioligand binding (ligand: [125I] Cyanopindolol) None 176.0 nM DRUGMATRIX: Adrenergic beta1 radioligand binding (ligand: [125I] Cyanopindolol) None 102.0 nM
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 28.1 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 19.8 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 30.5 %
Inhibition of Capra hircus (goat) brain DPP-3 using Arg-Arg-4mbetaNA as substrate assessed as liberation of 4mbetaNA from substrate at 0.5 mM Capra hircus 70.0 %
Antagonist activity against beta-1 adrenergic receptor (unknown origin) Homo sapiens 15.85 nM
Antagonist activity at rat beta1 adrenoceptor Rattus norvegicus 22.91 nM
Displacement of [3H]CGP12177 from mouse beta1 adrenoceptor expressed in HEK293T cell membranes Mus musculus 49.0 nM
Displacement of [3H]CGP12177 from human beta2 adrenoceptor expressed in CHO cell membranes Homo sapiens 220.0 nM
Displacement of [3H]CGP12177 from human beta1 adrenoceptor expressed in HEK293T cell membranes Homo sapiens 55.0 nM
Displacement of [3H]DHA from inactive/G protein-uncoupled human beta2-AR expressed in CHO cell membranes by liquid scintillation counting Homo sapiens 130.0 nM
Antiproliferative activity against human SK-MEL-5 cells assessed as cell growth inhibition at 100 uM incubated for 48 hrs by MTT assay relative to control Homo sapiens 38.8 %
Antiproliferative activity against human SK-MEL-28 cells assessed as cell growth inhibition at 100 uM measured after 48 hrs by MTT assay relative to control Homo sapiens 30.0 %
Antiproliferative activity against human A375 cells assessed as cell growth inhibition at 100 uM measured after 48 hrs by MTT assay relative to control Homo sapiens 26.3 %

Related Entries

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Cross References

Resources Reference
ChEBI 6904
ChEMBL CHEMBL13
DrugBank DB00264
DrugCentral 1786
FDA SRS GEB06NHM23
Human Metabolome Database HMDB0001932
Guide to Pharmacology 553
KEGG C07202
PharmGKB PA450480
PubChem 4171
SureChEMBL SCHEMBL4093
CONTENTS