ATENOLOL

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC C07AB03
UNII 50VV3VW0TI
EPA CompTox DTXSID2022628

Structure

InChI Key METKIMKYRPQLGS-UHFFFAOYSA-N
Smiles CC(C)NCC(O)COc1ccc(CC(N)=O)cc1
InChI
InChI=1S/C14H22N2O3/c1-10(2)16-8-12(17)9-19-13-5-3-11(4-6-13)7-14(15)18/h3-6,10,12,16-17H,7-9H2,1-2H3,(H2,15,18)

Physicochemical Descriptors

Property Name Value
Molecular Formula C14H22N2O3
Molecular Weight 266.34
AlogP 0.45
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 8.0
Polar Surface Area 84.58
Molecular species BASE
Aromatic Rings 1.0
Heavy Atoms 19.0

Metabolites Network

visNetwork

Bioactivity

Mechanism of Action Action Reference
Beta-1 adrenergic receptor antagonist ANTAGONIST DailyMed
Protein: Beta-1 adrenergic receptor
Description: Beta-1 adrenergic receptor
Organism : Homo sapiens
P08588 ENSG00000043591
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Adrenergic receptor
- 2-1740 24-159 150-1514 -
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
- - - - 21-78
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - -
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 23.99 nM
Activity at beta-1 adrenergic receptor Cavia porcellus 158.49 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 23.99 nM
Percent inhibition against Beta-1 adrenergic receptor at 1 uM Homo sapiens 1.77 nM
Displacement of radiolabeled atenolol from human adrenergic beta-1 receptor Homo sapiens 600.0 nM Displacement of radiolabeled atenolol from human adrenergic beta-1 receptor Homo sapiens 430.0 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 -4.6 %
Displacement of [3H](-)-CGP12177 from human adrenergic beta1 receptor Homo sapiens 170.0 nM
DRUGMATRIX: Adrenergic beta1 radioligand binding (ligand: [125I] Cyanopindolol) None 758.0 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 20.6 %
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 7.1 %
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 6.8 %
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 %
Binding affinity to human adrenergic alpha1 receptor by radioligand displacement assay Homo sapiens 230.0 nM
Binding affinity to human adrenergic beta1 receptor by radioligand displacement assay Homo sapiens 150.0 nM Binding affinity to human adrenergic beta1 receptor by radioligand displacement assay Homo sapiens 260.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 78.26 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 93.81 %
Antagonist activity at beta1 adrenoceptor in guinea pig atrium assessed as inhibition of isoproterenol-induced response after 20 mins Cavia porcellus 43.65 nM
Displacement of [3H](-)CGP12177 from human recombinant Beta-1 adrenergic receptor expressed in HEK293 cells Homo sapiens 210.0 nM
Displacement of [3H]CGP 12177 from human recombinant beta1 adrenergic receptor expressed in HEK293 cells measured after 60 mins by scintillation counting method Homo sapiens 210.0 nM
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 9.69 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 2.4 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 8.57 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 6.08 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 19.94 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 3.26 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans 1.62 %
Displacement of [3H]DHA from inactive/G protein-uncoupled human beta2-AR expressed in CHO cell membranes by liquid scintillation counting Homo sapiens 260.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 6.73 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 3.46 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.01 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.02 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.02 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.01 %
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 5.2 %
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 6.9 %
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 8.6 %

Related Entries

Environmental Exposure

Environmental Exposure Map
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Cross References

Resources Reference
ChEBI 2904
ChEMBL CHEMBL24
DrugBank DB00335
DrugCentral 255
FDA SRS 50VV3VW0TI
Human Metabolome Database HMDB0001924
Guide to Pharmacology 548
PharmGKB PA448499
PubChem 2249
SureChEMBL SCHEMBL4362
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