PINDOLOL

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC C07AA03
UNII BJ4HF6IU1D
EPA CompTox DTXSID8023476

Structure

InChI Key JZQKKSLKJUAGIC-UHFFFAOYSA-N
Smiles CC(C)NCC(O)COc1cccc2[nH]ccc12
InChI
InChI=1S/C14H20N2O2/c1-10(2)16-8-11(17)9-18-14-5-3-4-13-12(14)6-7-15-13/h3-7,10-11,15-17H,8-9H2,1-2H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C14H20N2O2
Molecular Weight 248.33
AlogP 1.91
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 6.0
Polar Surface Area 57.28
Molecular species BASE
Aromatic Rings 2.0
Heavy Atoms 18.0

Bioactivity

Mechanism of Action Action Reference
Beta-1 adrenergic receptor partial agonist PARTIAL AGONIST DailyMed
Protein: Beta-2 adrenergic receptor
Description: Beta-2 adrenergic receptor
Organism : Homo sapiens
P07550 ENSG00000169252
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
- - 1-1 0 84
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Serotonin receptor
27 - 63 22-110 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - -25-85
Assay Description Organism Bioactivity Reference
Stimulation of [35S]- GIPyS binding to cloned human 5-hydroxytryptamine 1A receptor stably expressed in HeLa cells Homo sapiens 27.0 nM
Evaluated for binding affinity towards rat cortical membranes at 5-hydroxytryptamine 1 receptor binding site by using [3H]-5-HT as a radioligand. None 100.0 nM
Displacement of specific [3H]- 5-HT binding to cloned human 5-hydroxytryptamine 1A receptor stably expressed in HeLa cells Homo sapiens 24.0 nM
Evaluated for the binding affinity to hippocampus striatal membranes at 5-hydroxytryptamine 1A receptor binding site by using [3H]-8-OH- DPAT as a radioligand. None 20.0 nM
Binding affinity of a compound to rat brain 5-hydroxytryptamine 1A (serotonin) receptor assayed by radiolabeled [3H]-8-OH-DPAT ligand displacement None 21.88 nM
Binding affinity (Ki) to rat cortical membranes at 5-HT1B binding site by using [125 I] ICYP as a radioligand. None 80.0 nM
In vitro for binding affinity against beta adrenergic receptor in rat cerebellum Rattus norvegicus 1.0 nM
In vitro for binding affinity against beta adrenergic receptor in rat cortex Rattus norvegicus 1.0 nM
Beta-adrenergic receptor blockade activity in conscious normotensive rats at a dose of 1.25 mg/kg Rattus norvegicus 84.0 %
Inhibition constant against 5-hydroxytryptamine 1A receptor Homo sapiens 110.0 nM
Displacement of [3H]DPAT from human 5HT1A receptor Homo sapiens 22.4 nM
Antagonist activity at human 5HT1A expressed in mouse LM(tK-) cells assessed as inhibition of 5-HT-stimulated [35S]GTP-gamma-S binding Homo sapiens 81.1 nM
Binding affinity at human adrenergic beta-1 receptor Homo sapiens 0.52 nM
Binding affinity at human adrenergic beta2 receptor Homo sapiens 0.4 nM
Binding affinity to 5HT1A receptor None 63.1 nM
Displacement of [3H]-CGP 12177 from human beta-1 adrenergic receptor expressed in CHOK1 cells Homo sapiens 2.63 nM
Displacement of [3H]-CGP 12177 from human beta-2 adrenergic receptor expressed in CHOK1 cells Homo sapiens 0.537 nM
Displacement of [3H]-CGP 12177 from human beta-3 adrenergic receptor expressed in CHOK1 cells Homo sapiens 165.96 nM
Antagonist activity at human beta-1 adrenergic receptor site 1 expressed in cimeterol-stimulated CHO-K1 cells assessed as CRE-SPAP level by fluorescence correlation spectroscopic analysis Homo sapiens 2.399 nM
Antagonist activity at human beta-2 adrenergic receptor expressed in salbutamol-stimulated CHO-K1 cells assessed as CRE-SPAP level by fluorescence correlation spectroscopic analysis Homo sapiens 0.6607 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: [3H] 8-OH-DPAT) None 48.0 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: [3H] 8-OH-DPAT) None 27.0 nM
DRUGMATRIX: Adrenergic beta1 radioligand binding (ligand: [125I] Cyanopindolol) None 0.921 nM DRUGMATRIX: Adrenergic beta1 radioligand binding (ligand: [125I] Cyanopindolol) None 0.532 nM
DRUGMATRIX: Adrenergic beta2 radioligand binding (ligand: [3H] CGP-12177) None 0.549 nM DRUGMATRIX: Adrenergic beta2 radioligand binding (ligand: [3H] CGP-12177) None 0.377 nM
DRUGMATRIX: Adrenergic beta3 radioligand binding (ligand: [125I] Cyanopindolol) None 88.0 nM DRUGMATRIX: Adrenergic beta3 radioligand binding (ligand: [125I] Cyanopindolol) None 66.0 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 -24.7 %
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 24.5 %
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 -10.8 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 85.04 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 97.58 %
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 7.44 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 5.35 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 17.1 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 13.32 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 24.44 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 3.5 %
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 -9.82 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 11.03 %
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 -0.11 % 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 -0.11 %

Related Entries

Cross References

Resources Reference
ChEBI 8214
ChEMBL CHEMBL500
DrugBank DB00960
DrugCentral 2176
FDA SRS BJ4HF6IU1D
Human Metabolome Database HMDB0015095
Guide to Pharmacology 91
KEGG C07445
PharmGKB PA450966
PubChem 4828
SureChEMBL SCHEMBL5219
ZINC ZINC00056646
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