TIMOLOL

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC C07AA06 S01ED01
UNII 5JKY92S7BR
EPA CompTox DTXSID4023674

Structure

InChI Key BLJRIMJGRPQVNF-JTQLQIEISA-N
Smiles CC(C)(C)NC[C@H](O)COc1nsnc1N1CCOCC1
InChI
InChI=1S/C13H24N4O3S/c1-13(2,3)14-8-10(18)9-20-12-11(15-21-16-12)17-4-6-19-7-5-17/h10,14,18H,4-9H2,1-3H3/t10-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C13H24N4O3S
Molecular Weight 316.43
AlogP 0.5
Hydrogen Bond Acceptor 8.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 6.0
Polar Surface Area 79.74
Molecular species BASE
Aromatic Rings 1.0
Heavy Atoms 21.0

Bioactivity

Mechanism of Action Action Reference
Beta-1 adrenergic receptor antagonist ANTAGONIST 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(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D6
- 11000 - - -
Ion channel Voltage-gated ion channel Voltage-gated sodium channel
- - - - 8
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Adrenergic receptor
- - 0-0 3-631 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Serotonin receptor
- - - 617 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 39
Assay Description Organism Bioactivity Reference
Binding affinity of a compound to rat brain 5-hydroxytryptamine 1A (serotonin) receptor assayed by radiolabeled [3H]-8-OH-DPAT ligand displacement None 616.6 nM
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 0.3631 nM
Beta-2 adrenergic receptor antagonistic activity on guinea pig tracheal chains Cavia porcellus 0.2399 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 0.2399 nM
In vitro inhibitory activity against beta-2 adrenoceptor was measured by the inhibition of isoproterenol-induced relaxation of PGF2-alpha contracted guinea pig trachea Cavia porcellus 0.166 nM
Compound was tested for its Beta-1 adrenergic receptor antagonistic activity on guinea pig atria Cavia porcellus 0.3631 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 0.3631 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 8.0 %
Antagonist activity at rat wild type beta-1 adrenergic receptor expressed in CHO cells Rattus norvegicus 3.162 nM
Antagonist activity at rat beta-1 adrenergic receptor Y356F mutant expressed in CHO cells Rattus norvegicus 15.85 nM
Antagonist activity at rat beta-1 adrenergic receptor Y356A mutant expressed in CHO cells Rattus norvegicus 630.96 nM
Antagonist activity at rat beta-1 adrenergic receptor W134A mutant expressed in CHO cells Rattus norvegicus 7.943 nM
Antagonist activity at rat beta-1 adrenergic receptor S190A mutant expressed in CHO cells Rattus norvegicus 31.62 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 39.0 %
DRUGMATRIX: Adrenergic beta1 radioligand binding (ligand: [125I] Cyanopindolol) None 2.603 nM DRUGMATRIX: Adrenergic beta1 radioligand binding (ligand: [125I] Cyanopindolol) None 1.503 nM
DRUGMATRIX: Adrenergic beta2 radioligand binding (ligand: [3H] CGP-12177) None 0.292 nM DRUGMATRIX: Adrenergic beta2 radioligand binding (ligand: [3H] CGP-12177) None 0.201 nM
DRUGMATRIX: Adrenergic beta3 radioligand binding (ligand: [125I] Cyanopindolol) None 452.0 nM DRUGMATRIX: Adrenergic beta3 radioligand binding (ligand: [125I] Cyanopindolol) None 339.0 nM
Displacement of [3H]-CGP12177 from human beta2 ADR expressed in HEK293T cell membrane after 90 mins by scintillation counting Homo sapiens 0.2089 nM
Displacement of [3H]-CGP12177 from human beta1 ADR expressed in HEK293T cell membranes after 90 mins by scintillation counting Homo sapiens 5.37 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 33.3 %
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 18.6 %
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 22.7 %

Cross References

Resources Reference
ChEBI 9599
ChEMBL CHEMBL499
DrugBank DB00373
DrugCentral 4061
FDA SRS 5JKY92S7BR
Guide to Pharmacology 565
KEGG C07141
PDB TIM
PharmGKB PA451690
PubChem 62933
SureChEMBL SCHEMBL4912
ZINC ZINC000000002176
CONTENTS