DARIFENACIN

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Synonyms
Status
Molecule Category Free-form
ATC G04BD10
UNII APG9819VLM
EPA CompTox DTXSID2048290

Structure

InChI Key HXGBXQDTNZMWGS-RUZDIDTESA-N
Smiles NC(=O)C(c1ccccc1)(c1ccccc1)[C@@H]1CCN(CCc2ccc3c(c2)CCO3)C1
InChI
InChI=1S/C28H30N2O2/c29-27(31)28(23-7-3-1-4-8-23,24-9-5-2-6-10-24)25-14-17-30(20-25)16-13-21-11-12-26-22(19-21)15-18-32-26/h1-12,19,25H,13-18,20H2,(H2,29,31)/t25-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C28H30N2O2
Molecular Weight 426.56
AlogP 3.96
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 7.0
Polar Surface Area 55.56
Molecular species BASE
Aromatic Rings 3.0
Heavy Atoms 32.0
Assay Description Organism Bioactivity Reference
Binding affinity (Ki) against binding of [3H]NMS using membranes from CHO cells expressing cloned human Muscarinic acetylcholine receptor M1 Homo sapiens 5.5 nM
Binding affinity (Ki) against binding of [3H]NMS using membranes from CHO cells expressing cloned human Muscarinic acetylcholine receptor M3 Homo sapiens 0.84 nM
Binding affinity (Ki) against binding of [3H]NMS using membranes from CHO cells expressing cloned human Muscarinic acetylcholine receptor M4 Homo sapiens 8.6 nM
Binding affinity (Ki) against binding of [3H]NMS using membranes from CHO cells expressing cloned human Muscarinic acetylcholine receptor M5 Homo sapiens 2.3 nM
Binding affinity (Ki) against binding of [3H]NMS to membranes from CHO cells expressing cloned human Muscarinic acetylcholine receptor M2 Homo sapiens 47.0 nM
Binding affinity to human muscarinic M3 receptor Homo sapiens 1.3 nM
Binding affinity to human muscarinic M2 receptor Homo sapiens 50.0 nM
Antagonism at muscarinic M2 receptor in isolated guinea pig urinary bladder Cavia porcellus 15.85 nM
Antagonism in muscarinic M3 receptor in guinea pig left atria Cavia porcellus 50.12 nM
Displacement of [3H]N-methylscopolamine from muscarinic M3 receptor in rat submandibular gland Rattus norvegicus 2.5 nM
Displacement of [3H]N-methylscopolamine from muscarinic M2 receptor in rat heart Rattus norvegicus 63.0 nM
Agonist activity at beta2 adrenoceptor in guinea pig tracheal rings assessed as vasorelaxation Cavia porcellus 1.0 nM
Bronchocoprotective activity in guinea pig assessed as inhibition of acetylcholine-induced bronchoconstriction administered by aerosol after 4 hrs Cavia porcellus 5.0 ug.mL-1
Bronchocoprotective activity in guinea pig assessed as inhibition of acetylcholine-induced bronchoconstriction administered by aerosol after 24 hrs Cavia porcellus 12.0 ug.mL-1
Displacement of [3H]-dihydroalprenolol from human beta2-adrenoceptor expressed in HEK cells after 4 hrs Homo sapiens 61.0 nM
Agonist activity at human beta2-adrenoceptor expressed in HEK cells assessed as increase of cAMP level after 10 mins by radioimmunoassay Homo sapiens 0.82 nM
Agonist activity at human adrenergic beta2 receptor expressed in H292 cells assessed as stimulation of cAMP accumulation after 60 mins Homo sapiens 15.85 nM
Binding affinity to adrenergic beta1 receptor None 316.23 nM
Agonist activity at adrenergic beta1 receptor None 39.81 nM
Agonist activity at beta2-adrenoceptor in human bronchial smooth-muscle cell by cAMP assay Homo sapiens 2.05 nM
Binding affinity to human beta2-adrenoceptor by radioligand binding assay Homo sapiens 15.9 nM
Binding affinity to human beta1-adrenoceptor by radioligand binding assay Homo sapiens 180.0 nM
Agonist activity at human beta2 adrenergic receptor expressed in HEK293 cells assessed as cAMP accumulation using [125I]cAMP by scintillation counting Homo sapiens 0.7943 nM
Inhibition of rapid delayed inward rectifying potassium current (IKr) measured using manual patch clamp assay None 79.43 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 7.91 %
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 0.2 % 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 0.2 %
Displacement of [3H]N-methylscopolamine from human muscarinic M1 receptor transiently expressed in HEK293T cell membranes incubated for 1 hr by scintillation counting method Homo sapiens 5.5 nM
Displacement of [3H]N-methylscopolamine from human muscarinic M2 receptor transiently expressed in HEK293T cell membranes incubated for 1 hr by scintillation counting method Homo sapiens 12.0 nM
Displacement of [3H]N-methylscopolamine from human muscarinic M3 receptor transiently expressed in HEK293T cell membranes incubated for 1 hr by scintillation counting method Homo sapiens 0.74 nM
Agonist activity at human muscarinic M3 receptor expressed in HEK293 cells assessed as increase in IP1 accumulation incubated for 90 min by TR-HTRF assay Homo sapiens 32.0 nM
Antagonist activity at human muscarinic M3 receptor expressed in HEK293 assessed as inhibition of carbachol-induced IP1 accumulation preincubated for 30 mins followed by carbachol addition and measured after 90 mins by TR-HTRF assay Homo sapiens 45.0 nM
Antagonist activity at muscarinic M3 receptor (unknown origin) expressed in HEK293 cells coexpressing EA tagged beta-arrestin2 assessed as inhibition of carbachol-induced beta-arrestin2 recruitment preincubated for 30 mins followed by carbachol addition and measured after 90 mins by PathHunter assay Homo sapiens 11.0 nM

Cross References

Resources Reference
ChEBI 391960
ChEMBL CHEMBL1346
DrugBank DB00496
DrugCentral 784
FDA SRS APG9819VLM
Human Metabolome Database HMDB0014639
Guide to Pharmacology 321
PharmGKB PA164774901
PubChem 444031
SureChEMBL SCHEMBL56574
ZINC ZINC000001996117
CONTENTS