Compound Detail

CHEMBL1346

DARIFENACIN

💊 Approved Drug

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💊 Approved Drug

NC(=O)C(c1ccccc1)(c1ccccc1)[C@@H]1CCN(CCc2ccc3c(c2)CCO3)C1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL1346
Name	DARIFENACIN
Phase	Approved
Structure Type	MOL
InChI Key	HXGBXQDTNZMWGS-RUZDIDTESA-N
Therapeutic	✓ Yes

Known Names

Darifenacin Darifenacin extended release Darifenacina Darifenacine UK-88525 UK88525

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

426.6

MW (Da)

3.96

ALogP

HBA

HBD

55.6

PSA (Å²)

0.62

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	2004
Availability	Prescription
Chirality	Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product

USAN Stem	-fenacin
USAN Year	2004

Extended Properties

Molecular Formula	C28H30N2O2
MW	426.56
Aromatic Rings	3
Heavy Atoms	32
NP-Likeness	-0.56

Indications

Polyuria Urinary Incontinence Urinary Bladder, Overactive Amyotrophic Lateral Sclerosis

ATC Classification

G04BD10

darifenacin

Level 1: GENITO URINARY SYSTEM AND SEX HORMONES

Level 2: UROLOGICALS

Activity Summary

Ki 15 meas. best 9.13

EC50 10 meas. best 9.1

IC50 8 meas. best 7.1

Kd 2 meas. best 7.8

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Muscarinic acetylcholine receptor M3 CHEMBL245	Ki	9.13	9.0333	0.7	3
Beta-2 adrenergic receptor CHEMBL210	EC50	9.1	8.67	0.8	4
Beta-2 adrenergic receptor CHEMBL5414	EC50	9.0	9.0	1.0	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	Ki	8.64	8.64	2.3	1
Muscarinic acetylcholine receptor M3 CHEMBL320	Ki	8.6	8.6	2.5	1
Muscarinic acetylcholine receptor M1 CHEMBL216	Ki	8.26	8.26	5.5	2
Muscarinic acetylcholine receptor M4 CHEMBL1821	Ki	8.07	8.07	8.6	1
Muscarinic acetylcholine receptor M3 CHEMBL245	EC50	7.96	7.6033	11.0	3
Muscarinic acetylcholine receptor M2 CHEMBL211	Ki	7.92	7.5167	12.0	3
Beta-2 adrenergic receptor CHEMBL210	Ki	7.8	7.505	15.9	2
Muscarinic acetylcholine receptor M2 CHEMBL211	Kd	7.8	7.8	15.8	1
Beta-1 adrenergic receptor CHEMBL213	EC50	7.4	7.4	39.8	1
Muscarinic acetylcholine receptor M3 CHEMBL5498	Kd	7.3	7.3	50.1	1
Muscarinic acetylcholine receptor M2 CHEMBL309	Ki	7.2	7.2	63.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	7.1	6.45	79.4	2
Beta-1 adrenergic receptor CHEMBL213	Ki	6.75	6.75	180.0	1
Beta-1 adrenergic receptor CHEMBL213	IC50	6.5	6.5	316.2	1
Sodium channel protein type 5 subunit alpha CHEMBL1980	IC50	5.8	5.8	1584.9	1
Beta-1 adrenergic receptor CHEMBL3252	EC50	5.64	5.64	2310.0	1
A-type voltage-gated potassium channel KCND3 CHEMBL1964	IC50	4.9	4.9	12589.2	1
Voltage-gated potassium channel, IKs; KCNQ1(Kv7.1)/KCNE1(MinK) CHEMBL2221347	IC50	4.7	4.7	19952.6	1
D(2) dopamine receptor CHEMBL217	IC50	4.6	4.6	25118.9	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	12.0	mL.min-1.kg-1	Homo sapiens
CL	5.05	uL.min-1.(10^6cells)-1	Homo sapiens
CL	9.5	mL.min-1.g-1	Homo sapiens
CL	50.96	uL.min-1.(10^6cells)-1	Rattus norvegicus
CL	594.0	mL.min-1.kg-1	Homo sapiens
CL	6.0	mL.min-1.kg-1	Homo sapiens
CL	12.0	mL.min-1.kg-1	Homo sapiens
Fu	0.02	-	Homo sapiens
Fu	0.02	-	Homo sapiens
MRT	3.6	hr	Homo sapiens
T1/2	3.6	hr	Homo sapiens
T1/2	7.6	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Muscarinic acetylcholine receptor M3	Ki	=	0.74	nM	9.13	Displacement of [3H]N-methylscopolamine from human muscarinic M3 receptor transi...	32202101
Beta-2 adrenergic receptor	EC50	=	0.7943	nM	9.1	Agonist activity at human beta2 adrenergic receptor expressed in HEK293 cells as...	25629394
Beta-2 adrenergic receptor	EC50	=	0.82	nM	9.09	Agonist activity at human beta2-adrenoceptor expressed in HEK cells assessed as ...	21310610
Muscarinic acetylcholine receptor M3	Ki	=	0.84	nM	9.08	Binding affinity (Ki) against binding of [3H]NMS using membranes from CHO cells ...	11831911
Beta-2 adrenergic receptor	EC50	=	1.0	nM	9.0	Agonist activity at beta2 adrenoceptor in guinea pig tracheal rings assessed as ...	21277205
Muscarinic acetylcholine receptor M3	Ki	=	1.3	nM	8.89	Binding affinity to human muscarinic M3 receptor	16275087
Beta-2 adrenergic receptor	EC50	=	2.05	nM	8.69	Agonist activity at beta2-adrenoceptor in human bronchial smooth-muscle cell by ...	22932315
Muscarinic acetylcholine receptor M5	Ki	=	2.3	nM	8.64	Binding affinity (Ki) against binding of [3H]NMS using membranes from CHO cells ...	11831911
Muscarinic acetylcholine receptor M3	Ki	=	2.5	nM	8.6	Displacement of [3H]N-methylscopolamine from muscarinic M3 receptor in rat subma...	17629699
Muscarinic acetylcholine receptor M1	Ki	=	5.5	nM	8.26	Displacement of [3H]N-methylscopolamine from human muscarinic M1 receptor transi...	32202101
Muscarinic acetylcholine receptor M1	Ki	=	5.5	nM	8.26	Binding affinity (Ki) against binding of [3H]NMS using membranes from CHO cells ...	11831911
Muscarinic acetylcholine receptor M4	Ki	=	8.6	nM	8.07	Binding affinity (Ki) against binding of [3H]NMS using membranes from CHO cells ...	11831911
Muscarinic acetylcholine receptor M3	EC50	=	11.0	nM	7.96	Antagonist activity at muscarinic M3 receptor (unknown origin) expressed in HEK2...	32202101
Muscarinic acetylcholine receptor M2	Ki	=	12.0	nM	7.92	Displacement of [3H]N-methylscopolamine from human muscarinic M2 receptor transi...	32202101
Muscarinic acetylcholine receptor M2	Kd	=	15.85	nM	7.8	Antagonism at muscarinic M2 receptor in isolated guinea pig urinary bladder	16275087
Beta-2 adrenergic receptor	Ki	=	15.9	nM	7.8	Binding affinity to human beta2-adrenoceptor by radioligand binding assay	22932315
Beta-2 adrenergic receptor	EC50	=	15.85	nM	7.8	Agonist activity at human adrenergic beta2 receptor expressed in H292 cells asse...	21723724
Muscarinic acetylcholine receptor M3	EC50	=	32.0	nM	7.5	Agonist activity at human muscarinic M3 receptor expressed in HEK293 cells asses...	32202101
Beta-1 adrenergic receptor	EC50	=	39.81	nM	7.4	Agonist activity at adrenergic beta1 receptor	21723724
Muscarinic acetylcholine receptor M3	EC50	=	45.0	nM	7.35	Antagonist activity at human muscarinic M3 receptor expressed in HEK293 assessed...	32202101

Literature References

PubMed	DOI	Target Context	# Activities
-	10.5281/zenodo.13943903	ADMET	89
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
32202101	10.1021/acs.jmedchem.0c00297	Muscarinic acetylcholine receptor M3	8
-	10.6019/CHEMBL3301361	ADMET	6
25629394	10.1021/jm501915g	Cavia porcellus	6
-	10.6019/CHEMBL3301361	No relevant target	4
22932315	10.1016/j.bmcl.2012.07.096	Beta-2 adrenergic receptor	4
18426954	10.1124/dmd.108.020479	ADMET	4
-	10.6019/CHEMBL4651402	SARS-CoV-2	4
23454828	10.1124/dmd.112.050278	Homo sapiens	3
21723724	10.1016/j.bmcl.2011.05.097	Unchecked	3
37468498	10.1038/s41467-023-40064-9	Cannabinoid receptor 1	3
37468498	10.1038/s41467-023-40064-9	5-hydroxytryptamine receptor 2A	3
37468498	10.1038/s41467-023-40064-9	Alpha-2A adrenergic receptor	3
37468498	10.1038/s41467-023-40064-9	Muscarinic acetylcholine receptor M2	3
16220976	10.1021/jm050099q	Rattus norvegicus	3
37468498	10.1038/s41467-023-40064-9	5-hydroxytryptamine receptor 2B	3
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
16275087	10.1016/j.bmcl.2005.09.079	Muscarinic acetylcholine receptor M2	2
25087753	10.1016/j.vascn.2014.07.002	Voltage-gated inwardly rectifying potassium channel KCNH2	2

Data from ChEMBL 36 via Core Engine