Compound Detail

CHEMBL631

PROPAFENONE

💊 Approved Drug

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💊 Approved Drug

CCCNCC(O)COc1ccccc1C(=O)CCc1ccccc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL631
Name	PROPAFENONE
Phase	Approved
Structure Type	MOL
InChI Key	JWHAUXFOSRPERK-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

GNF-Pf-4594 Propafenon hexal Propafenona Propafenone

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

341.4

MW (Da)

3.24

ALogP

HBA

HBD

58.6

PSA (Å²)

0.49

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1989
Availability	Prescription
Chirality	Racemic

Routes of Administration

Oral

Flags

Black Box Warning Natural Product

USAN Stem	-afenone
USAN Year	1988

Extended Properties

Molecular Formula	C21H27NO3
MW	341.45
Aromatic Rings	2
Heavy Atoms	25
NP-Likeness	-0.36

Indications

Arrhythmias, Cardiac Atrial Fibrillation Death, Sudden, Cardiac Heart Failure Myocardial Infarction Ventricular Fibrillation

ATC Classification

C01BC03

propafenone

Level 1: CARDIOVASCULAR SYSTEM

Level 2: CARDIAC THERAPY

Activity Summary

IC50 45 meas. best 7.28

Ki 17 meas. best 7.44

EC50 10 meas. best 6.93

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Beta-2 adrenergic receptor CHEMBL210	Ki	7.44	7.44	36.0	1
Beta-2 adrenergic receptor CHEMBL210	IC50	7.28	7.28	52.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	7.24	7.24	58.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	IC50	7.04	7.04	92.0	1
Plasmodium falciparum CHEMBL364	EC50	6.93	6.3067	116.5	6
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	6.73	6.73	187.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	6.7	6.7	201.0	1
Beta-1 adrenergic receptor CHEMBL213	Ki	6.69	6.69	205.0	1
ATP-dependent translocase ABCB1 CHEMBL4302	EC50	6.5	6.4867	320.0	3
Beta-3 adrenergic receptor CHEMBL246	Ki	6.5	6.5	318.0	1
ATP-dependent translocase ABCB1 CHEMBL4302	IC50	6.48	6.48	331.1	1
Beta-1 adrenergic receptor CHEMBL213	IC50	6.45	6.45	354.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	IC50	6.42	6.42	384.0	1
Beta-3 adrenergic receptor CHEMBL246	IC50	6.37	6.37	424.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	6.36	6.0	440.0	3
5-hydroxytryptamine receptor 2A CHEMBL224	IC50	6.18	6.18	654.0	1
Unchecked CHEMBL612545	Ki	6.16	5.9533	689.0	3
Unchecked CHEMBL612545	IC50	6.11	5.095	775.0	10
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	6.06	6.06	865.0	1
5-hydroxytryptamine receptor 1A CHEMBL273	Ki	6.03	6.03	935.0	1
CCRF-CEM/VCR-1000 CHEMBL614540	IC50	5.97	5.97	1080.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	5.96	5.96	1097.0	1
Sodium channel protein type 5 subunit alpha CHEMBL1980	IC50	5.92	5.7	1190.0	2
Alpha-1B adrenergic receptor CHEMBL315	Ki	5.85	5.85	1416.0	1
Sodium-dependent dopamine transporter CHEMBL238	Ki	5.83	5.83	1484.0	1
5-hydroxytryptamine receptor 1A CHEMBL273	IC50	5.79	5.79	1637.0	1
Voltage-dependent L-type calcium channel subunit alpha-1C CHEMBL2366456	IC50	5.75	5.75	1800.0	2
Sodium-dependent dopamine transporter CHEMBL238	IC50	5.73	5.73	1868.0	1
5-hydroxytryptamine receptor 6 CHEMBL3371	IC50	5.73	5.73	1863.0	1
Sulfonylurea receptor 2, Kir6.2 CHEMBL2095198	IC50	5.66	5.66	2200.0	1
Alpha-1A adrenergic receptor CHEMBL319	Ki	5.6	5.6	2488.0	1
Alpha-1B adrenergic receptor CHEMBL315	IC50	5.59	5.59	2558.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	IC50	5.58	5.58	2610.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	Ki	5.52	5.52	2991.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	IC50	5.52	5.52	3016.0	1
Cytochrome P450 1A2 CHEMBL3356	IC50	5.48	5.48	3292.0	1
ATP-dependent translocase ABCB1 CHEMBL4302	Ki	5.38	5.38	4200.0	1
Cytochrome P450 2D6 CHEMBL289	IC50	5.34	5.34	4603.4	1
Potassium channel subfamily K member 3 CHEMBL2321613	IC50	5.29	5.29	5100.0	1
Alpha-1A adrenergic receptor CHEMBL319	IC50	5.21	5.21	6147.0	1
Potassium channel subfamily K member 2 CHEMBL2321615	IC50	5.12	5.12	7600.0	1
Solute carrier family 22 member 1 CHEMBL5685	IC50	4.96	4.885	11100.0	2
CRMM-2 CHEMBL5465459	IC50	4.87	4.87	13400.0	2
CRMM-1 CHEMBL5441368	IC50	4.61	4.61	24700.0	2
Nuclear receptor subfamily 2 group E member 1 CHEMBL1961788	EC50	4.33	4.33	47000.0	1
L02 CHEMBL4296457	IC50	4.32	4.32	48200.0	1
Bile salt export pump CHEMBL6020	IC50	4.27	4.27	53700.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	44.1	mL.min-1.kg-1	Macaca
CL	62.0	mL.min-1.kg-1	Rattus norvegicus
CL	8.8	mL.min-1.kg-1	Homo sapiens
CL	16.0	mL.min-1.kg-1	Homo sapiens
CL	30.8	mL.min-1.kg-1	Canis lupus familiaris
CL	45.9	mL.min-1.kg-1	Mus musculus
CL	4.4	mL.min-1.kg-1	Homo sapiens
CL	46.0	mL.min-1.kg-1	Mus musculus
CL	4.0	mL.min-1.kg-1	Homo sapiens
CL	38.02	uL.min-1.(10^6cells)-1	Homo sapiens
CL	328.0	mL.min-1.kg-1	Homo sapiens
CL	47.8	uL.min-1.(10^6cells)-1	Homo sapiens
CL	10.0	mL.min-1.kg-1	Homo sapiens
CL	444.0	mL.min-1.g-1	Rattus norvegicus
CL	260.0	mL.min-1.g-1	Homo sapiens
CL	194.3	mL.min-1.kg-1	Homo sapiens
CL	180.9	mL.min-1.g-1	Homo sapiens
CL	162.8	mL.min-1.kg-1	Homo sapiens
CL	204.2	mL.min-1.kg-1	Homo sapiens
CL	226.9	mL.min-1.g-1	Homo sapiens
CL	106.3	mL.min-1.g-1	Homo sapiens
CL	0.0956	mL.min-1.kg-1	Homo sapiens
CL	193.2	mL.min-1.g-1	Homo sapiens
CL	173.8	mL.min-1.kg-1	Homo sapiens
CL	0.19	mL.min-1.kg-1	Homo sapiens
CL	1.184	mL.min-1.kg-1	Rattus norvegicus
CL	219.6	mL.min-1.g-1	Homo sapiens
CL	1145.8	mL.min-1.g-1	Mus musculus
CL	265.9	mL.min-1.g-1	Homo sapiens
CL	239.3	mL.min-1.kg-1	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Beta-2 adrenergic receptor	Ki	=	36.0	nM	7.44	DRUGMATRIX: Adrenergic beta2 radioligand binding (ligand: [3H] CGP-12177)	-
Beta-2 adrenergic receptor	IC50	=	52.0	nM	7.28	DRUGMATRIX: Adrenergic beta2 radioligand binding (ligand: [3H] CGP-12177)	-
5-hydroxytryptamine receptor 2B	Ki	=	58.0	nM	7.24	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ...	-
5-hydroxytryptamine receptor 2B	IC50	=	92.0	nM	7.04	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ...	-
Plasmodium falciparum	EC50	=	116.5	nM	6.93	NOVARTIS: Inhibition of Plasmodium falciparum W2 (drug-resistant) proliferation ...	18579783
5-hydroxytryptamine receptor 2A	Ki	=	187.0	nM	6.73	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ...	-
5-hydroxytryptamine receptor 2C	Ki	=	201.0	nM	6.7	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ...	-
Plasmodium falciparum	EC50	=	200.0	nM	6.7	Antimalarial activity against erythrocytic stage of chloroquine-resistant Plasmo...	21955244
Beta-1 adrenergic receptor	Ki	=	205.0	nM	6.69	DRUGMATRIX: Adrenergic beta1 radioligand binding (ligand: [125I] Cyanopindolol)	-
Plasmodium falciparum	EC50	=	252.1	nM	6.6	NOVARTIS: Inhibition of Plasmodium falciparum 3D7 (drug-susceptible) proliferati...	18579783
Beta-3 adrenergic receptor	Ki	=	318.0	nM	6.5	DRUGMATRIX: Adrenergic beta3 radioligand binding (ligand: [125I] Cyanopindolol)	-
ATP-dependent translocase ABCB1	EC50	=	320.0	nM	6.5	Compound was tested for inhibition of daunomycin efflux in the resistant human T...	9767638
ATP-dependent translocase ABCB1	IC50	=	331.13	nM	6.48	Inhibition of P-glycoprotein-mediated daunorubicin efflux from human CCRF-CEM/VC...	22452412
ATP-dependent translocase ABCB1	EC50	=	331.13	nM	6.48	SUPPLEMENTARY: Inhibition of P-glycoprotein expressed in MDR CCRF vcr1000 cells ...	-
ATP-dependent translocase ABCB1	EC50	=	329.0	nM	6.48	Inhibition of P-glycoprotein expressed in MDR CCRF vcr1000 cells by daunorubicin...	17352460
Beta-1 adrenergic receptor	IC50	=	354.0	nM	6.45	DRUGMATRIX: Adrenergic beta1 radioligand binding (ligand: [125I] Cyanopindolol)	-
5-hydroxytryptamine receptor 2C	IC50	=	384.0	nM	6.42	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ...	-
Beta-3 adrenergic receptor	IC50	=	424.0	nM	6.37	DRUGMATRIX: Adrenergic beta3 radioligand binding (ligand: [125I] Cyanopindolol)	-
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	440.0	nM	6.36	Inhibition of hERG K channel	21300721
5-hydroxytryptamine receptor 2A	IC50	=	654.0	nM	6.18	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ...	-

Literature References

PubMed	DOI	Target Context	# Activities
16472241	10.2174/1570163043334794	Hepatotoxicity	18
36868105	10.1016/j.ejmech.2023.115238	Unchecked	15
36868105	10.1016/j.ejmech.2023.115238	CRMM-1	15
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
18024584	10.1073/pnas.0709695104	H4	11
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
36680883	10.1016/j.ejmech.2022.115076	ADMET	10
3005568	10.1021/jm00152a013	Rattus norvegicus	9
36520541	10.1021/acs.jmedchem.2c01368	ADMET	9
30266543	10.1016/j.bmcl.2018.09.014	ADMET	9
30996859	10.1039/C8MD00556G	ADMET	8
16621936	10.1124/dmd.105.006619	ADMET	8
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
36868105	10.1016/j.ejmech.2023.115238	CRMM-2	7
32512482	10.1016/j.ejmech.2020.112423	ADMET	6
38385364	10.1021/acs.jmedchem.3c02153	ADMET	6
31855426	10.1021/acs.jmedchem.9b01269	ADMET	6
33314925	10.1021/acs.jmedchem.0c01647	ADMET	5
34653770	10.1016/j.ejmech.2021.113903	ADMET	5
30365885	10.1021/acs.jmedchem.8b01065	ADMET	5

Data from ChEMBL 36 via Core Engine