Compound Detail

CHEMBL633

AMIODARONE

💊 Approved Drug

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💊 Approved Drug

CCCCc1oc2ccccc2c1C(=O)c1cc(I)c(OCCN(CC)CC)c(I)c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL633
Name	AMIODARONE
Phase	Approved
Structure Type	MOL
InChI Key	IYIKLHRQXLHMJQ-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Amiodarona Amiodarone

Targets

139

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

645.3

MW (Da)

6.94

ALogP

HBA

HBD

42.7

PSA (Å²)

0.17

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1985
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product

USAN Stem	-arone
USAN Year	1987

Extended Properties

Molecular Formula	C25H29I2NO3
MW	645.32
Aromatic Rings	3
Heavy Atoms	31
NP-Likeness	-0.38

Indications

Arrhythmias, Cardiac Arrhythmias, Cardiac Atrial Fibrillation Atrial Flutter Cardiomyopathies Death, Sudden, Cardiac Heart Arrest Heart Diseases Heart Failure Heart Failure Myocardial Infarction Tachycardia, Ventricular Ventricular Fibrillation Amyloidosis, Familial Hemorrhagic Fever, Ebola Severe Acute Respiratory Syndrome Tachycardia, Supraventricular Coronary Disease

ATC Classification

C01BD01

amiodarone

Level 1: CARDIOVASCULAR SYSTEM

Level 2: CARDIAC THERAPY

Activity Summary

IC50 80 meas. best 7.52

Ki 52 meas. best 9.0

EC50 7 meas. best 6.1

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	9.0	8.195	1.0	2
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase CHEMBL4931	Ki	7.6	7.6	25.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	7.52	5.704	30.0	5
Unchecked CHEMBL612545	Ki	7.32	6.535	48.0	6
Unchecked CHEMBL612545	IC50	7.27	6.03	54.0	8
C-8 sterol isomerase ERG2 CHEMBL3224	Ki	7.21	7.21	62.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	IC50	7.01	7.01	97.0	1
Alpha-2A adrenergic receptor CHEMBL1867	Ki	6.93	6.93	117.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	6.67	6.67	212.0	1
Voltage-gated L-type calcium channel CHEMBL2095229	IC50	6.57	6.145	270.0	2
Alpha-2A adrenergic receptor CHEMBL1867	IC50	6.51	6.51	312.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	IC50	6.39	6.39	404.0	1
D(3) dopamine receptor CHEMBL234	Ki	6.39	6.39	410.0	1
Muscarinic acetylcholine receptor M4 CHEMBL1821	Ki	6.3	6.3	506.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	6.23	6.23	587.0	1
Thyroid hormone receptor beta CHEMBL1947	IC50	6.22	6.22	600.0	1
Muscarinic acetylcholine receptor M1 CHEMBL216	Ki	6.2	6.2	629.0	1
Thyroid hormone receptor alpha CHEMBL1860	IC50	6.19	6.19	650.0	1
Muscarinic acetylcholine receptor M3 CHEMBL245	Ki	6.17	6.17	679.0	1
Trypanosoma cruzi CHEMBL368	EC50	6.1	6.1	800.0	1
Tyrosine-protein kinase Fyn CHEMBL1841	IC50	6.09	6.09	817.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	IC50	6.04	6.04	923.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	5.99	5.99	1026.0	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	Ki	5.97	5.97	1077.0	1
D(3) dopamine receptor CHEMBL234	IC50	5.92	5.92	1208.0	1
Sodium-dependent serotonin transporter CHEMBL228	Ki	5.91	5.91	1224.0	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	IC50	5.82	5.82	1499.0	1
Cytochrome P450 2C8 CHEMBL3721	Ki	5.82	5.055	1500.0	2
Solute carrier organic anion transporter family member 1A4 CHEMBL1781860	Ki	5.75	5.75	1800.0	1
Muscarinic acetylcholine receptor M2 CHEMBL211	Ki	5.74	5.74	1806.0	1
Sodium-dependent dopamine transporter CHEMBL238	Ki	5.7	5.7	1990.0	1
ATP-dependent translocase ABCB1 CHEMBL2573	Ki	5.68	5.68	2100.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	Ki	5.65	5.65	2252.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	IC50	5.64	5.64	2271.0	1
Sodium-dependent serotonin transporter CHEMBL228	IC50	5.64	5.64	2305.0	1
CHRC5 cell line CHEMBL614457	EC50	5.64	5.64	2300.0	1
Sodium-dependent dopamine transporter CHEMBL238	IC50	5.6	5.6	2505.0	1
Plasmodium falciparum CHEMBL364	IC50	5.6	5.6	2500.0	1
Muscarinic acetylcholine receptor M1 CHEMBL216	IC50	5.58	5.58	2613.0	1
Trypanosoma cruzi CHEMBL368	IC50	5.57	5.31	2700.0	2
Delta-type opioid receptor CHEMBL236	Ki	5.55	5.55	2825.0	1
Muscarinic acetylcholine receptor M3 CHEMBL245	IC50	5.5	5.5	3201.0	1
ATP-dependent translocase ABCB1 CHEMBL4302	Ki	5.5	5.37	3200.0	2
NAD-dependent protein deacetylase sirtuin-3, mitochondrial CHEMBL4461	EC50	5.49	5.49	3250.0	1
Lethal factor CHEMBL4372	IC50	5.46	5.46	3500.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	IC50	5.45	5.45	3590.0	1
Muscarinic acetylcholine receptor M4 CHEMBL1821	IC50	5.44	5.44	3630.0	1
C-C chemokine receptor type 2 CHEMBL4015	Ki	5.37	5.37	4285.0	1
D(1A) dopamine receptor CHEMBL2056	Ki	5.34	5.34	4571.0	1
Sodium channel alpha subunit CHEMBL2331043	IC50	5.32	5.32	4800.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	21121.32	ng.hr.mL-1	Homo sapiens
CL	1.9	mL.min-1.kg-1	Homo sapiens
CL	1.9	mL.min-1.kg-1	Homo sapiens
CL	1.9	mL.min-1.kg-1	Homo sapiens
CL	1.9	mL.min-1.kg-1	Homo sapiens
CL	1.9	mL.min-1.kg-1	Homo sapiens
CL	10.7	mL.min-1.kg-1	Macaca
CL	14.7	mL.min-1.kg-1	Rattus norvegicus
CL	14.7	mL.min-1.kg-1	Canis lupus familiaris
CL	11.0	uL.min-1.(10^6cells)-1	Rattus norvegicus
CL	27.0	mL.min-1.g-1	Homo sapiens
F	79.0	%	Homo sapiens
F	50.0	%	Homo sapiens
Fu	0.0002	-	-
Fu	1e-06	-	-
Fu	0.0002	-	Homo sapiens
Fu	0.0002	-	Homo sapiens
Fu	0.0002	-	Homo sapiens
Fu	0.0001	-	Homo sapiens
Fu	0.0012	-	Canis lupus familiaris
MRT	620.0	hr	Homo sapiens
T1/2	820.0	hr	Homo sapiens
T1/2	720.0	hr	Homo sapiens
T1/2	35.0	hr	Homo sapiens
T1/2	4.0	hr	Homo sapiens
T1/2	17.0	hr	Homo sapiens
Tmax	7.3	hr	Homo sapiens
Vd	0.9	L.kg-1	Oryctolagus cuniculus
Vd	148.0	L.kg-1	Oryctolagus cuniculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Sigma non-opioid intracellular receptor 1	Ki	=	1.0	nM	9.0	Affinity for sigma receptor type 1 of guinea pig using [3H]ifenprodil or (+)-[3H...	16033255
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase	Ki	=	25.0	nM	7.6	Affinity for human EMP expressed in ERG2 deficient strain of Saccharomyces cerev...	16033255
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	30.0	nM	7.52	Inhibition of potassium current (Ikr) measured using whole-cell patch clamp expe...	21300721
Sigma non-opioid intracellular receptor 1	Ki	=	41.0	nM	7.39	DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol)	-
Unchecked	Ki	=	48.0	nM	7.32	DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand:...	-
Unchecked	IC50	=	54.0	nM	7.27	DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand:...	-
C-8 sterol isomerase ERG2	Ki	=	62.0	nM	7.21	Affinity for ERG2 of Saccharomyces cerevisiae using [3H]ifenprodil or (+)-[3H]pe...	16033255
Unchecked	Ki	=	72.0	nM	7.14	DRUGMATRIX: Sigma2 radioligand binding (ligand: [3H] Ifenprodil)	-
Sigma non-opioid intracellular receptor 1	IC50	=	97.0	nM	7.01	DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol)	-
Unchecked	Ki	=	106.0	nM	6.97	DRUGMATRIX: Calcium Channel Type L, Dihydropyridine radioligand binding (ligand:...	-
Alpha-2A adrenergic receptor	Ki	=	117.0	nM	6.93	DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912)	-
Unchecked	IC50	=	117.0	nM	6.93	DRUGMATRIX: Sigma2 radioligand binding (ligand: [3H] Ifenprodil)	-
Unchecked	IC50	=	165.0	nM	6.78	DRUGMATRIX: Calcium Channel Type L, Dihydropyridine radioligand binding (ligand:...	-
5-hydroxytryptamine receptor 2C	Ki	=	212.0	nM	6.67	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ...	-
Voltage-gated L-type calcium channel	IC50	=	270.0	nM	6.57	Inhibition of voltage-gated L-type Ca channel (species unknown)	21300721
Alpha-2A adrenergic receptor	IC50	=	312.0	nM	6.51	DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912)	-
D(3) dopamine receptor	Ki	=	410.0	nM	6.39	DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone)	-
5-hydroxytryptamine receptor 2C	IC50	=	404.0	nM	6.39	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ...	-
Muscarinic acetylcholine receptor M4	Ki	=	506.0	nM	6.3	DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine)	-
Unchecked	Ki	=	524.0	nM	6.28	DRUGMATRIX: Calcium Channel Type L, Phenylalkylamine radioligand binding (ligand...	-

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885861	Rattus norvegicus	1437
-	10.6019/CHEMBL3885881	Rattus norvegicus	224
11806713	10.1021/jm001126+	Rattus norvegicus	27
17228875	10.1021/jm060878m	Heart	20
16472241	10.2174/1570163043334794	Hepatotoxicity	18
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
18024584	10.1073/pnas.0709695104	H4	13
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
20509610	10.1021/jm100298d	Molecular identity unknown	10
20509610	10.1021/jm100298d	NON-PROTEIN TARGET	9
7286032	10.1007/bf00562807	Homo sapiens	9
20070106	10.1021/jm901371v	Homo sapiens	8
16621936	10.1124/dmd.105.006619	ADMET	8
25544686	10.1016/j.ejmech.2014.12.028	HepG2	8
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
22328583	10.1124/dmd.111.043505	Cytochrome P450 2J2	7
16451055	10.1021/jm050691f	Trypanosoma cruzi	6
11806713	10.1021/jm001126+	CHO-K1	5
20509610	10.1021/jm100298d	Heart	5
12061889	10.1021/jm0200409	ADMET	5

Data from ChEMBL 36 via Core Engine