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Compound Detail

CHEMBL1083993

AMIODARONE HYDROCHLORIDE
💊 Approved Drug
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💊 Approved Drug
CCCCc1oc2ccccc2c1C(=O)c1cc(I)c(OCCN(CC)CC)c(I)c1.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1083993
Name AMIODARONE HYDROCHLORIDE
Phase Approved
Structure Type MOL
InChI Key ITPDYQOUSLNIHG-UHFFFAOYSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL633
Active Moiety CHEMBL633

Known Names

Amidox Amiodar Amiodarone hcl Amiodarone hydrochloride Amyben Cordarone Cordarone x Cordarone x 100 Cordarone x 200 Darmil L-3428 Miodaron +11 more
3
Targets
13
Activities
2
Assay Types
11
PK Parameters
20
Publications
23
Known Names
7
Indications
1
Mechanisms

Molecular Properties

645.3
MW (Da)
6.94
ALogP
4
HBA
0
HBD
42.7
PSA (Ų)
0.17
QED
2
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1985
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral

Flags

Black Box Warning
USAN Stem -arone

Extended Properties

Molecular Formula C25H30ClI2NO3
MW 681.78
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness -0.38

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
HERG blocker BLOCKER Voltage-gated inwardly rectifying potassium channel KCNH2 ✓ ✓

Indications

Arrhythmias, Cardiac Tachycardia, Ventricular Ventricular Fibrillation Atrial Fibrillation Chagas Cardiomyopathy Heart Failure Amyloidosis, Familial

Drug Warnings

Black Box Warning
cardiotoxicity
Country: United States
Black Box Warning
respiratory toxicity
Country: United States
Black Box Warning
hepatotoxicity
Country: United States
Black Box Warning
musculoskeletal toxicity
Country: United States
Black Box Warning
nephrotoxicity
Country: United States
Black Box Warning
dermatological toxicity
Country: United States

Activity Summary

IC50 11 meas. best 5.7
EC50 2 meas. best 5.18

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 5.7 5.4714 1995.3 7
Unchecked
CHEMBL612545
 IC50 5.5 5.5 3170.0 1
Cruzipain
CHEMBL3563
 IC50 5.4 5.4 4000.0 1
Unchecked
CHEMBL612545
 EC50 5.18 5.145 6530.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 1.667 mL.min-1.kg-1 Homo sapiens
CL 3.667 mL.min-1.kg-1 Homo sapiens
CL 2.5 mL.min-1.kg-1 Homo sapiens
F 50.0 % Homo sapiens
PPB 96.0 % Homo sapiens
T1/2 1272.0 hr Homo sapiens
T1/2 1392.0 hr Homo sapiens
T1/2 480.0 hr Homo sapiens
T1/2 1128.0 hr Homo sapiens
Tmax 3.0 hr Homo sapiens
Vd 60.0 L.kg-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 1995.26 nM 5.7 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
Plasmodium falciparum IC50 = 2511.89 nM 5.6 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 2511.89 nM 5.6 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 3162.28 nM 5.5 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 3162.28 nM 5.5 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910
Unchecked IC50 = 3170.0 nM 5.5 PUBCHEM_BIOASSAY: High Throughput Screen to Identify Inhibitors of Mycobacterium... -
Cruzipain IC50 = 4000.0 nM 5.4 Inhibition of Trypanosoma cruzi cruzaine preincubated for 5 mins before substrat... 20426472
Plasmodium falciparum IC50 = 5011.87 nM 5.3 Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR g... 19734910
Unchecked EC50 = 6530.0 nM 5.18 PUBCHEM_BIOASSAY: Fluorescent HTS Cytotoxicity/Cell viability assay (HPDE-C7 cel... -
Unchecked EC50 = 7820.0 nM 5.11 PUBCHEM_BIOASSAY: Fluorescent HTS Cytotoxicity/Cell viability assay (HPDE-C7K ce... -
Plasmodium falciparum IC50 = 7943.28 nM 5.1 Antiplasmodial activity against Plasmodium falciparum Dd2 after 72 hrs by SYBR g... 19734910

Literature References

PubMed DOI Target Context # Activities
21398391 10.1124/dmd.110.037671 ADMET 21
- 10.6019/CHEMBL5303304 HEK-293T 9
- 10.6019/CHEMBL5303304 Fibroblast 8
19734910 10.1038/nchembio.215 Plasmodium falciparum 7
21398391 10.1124/dmd.110.037671 Liver microsome 6
- 10.6019/CHEMBL5303304 U2OS 4
- 10.6019/CHEMBL5724696 TERT-RPE1 4
20426472 10.1021/jm100254w Cruzipain 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
20426472 10.1021/jm100254w No relevant target 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1
- 10.1101/2020.04.03.023846 SARS-CoV-2 1
- 10.6019/CHEMBL4513141 Candida albicans 1
- 10.6019/CHEMBL4513141 Cryptococcus neoformans 1
- 10.6019/CHEMBL4513141 Escherichia coli 1
- 10.6019/CHEMBL4513141 Klebsiella pneumoniae 1
27048942 10.1016/j.bmcl.2016.03.054 Thoracic aorta 1
- 10.6019/CHEMBL4513141 Acinetobacter baumannii 1
21398391 10.1124/dmd.110.037671 No relevant target 1

Data from ChEMBL 36 via Core Engine