amiodarone   Click here for help

GtoPdb Ligand ID: 2566

Synonyms: amiodarone hydrochloride | Cordarone®
Approved drug PDB Ligand
amiodarone is an approved drug (FDA (1985))
Compound class: Synthetic organic
Comment: Amiodarone is a class III antiarrhythmic drug and acts as a positive inotropic agent. The prescription drug contains amiodarone hydrochloride (PubChem CID 441325).
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: amiodarone

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 11
Topological polar surface area 42.68
Molecular weight 645.02
XLogP 7.91
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CCCCc1oc2c(c1C(=O)c1cc(I)c(c(c1)I)OCCN(CC)CC)cccc2
Isomeric SMILES CCCCc1oc2c(c1C(=O)c1cc(I)c(c(c1)I)OCCN(CC)CC)cccc2
InChI InChI=1S/C25H29I2NO3/c1-4-7-11-22-23(18-10-8-9-12-21(18)31-22)24(29)17-15-19(26)25(20(27)16-17)30-14-13-28(5-2)6-3/h8-10,12,15-16H,4-7,11,13-14H2,1-3H3
InChI Key IYIKLHRQXLHMJQ-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1985))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(2-butyl-1-benzofuran-3-yl)-[4-(2-diethylaminoethoxy)-3,5-diiodophenyl]methanone
International Nonproprietary Names Click here for help
INN number INN
2012 amiodarone
Synonyms Click here for help
amiodarone hydrochloride | Cordarone®
Database Links Click here for help
Specialist databases
GPCRdb Ligand amiodarone
Other databases
BindingDB Ligand 18957
CAS Registry No. 1951-25-3
ChEBI CHEBI:2663
ChEMBL Ligand CHEMBL633
DrugBank Ligand DB01118
DrugCentral Ligand 176
GtoPdb PubChem SID 135649937
PubChem CID 2157
RCSB PDB Ligand BBI
Search Google for chemical match using the InChIKey IYIKLHRQXLHMJQ-UHFFFAOYSA-N
Search Google for chemicals with the same backbone IYIKLHRQXLHMJQ
Search PubMed clinical trials amiodarone
Search PubMed titles amiodarone
Search PubMed titles/abstracts amiodarone
UniChem Compound Search for chemical match using the InChIKey IYIKLHRQXLHMJQ-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey IYIKLHRQXLHMJQ-UHFFFAOYSA-N
Wikipedia Amiodarone