dronedarone   Click here for help

GtoPdb Ligand ID: 7465

Synonyms: Multaq® | SR-33598B
Approved drug
dronedarone is an approved drug (FDA and EMA (2009))
Compound class: Synthetic organic
Comment: Dronedarone is a class III antiarrhythmic drug. It is a noniodinated analogue of amiodarone. The marketed formulation contains the hydrochloride salt (PubChem CID 219025).
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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: dronedarone

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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 5
Hydrogen bond donors 1
Rotatable bonds 18
Topological polar surface area 97.23
Molecular weight 556.3
XLogP 7.23
No. Lipinski's rules broken 2

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCCCc1oc2c(c1C(=O)c1ccc(cc1)OCCCN(CCCC)CCCC)cc(cc2)NS(=O)(=O)C
Isomeric SMILES CCCCc1oc2c(c1C(=O)c1ccc(cc1)OCCCN(CCCC)CCCC)cc(cc2)NS(=O)(=O)C
InChI InChI=1S/C31H44N2O5S/c1-5-8-12-29-30(27-23-25(32-39(4,35)36)15-18-28(27)38-29)31(34)24-13-16-26(17-14-24)37-22-11-21-33(19-9-6-2)20-10-7-3/h13-18,23,32H,5-12,19-22H2,1-4H3
InChI Key ZQTNQVWKHCQYLQ-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Bogdan R, Goegelein H, Ruetten H. (2011)
Effect of dronedarone on Na+, Ca2+ and HCN channels.
Naunyn Schmiedebergs Arch Pharmacol, 383 (4): 347-56. [PMID:21279331]
2. Guo X, Ma X, Yang Q, Xu J, Huang L, Jia J, Shan J, Liu L, Chen W, Chu H et al.. (2014)
Discovery of 1-aryloxyethyl piperazine derivatives as Kv1.5 potassium channel inhibitors (part I).
Eur J Med Chem, 81: 89-94. [PMID:24824064]
3. Gómez R, Caballero R, Barana A, Amorós I, De Palm SH, Matamoros M, Núñez M, Pérez-Hernández M, Iriepa I, Tamargo J et al.. (2014)
Structural basis of drugs that increase cardiac inward rectifier Kir2.1 currents.
Cardiovasc Res, 104 (2): 337-46. [PMID:25205296]
4. Sobrado LF, Varone BB, Machado AD, Nearing BD, Zeng D, Belardinelli L, Verrier RL. (2013)
Dronedarone's inhibition of If current is the primary mechanism responsible for its bradycardic effect.
J Cardiovasc Electrophysiol, 24 (8): 914-8. [PMID:23647933]
5. Verrier RL, Sobrado MF, Pagotto VP, Kanas AF, Machado AD, Varone BB, Sobrado LF, Nearing BD, Zeng D, Belardinelli L. (2013)
Inhibition of I(f) in the atrioventricular node as a mechanism for dronedarone's reduction in ventricular rate during atrial fibrillation.
Heart Rhythm, 10 (11): 1692-7. [PMID:23933296]
6. Xynogalos P, Seyler C, Scherer D, Koepple C, Scholz EP, Thomas D, Katus HA, Zitron E. (2014)
Class III antiarrhythmic drug dronedarone inhibits cardiac inwardly rectifying Kir2.1 channels through binding at residue E224.
Naunyn Schmiedebergs Arch Pharmacol, 387 (12): 1153-61. [PMID:25182566]