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 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/)
No information available.
Summary of Clinical Use Click here for help
Approved to treat life-threatening atrial flutter and fibrilation by restoring synus rhythm.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Dronedarone's mechanism of action is complex, with clinical efficacy arising from actions as a multi-channel blocker, affecting potassium, sodium and calcium currents, as well as antagonism of α- and β-adrenoceptors. Inhibition of sodium and potassium currents appears to prolong the duration of action potential and refractory period in myocardial tissue. Additionally, inhibition of calcium channels and antagonism of β1-adrenoceptors may decrease the abnormal AV conduction and sinus node function associated with atrial fibrillation. Studies in pigs suggest that inhibition of the sinoatrial node If current via HCN channels is the principal mechanism underlying dronedarone's bradycardic action [4]. Dronedarone's antifibrillatory action may also be attributed, in part, to inhibition of inward-rectifier potassium channels, especially Kir2.1 [3,6].
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com
European Medicines Agency (EMA)