dronedarone   

GtoPdb Ligand ID: 7465

Synonyms: Multaq® | SR-33598B
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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2D Structure
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Physico-chemical Properties
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
SMILES / InChI / InChIKey
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
No information available.
Summary of Clinical Use
Approved to treat life-threatening atrial flutter and fibrilation by restoring synus rhythm.
Mechanism Of Action and Pharmacodynamic Effects
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].
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