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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2D Structure
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Physico-chemical Properties
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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
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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
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]