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Details

Stereochemistry ACHIRAL
Molecular Formula C31H44N2O5S
Molecular Weight 556.756
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DRONEDARONE

SMILES

CCCCN(CCCC)CCCOC1=CC=C(C=C1)C(=O)C2=C(CCCC)OC3=C2C=C(NS(C)(=O)=O)C=C3

InChI

InChIKey=ZQTNQVWKHCQYLQ-UHFFFAOYSA-N
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

HIDE SMILES / InChI
Molecular Formula C31H44N2O5S
Molecular Weight 556.756
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Dronedarone is an antiarrhythmic that is FDA approved for the treatment of atrial fibrillation in patients in sinus rhythm with a history of paroxysmal or persistent atrial fibrillation (AF). Dronedarone is multichannel blocker. Common adverse reactions include abdominal pain, diarrhea, indigestion, nausea, vomiting, asthenia and raised serum creatinine. Dronedarone has potentially important pharmacodynamics interactions: Digoxin: Consider discontinuation or halve dose of digoxin before treatment and monitor; Calcium channel blockers (CCB): Initiate CCB with low dose and increase after ECG verification of tolerability; Beta-blockers: May provoke excessive bradycardia, Initiate with low dose and increase after ECG verification of tolerability.

CNS Activity

Originator

Approval Year

2009
68
Targets

Targets

Primary TargetPharmacologyConditionPotency
Substrate
587
Blocker
496
Atrial Fibrillation
Blocker
496
Atrial Fibrillation
 1.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Inward rectifier potassium channel 2
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4
Approved
7883
MULTAQ
Primary
Inward rectifier potassium channel 2
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4
Approved
7883
MULTAQ
Approved (off-label)
8
PubMed

PubMed

TitleDatePubMed
Electrophysiological effects of dronedarone (SR 33589), a noniodinated amiodarone derivative in the canine heart: comparison with amiodarone.
2001 Jul
Dronedarone (Sanofi-Synthélabo).
2001 May
Dronedarone for prevention of atrial fibrillation: a dose-ranging study.
2003 Aug
Effects of amiodarone and dronedarone on voltage-dependent sodium current in human cardiomyocytes.
2003 Aug
Electrophysiologic characterization of dronedarone in guinea pig ventricular cells.
2003 Feb
Dronerarone acts as a selective inhibitor of 3,5,3'-triiodothyronine binding to thyroid hormone receptor-alpha1: in vitro and in vivo evidence.
2003 Feb
Chronic amiodarone-induced inhibition of the Na+-K+ pump in rabbit cardiac myocytes is thyroid-dependent: comparison with dronedarone.
2003 Jan
Old and new antiarrhythmic drugs for converting and maintaining sinus rhythm in atrial fibrillation: comparative efficacy and results of trials.
2003 Mar 20
IKr channel blockers: novel antiarrhythmic agents.
2003 Oct
Trials of new antiarrhythmic drugs for maintenance of sinus rhythm in patients with atrial fibrillation.
2004
Involvement of nitric oxide in amiodarone- and dronedarone-induced coronary vasodilation in guinea pig heart.
2004 Aug 2
Pharmacokinetic and pharmacodynamic interactions between metoprolol and dronedarone in extensive and poor CYP2D6 metabolizers healthy subjects.
2004 Feb
Oral class III antiarrhythmics: what is new?
2004 Jan
[Safety of new anti-arrhythmic drugs].
2005 Apr
The novel antiarrhythmic drug dronedarone: comparison with amiodarone.
2005 Fall
This DAFNE is definitely not that DAFNE.
2005 May 25
Pharmacological treatment of atrial fibrillation: mechanisms of action and efficacy of class III drugs.
2006
[Dronedarone--a new therapeutic option for controlling atrial rhythm and ventricular frequency].
2006 Aug 25
Dronedarone: a new antiarrhythmic agent.
2006 Feb
Amiodarone inhibits thyroidal iodide transport in vitro by a cyclic adenosine 5'-monophosphate- and iodine-independent mechanism.
2006 Jun
Amiodarone: a multifaceted antiarrhythmic drug.
2006 Sep
Dronedarone: an emerging agent with rhythm- and rate-controlling effects.
2006 Sep
Inhibition of the HERG potassium channel by the tricyclic antidepressant doxepin.
2007 Aug 1
Effect of dronedarone on renal function in healthy subjects.
2007 Dec
Dronedarone in atrial fibrillation.
2007 Dec 6
Dronedarone: in quest of the ideal antiarrhythmic drug.
2007 Fall
New antiarrhythmic treatment of atrial fibrillation.
2007 Jul
Effect of amiodarone and dronedarone administration in rats on thyroid hormone-dependent gene expression in different cardiac components.
2007 Jun
New antiarrhythmic drugs for establishing sinus rhythm in atrial fibrillation: what are our therapies likely to be by 2010 and beyond?
2007 Nov
Dronedarone for maintenance of sinus rhythm in atrial fibrillation or flutter.
2007 Sep 6
Relationship among amiodarone, new class III antiarrhythmics, miscellaneous agents and acquired long QT syndrome.
2008
Rationale and design of ATHENA: A placebo-controlled, double-blind, parallel arm Trial to assess the efficacy of dronedarone 400 mg bid for the prevention of cardiovascular Hospitalization or death from any cause in patiENts with Atrial fibrillation/atrial flutter.
2008 Jan
Anti-arrhythmic drug therapy for atrial fibrillation: current anti-arrhythmic drugs, investigational agents, and innovative approaches.
2008 Jun
Pharmacotherapy for atrial arrhythmias: present and future.
2008 Jun
Acute inhibitory effect of dronedarone, a noniodinated benzofuran analogue of amiodarone, on Na+/Ca2+ exchange current in guinea pig cardiac ventricular myocytes.
2008 Jun
Increased mortality after dronedarone therapy for severe heart failure.
2008 Jun 19
Is dronedarone effective for the prevention of recurrent atrial fibrillation?
2008 Mar
New antiarrhythmic drugs for atrial fibrillation: focus on dronedarone and vernakalant.
2008 Oct
[Current pharmacological management of atrial fibrillation management by practice cardiologists - news from congress in Munich].
2008 Sep
Trial watch: novel antiarrhythmic agent shows promise in Phase III trial.
2009 Apr
Dronedarone for atrial fibrillation--an odyssey.
2009 Apr 30
Clinical trials update from the Heart Failure Society of America and the American Heart Association meetings in 2008: SADHART-CHF, COMPARE, MOMENTUM, thyroid hormone analogue study, HF-ACTION, I-PRESERVE, beta-interferon study, BACH, and ATHENA.
2009 Feb
Major recent trials in cardiovascular diseases.
2009 Mar
New pharmacological options for patients with atrial fibrillation: the ATHENA trial.
2009 May
The role of thyroid hormone nuclear receptors in the heart: evidence from pharmacological approaches.
2010 Mar
Patents

Patents

20020150622
2
JP2011529958A
2

Sample Use Guides

In Vivo Use Guide
One tablet of 400 mg twice a day with morning and evening meals.
Route of Administration: Oral
In Vitro Use Guide
In isolated ventricular myocytes, dronedarone inhibited rapidly activating delayed-rectifier K+ current (I(Kr)) (median inhibitory concentration [IC50] /= 30 uM).
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:13:31 UTC 2019
Edited
by admin
on Mon Oct 21 20:13:31 UTC 2019
Record UNII
JQZ1L091Y2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DRONEDARONE
EMA EPAR   INN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
DRONEDARONE [INN]
Common Name English
METHANESULFONAMIDE, N-(2-BUTYL-3-(4-(3-(DIBUTYLAMINO)PROPOXY)BENZOYL)-5-BENZOFURANYL)-
Systematic Name English
SR33589
Code English
SR-33589
Code English
DRONEDARONE [VANDF]
Common Name English
N-(2-BUTYL-3-(4-(3-(DIBUTYLAMINO)PROPROXY)BENZOYL)BENZOFURAN-5-YL)METHANESULFONAMIDE
Common Name English
DRONEDARONE [EMA EPAR]
Common Name English
DRONEDARONE [MI]
Common Name English
DRONEDARONE [MART.]
Common Name English
DRONEDARONE [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QC01BD07
Created by admin on Mon Oct 21 20:13:31 UTC 2019 , Edited by admin on Mon Oct 21 20:13:31 UTC 2019
LIVERTOX 331
Created by admin on Mon Oct 21 20:13:31 UTC 2019 , Edited by admin on Mon Oct 21 20:13:31 UTC 2019
NDF-RT N0000175426
Created by admin on Mon Oct 21 20:13:31 UTC 2019 , Edited by admin on Mon Oct 21 20:13:31 UTC 2019
WHO-ATC C01BD07
Created by admin on Mon Oct 21 20:13:31 UTC 2019 , Edited by admin on Mon Oct 21 20:13:31 UTC 2019
NCI_THESAURUS C47793
Created by admin on Mon Oct 21 20:13:31 UTC 2019 , Edited by admin on Mon Oct 21 20:13:31 UTC 2019
Code System Code Type Description
WIKIPEDIA
DRONEDARONE
Created by admin on Mon Oct 21 20:13:31 UTC 2019 , Edited by admin on Mon Oct 21 20:13:31 UTC 2019
PRIMARY
DRUG BANK
DB04855
Created by admin on Mon Oct 21 20:13:31 UTC 2019 , Edited by admin on Mon Oct 21 20:13:31 UTC 2019
PRIMARY
NDF-RT
N0000185503
Created by admin on Mon Oct 21 20:13:31 UTC 2019 , Edited by admin on Mon Oct 21 20:13:31 UTC 2019
PRIMARY P-Glycoprotein Inhibitors [MoA]
RXCUI
233698
Created by admin on Mon Oct 21 20:13:31 UTC 2019 , Edited by admin on Mon Oct 21 20:13:31 UTC 2019
PRIMARY RxNorm
PUBCHEM
208898
Created by admin on Mon Oct 21 20:13:31 UTC 2019 , Edited by admin on Mon Oct 21 20:13:31 UTC 2019
PRIMARY
MESH
C118667
Created by admin on Mon Oct 21 20:13:31 UTC 2019 , Edited by admin on Mon Oct 21 20:13:31 UTC 2019
PRIMARY
EPA CompTox
141626-36-0
Created by admin on Mon Oct 21 20:13:31 UTC 2019 , Edited by admin on Mon Oct 21 20:13:31 UTC 2019
PRIMARY
HSDB
141626-36-0
Created by admin on Mon Oct 21 20:13:31 UTC 2019 , Edited by admin on Mon Oct 21 20:13:31 UTC 2019
PRIMARY
MERCK INDEX
M4768
Created by admin on Mon Oct 21 20:13:31 UTC 2019 , Edited by admin on Mon Oct 21 20:13:31 UTC 2019
PRIMARY Merck Index
NDF-RT
N0000182137
Created by admin on Mon Oct 21 20:13:31 UTC 2019 , Edited by admin on Mon Oct 21 20:13:31 UTC 2019
PRIMARY Cytochrome P450 2D6 Inhibitors [MoA]
IUPHAR
7465
Created by admin on Mon Oct 21 20:13:31 UTC 2019 , Edited by admin on Mon Oct 21 20:13:31 UTC 2019
PRIMARY
CAS
141626-36-0
Created by admin on Mon Oct 21 20:13:31 UTC 2019 , Edited by admin on Mon Oct 21 20:13:31 UTC 2019
PRIMARY
EVMPD
SUB06408MIG
Created by admin on Mon Oct 21 20:13:31 UTC 2019 , Edited by admin on Mon Oct 21 20:13:31 UTC 2019
PRIMARY
ChEMBL
CHEMBL184412
Created by admin on Mon Oct 21 20:13:31 UTC 2019 , Edited by admin on Mon Oct 21 20:13:31 UTC 2019
PRIMARY
NDF-RT
N0000190114
Created by admin on Mon Oct 21 20:13:31 UTC 2019 , Edited by admin on Mon Oct 21 20:13:31 UTC 2019
PRIMARY Cytochrome P450 3A Inhibitors [MoA]
NCI_THESAURUS
C65485
Created by admin on Mon Oct 21 20:13:31 UTC 2019 , Edited by admin on Mon Oct 21 20:13:31 UTC 2019
PRIMARY
INN
7382
Created by admin on Mon Oct 21 20:13:31 UTC 2019 , Edited by admin on Mon Oct 21 20:13:31 UTC 2019
PRIMARY
Related Record Type Details
CYTOCHROME P450 2D6
METABOLIC ENZYME -> SUBSTRATE
MINOR
Structure of DRONEDARONE
EXCRETED UNCHANGED
Mass balance indicates that orally administered dronedarone is ultimately excreted in the urine (6 %) and feces (84 %) primarily as metabolites. Dronedarone was extensively metabolized; only low amounts of dronedarone were detected in feces and dronedarone was non-existent in urine.
AMOUNT EXCRETED
URINE
Structure of DRONEDARONE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> INHIBITOR
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
CYTOCHROME P450 2D6
METABOLIC ENZYME -> INHIBITOR
LOW
Ki
CYTOCHROME P450 2C8
METABOLIC ENZYME -> INHIBITOR
LOW
Ki
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
MAJOR
Related Record Type Details
Structure of DEBUTYLDRONEDARONE
METABOLITE LESS ACTIVE -> PARENT
Dronedarone is extensively metabolized, mainly by CYP 3A
MAJOR
PLASMA
Related Record Type Details
Structure of DRONEDARONE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Tmax PHARMACOKINETIC IN HEPATICALLY IMPAIRED PATIENTS

DOSE

Biological Half-life PHARMACOKINETIC
Tmax PHARMACOKINETIC IN HEALTHY SUBJECTS

DOSE

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