Dronedarone hydrochlorideProduct ingredient for Dronedarone

Name
Dronedarone hydrochloride
Drug Entry
Dronedarone

Dronedarone is a Class III antiarrhythmic drug that works to restore the normal sinus rhythm in patients with paroxysmal or persistent atrial fibrillation. Atrial fibrillation is a common sustained arrhythmia where the treatment primarily focuses on stroke prevention and symptom management. It is managed by rate control, rhythm control, prevention of thromboembolic events, and treatment of the underlying disease.1 Similar to amiodarone, dronedarone is a multichannel blocker that works to control rhythm and rate in atrial fibrillation.2 It meets criteria of all four Vaughan Williams antiarrhythmic drug classes by blocking sodium, potassium, and calcium ion channels and inhibiting β-adrenergic receptors.1,13

Dronedarone is a related benzofuran compound to amiodarone but its chemical structure lacks iodine moieties which are associated with amiodarone-induced thyroid problems.1,8 Additionally, the methyl sulfonyl group in its structure renders dronedarone to be more lipophilic with a shorter half-life than amiodarone.1 This ultimately leads to reduced tissue accumulation of the drug and decreased risk for organ toxicities, such as thyroid and pulmonary toxicities.8 Commonly marketed as Multaq®, dronedarone was approved by the FDA in July 2009 and Health Canada in August 2009. A safety concern for the risk of drug-induced hepatocellular injury has been issued following marketing of dronedarone.11

Accession Number
DBSALT000061
Structure
Synonyms
Not Available
UNII
FA36DV299Q
CAS Number
141625-93-6
Weight
Average: 593.217
Monoisotopic: 592.273770957
Chemical Formula
C31H45ClN2O5S
InChI Key
DWKVCQXJYURSIQ-UHFFFAOYSA-N
InChI
InChI=1S/C31H44N2O5S.ClH/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;1H
IUPAC Name
N-(2-butyl-3-{4-[3-(dibutylamino)propoxy]benzoyl}-1-benzofuran-5-yl)methanesulfonamide hydrochloride
SMILES
Cl.CCCCN(CCCC)CCCOC1=CC=C(C=C1)C(=O)C1=C(CCCC)OC2=C1C=C(NS(C)(=O)=O)C=C2
PubChem Compound
219025
ChemSpider
189860
ChEBI
775680
ChEMBL
CHEMBL1201729
Wikipedia
Dronedarone
Predicted Properties
PropertyValueSource
Water Solubility0.00201 mg/mLALOGPS
logP6.46ALOGPS
logP5.18Chemaxon
logS-5.4ALOGPS
pKa (Strongest Acidic)9.18Chemaxon
pKa (Strongest Basic)10.31Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area88.85 Å2Chemaxon
Rotatable Bond Count17Chemaxon
Refractivity158.13 m3·mol-1Chemaxon
Polarizability66.28 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon