DRONEDARONE HYDROCHLORIDE

DRONEDARONE HYDROCHLORIDE Basic information
Product Name:DRONEDARONE HYDROCHLORIDE
Synonyms:Dronedarone hydrochloride(SR33589B);MethanesulfonaMide,N-[2-butyl-3-[4-[3-(dibutylaMino)propoxy]benz;N-[2-butyl-3-[4-(3-dibutyl-aminopropoxy) benzoyl] methanesulfonamide hydrochloride;SR-33589B;DRONEDARONE HYDROCHLORIDE;N-[2-butyl-3-[4-[3-(dibutylamino)propoxy]benzoyl]-5-benzofuranyl]-methanesulfonamide,hydrochloride (1:1);SR33589;Dronedarone HCl, >=99%
CAS:141625-93-6
MF:C31H44N2O5S.ClH
MW:593.224
EINECS:630-355-2
Product Categories:Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;API;141625-93-6
Mol File:141625-93-6.mol
DRONEDARONE HYDROCHLORIDE Structure
DRONEDARONE HYDROCHLORIDE Chemical Properties
Melting point NA (low-melting)
storage temp. 2-8°C
solubility DMSO: soluble15mg/mL, clear
form powder
color white to off-white
Merck 14,3449
Stability:Hygroscopic
InChIKeyDWKVCQXJYURSIQ-UHFFFAOYSA-N
Safety Information
RIDADR UN 3077 9 / PGIII
WGK Germany 3
HS Code 2935904000
MSDS Information
DRONEDARONE HYDROCHLORIDE Usage And Synthesis
Chemical PropertiesPale Yellow Solid
UsesDronedarone Hydrochloride can be used for the treatment of atrial fibrillation and atrial flutter in patients who have suffered cardiac arrhythmias.
UsesCardiovascular Drugs
UsesDronedarone Hydrochloride is a therapy for the treatment of patients with paroxysmal and persistent atrial fibrillation or atrial flutter.
Biological Activitydronedarone hcl is an amiodarone analogue which has been shown an effective and promising treatment for atrial fibrillation (af) [1].
Biochem/physiol ActionsDronedarone is a Class III antiarrhythmic and a multi-channel blocker for atrial fibrillation. It blocks potassium, sodium, and calcium channels and also exhibits antiadrenergic properties.
Clinical UseDronedarone hydrochloride (also known as SR33589 and marketed as Multaq) is a drug developed by Sanofi-Aventis for cardiac arrhythmias (irregular heartbeat) that was approved by the FDA in July 2009. Dronedarone is used for the treatment of atrial fibrillation and atrial flutter in patients whose hearts have either returned to normal rhythm or who undergo drug therapy or electroshock treatment to maintain normal cardio rhythm. Dronedarone is less lipophilic than amiodarone, exhibits a much smaller volume of distribution and a half-life of 24 h, this stands in contrast to competitor amiodarone’s half-life of several weeks. As a result of these pharmacokinetic characteristics, dronedarone dosing may be less complicated than amiodarone.
SynthesisThe synthesis of dronedarone relies on the preparation of the benzofuran core 34, of which three main routes have been reported, but two possess obvious overlap and are considered more process-amenable. Starting from methyl 2-(2-formylphenoxy)hexanoate (32), this aldehyde can either be nitrated, then saponified or saponified and then nitrated to procure nitroacid 33 (the Scheme). The benzofuran ring is then secured through the use of acetic anhydride and base in the presence of DMF at elevated temperature. The key benzofuran 34 can be produced by either route in 62% yield on gramscale by this method. Friedel¨CCrafts acylation involving anisoyl chloride and tin tetrachloride constructed the diaryl ketone 35. Cleavage of the methyl ether through the use of aluminum trichloride in refluxing DCE provided phenol 36. Alkylation of phenol 36 with aminoalkyl chloride 37 gave ether 38. Subsequent reduction of the nitro group via catalytic hydrogenation and sulfonylation of the resulting amine provided dronedarone (VII) which was isolated as its HCl salt.

Synthesis_141625-93-6

in vitrodronedarone has been demonstrated to inhibit muscarinic acetylcholine receptor-operated k+ current ik(ach) induced by carbachol or gtp-gamma-s with ic50 values of 10nm and <100nm, respectively, in cells isolated from guinea pig atria. notably, dronedarone was 100-fold potent and selective over amiodarone in inhibiting ik(ach) [1].
in vivodronedarone has shown to block arterial thrombus formation, decrease platelet aggregation and reduce plasminogen activator inhibitor-1 (pai1) expression in c57bl/6 mice [2].
references[1] guillemare e1, marion a, nisato d, gautier p. inhibitory effects of dronedarone on muscarinic k+ current in guinea pig atrial cells. j cardiovasc pharmacol. 2000 dec;36(6):802-5.
[2] breitenstein a1, sluka sh, akhmedov a, stivala s, steffel j, camici gg, riem hh, beer hj, studt jd, duru f, luscher tf, tanner fc. dronedarone reduces arterial thrombus formation. basic res cardiol. 2012 nov;107(6):302.
DRONEDARONE HYDROCHLORIDE Preparation Products And Raw materials
Dronedarone Hydrochloride IMpurity C Des(Methylsulfonyl) Dronedarone Oxalate Tolvaptan SR 35021 Dronedarone Hydrochloride IMpurity E Dronedarone Hydrochloride IMpurity B 3-(4-HYDROXYBENZOYL)-2-METHYL-BENZOFURAN 4-[3-(Dimethylamino)propoxy]benzaldehyde 2-METHYL-5-BENZOFURANAMINE 1-BENZOFURAN-5-AMINE 2-Butyl-3-(4-hydroxybenzoyl)benzofuran 3-Acetyl-2-ethylbenzofuran 2-Butylbenzofuran 3-(4-METHOXYBENZOYL)-2-METHYLBENZOFURAN 3-ACETYLBENZO[B]FURAN Benzarone DRONEDARONE HYDROCHLORIDE 2-Ethylbenzofuran-3-carbaldehyde

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