Dronedarone HCl

Antiarrhythmic drugs CAS# 141625-93-6

Dronedarone HCl

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Quality Control of Dronedarone HCl

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Chemical structure

Dronedarone HCl

3D structure

Chemical Properties of Dronedarone HCl

Cas No. 141625-93-6 SDF Download SDF
PubChem ID 219025 Appearance Powder
Formula C31H45ClN2O5S M.Wt 593.22
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : ≥ 50 mg/mL (84.29 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name N-[2-butyl-3-[4-[3-(dibutylamino)propoxy]benzoyl]-1-benzofuran-5-yl]methanesulfonamide;hydrochloride
SMILES CCCCC1=C(C2=C(O1)C=CC(=C2)NS(=O)(=O)C)C(=O)C3=CC=C(C=C3)OCCCN(CCCC)CCCC.Cl
Standard InChIKey DWKVCQXJYURSIQ-UHFFFAOYSA-N
Standard 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Dronedarone HCl

DescriptionDronedarone hydrochloride is a non-iodinated amiodarone derivative that inhibits Na+, K+ and Ca2+ currents.In Vitro:Dronedarone (SR-33589) is a multichannel blocker for atrial fibrillation . It is a potent inhibitor of the acetylcholine-activated K+ current from atrial and sinoatrial nodal tissue, and inhibits the rapid delayed rectifier more potently than slow and inward rectifier K+ currents and inhibits L-type calcium current. Under whole-cell patch clamp, it blocks IKr (IC50=3 μM) and ICa-L (IC50=0.18 μM). The effects on ICa-L are use- and frequency-dependent. Dronedarone inhibits current carried by human ether-a-go-go gene (HERG)-expressing oocytes (analagous to IKr) with an IC50 of 9 μM[1]. In guinea pig ventricular myocytes, dronedarone exhibits a state dependent inhibition of the fast Na+ channel current with an IC50 of 0.7±0.1 μM, when the holding potential is −80 mV[2].In Vivo:Dronedarone (Hydrochloride) reduces significantly the incidence of ventricular fibrillation (VF) from 80 to 30% (p < 0.05) at 3 mg/kg i.v. and eliminated VF and mortality at 10 mg/kg i.v. [3]. Dronedarone inhibited carotid artery thrombus formation in vivo. Thrombin- and collagen-induced platelet aggregation is impaired indronedarone-treated mice (P.05), and expression ofplasminogen activator inhibitor-1 (PAI1), an inhibitor of the fibrinolytic system, is reduced in the arterial wall[4].

References:
[1]. Bogdan R, et al. Effect of?dronedarone?on Na+, Ca2+ and HCN channels. Naunyn Schmiedebergs Arch Pharmacol.?2011 Apr;383(4):347-56.? [2]. Doggrell SA, et al. Dronedarone: an amiodarone analogue. Expert Opin Investig Drugs. 2004 Apr;13(4):415-26. [3]. Manning AS, et al. SR 33589, a new amiodarone-like agent: effect on ischemia- and reperfusion-induced arrhythmias in anesthetized rats. J Cardiovasc Pharmacol. 1995 Sep;26(3):453-61. [4]. Breitenstein A, et al. Dronedarone reduces arterial thrombus formation. Basic Res Cardiol. 2012 Nov;107(6):302.

Protocol

Animal Administration [3][4]
Rats: Rats are anesthetized, artificially ventilated, and the thorax opened by a left thoracotomy. Ischemia is induced by left coronary artery ligation, and reperfusion is achieved (after a 5-min period of ischemia) in a separate group of rats by removing the ligature. Agents are given intravenously 5 min before occlusion or orally 4 h before study[3]. Mice: Twelve-week-old C57Bl/6 mice are divided into two groups: dronedarone (200 mg/kg body weight with a once daily oral gavage for 14 days) or control (1.4 % methylcellulose). Twenty-four hours after the last application, mice are anesthetized by intraperitoneal injection of 87 mg/kg sodium pentobarbital. Rose bengal is diluted to 12 mg/mL in phosphate-buffered saline and then injected into the tail vein at a concentration of 63 mg/kg[4].

References:
[1]. Bogdan R, et al. Effect of?dronedarone?on Na+, Ca2+ and HCN channels. Naunyn Schmiedebergs Arch Pharmacol.?2011 Apr;383(4):347-56.? [2]. Doggrell SA, et al. Dronedarone: an amiodarone analogue. Expert Opin Investig Drugs. 2004 Apr;13(4):415-26. [3]. Manning AS, et al. SR 33589, a new amiodarone-like agent: effect on ischemia- and reperfusion-induced arrhythmias in anesthetized rats. J Cardiovasc Pharmacol. 1995 Sep;26(3):453-61. [4]. Breitenstein A, et al. Dronedarone reduces arterial thrombus formation. Basic Res Cardiol. 2012 Nov;107(6):302.

Dronedarone HCl Dilution Calculator

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Dronedarone HCl Molarity Calculator

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Preparing Stock Solutions of Dronedarone HCl

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.6857 mL 8.4286 mL 16.8572 mL 33.7143 mL 42.1429 mL
5 mM 0.3371 mL 1.6857 mL 3.3714 mL 6.7429 mL 8.4286 mL
10 mM 0.1686 mL 0.8429 mL 1.6857 mL 3.3714 mL 4.2143 mL
50 mM 0.0337 mL 0.1686 mL 0.3371 mL 0.6743 mL 0.8429 mL
100 mM 0.0169 mL 0.0843 mL 0.1686 mL 0.3371 mL 0.4214 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Dronedarone HCl

Dronedarone HCL is an amiodarone analogue which has been shown an effective and promising treatment for Atrial fibrillation (AF) [1].

In vitro, dronedarone 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 vivo, dronedarone 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.

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References on Dronedarone HCl

Identification and characterization of stress degradation products of dronedarone hydrochloride employing LC-UV/PDA, LC-MS/TOF and MS(n) studies.[Pubmed:26547261]

J Pharm Biomed Anal. 2016 Jan 25;118:139-148.

Dronedarone HCl was subjected to forced decomposition conditions of hydrolysis (neutral, acidic and alkaline), oxidation, photolysis and thermal stress, as suggested in the ICH guideline Q1A(R2). The drug showed significant degradation under alkaline hydrolytic and alkaline photolytic conditions while it remained stable in neutral, acidic, thermal and oxidative conditions. In total, six degradation products (I-VI) were formed, which could be separated by chromatography on C18 (250 mm x 4.6 mm; 5 mu, Xterra) column using isocratic elution method. Detection wavelength was selected as 288 nm. Multi-stage (MS(n)) and MS/TOF accurate mass studies were carried out to establish the complete fragmentation pathway of the drug which in turn was utilized in characterization of the products. The degradation pathway of the drug leading to generation of products I-VI was postulated and this has not been reported so far.

Description

Dronedarone Hydrochloride is a non-iodinated amiodarone derivative that inhibits Na+, K+ and Ca2+ currents.

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