Sotalol hydrochloride Chemical Properties

Melting point:

218-220°C

storage temp. 

2-8°C

solubility 

H₂O: 20 mg/mL

form 

powder

color 

white to off-white

Water Solubility 

Soluble in phosphate buffered saline, DMSO, ethanol, water, and methanol.

CAS DataBase Reference

959-24-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

PB0826000

HS Code 

2935904000

Toxicity

LD50 in male mice, rats (mg/kg): 2600, 3450 orally; 670, 680 i.p.; LD50 orally in rabbits: 1000 mg/kg; LD50 i.p. in dogs: 330 mg/kg (Lish)

MSDS

• Language:English Provider:SigmaAldrich

Sotalol hydrochloride Usage And Synthesis

Description

Sotalol is a non-selective antagonist of β-adrenergic receptors (β-ARs; IC₅₀s = 8.9 and 5.2 μM for β1- and β2-ARs, respectively) and a class III antiarrhythmic agent. It decreases delayed outward potassium currents (IK) in guinea pig ventricular cells and prolongs action potential duration in electrically stimulated isolated guinea pig papillary muscles when used at a concentration of 100 μM. Sotalol decreases heart rate and increases blood pressure and the cardiac functional refractory period (FRP) in a canine model of ventricular tachycardia induced by programmed electrical stimulation (PES). Formulations containing sotalol have been used in the treatment of ventricular arrhythmias and maintenance of normal sinus rhythm in patients with atrial fibrillation or flutter (AFIB/AFL).

Description

Sotalol (hydrochloride) (Item No. 26291) is an analytical reference standard categorized as a β-adrenergic receptor antagonist. It has been detected as an adverse analytical finding (AAF) during anti-doping testing. This product is intended for use in analytical forensic applications. This product is also available as a general research tool .

Chemical Properties

White Crystalline Solid

Originator

Sotagard,Glaxo

Uses

Sotalol hydrochloride is used as a potent beta adrenergic antagonist, prolongs the action potential and increases the refractory period. Sotalol hydrochloride is also considered a non-selective β blocker and a potassium channel blocker with an IC50 of 43 μM.

Uses

A potent -adrenergic receptor antagonist. A class III antiarrythmic. It has been shown to prolong action potential and increases the refractory period

Uses

A potent α-adrenergic receptor antagonist. A class III antiarrythmic. It has been shown to prolong action potential and increases the refractory period.

Uses

antibacterial

Definition

ChEBI: A hydrochloride salt that is the monohydrochloride of sotalol. It has both beta-adrenoreceptor blocking (Vaughan Williams Class II) and cardiac action potential duration prolongation (Vaughan Williams Class III) antiarrhythmic properties. It is used (usually as the hydrochloride salt) for the management of ventricular and supraventricular arrhythmias.

Manufacturing Process

As a resulting of reaction of methansulfonylchloride reacted with aniline methansulfonanilide was obtained. The methansulfonanilide reacted with bromacetylbromide at the presence of AlCl3 and CS2 and 4-(bromacetyl)- methansulfonanilide was prepeared.
Then to the 4-(bromacetyl)-methansulfonanilide isopropylamine was added to give 4-(1-oxo-2-isopropylaminoethyl)methansulfonanilide.The 4-(1-oxo-2-isopropylaminoethyl)methansulfonanilide was reduced by hydrogenesation in the presence of Pd-C catalyst and sodium borohydride. So 4-(1-hydroxy-2-isopropylaminoethyl)methansulfonanilide was obtained.
The 4-(1-hydroxy-2-isopropylaminoethyl)methansulfonanilide hydrochloride may be prepared by treatment of base with hydrochloric acid.

brand name

Betapace(Berlex); Sorine (Upsher Smith).

Therapeutic Function

Beta-adrenergic blocker, Antiarrhythmic

Biological Activity

A relatively potent pure β adrenergic antagonist, unique in possessing additional class III antiarrhythmic activity. Also available as part of the Mixed Adrenergic Tocriset™ .

Clinical Use

Beta-adrenoceptor blocker:
Treatment of life-threatening ventricular arrhythmias
Prophylaxis of SVT

Veterinary Drugs and Treatments

Sotalol may be useful in the treatment of ventricular tachycardias and, possibly, supraventricular tachycardias in dogs.

Drug interactions

Potentially hazardous interactions with other drugs
Anaesthetics: enhanced hypotensive effect.
Analgesics: NSAIDs antagonise hypotensive effect.
Anti-arrhythmics: increased risk of myocardial depression and bradycardia; increased risk ofbradycardia, myocardial depression and AV block with amiodarone; increased risk of ventricular arrhythmias with amiodarone, dronedarone, disopyramide or procainamide - avoid; increased risk of myocardial depression and bradycardia with flecainide.
Antibacterials: increased risk of ventricular arrhythmias with moxifloxacin - avoid; increased risk of ventricular arrhythmias with delamanid.
Antidepressants: enhanced hypotensive effect with MAOIs; increased risk of ventricular arrhythmias with tricyclics; increased risk of ventricular arrhythmias with citalopram, escitalopram and venlafaxine - avoid.
Antihistamines: increased risk of ventricular arrhythmias with mizolastine - avoid.
Antihypertensives: enhanced hypotensive effect; increased risk of withdrawal hypertension with clonidine; increased risk of first dose hypotensive effect with post-synaptic alpha-blockers such as prazosin.
Antimalarials: increased risk of bradycardia with mefloquine; avoid with artemether and lumefantrine and piperaquine with artenimol - increased risk of ventricular arrhythmias.
Antimuscarinics: increased risk of ventricular arrhythmias with tolterodine.
Antipsychotics: enhanced hypotensive effect with phenothiazines; increased risk of ventricular arrhythmias with amisulpride, droperidol, haloperidol, phenothiazines, pimozide, risperidone, sulpiride or zuclopenthixol - avoid with droperidol and zuclopenthixol.
Antivirals: increased risk of ventricular arrhythmias with saquinavir or telaprevir - avoid.
Atomoxetine: increased risk of ventricular arrhythmias.
Calcium-channel blockers: increased risk of bradycardia and AV block with diltiazem; hypotension and heart failure possible with nifedipine and nisoldipine; asystole, severe hypotension and heart failure with verapamil.
Cytotoxics: possible increased risk of bradycardia with crizotinib; increased risk of ventricular arrhythmias with vandetanib - avoid; increased risk of ventricular arrhythmias with arsenic trioxide, bosutinib, ceritinib, panobinostat and vandetanib.
Diuretics: enhanced hypotensive effect; increased risk of ventricular arrhythmias due to hypokalaemia.
Fingolimod: possibly increased risk of bradycardia.
Ivabradine: increased risk of ventricular arrhythmias.
Moxisylyte: possible severe postural hypotension. Ranolazine: avoid concomitant use.
Sympathomimetics: severe hypertension with adrenaline and noradrenaline and possibly with dobutamine.

Metabolism

Metabolism of sotalol is negligible, and it is excreted unchanged in the urine.

storage

Store at RT

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