| Identification | More | [Name]
Sotalol hydrochloride | [CAS]
959-24-0 | [Synonyms]
4'-(1-hydroxy-2-isopropylaminoethyl)methanesulphonanilide hydrochloride
BETAPACE
DAROB
MJ-1999
N-[4-[1-HYDROXY-2-[(1-METHYLETHYL)AMINO]ETHYL]PHENYL]METHANESULFONAMIDE HYDROCHLORIDE
N-[4-(1-HYDROXY-2-[ISOPROPYLAMINO]ETHYL)-PHENYL]METHANESULFONAMIDE HYDROCHLORIDE
SOTACOR
SOTALEX
SOTALOL HCL
(+/-)-SOTALOL HYDROCHLORIDE
SOTALOL HYDROCHLORIDE
4-(2-isopropylamino-1-hydroxyaethyl)methanesulfonailidhydrochlorid
4’-(1-hydroxy-2-(isopropylamino)ethyl)methanesulfonanilidemonohydrochloride
4’-(1-hydroxy-2-(isopropylamino)ethyl)-methanesulfonanilidmonohydrochlorid
isopropylaminohydroxyethylmethanesulfonanilidehydrochloride
meadjohnson1999
n-isopropyl-beta-(4-methanesulfonamidophenyl)ethanolaminehydrochloride
SOLATOL HCL
(-N-[4-[1-Hydroxy-2-[(1-Methyl Ethyl) Amino]-ethyl]phenyl]methanesulfonamide
D,L-Sotalol, Hydrochloride | [EINECS(EC#)]
213-496-0 | [Molecular Formula]
C12H21ClN2O3S | [MDL Number]
MFCD00242937 | [Molecular Weight]
308.82 | [MOL File]
959-24-0.mol |
| Chemical Properties | Back Directory | [Appearance]
White Crystalline Solid | [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. | [Usage]
A potent-adrenergic receptor antagonist. A class III antiarrythmic. It has been shown to prolong action potential and increases the refractory period | [Major Application]
pharmaceutical small molecule | [InChI]
InChI=1S/C12H20N2O3S.ClH/c1-9(2)13-8-12(15)10-4-6-11(7-5-10)14-18(3,16)17;/h4-7,9,12-15H,8H2,1-3H3;1H | [InChIKey]
VIDRYROWYFWGSY-UHFFFAOYSA-N | [SMILES]
C(C1C=CC(=CC=1)NS(=O)(=O)C)(O)CNC(C)C.Cl | [CAS DataBase Reference]
959-24-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H303-H315-H319-H335 | [Precautionary statements ]
P261-P280a-P304+P340-P405-P501a-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
PB0826000
| [HS Code ]
2935904000 | [Storage Class]
11 - Combustible Solids | [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) |
| Hazard Information | Back Directory | [Description]
Sotalol (hydrochloride) (Item No. 26291) is an analytical reference standard categorized as a β-adrenergic receptor antagonist.1,2,3 It has been detected as an adverse analytical finding (AAF) during anti-doping testing.4 This product is intended for use in analytical forensic applications. This product is also available as a general research tool (Item No. 16136). | [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.1,2 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.3 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).1 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). | [Chemical Properties]
White Crystalline Solid | [Originator]
Sotagard,Glaxo | [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 | [References]
[1] H. TSUCHIHASHI. Characteristics of 125I-iodocyanopindolol binding to β-adrenergic and serotonin-1B receptors of rat brain: selectivity of β-adrenergic agents[J]. European journal of pharmacology, 1990, 183 1: 404. DOI: 10.1016/0014-2999(90)93286-y |
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