Basic information
- CAS
959-24-0- Standard SMILES
CC(C)NCC(O)c1ccc(NS(C)(=O)=O)cc1.Cl- InChIKey
VIDRYROWYFWGSY-UHFFFAOYSA-N- Molecular formula
- C12H21ClN2O3S
- Average molar mass
- 308.83 g/mol
Overview
Sotalol hydrochloride is 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. It has a role as a beta-adrenergic antagonist and an anti-arrhythmia drug. It contains a sotalol(1+).
Names & identifiers
- Preferred name
- Sotalol Hydrochloride
- IUPAC
- N-[4-[1-hydroxy-2-(propan-2-ylamino)ethyl]phenyl]methanesulfonamide;hydrochloride
- English name
- Sotalol hydrochloride
- Molecular formula
- C12H20N2O3S.ClH
- Molecular weight
- 308.83
Names & synonyms
Sotalol hydrochloride959-24-0Sotalol HCLBetapaceBetapace AFSotacorSotalexSorineSotylizeBerlexMJ 1999Darob
Show more names
MJ-1999DL-MJ 1999SOLATOL HCLmeadjohnson1999
Sotalol MonohydrochlorideHEC37C70XXIsopropylaminohydroxyethylmethanesulfonanilide hydrochloride4'-(1-Hydroxy-2-(isopropylamino)ethyl)methanesulfonanilide monohydrochlorideNSC-337251NSC-760358DTXSID8021278N-Isopropyl-beta-(4-methanesulfonamidophenyl)ethanolamine hydrochloride
Database identifiers
- CAS
959-24-0- PubChem CID
- 66245
- ChEMBL
CHEMBL1700- ChEBI
CHEBI:9207- UNII
- HEC37C70XX
- EC Number
- 213-496-0
Properties
Computed structural properties
- Topological polar surface area
- 86.8 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 6
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 330
Experimental & physicochemical properties
Solubility>46.3 [ug/mL] (The mean of the results at pH 7.4)
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Adrenergic Beta-Antagonists; Antiarrhythmics
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Collision Cross Section166.3 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 218 · 218-220°C
- storage temp.
- 2 · 2-8°C
- solubility
- 2 O: · H2O: 20 mg/mL
- form
- powder
- color
- white to off-white
- Water Solubility
- Soluble in phosphate buffered saline, DMSO, ethanol, water, and methanol.
- 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
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 1.4% (1 of 73) of reports.
Warning
H315 (94.5%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 73 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Other Safety InformationIMAP assessments - Methanesulfonamide, N-[4-[1-hydroxy-2-[(1-methylethyl)amino]ethyl]phenyl]-, monohydrochloride: Environment tier I assessment
Hazard Classes and CategoriesSkin Irrit. 2 (94.5%)
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Sotalol hydrochloride
Ambiguous-DILI-concern
3
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- wgk
- 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)
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
SOTALOL HYDROCHLORIDE
Cardiac Rhythm Alteration [PE]; Antiarrhythmic [EPC]; Adrenergic beta-Antagonists [MoA]
SOTALOL HYDROCHLORIDE TABLES AF
Adrenergic beta-Antagonists [MoA]; Antiarrhythmic [EPC]; Cardiac Rhythm Alteration [PE]
SOTALOL HYDROCHLORIDE TABLETS AF
Antiarrhythmic [EPC]; Adrenergic beta-Antagonists [MoA]; Cardiac Rhythm Alteration [PE]
MeSH Pharmacological Classification
Drugs that bind to but do not activate beta-adrenergic receptors thereby blocking the actions of beta-adrenergic agonists. Adrenergic beta-antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches, and anxiety.
Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade.
Drugs that inhibit the actions of the sympathetic nervous system by any mechanism. The most common of these are the ADRENERGIC ANTAGONISTS and drugs that deplete norepinephrine or reduce the release of transmitters from adrenergic postganglionic terminals (see ADRENERGIC AGENTS). Drugs that act in the central nervous system to reduce sympathetic activity (e.g., centrally acting alpha-2 adrenergic agonists, see ADRENERGIC ALPHA-AGONISTS) are included here.
Applications
DescriptionSotalol 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).
Related reactions
4 records
Compound notes
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