Sotalol

HCID 5253CAS 3930-20-9

Basic information

Standard SMILES
CC(C)NCC(O)c1ccc(NS(C)(=O)=O)cc1
InChIKey
ZBMZVLHSJCTVON-UHFFFAOYSA-N
Molecular formula
C12H20N2O3S
Average molar mass
272.37 g/mol
Monoisotopic mass
272.1194635

Overview

Sotalol is a sulfonamide that is N-phenylmethanesulfonamide in which the phenyl group is substituted at position 4 by a 1-hydroxy-2-(isopropylamino)ethyl group. 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, a xenobiotic, an anti-arrhythmia drug and an environmental contaminant. It is a member of ethanolamines, a sulfonamide, a secondary alcohol and a secondary amino compound. It is a conjugate base of a sotalol(1+).

Names & identifiers

Preferred name
Sotalol
IUPAC
N-[4-[1-hydroxy-2-(propan-2-ylamino)ethyl]phenyl]methanesulfonamide
English name
Sotalol
Molecular formula
C12H20N2O3S
Molecular weight
272.36

Names & synonyms

sotalol3930-20-9beta-CardoneDL-SotalolSotalolumDarob miteDTXSID00235894'-(1-Hydroxy-2-(isopropylamino)ethyl)methane sulfonanilideMethanesulfonanilide, 4'-(1-hydroxy-2-(isopropylamino)ethyl)-C07AA07A6D97U294IN-(4-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}phenyl)methanesulfonamide
Show more names
SORBITOLSotalol (base and/or unspecified salts)SotololBetacotdoneAURORA KA-855Sotalol USP/EP/BPSotalol Intermediate
Methanesulfonamide, N-(4-(1-hydroxy-2-((1-methylethyl)amino)ethyl)phenyl)-DTXCID303589CHEBI:63622Methanesulfonamide, N-[4-[1-hydroxy-2-[(1-methylethyl)amino]ethyl]phenyl]-SotaloloN-(4-(1-hydroxy-2-((propan-2-yl)amino)ethyl)phenyl)methanesulfonamideRefChem:56607MJ1999

Database identifiers

CAS
3930-20-9
PubChem CID
5253
DTXSID
DTXSID0023589
ChEMBL
CHEMBL471
ChEBI
CHEBI:63622
UNII
A6D97U294I
EC Number
977-025-7
Nikkaji
J10.583J

Properties

Computed structural properties

XLogP
0.2
Topological polar surface area
86.8 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
5
Rotatable bonds
6
Heavy atoms
18

Experimental & physicochemical properties

Drugs · 2 items

Pharmaceuticals

Pharmaceuticals -> Used in Switzerland

LogP · 2 items

1.1

0.53

Solubility7.82e-01 g/L
Human Drugs · 2 items

Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Adrenergic Beta-Antagonists; Antiarrhythmics

Pharmaceuticals

Melting Point206.5 - 207 °C
Physical DescriptionSolid

Physicochemical properties

Melting point
206.5 · 206.5-207 °C
Boiling point
443.3 · 443.3±55.0 °C(Predicted)
Density
1.298 g/cm3 · 1.298 g/cm3
storage temp.
-20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
solubility
Chloroform (Slightly, Heated), Methanol (Slightly, Sonicated)
form
Solid

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P203, P260, P263, P264, P264+P265, P270, P280, P302+P352, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Toxicology

Hepatotoxicity · 1 item

Mild-to-moderate elevations in serum aminotransferase levels occur in less than 2% of patients on sotalol and are usually transient and asymptomatic, resolving even with continuation of therapy. Sotalol has been linked to a single case of clinically apparent liver injury, with onset of an acute hepatitis-like syndrome with prolonged jaundice 12 weeks after sotalol was initiated. The injury improved but did not resolve with discontinuation of sotalol. In large case series of drug induced liver disease and acute liver failure, sotalol has not been listed as a cause. Other beta-blockers have been linked to rare instances of acute clinically apparent liver injury with a latency to onset ranging from 4 to 24 weeks, a hepatocellular pattern of serum enzyme elevations and a mild, self-limiting course without evidence of hypersensitivity or autoimmune reactions.

Adverse Effects · 1 item

Sotalol's adverse effect profile is inherent in the mechanisms of action as both a potassium channel blocker and a non-cardioselective β-blocker. The potassium channel blockade, primarily in phase 3 of the cardiac action potential, prolongs the QTc. Thus, the electrocardiogram (ECG) must be monitored upon initiating sotalol or adding other QTc-prolonging medications. Prolongation of the QT interval occurs in 1% to 2% of cases, which could lead to torsades de pointes or new ventricular tachycardia/ventricular fibrillation.

Toxicity Summary · 1 item

Sotalol toxicity is inherent due to the mechanism of action as both a potassium channel blocker and a non-cardioselective β-blocker and mirrors the adverse effect profile. The most obvious and potentially problematic sign of toxicity is concentration-related QTc prolongation. If QTc is over 500 ms during initiation, the sotalol dose should be reduced or discontinued. If QTc exceeds 520 ms during the maintenance phase of dosing, the clinician should either reduce the dose or discontinue sotalol.

Drug Induced Liver Injury · 5 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

sotalol

DILI Negative

Oral

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Safety data

risk_code
36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
26-36
Hazard statements
H319

Chemistry & industry

Pharmacology

ATC Code · 3 items

C07AA07

C - Cardiovascular system

QC - Cardiovascular system

Protein Binding0%.
Pharmacodynamics · 1 item

Sotalol is a competitive inhibitor of the rapid potassium channel. This inhibition lengthens the duration of action potentials and the refractory period in the atria and ventricles. The inhibition of rapid potassium channels is increases as heart rate decreases, which is why adverse effects like torsades de points is more likely to be seen at lower heart rates. L-sotalol also has beta adrenergic receptor blocking activity seen above plasma concentrations of 800ng/L. The beta blocking ability of sotalol further prolongs action potentials. D-sotalol does not have beta blocking activity but also reduces a patient's heart rate while standing or exercising. These actions combine to produce a negative inotropic effect that reduces the strength of contractility of muscle cells in the heart. Extension of the QT interval is also adversely associated with the induction of arrhythmia in patients. Hyperglycemia is a greater risk for non insulin dependant diabetics than insulin dependant diabetics. Beta blockers inhibit insulin secretion which may cause hyperglycemia in type II diabetes mellitus. The risk of hypoglycemia is higher in insulin dependant diabetes than non insulin dependant diabetics. Beta blockers decrease secretion of insulin, which may mask hypoglycemia in an insulin dependant patient. Beta blockers also increase glucose uptake into cells which may prolong or potentiate hypoglycemia. Further information regarding adverse reactions can be found here.

Mechanism of Action · 1 item

Sotalol inhibits beta-1 adrenoceptors in the myocardium as well as rapid potassium channels to slow repolarization, lengthen the QT interval, and slow and shorten conduction of action potentials through the atria. The action of sotalol on beta adrenergic receptors lengthens the sinus node cycle, conduction time through the atrioventricular node, refractory period, and duration of action potentials.

Biological Half-Life · 1 item

The terminal elimination half life is 10-20 hours in healthy patients. In patients with a creatinine clearance >80mL/min, the half life is 17.5±0.97h. In patients with a creatinine clearance 30-80mL/min, the half life is 22.7±6.4h. In patients with a creatinine clearance 10-30mL/min, the half life is 64±27.2h. In patients with a creatinine clearance <10mL/min, the half life is 97.9±57.3h.

Metabolism/MetabolitesSotalol is not metabolized.

Uses & manufacturing

UsesUse (kg) in Switzerland (2009): >250
Use ClassificationPharmaceuticals
Applications · 1 item

General DescriptionSotalol, 4'[1-hydroxy-2-(isopropylamino)ethyl]methylsulfonanilide (Betapace), is a relatively new antiarrhythmicdrug, characterized most often as a class IIIagent, and although it has effects that are related to the classII agents, it is not therapeutically considered a class II antiarrhythmic.It contains a chiral center and is marketed as theracemic mixture. Because of its enantiomers, its mechanismof action spans two of the antiarrhythmic drug classes. Thel(-) enantiomer has both β-blocking (class II) and potassiumchannel-blocking (class III) activities. The d(+) enantiomerhas class III properties similar to those of the (-) isomer,but its affinity for the -adrenergic receptor is 30 to 60 timeslower.

Upstream & downstream products

Upstream raw materials

Suppliers24 total

陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]
Anhui Zhongda Biotechnology Co., Ltd+86-15689548120 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
Anhui Zhongda Biotechnology Co., Ltd+86-19956560829 · [email protected]
医恩医疗系统研发(上海)有限公司021-58958002 18930822973 · [email protected]
Additional notes · 1 item

DefinitionChEBI: A sulfonamide that is N-phenylmethanesulfonamide in which the phenyl group is sustituted at position 4 by a 1-hydroxy-2-(isopropylamino)ethyl group. It has both beta-adrenoreceptor blocking (Vaughan Williams Class II) and ardiac 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.

Related reactions

5 records

Linked notes

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