CHEBI:63622 - sotalol

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ChEBI Name sotalol
ChEBI ID CHEBI:63622
Definition 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 β-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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Anonymous
Secondary ChEBI IDs CHEBI:9206
Supplier Information
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Formula C12H20N2O3S
Net Charge 0
Average Mass 272.36400
Monoisotopic Mass 272.119
InChI InChI=1S/C12H20N2O3S/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
InChIKey ZBMZVLHSJCTVON-UHFFFAOYSA-N
SMILES CC(C)NCC(O)c1ccc(NS(C)(=O)=O)cc1
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
beta-adrenergic antagonist
An agent that binds to but does not activate beta-adrenergic receptors thereby blocking the actions of endogenous or exogenous beta-adrenergic agonists. beta-Adrenergic antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches and anxiety.
Application(s): beta-adrenergic antagonist
An agent that binds to but does not activate beta-adrenergic receptors thereby blocking the actions of endogenous or exogenous beta-adrenergic agonists. beta-Adrenergic antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches and anxiety.
anti-arrhythmia drug
A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.
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ChEBI Ontology
Outgoing sotalol (CHEBI:63622) has role β-adrenergic antagonist (CHEBI:35530)
sotalol (CHEBI:63622) has role anti-arrhythmia drug (CHEBI:38070)
sotalol (CHEBI:63622) has role environmental contaminant (CHEBI:78298)
sotalol (CHEBI:63622) has role xenobiotic (CHEBI:35703)
sotalol (CHEBI:63622) is a ethanolamines (CHEBI:23981)
sotalol (CHEBI:63622) is a secondary alcohol (CHEBI:35681)
sotalol (CHEBI:63622) is a secondary amino compound (CHEBI:50995)
sotalol (CHEBI:63622) is a sulfonamide (CHEBI:35358)
sotalol (CHEBI:63622) is conjugate base of sotalol(1+) (CHEBI:63647)
Incoming sotalol(1+) (CHEBI:63647) is conjugate acid of sotalol (CHEBI:63622)
IUPAC Name
N-{4-[1-hydroxy-2-(propan-2-ylamino)ethyl]phenyl}methanesulfonamide
INNs Sources
sotalol ChemIDplus
sotalolum ChemIDplus
Synonyms Sources
4'-(1-hydroxy-2-(isopropylamino)ethyl)methane sulfonanilide ChemIDplus
β-cardone ChemIDplus
Sotalol KEGG COMPOUND
Manual Xrefs Databases
2464 DrugCentral
C07309 KEGG COMPOUND
D08525 KEGG DRUG
DB00489 DrugBank
HMDB0014632 HMDB
LSM-1465 LINCS
Sotalol Wikipedia
View more database links
Registry Numbers Types Sources
2380820 Reaxys Registry Number Reaxys
3930-20-9 CAS Registry Number KEGG COMPOUND
3930-20-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
20562595 PubMed citation Europe PMC
21553267 PubMed citation Europe PMC
21854895 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comment
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag