Sotalol (CED0003327)

Record Information
Version1.0
Creation Date2016-05-22 03:46:07 UTC
Update Date2026-08-18 20:06:37 UTC
Accession NumberCHEM016874
Identification
Common NameSotalol
ClassSmall Molecule
Description
Sotalol is an organic compound with the chemical formula C12H20N2O3S and an average molecular weight of 272.36 g/mol. Sotalol belongs to the sulfanilides, a subclass of benzene and substituted derivatives within the organic compounds. The compound is recorded as being found in or released from nine different sources. Within the category of healthcare, pharmaceuticals, and veterinary products, it is utilized as a beta blocking agent. Other identified sources include drinking water and water supply, as well as various electrical and electronic equipment such as electrodes, antennas, and electrically stimulated smoking devices. Additionally, it is associated with household cleaning and consumer products, specifically perfumes within detergents and soaps, tobacco smoke filters, cigar cigarettes, and other smoking requisites. Exposure to this substance occurs through oral and intravenous routes. At the molecular level, sotalol interacts with three recorded protein targets. It functions as an antagonist or inhibitor of the Beta-1 adrenergic receptor (ADRB1), the Beta-2 adrenergic receptor (ADRB2), and the voltage-gated inwardly rectifying potassium channel KCNH2.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
4'-(1-Hydroxy-2-(isopropylamino)ethyl)methane sulfonanilideChEBI
beta-CardoneChEBI
SotalolumChEBI
Darob miteKegg
4'-(1-Hydroxy-2-(isopropylamino)ethyl)methane sulphonanilideGenerator
b-CardoneGenerator
Β-cardoneGenerator
Sotalol HCLHMDB
Sotalol hydrochlorideMeSH, HMDB
Sotalol monohydrochlorideMeSH, HMDB
DarobMeSH, HMDB
Knoll pharmaceutical brand OF sotalolMeSH, HMDB
Chemical FormulaC12H20N2O3S
Average Molecular Mass272.364 g/mol
Monoisotopic Mass272.119 g/mol
CAS Registry Number3930-20-9
IUPAC NameN-(4-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}phenyl)methanesulfonamide
Traditional Namesotalol
SMILESCC(C)NCC(O)C1=CC=C(NS(C)(=O)=O)C=C1
InChI IdentifierInChI=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
InChI KeyZBMZVLHSJCTVON-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sulfanilides. These are organic aromatic compounds containing a sulfanilide moiety, with the general structure RS(=O)(=O)NC1=CC=CC=C1.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassSulfanilides
Direct ParentSulfanilides
Alternative Parents
Substituents
  • Sulfanilide
  • Aralkylamine
  • Organic sulfonic acid amide
  • Organosulfonic acid amide
  • Aminosulfonyl compound
  • Sulfonyl
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Secondary aliphatic amine
  • Secondary amine
  • Organopnictogen compound
  • Alcohol
  • Organic nitrogen compound
  • Aromatic alcohol
  • Organic oxygen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.78 g/LALOGPS
logP0.85ALOGPS
logP-0.4ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)10.07ChemAxon
pKa (Strongest Basic)9.43ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area78.43 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity71.12 m³·mol⁻¹ChemAxon
Polarizability29.34 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0zn9-9570000000-d4b8eccd09c6d9bdc80cNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0uk9-5982000000-a7262c3ec90ea5ecf7a8Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0090000000-b3dca1dbda7d2457ee97Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0090000000-a29ae691c7c3aac0cd25Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0090000000-3826232ebd5c11e1fb09Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0uk9-0590000000-c1cd421f642943a3e40dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0090000000-62e0058eee644436c974Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0090000000-1c2e1183f392f02dd2f3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-467f723fa9c5b11ac3a0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0090000000-ec702c0822212cb2e764Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0090000000-3fe820b16cdb741dfa3eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ab9-0090000000-ba1b9c76db4e9239d8ffNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0090000000-9855a87a9a317eccb37eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03e9-0690000000-0c5b752605586d60828aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0910000000-399c8ea4647bc5a24781Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-f44d2d18cd4dfd9b2756Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-053r-0900000000-422f178f83cadcda84d7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ab9-0090000000-06e3079747baad9d6087Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0090000000-69df046b345e5e50d742Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03e9-0690000000-94ba050da9e6a24f29b1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0910000000-0ef0a4777ff5e99c8462Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-52c0f117b0c8ef4e0b76Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-053r-0900000000-ade6b1782a916acc1d7eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0090000000-ef1bcb821ca9cd1627a8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0090000000-75d846e48f9d41af615cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03e9-0790000000-610bf5222b1cb6f67b93Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-053r-0900000000-943fd2d5d938aa51d8d5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0920000000-7400cd81d8ca70325a62Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-053r-0900000000-3b49e7b47aa69566cb3aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0090000000-36ad35b8c37f5c9f4e91Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0090000000-1f8f59e1c29a48907b1dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0390000000-7e44e05711b4dc722309Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0090000000-6c61b70deef88c62ee35Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0090000000-b3dca1dbda7d2457ee97Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0090000000-75d846e48f9d41af615cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0090000000-602a6608eea251ed269eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0090000000-c70ff95e23856f99502aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0229-0980000000-5f1ef8c732be6fe68dbdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03e9-0790000000-610bf5222b1cb6f67b93Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-97ce0758dcb0e6a91532Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03e9-0790000000-2e50f1ae664bc3d64e8cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-06si-0950000000-889e7f2903504b370b4fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0fk9-0190000000-f6b9b5bba4b95da2c0b2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0930000000-b392368dc754e752c258Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0bt9-0190000000-916c223f241777450719Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0229-0290000000-4ac0b432aa04a88f8c87Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-053r-0900000000-69cc6a1fdde7855a2a62Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-053r-0900000000-fc32464999b727c16ac8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0229-0290000000-9e686e3bd1aef55cf855Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0090000000-f33265d05bcf6ddaef3eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0090000000-68f9b5a6fe5ae6383dbeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ab9-0090000000-4e119186ee400eb04378Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ab9-0090000000-3931f0c8e7358949ff86Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03e9-0690000000-642a67022188b4dbd7bdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03e9-0690000000-f214ac8459f41668f1d0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0910000000-04251164509f3911097fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0910000000-38746a4b88a9631268baNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0090000000-a29ae691c7c3aac0cd25Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0090000000-ec702c0822212cb2e764Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-7238fbbd82148a19aad4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-07af6261fb6fdd955768Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0090000000-3826232ebd5c11e1fb09Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0090000000-1c2e1183f392f02dd2f3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-467f723fa9c5b11ac3a0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0090000000-62e0058eee644436c974Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-053r-0900000000-98fcdad89208a861cdf1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-d718b4edfa8d3db2f095Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0uk9-0590000000-c1cd421f642943a3e40dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0adi-0590000000-09098535885ecdd33e06Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01t9-0910000000-fe5e3cea1910aa494493Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0079-4900000000-f69c1721a736a690e1f8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00fr-7090000000-8f2d5c2fc4cd2a32e84eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9120000000-51d630654bc798397a72Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9000000000-c9c1175194f72014c120Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ab9-0090000000-c93e9788a97919b32703Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0090000000-8e8021523ee35f8f033bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-08g3-3920000000-488675b1d11d403fd583Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0090000000-8e3453399b96e94668acNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-1390000000-c83a07325e2dbec62a2cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9510000000-17d53aa01717830b1f60Not AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2459.0Log mg/kg[1400:4400]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
115Drinking waterDrinking water & water supplyNot Available
233BrushesPersonal care & cosmeticsNot Available
293Beta blocking agentsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
Pathways
4 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Beta-2 adrenergic receptor structureClick to view 3D structureBeta-2 adrenergic receptorP07550HumansPredicted (SEA)1.86838
Click to view 3D structureBeta-2 adrenergic receptorQ28044Bos taurusPredicted (SEA)0.0778492
Beta-1 adrenergic receptor structureClick to view 3D structureBeta-1 adrenergic receptorP08588HumansPredicted (SEA)3.34752
Click to view 3D structureTaste receptor type 2 member 50P59544HumansPredicted (SEA)0.622794
Click to view 3D structureTaste receptor type 2 member 45P59539HumansPredicted (SEA)0.622794
Click to view 3D structureTaste receptor type 2 member 42Q7RTR8HumansPredicted (SEA)0.622794
Click to view 3D structureTaste receptor type 2 member 41P59536HumansPredicted (SEA)0.622794
Click to view 3D structureTaste receptor type 2 member 7Q9NYW3HumansPredicted (SEA)0.622794
Click to view 3D structureTaste receptor type 2 member 30P59541HumansPredicted (SEA)0.622794
Click to view 3D structureTaste receptor type 2 member 60P59551HumansPredicted (SEA)0.622794
Click to view 3D structureTaste receptor type 2 member 19P59542HumansPredicted (SEA)0.622794
Click to view 3D structureTaste receptor type 2 member 20P59543HumansPredicted (SEA)0.622794
Click to view 3D structureTaste receptor type 2 member 1Q9NYW7HumansPredicted (SEA)0.622794
Click to view 3D structureTaste receptor type 2 member 40P59535HumansPredicted (SEA)0.622794
Click to view 3D structureTaste receptor type 2 member 3Q9NYW6HumansPredicted (SEA)0.622794
Click to view 3D structureTaste receptor type 2 member 13Q9NYV9HumansPredicted (SEA)0.622794
Click to view 3D structureTaste receptor type 2 member 39P59534HumansPredicted (SEA)0.622794
Click to view 3D structureTaste receptor type 2 member 5Q9NYW4HumansPredicted (SEA)0.622794
Click to view 3D structureTaste receptor type 2 member 9Q9NYW1HumansPredicted (SEA)0.622794
Click to view 3D structureTaste receptor type 2 member 43P59537HumansPredicted (SEA)0.622794
Click to view 3D structureBeta-2 adrenergic receptorP54833Canis lupus familiarisPredicted (SEA)0.0778492
Click to view 3D structureBeta-2 adrenergic receptorQ8K4Z4Cavia porcellusPredicted (SEA)4.9045
Click to view 3D structureBeta-1 adrenergic receptorB0FL73Cavia porcellusPredicted (SEA)3.34752
Beta-3 adrenergic receptor structureClick to view 3D structureBeta-3 adrenergic receptorP13945HumansPredicted (SEA)9.26406
Click to view 3D structureBeta-1 adrenergic receptorP18090Rattus norvegicusPredicted (SEA)3.89246
Concentrations
StatusValueUnitSample LocationReference
Detected and Quantified410ng/LBioggio,Lugano
Detected and Quantified330ng/LBussigny-prés-Lausanne
Detected and Quantified550ng/LHallau,Klettgau
Detected and Quantified140ng/LThal,Altenrhein
Detected and Quantified640ng/LUetendorf,Thun
Detected and Quantified330ng/LVernier,Aïre
Detected and Quantified480ng/LWinterthur
Detected and Quantified300ng/LWerdhölzli,Zürich
Detected and Quantified210ng/LSchönau,Zug
Detected and Quantified140ng/LAffoltern,Zwillikon
External Links
DrugBank IDDB00489
HMDB IDHMDB0253916
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSotalol
Chemspider ID5063
ChEBI ID63622
PubChem Compound IDNot Available
Kegg Compound IDC07309
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20562595
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21553267
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21854895