Identification

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Name
Sotalol
Accession Number
DB00489  (APRD01230)
Type
Small Molecule
Groups
Approved
Description

Sotalol is a methanesulfonanilide developed in 1960.6 It was the first of the class III anti arrhythmic drugs.6 Sotalol was first approved as an oral tablet on 30 October 1992.8 A racemic mixture of sotalol is currently formulated as a tablet, oral solution, and intravenous injection indicated for life threatening ventricular arrhythmias and maintaining normal sinus rhythm in atrial fibrillation or flutter.Label,9,10

Structure
Thumb
Synonyms
  • 4'-(1-hydroxy-2-(isopropylamino)ethyl)methane sulfonanilide
  • Sotalol
  • Sotalolo
  • Sotalolum
  • β-cardone
External IDs
MJ 1999
Product Ingredients
IngredientUNIICASInChI Key
Sotalol hydrochlorideHEC37C70XX959-24-0VIDRYROWYFWGSY-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BetapaceTablet120 mg/1OralCovis Pharma2016-09-01Not applicableUs
BetapaceTablet160 mg/1OralBayer1992-10-302017-11-10Us50419 0106 10 nlmimage10 10190868
BetapaceTablet80 mg/1OralPhysicians Total Care, Inc.1992-10-302000-10-30Us
BetapaceTablet80 mg/1OralCovis Pharma2016-09-01Not applicableUs
BetapaceTablet120 mg/1OralBayer1992-10-302017-11-10Us50419 0109 10 nlmimage10 19190cb8
BetapaceTablet80 mg/1OralBayer1992-10-302017-11-10Us50419 0105 10 nlmimage10 16190b68
BetapaceTablet160 mg/1OralCovis Pharma2016-09-01Not applicableUs
Betapace AFTablet160 mg/1OralCovis Pharma2016-09-01Not applicableUs
Betapace AFTablet80 mg/1OralPhysicians Total Care, Inc.2005-10-312008-01-30Us
Betapace AFTablet120 mg/1OralCovis Pharma2016-09-01Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-sotalol - Tab 160mgTabletOralApotex Corporation1995-12-31Not applicableCanada
Apo-sotalol 80mg TabletsTabletOralApotex Corporation1996-12-31Not applicableCanada
Ava-sotalolTabletOralAvanstra Inc2011-08-112014-08-21Canada
Ava-sotalolTabletOralAvanstra Inc2011-08-112014-08-21Canada
Dom-sotalolTabletOralDominion Pharmacal1998-09-17Not applicableCanada
Dom-sotalolTabletOralDominion Pharmacal1998-09-17Not applicableCanada
Ftp-sotalolTabletOralFtp Pharmacal Inc.1998-10-092004-08-03Canada
Ftp-sotalolTabletOralFtp Pharmacal Inc.1998-10-092004-08-03Canada
Gen-sotalol 240mgTabletOralGenpharm Ulc1996-10-212009-08-05Canada
Jamp-sotalolTabletOralJamp Pharma Corporation2011-10-20Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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International/Other Brands
Biosotal (Sanofi-Aventis) / Cardol (Alphapharm) / Darob (Abbott) / Darob mite (Abbott) / Hipecor (Merck) / Loritmik (Krka) / Rytmobeta (Abbott) / Sotacor (Bristol-Myers Squibb) / Sotagard (GlaxoSmithKline) / Sotalex (Bristol-Myers Squibb) / Sotapor (Bristol-Myers Squibb) / Talozin (Adeka) / Tan Shi (Chia Tai Tianqing) / Xi An Lin (Changzhou Pharmaceutical Factory)
Categories
UNII
A6D97U294I
CAS number
3930-20-9
Weight
Average: 272.364
Monoisotopic: 272.119463206
Chemical Formula
C12H20N2O3S
InChI Key
ZBMZVLHSJCTVON-UHFFFAOYSA-N
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
IUPAC Name
N-(4-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}phenyl)methanesulfonamide
SMILES
CC(C)NCC(O)C1=CC=C(NS(C)(=O)=O)C=C1

Pharmacology

Indication

Sotalol is indicated to treat life threatening ventricular arrhytmias and maintain normal sinus rhythm in patients with atrial fibrillation or flutter.Label There are also oral solutions and intravenous injections indicated for patients requiring sotalol, but for whom a tablet would not be appropriate.Label,9,10

Associated Conditions
Pharmacodynamics

Sotalol is a competitive inhibitor of the rapid potassium channel.2 This inhibition lengthens the duration of action potentials and the refractory period in the atria and ventricles.3,4 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.6 L-sotalol also has beta adrenergic receptor blocking activity seen above plasma concentrations of 800ng/L.6 The beta blocking ability of sotalol further prolongs action potentials.6 D-sotalol does not have beta blocking activity but also reduces a patient's heart rate while standing or exercising.6 These actions combine to produce a negative inotropic effect that reduces the strength of contractility of muscle cells in the heart.2 Extension of the QT interval is also adversely associated with the induction of arrhythmia in patients.4

Hyperglycemia is a greater risk for non insulin dependant diabetics than insulin dependant diabetics.7 Beta blockers inhibit insulin secretion which may cause hyperglycemia in type II diabetes mellitus.7 The risk of hypoglycemia is higher in insulin dependant diabetes than non insulin dependant diabetics.7 Beta blockers decrease secretion of insulin, which may mask hypoglycemia in an insulin dependant patient.7 Beta blockers also increase glucose uptake into cells which may prolong or potentiate hypoglycemia.7

Further information regarding adverse reactions can be found here.11

Mechanism of action

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.2,3,4,5 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.6

TargetActionsOrganism
APotassium voltage-gated channel subfamily H member 2
inhibitor
Humans
ABeta-1 adrenergic receptor
antagonist
Humans
ABeta-2 adrenergic receptor
antagonist
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Sotalol is 90-100% bioavailable.Label,1 When taken with a meal, adsorption is lowered by 18%.Label,1 In patients with a creatinine clearance >80mL/min, the maximum concentration is 6.25±2.19.1

Volume of distribution

The apparent volume of distribution is 1.2-2.4L/kg.Label,1

Protein binding

0%.Label,1

Metabolism

Sotalol is not metabolized.Label,1

Route of elimination

80-90% of a given dose is excreted in the urine as unchanged sotalol.Label,1 A small fraction of the doses is excreted in the feces as unchanged sotalol.Label,1

Half life

The terminal elimination half life is 10-20 hours in healthy patients.Label,1 In patients with a creatinine clearance >80mL/min, the half life is 17.5±0.97h.1 In patients with a creatinine clearance 30-80mL/min, the half life is 22.7±6.4h.1 In patients with a creatinine clearance 10-30mL/min, the half life is 64±27.2h.1 In patients with a creatinine clearance <10mL/min, the half life is 97.9±57.3h.1

Clearance

In patients with a creatinine clearance >80mL/min, the plasma clearance is 6.78±2.72L/h and the renal clearance is 4.99±1.43L/h.1 In patients with a creatinine clearance 30-80mL/min, the plasma clearance is 2.74±0.53L/h and the renal clearance is 2.00±0.67L/h.1 In patients with a creatinine clearance 10-30mL/min, the plasma clearance is 1.56±0.44L/h and the renal clearance is 0.65±0.31L/h.1 In patients with a creatinine clearance <10mL/min, the plasma clearance is 0.65±0.20L/h and the renal clearance is 0.27±0.13L/h.1

Toxicity

Patients experiencing an overdose may present with bradycardia, congestive heart failure, hypotension, bronchospasm, and hypoglycemia.Label Larger intentional overdoses may present as hypotension, bradycardia, cardiac asystole, prolonged QT interval, torsade de pointes, ventricular tachycardia, and premature ventricular complexes.Label Stop administering sotalol and observe the patient until the QT interval returns to normal and the heart rate rises above 50 beats per minute.Label Hemodialysis may help lower plasma concentrations of sotalol as it is not bound to plasma proteins.Label Bradycardia and cardiac asystole may be treated with atropine, other anticholinergic drugs, beta adrenergic agonists, or transvenous cardiac pacing.Label. Second or third degree heart block may be treated with a transvenous cardiac pacemaker.Label Hypotension may be treated with epinephrine or norepinephrine.Label Bronchospasm may be treated with aminophylline or a beta-2 agonist, possibly at higher than normal doses.Label Torsade de pointes may be treated with DC cardioversion, transvenous cardiac pacing, epinephrine, or magnesium sulfate.Label

The oral LD50 for rats is 3450mg/kg, intraperitoneal LD50 for rats is 680mg/kg, oral LD50 for mice is 2600mg/kg, and intraperitoneal LD50 for mice is 670mg/kg.MSDS

Pregnant rabbits given 6 times the maximum recommended human dose showed an increase in fetal death and maternal toxicity, while rats given 18 times the maximum recommended human dose had an increased number of fetal resorptions.Label Sotalol is present in human breast milk so patients taking sotalol should not breast feed.Label

Sotalol has not been found to be carcinogenic.Label No studies have been performed regarding mutagenicity or clastogenicity.Label In animal studies, sotalol was not associated with a reduction in fertility aside from smaller litter sizes.Label

Further information regarding adverse reactions can be found here.11

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Sotalol Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidineThe metabolism of Sotalol can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine.
1,10-Phenanthroline1,10-Phenanthroline may increase the bradycardic activities of Sotalol.
2,4-thiazolidinedioneThe risk or severity of hypoglycemia can be increased when Sotalol is combined with 2,4-thiazolidinedione.
2,5-Dimethoxy-4-ethylamphetamineThe therapeutic efficacy of Sotalol can be decreased when used in combination with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe therapeutic efficacy of Sotalol can be decreased when used in combination with 2,5-Dimethoxy-4-ethylthioamphetamine.
25-desacetylrifapentineThe metabolism of Sotalol can be increased when combined with 25-desacetylrifapentine.
3-isobutyl-1-methyl-7H-xanthineThe risk or severity of adverse effects can be increased when Sotalol is combined with 3-isobutyl-1-methyl-7H-xanthine.
4-Bromo-2,5-dimethoxyamphetamineThe therapeutic efficacy of Sotalol can be decreased when used in combination with 4-Bromo-2,5-dimethoxyamphetamine.
4-Bromo-2,5-dimethoxyphenethylamineThe therapeutic efficacy of 4-Bromo-2,5-dimethoxyphenethylamine can be decreased when used in combination with Sotalol.
4-MethoxyamphetamineThe metabolism of Sotalol can be decreased when combined with 4-Methoxyamphetamine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

General References
  1. Hanyok JJ: Clinical pharmacokinetics of sotalol. Am J Cardiol. 1993 Aug 12;72(4):19A-26A. [PubMed:8346722]
  2. Valdes SO, Miyake CY, Niu MC, de la Uz CM, Asaki SY, Landstrom AP, Schneider AE, Rusin CG, Patel R, Lam WW, Kim JJ: Early experience with intravenous sotalol in children with and without congenital heart disease. Heart Rhythm. 2018 Dec;15(12):1862-1869. doi: 10.1016/j.hrthm.2018.07.010. Epub 2018 Jul 10. [PubMed:30003959]
  3. Staudacher I, Illg C, Chai S, Deschenes I, Seehausen S, Gramlich D, Muller ME, Wieder T, Rahm AK, Mayer C, Schweizer PA, Katus HA, Thomas D: Cardiovascular pharmacology of K2P17.1 (TASK-4, TALK-2) two-pore-domain K(+) channels. Naunyn Schmiedebergs Arch Pharmacol. 2018 Oct;391(10):1119-1131. doi: 10.1007/s00210-018-1535-z. Epub 2018 Jul 14. [PubMed:30008082]
  4. Orvos P, Kohajda Z, Szlovak J, Gazdag P, Arpadffy-Lovas T, Toth D, Geramipour A, Talosi L, Jost N, Varro A, Virag L: Evaluation of Possible Proarrhythmic Potency: Comparison of the Effect of Dofetilide, Cisapride, Sotalol, Terfenadine, and Verapamil on hERG and Native IKr Currents and on Cardiac Action Potential. Toxicol Sci. 2019 Apr 1;168(2):365-380. doi: 10.1093/toxsci/kfy299. [PubMed:30561737]
  5. Gorre F, Vandekerckhove H: Beta-blockers: focus on mechanism of action. Which beta-blocker, when and why? Acta Cardiol. 2010 Oct;65(5):565-70. doi: 10.2143/AC.65.5.2056244. [PubMed:21125979]
  6. Kpaeyeh JA Jr, Wharton JM: Sotalol. Card Electrophysiol Clin. 2016 Jun;8(2):437-52. doi: 10.1016/j.ccep.2016.02.007. [PubMed:27261833]
  7. Mills GA, Horn JR: Beta-blockers and glucose control. Drug Intell Clin Pharm. 1985 Apr;19(4):246-51. [PubMed:2861072]
  8. FDA Approved Drug Products: Sotalol [Link]
  9. FDA Approved Drug Products: Sotalol Intravenous [Link]
  10. FDA Approved Drug Products: Sotalol Oral Solution [Link]
  11. Dailymed: Sotalol Tablets [Link]
External Links
Human Metabolome Database
HMDB0014632
KEGG Compound
C07309
PubChem Compound
5253
PubChem Substance
46505012
ChemSpider
5063
BindingDB
25762
ChEBI
63622
ChEMBL
CHEMBL471
Therapeutic Targets Database
DAP000372
PharmGKB
PA451457
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Sotalol
ATC Codes
C07AA07 — SotalolC07BA07 — Sotalol and thiazidesC07FX02 — Sotalol and acetylsalicylic acid
AHFS Codes
  • 24:24.00 — Beta-adrenergic Blocking Agents
FDA label
Download (93.8 KB)
MSDS
Download (24.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedOtherBioequivalence1
1CompletedTreatmentHealthy Volunteers1
1TerminatedBasic ScienceAtrial Fibrillation (AF)1
2CompletedTreatmentFailed First Radiofrequency Ablation Procedure / Paroxysmal Atrial Fibrillation (PAF)1
3CompletedPreventionArrhythmia / Cardiovascular Disease (CVD) / Heart Arrest / Heart Diseases / Myocardial Infarction / Ventricular Fibrillation1
3CompletedTreatmentArrhythmia / Atrial Fibrillation (AF) / Cardiovascular Disease (CVD) / Heart Diseases1
3CompletedTreatmentArrhythmia / Cardiovascular Disease (CVD) / Death, Sudden,Cardiac / Heart Diseases / Ventricular Fibrillation / Ventricular Tachycardia (VT)1
3CompletedTreatmentArrhythmia / Arrhythmia of ventricular origin / Cardiovascular Disease (CVD) / Death, Sudden,Cardiac / Heart Diseases / Ventricular Fibrillation / Ventricular Tachycardia (VT)1
3CompletedTreatmentAtrial Fibrillation (AF)1
3CompletedTreatmentAtrial Fibrillation (AF) / Cerebrovascular Accident / Sudden Death1
3CompletedTreatmentParoxysmal Atrial Fibrillation (PAF)1
3RecruitingTreatmentFetal Atrial Flutter Without Hydrops / Fetal Supraventricular Tachycardia With Hydrops / Fetal Supraventricular Tachycardia Without Hydrops1
3SuspendedTreatmentAtrial Fibrillation (AF)1
3TerminatedTreatmentAtrial Fibrillation (AF) / Heart Failure1
3WithdrawnTreatmentCoronary Artery Disease / Ventricular Tachycardia (VT)1
4CompletedNot AvailableParoxysmal Atrial Fibrillation (PAF)1
4CompletedPreventionVentricular Tachycardia (VT)1
4CompletedTreatmentAtrial Fibrillation (AF)1
4Not Yet RecruitingTreatmentArrhythmia1
4Not Yet RecruitingTreatmentAtrial Fibrillation (AF)1
4RecruitingTreatmentAtrial Fibrillation (AF)2
4RecruitingTreatmentMyocardial Infarction / Ventricular Tachyarrhythmias1
4RecruitingTreatmentVentricular Tachycardia (VT)1
4TerminatedTreatmentArrhythmia of ventricular origin / Ventricular Tachycardia (VT)1
4Unknown StatusNot AvailableVentricular Premature Complexes / Ventricular Tachycardia (VT)1
4WithdrawnTreatmentAtrial Fibrillation (AF)1
Not AvailableActive Not RecruitingTreatmentAtrial Fibrillation (AF)1
Not AvailableActive Not RecruitingTreatmentAtrial Fibrillation (AF) / Quality of Life1
Not AvailableCompletedTreatmentArrhythmia / Atrial Fibrillation (AF)1
Not AvailableCompletedTreatmentAtrial Fibrillation (AF)1
Not AvailableCompletedTreatmentHeart Failure / Recurrent Atrial Fibrillation1
Not AvailableCompletedTreatmentMonomorphic Ventricular Tachycardia1
Not AvailableRecruitingNot AvailableAtrial Fibrillation (AF)1
Not AvailableRecruitingNot AvailableLong qt Syndrome / Therapeutic Agent Toxicity1
Not AvailableRecruitingTreatmentVentricular premature beats1
Not AvailableTerminatedTreatmentVentricular Tachycardia (VT)1

Pharmacoeconomics

Manufacturers
  • Academic pharmaceuticals inc
  • Bayer healthcare pharmaceuticals inc
  • Upsher smith laboratories inc
  • Amneal pharmaceutical
  • Apotex inc
  • Apotex inc etobicoke site
  • Impax pharmaceuticals
  • Mutual pharmaceutical co inc
  • Mylan pharmaceuticals inc
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Vintage pharmaceuticals inc
  • Watson laboratories inc
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Amerisource Health Services Corp.
  • Amneal Pharmaceuticals
  • Apotex Inc.
  • Atlantic Biologicals Corporation
  • Bayer Healthcare
  • Bioniche Pharma
  • Cardinal Health
  • Caremark LLC
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Eon Labs
  • Genpharm LP
  • Global Pharmaceuticals
  • Golden State Medical Supply Inc.
  • Heartland Repack Services LLC
  • Kaiser Foundation Hospital
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Novopharm Ltd.
  • Physicians Total Care Inc.
  • Promex Medical Inc.
  • Qualitest
  • Rebel Distributors Corp.
  • Resource Optimization and Innovation LLC
  • Teva Pharmaceutical Industries Ltd.
  • Torpharm Inc.
  • Upsher Smith Laboratories
  • Vangard Labs Inc.
Dosage forms
FormRouteStrength
TabletOral
TabletOral160 mg
TabletOral80 mg
InjectionIntravenous15 mg/1mL
TabletOral120 mg/1
TabletOral160 mg/1
TabletOral240 mg/1
TabletOral80 mg/1
SolutionOral5 mg/1mL
Prices
Unit descriptionCostUnit
Betapace AF 100 160 mg tablet Box538.2USD box
Betapace AF 60 120 mg tablet Bottle311.06USD bottle
Betapace 240 mg tablet8.94USD tablet
Sotalol hcl 150 mg/10 ml vial7.8USD ml
Betapace 160 mg tablet6.87USD tablet
Betapace af 160 mg tablet6.24USD tablet
Sorine 240 mg tablet5.6USD tablet
Betapace 120 mg tablet5.5USD tablet
Sotalol HCl 240 mg tablet5.29USD tablet
Sotalol 240 mg tablet5.09USD tablet
Betapace af 120 mg tablet4.99USD tablet
Sotalol HCl (AF) 160 mg tablet4.45USD tablet
Sorine 160 mg tablet4.31USD tablet
Sotalol af 160 mg tablet4.27USD tablet
Betapace 80 mg tablet4.12USD tablet
Sotalol HCl 160 mg tablet4.07USD tablet
Sotalol 160 mg tablet3.92USD tablet
Betapace af 80 mg tablet3.74USD tablet
Sotalol HCl (AF) 120 mg tablet3.56USD tablet
Sorine 120 mg tablet3.46USD tablet
Sotalol af 120 mg tablet3.42USD tablet
Sotalol HCl 120 mg tablet3.26USD tablet
Sotalol 120 mg tablet3.13USD tablet
Sotalol HCl 80 mg tablet2.67USD tablet
Sotalol HCl (AF) 80 mg tablet2.67USD tablet
Sorine 80 mg tablet2.61USD tablet
Sotalol af 80 mg tablet2.56USD tablet
Sotalol 80 mg tablet2.35USD tablet
Apo-Sotalol 160 mg Tablet0.68USD tablet
Co Sotalol 160 mg Tablet0.68USD tablet
Mylan-Sotalol 160 mg Tablet0.68USD tablet
Novo-Sotalol 160 mg Tablet0.68USD tablet
Nu-Sotalol 160 mg Tablet0.68USD tablet
Pms-Sotalol 160 mg Tablet0.68USD tablet
Ratio-Sotalol 160 mg Tablet0.68USD tablet
Sandoz Sotalol 160 mg Tablet0.68USD tablet
Apo-Sotalol 80 mg Tablet0.62USD tablet
Co Sotalol 80 mg Tablet0.62USD tablet
Mylan-Sotalol 80 mg Tablet0.62USD tablet
Novo-Sotalol 80 mg Tablet0.62USD tablet
Nu-Sotalol 80 mg Tablet0.62USD tablet
Pms-Sotalol 80 mg Tablet0.62USD tablet
Ratio-Sotalol 80 mg Tablet0.62USD tablet
Sandoz Sotalol 80 mg Tablet0.62USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US9724297No2017-08-082035-08-31Us
US10206895No2019-02-192034-04-01Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)206.75http://www.chemspider.com/Chemical-Structure.5063.html
boiling point (°C)443.3http://www.chemspider.com/Chemical-Structure.5063.html
Predicted Properties
PropertyValueSource
Water Solubility0.782 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity71.12 m3·mol-1ChemAxon
Polarizability29.34 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.995
Blood Brain Barrier+0.9382
Caco-2 permeable-0.8957
P-glycoprotein substrateNon-substrate0.6708
P-glycoprotein inhibitor INon-inhibitor0.8881
P-glycoprotein inhibitor IINon-inhibitor0.9638
Renal organic cation transporterNon-inhibitor0.9514
CYP450 2C9 substrateNon-substrate0.7392
CYP450 2D6 substrateNon-substrate0.8296
CYP450 3A4 substrateNon-substrate0.6194
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8807
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8276
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.587
BiodegradationNot ready biodegradable0.9949
Rat acute toxicity2.2873 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.846
hERG inhibition (predictor II)Non-inhibitor0.8701
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-0090000000-b3dca1dbda7d2457ee97
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-00di-0090000000-a29ae691c7c3aac0cd25
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-00di-0090000000-3826232ebd5c11e1fb09
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0uk9-0590000000-c1cd421f642943a3e40d
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-00di-0090000000-62e0058eee644436c974
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-00di-0090000000-1c2e1183f392f02dd2f3
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-00di-0900000000-467f723fa9c5b11ac3a0
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-0090000000-ec702c0822212cb2e764
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0090000000-3fe820b16cdb741dfa3e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0ab9-0090000000-ba1b9c76db4e9239d8ff
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0090000000-9855a87a9a317eccb37e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03e9-0690000000-0c5b752605586d60828a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0910000000-399c8ea4647bc5a24781
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-f44d2d18cd4dfd9b2756
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-053r-0900000000-422f178f83cadcda84d7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0ab9-0090000000-06e3079747baad9d6087
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0090000000-69df046b345e5e50d742
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03e9-0690000000-94ba050da9e6a24f29b1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0910000000-0ef0a4777ff5e99c8462
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-52c0f117b0c8ef4e0b76
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-053r-0900000000-ade6b1782a916acc1d7e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0090000000-ef1bcb821ca9cd1627a8
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0090000000-75d846e48f9d41af615c
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03e9-0790000000-610bf5222b1cb6f67b93
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-053r-0900000000-943fd2d5d938aa51d8d5
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0920000000-7400cd81d8ca70325a62
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-053r-0900000000-3b49e7b47aa69566cb3a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0090000000-36ad35b8c37f5c9f4e91
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0090000000-1f8f59e1c29a48907b1d
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-0390000000-7e44e05711b4dc722309

Taxonomy

Description
This compound 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Sulfanilides
Direct Parent
Sulfanilides
Alternative Parents
Aralkylamines / Organosulfonamides / Organic sulfonamides / Aminosulfonyl compounds / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
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
show 14 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
sulfonamide, secondary alcohol, secondary amino compound, ethanolamines (CHEBI:63622)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization
Specific Function
Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the ...
Gene Name
KCNH2
Uniprot ID
Q12809
Uniprot Name
Potassium voltage-gated channel subfamily H member 2
Molecular Weight
126653.52 Da
References
  1. Shimizu W, Antzelevitch C: Effects of a K(+) channel opener to reduce transmural dispersion of repolarization and prevent torsade de pointes in LQT1, LQT2, and LQT3 models of the long-QT syndrome. Circulation. 2000 Aug 8;102(6):706-12. [PubMed:10931813]
  2. Numaguchi H, Mullins FM, Johnson JP Jr, Johns DC, Po SS, Yang IC, Tomaselli GF, Balser JR: Probing the interaction between inactivation gating and Dd-sotalol block of HERG. Circ Res. 2000 Nov 24;87(11):1012-8. [PubMed:11090546]
  3. Wolpert C, Schimpf R, Giustetto C, Antzelevitch C, Cordeiro J, Dumaine R, Brugada R, Hong K, Bauersfeld U, Gaita F, Borggrefe M: Further insights into the effect of quinidine in short QT syndrome caused by a mutation in HERG. J Cardiovasc Electrophysiol. 2005 Jan;16(1):54-8. [PubMed:15673388]
  4. Wolpert C, Schimpf R, Veltmann C, Giustetto C, Gaita F, Borggrefe M: Clinical characteristics and treatment of short QT syndrome. Expert Rev Cardiovasc Ther. 2005 Jul;3(4):611-7. [PubMed:16076272]
  5. Fedida D, Orth PM, Hesketh JC, Ezrin AM: The role of late I and antiarrhythmic drugs in EAD formation and termination in Purkinje fibers. J Cardiovasc Electrophysiol. 2006 May;17 Suppl 1:S71-S78. [PubMed:16686685]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Receptor signaling protein activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
Gene Name
ADRB1
Uniprot ID
P08588
Uniprot Name
Beta-1 adrenergic receptor
Molecular Weight
51322.1 Da
References
  1. Lowe MD, Lynham JA, Grace AA, Kaumann AJ: Comparison of the affinity of beta-blockers for two states of the beta 1-adrenoceptor in ferret ventricular myocardium. Br J Pharmacol. 2002 Jan;135(2):451-61. [PubMed:11815381]
  2. Joseph SS, Lynham JA, Colledge WH, Kaumann AJ: Binding of (-)-[3H]-CGP12177 at two sites in recombinant human beta 1-adrenoceptors and interaction with beta-blockers. Naunyn Schmiedebergs Arch Pharmacol. 2004 May;369(5):525-32. Epub 2004 Apr 2. [PubMed:15060759]
  3. Yalcin I, Choucair-Jaafar N, Benbouzid M, Tessier LH, Muller A, Hein L, Freund-Mercier MJ, Barrot M: beta(2)-adrenoceptors are critical for antidepressant treatment of neuropathic pain. Ann Neurol. 2009 Feb;65(2):218-25. doi: 10.1002/ana.21542. [PubMed:19259968]
  4. Doggrell SA: The effects of (+/-)-, (+)-, and (-)-atenolol, sotalol, and amosulalol on the rat left atria and portal vein. Chirality. 1993;5(1):8-14. [PubMed:8095397]
  5. Juberg EN, Minneman KP, Abel PW: Beta 1- and beta 2-adrenoceptor binding and functional response in right and left atria of rat heart. Naunyn Schmiedebergs Arch Pharmacol. 1985 Sep;330(3):193-202. [PubMed:2865685]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Protein homodimerization activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
Gene Name
ADRB2
Uniprot ID
P07550
Uniprot Name
Beta-2 adrenergic receptor
Molecular Weight
46458.32 Da
References
  1. Lowe MD, Lynham JA, Grace AA, Kaumann AJ: Comparison of the affinity of beta-blockers for two states of the beta 1-adrenoceptor in ferret ventricular myocardium. Br J Pharmacol. 2002 Jan;135(2):451-61. [PubMed:11815381]
  2. Joseph SS, Lynham JA, Colledge WH, Kaumann AJ: Binding of (-)-[3H]-CGP12177 at two sites in recombinant human beta 1-adrenoceptors and interaction with beta-blockers. Naunyn Schmiedebergs Arch Pharmacol. 2004 May;369(5):525-32. Epub 2004 Apr 2. [PubMed:15060759]
  3. Yalcin I, Choucair-Jaafar N, Benbouzid M, Tessier LH, Muller A, Hein L, Freund-Mercier MJ, Barrot M: beta(2)-adrenoceptors are critical for antidepressant treatment of neuropathic pain. Ann Neurol. 2009 Feb;65(2):218-25. doi: 10.1002/ana.21542. [PubMed:19259968]
  4. Doggrell SA: The effects of (+/-)-, (+)-, and (-)-atenolol, sotalol, and amosulalol on the rat left atria and portal vein. Chirality. 1993;5(1):8-14. [PubMed:8095397]
  5. Juberg EN, Minneman KP, Abel PW: Beta 1- and beta 2-adrenoceptor binding and functional response in right and left atria of rat heart. Naunyn Schmiedebergs Arch Pharmacol. 1985 Sep;330(3):193-202. [PubMed:2865685]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Iwaki M, Niwa T, Bandoh S, Itoh M, Hirose H, Kawase A, Komura H: Application of substrate depletion assay to evaluation of CYP isoforms responsible for stereoselective metabolism of carvedilol. Drug Metab Pharmacokinet. 2016 Dec;31(6):425-432. doi: 10.1016/j.dmpk.2016.08.007. Epub 2016 Sep 2. [PubMed:27836712]
  2. Brodde OE, Kroemer HK: Drug-drug interactions of beta-adrenoceptor blockers. Arzneimittelforschung. 2003;53(12):814-22. [PubMed:14732961]
  3. Sternieri E, Coccia CP, Pinetti D, Guerzoni S, Ferrari A: Pharmacokinetics and interactions of headache medications, part II: prophylactic treatments. Expert Opin Drug Metab Toxicol. 2006 Dec;2(6):981-1007. doi: 10.1517/17425255.2.6.981 . [PubMed:17125412]

Drug created on June 13, 2005 07:24 / Updated on November 12, 2019 19:43