Identification

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

An adrenergic beta-antagonist that is used in the treatment of life-threatening arrhythmias. [PubChem]

Structure
Thumb
Synonyms
  • 4'-(1-Hydroxy-2-(isopropylamino)ethyl)methane sulfonanilide
  • Sotalol
  • Sotalolo
  • Sotalolum
External IDs
MJ 1999
Product Ingredients
IngredientUNIICASInChI Key
Sotalol HydrochlorideHEC37C70XX959-24-0VIDRYROWYFWGSY-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BetapaceTablet160 mg/1OralBayer1992-10-302017-11-10Us50419 0106 10 nlmimage10 10190868
BetapaceTablet120 mg/1OralCovis Pharma2016-09-01Not applicableUs
BetapaceTablet120 mg/1OralBayer1992-10-302017-11-10Us50419 0109 10 nlmimage10 19190cb8
BetapaceTablet80 mg/1OralPhysicians Total Care, Inc.1992-10-302000-10-30Us
BetapaceTablet80 mg/1OralCovis Pharma2016-09-01Not applicableUs
BetapaceTablet80 mg/1OralBayer1992-10-302017-11-10Us50419 0105 10 nlmimage10 16190b68
BetapaceTablet160 mg/1OralCovis Pharma2016-09-01Not applicableUs
Betapace AFTablet120 mg/1OralCovis Pharma2016-09-01Not applicableUs
Betapace AFTablet120 mg/1OralBayer2000-02-222017-11-10Us50419 0119 06 nlmimage10 59192cc9
Betapace AFTablet80 mg/1OralCovis Pharma2016-09-01Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-sotalol - Tab 160mgTablet160 mgOralApotex Corporation1995-12-31Not applicableCanada
Apo-sotalol 80mg TabletsTablet80 mgOralApotex Corporation1996-12-31Not applicableCanada
Ava-sotalolTablet160 mgOralAvanstra Inc2011-08-112014-08-21Canada
Ava-sotalolTablet80 mgOralAvanstra Inc2011-08-112014-08-21Canada
Dom-sotalolTablet160 mgOralDominion Pharmacal1998-09-17Not applicableCanada
Dom-sotalolTablet80 mgOralDominion Pharmacal1998-09-17Not applicableCanada
Ftp-sotalolTablet160 mgOralFtp Pharmacal Inc.1998-10-092004-08-03Canada
Ftp-sotalolTablet80 mgOralFtp Pharmacal Inc.1998-10-092004-08-03Canada
Gen-sotalol 240mgTablet240 mgOralGenpharm Ulc1996-10-212009-08-05Canada
Jamp-sotalolTablet160 mgOralJamp Pharma Corporation2011-10-20Not applicableCanada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
SotalolSotalol (120 mg/1)TabletOralMutual Pharmaceutical2007-01-22Not applicableUs
SotalolSotalol (80 mg/1)TabletOralMutual Pharmaceutical2007-01-22Not applicableUs
SotalolSotalol (160 mg/1)TabletOralMutual Pharmaceutical2007-01-22Not applicableUs
Sotalol HydrochlorideSotalol Hydrochloride (240 mg/1)TabletOralMutual Pharmaceutical2006-12-01Not applicableUs
Sotalol HydrochlorideSotalol Hydrochloride (80 mg/1)TabletOralMutual Pharmaceutical2006-12-01Not applicableUs
Sotalol HydrochlorideSotalol Hydrochloride (160 mg/1)TabletOralMutual Pharmaceutical2006-12-01Not applicableUs
Sotalol HydrochlorideSotalol Hydrochloride (120 mg/1)TabletOralMutual Pharmaceutical2006-12-01Not applicableUs
International/Other Brands
beta-Cardone / 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

For the maintenance of normal sinus rhythm [delay in time to recurrence of atrial fibrillation/atrial flutter (AFIB/AFL)] in patients with symptomatic AFIB/AFL who are currently in sinus rhythm. Also for the treatment of documented life-threatening ventricular arrhythmias.

Associated Conditions
Pharmacodynamics

Sotalol is an antiarrhythmic drug. It falls into the class of beta blockers (and class II antiarrhythmic agents) because of its primary action on the β-adrenergic receptors in the heart. In addition to its actions on the beta receptors in the heart, sotalol inhibits the inward potassium ion channels of the heart. In so doing, sotalol prolongs repolarization, therefore lengthening the QT interval and decreasing automaticity. It also slows atrioventricular (AV) nodal conduction. Because of these actions on the cardiac action potential, it is also considered a class III antiarrhythmic agent. The beta-blocking effect of sotalol is non-cardioselective, half maximal at about 80mg/day and maximal at doses between 320 and 640 mg/day. Sotalol does not have partial agonist or membrane stabilizing activity. Although significant beta-blockade occurs at oral doses as low as 25 mg, significant Class Ieffects are seen only at daily doses of 160 mg and above.

Mechanism of action

Sotalol has both beta-adrenoreceptor blocking (Vaughan Williams Class I) and cardiac action potential duration prolongation (Vaughan Williams Class I) antiarrhythmic properties. Sotalol is a racemic mixture of d- and l-sotalol. Both isomers have similar Class I antiarrhythmic effects, while the l-isomer is responsible for virtually all of the beta-blocking activity. Sotalol inhibits response to adrenergic stimuli by competitively blocking β1-adrenergic receptors within the myocardium and β2-adrenergic receptors within bronchial and vascular smooth muscle. The electrophysiologic effects of sotalol may be due to its selective inhibition of the rapidly activating component of the potassium channel involved in the repolarization of cardiac cells. The class II electrophysiologic effects are caused by an increase in sinus cycle length (slowed heart rate), decreased AV nodal conduction, and increased AV nodal refractoriness, while the class III electrophysiological effects include prolongation of the atrial and ventricular monophasic action potentials, and effective refractory period prolongation of atrial muscle, ventricular muscle, and atrio-ventricular accessory pathways (where present) in both the anterograde and retrograde directions.

TargetActionsOrganism
APotassium voltage-gated channel subfamily H member 2
inhibitor
Human
ABeta-1 adrenergic receptor
antagonist
Human
ABeta-2 adrenergic receptor
antagonist
Human
Absorption

In healthy subjects, the oral bioavailability of sotalol is 90-100%. Absorption is reduced by approximately 20% compared to fasting when administered with a standard meal.

Volume of distribution
Not Available
Protein binding

Sotalol does not bind to plasma proteins.

Metabolism

Sotalol is not metabolized.

Route of elimination

Excretion is predominantly via the kidney in the unchanged form. Sotalol is excreted in the milk of laboratory animals and has been reported to be present in human milk.

Half life

Mean elimination half-life is 12 hours. Impaired renal function in geriatric patients can increase the terminal elimination half-life.

Clearance
Not Available
Toxicity

The most common signs to be expected are bradycardia, congestive heart failure, hypotension, bronchospasm and hypoglycemia. In cases of massive intentional overdosage (2-16 grams) of sotalol the following clinical findings were seen: hypotension, bradycardia, cardiac asystole, prolongation of QT interval, Torsade de Pointes, ventricular tachy-cardia, and premature ventricular complexes.

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

Interactions

Drug Interactions
DrugInteraction
(4R)-limonene(4R)-limonene may decrease the antihypertensive activities of Sotalol.
1,10-Phenanthroline1,10-Phenanthroline may increase the bradycardic activities of Sotalol.
4-Methoxyamphetamine4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Sotalol.
AbediterolSotalol may decrease the bronchodilatory activities of Abediterol.
AcebutololThe risk or severity of adverse effects can be increased when Sotalol is combined with Acebutolol.
AceclofenacAceclofenac may decrease the antihypertensive activities of Sotalol.
AcemetacinAcemetacin may decrease the antihypertensive activities of Sotalol.
AcepromazineSotalol may increase the orthostatic hypotensive activities of Acepromazine.
AceprometazineAceprometazine may increase the hypotensive activities of Sotalol.
AcetohexamideSotalol may increase the hypoglycemic activities of Acetohexamide.
Food Interactions
Not Available

References

General References
  1. Waldo AL, Camm AJ, deRuyter H, Friedman PL, MacNeil DJ, Pauls JF, Pitt B, Pratt CM, Schwartz PJ, Veltri EP: Effect of d-sotalol on mortality in patients with left ventricular dysfunction after recent and remote myocardial infarction. The SWORD Investigators. Survival With Oral d-Sotalol. Lancet. 1996 Jul 6;348(9019):7-12. [PubMed:8691967]
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
C07AA57 — Sotalol, combinationsC07AA07 — SotalolC07BA07 — Sotalol and thiazides
AHFS Codes
  • 24:24.00 — Beta-adrenergic Blocking Agents
FDA label
Download (93.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHealthy Volunteers1
1TerminatedBasic ScienceNonvalvular Atrial Fibrillation1
3CompletedPreventionArrythmias / Cardiovascular Disease (CVD) / Heart Arrest / Heart Diseases / Myocardial Infarction / Severe ventricular arrhythmias1
3CompletedTreatmentArrythmias / Cardiovascular Disease (CVD) / Death, Sudden,Cardiac / Heart Diseases / Severe ventricular arrhythmias / Ventricular Arrythmias / Ventricular Tachycardia (VT)1
3CompletedTreatmentArrythmias / Cardiovascular Disease (CVD) / Death, Sudden,Cardiac / Heart Diseases / Severe ventricular arrhythmias / Ventricular Tachycardia (VT)1
3CompletedTreatmentArrythmias / Cardiovascular Disease (CVD) / Heart Diseases / Nonvalvular Atrial Fibrillation1
3CompletedTreatmentCerebrovascular Accidents / Nonvalvular Atrial Fibrillation / Sudden Death1
3CompletedTreatmentNonvalvular Atrial Fibrillation1
3CompletedTreatmentParoxysmal Atrial Fibrillation (PAF)1
3Enrolling by InvitationTreatmentFetal Atrial Flutter Without Hydrops / Fetal Supraventricular Tachycardia With Hydrops / Fetal Supraventricular Tachycardia Without Hydrops1
3SuspendedTreatmentNonvalvular Atrial Fibrillation1
3TerminatedTreatmentHeart Failure, Unspecified / Nonvalvular Atrial Fibrillation1
4Not Yet RecruitingTreatmentNonvalvular Atrial Fibrillation1
4RecruitingTreatmentMyocardial Infarction / Ventricular Tachyarrhythmias1
4RecruitingTreatmentNonvalvular Atrial Fibrillation1
4WithdrawnTreatmentNonvalvular Atrial Fibrillation1
Not AvailableActive Not RecruitingTreatmentNonvalvular Atrial Fibrillation / Quality of Life1
Not AvailableCompletedTreatmentArrythmias / Nonvalvular Atrial Fibrillation1
Not AvailableCompletedTreatmentNonvalvular Atrial Fibrillation1
Not AvailableRecruitingTreatmentHeart Failure, Unspecified / Recurrent Atrial Fibrillation1
Not AvailableRecruitingTreatmentNonvalvular Atrial Fibrillation1
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
TabletOral160 mg
TabletOral80 mg
TabletOral240 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)
US9724297No2015-08-312035-08-31Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)206.5-207 °CPhysProp
water solubilitySoluble (5510 mg/L)Not Available
logP0.24BURGOT,G ET AL. (1990)
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
Human
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
Human
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
Human
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
Human
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 September 18, 2018 23:02