Ibutilide

Identification

Summary

Ibutilide is a class III antiarrhythmic agent used to correct atrial fibrillation and atrial flutter, which can be considered as an alternative to cardioversion.

Brand Names
Corvert
Generic Name
Ibutilide
DrugBank Accession Number
DB00308
Background

Ibutilide is a Class III antiarrhythmic agent available in intravenous formulations. It is indicated for the conversion of acute atrial flutter and recent onset atrial fibrillation to normal sinus rhythm (NSR).

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 384.576
Monoisotopic: 384.244663718
Chemical Formula
C20H36N2O3S
Synonyms
  • Ibutilid
  • Ibutilida
  • Ibutilide
  • Ibutilidum
  • N-(4-{4-[ethyl(heptyl)amino]-1-hydroxybutyl}phenyl)methanesulfonamide
External IDs
  • U 70226 E

Pharmacology

Indication

Indicated for the rapid conversion of atrial fibrillation or atrial flutter of recent onset to sinus rhythm.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofAtrial fibrillation••••••••••••
Management ofAtrial flutter••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Ibutilide prolongs the action potential duration and increases both atrial and ventricular refractoriness in vivo, i.e., class III electrophysiologic effects. Voltage clamp studies indicate that ibutilide, at nanomolar concentrations, delays repolarization by activation of a slow, inward current (predominantly sodium), rather than by blocking outward potassium currents, which is the mechanism by which most other class III antiarrhythmics act.

Mechanism of action

Ibutilide is a 'pure' class III antiarrhythmic drug, used intravenously against atrial flutter and fibrillation. At a cellular level it exerts two main actions: induction of a persistent Na+ current sensitive to dihydropyridine Ca2+ channel blockers and potent inhibition of the cardiac rapid delayed rectifier K+ current, by binding within potassium channel pores. In other words, Ibutilide binds to and alters the activity of hERG potassium channels, delayed inward rectifier potassium (IKr) channels and L-type (dihydropyridine sensitive) calcium channels

TargetActionsOrganism
AVoltage-dependent L-type calcium channel subunit alpha-1C
activator
Humans
AVoltage-dependent L-type calcium channel subunit beta-1
activator
Humans
APotassium voltage-gated channel subfamily H member 2
inhibitor
Humans
UVoltage-dependent calcium channel subunit alpha-2/delta-1
activator
Humans
UVoltage-dependent calcium channel gamma-1 subunit
activator
Humans
UPotassium channel subfamily K member 1
inhibitor
Humans
UPotassium channel subfamily K member 6
inhibitor
Humans
UPotassium voltage-gated channel subfamily H member 6
inhibitor
Humans
UPotassium voltage-gated channel subfamily H member 7
inhibitor
Humans
UATP-sensitive inward rectifier potassium channel 11
inhibitor
Humans
Absorption

Rapid after intravenous injection

Volume of distribution
  • 11 L/kg
Protein binding

40%

Metabolism

Primarily hepatic. Eight metabolites of ibutilide were detected in metabolic profiling of urine. These metabolites are thought to be formed primarily by o-oxidation followed by sequential b-oxidation of the heptyl side chain of ibutilide. Of the eight metabolites, only the o-hydroxy metabolite possesses class III electrophysiologic properties similar to that of ibutilide in an in vitro isolated rabbit myocardium model.

Route of elimination

In healthy male volunteers, about 82% of a 0.01 mg/kg dose of [14C] ibutilide fumarate was excreted in the urine (about 7% of the dose as unchanged ibutilide) and the remainder (about 19%) was recovered in the feces.

Half-life

6 hours (ranges from 2-12 hours)

Clearance
  • 29 mL/min/kg
Adverse Effects
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Toxicity

Acute overdose in animals results in CNS toxicity; notably, CNS depression, rapid gasping breathing, and convulsions. The intravenous median lethal dose in the rat was more than 50 mg/kg which is, on a mg/m2 basis, at least 250 times the maximum recommended human dose.

Pathways
PathwayCategory
Ibutilide 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
AbacavirIbutilide may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcebutololIbutilide may increase the arrhythmogenic activities of Acebutolol.
AceclofenacAceclofenac may decrease the excretion rate of Ibutilide which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Ibutilide which could result in a higher serum level.
AcetaminophenIbutilide may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Ibutilide fumarate9L5X4M5L6I122647-32-9PCIOHQNIRPWFMV-WXXKFALUSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CorvertInjection, solution0.1 mg/1mLIntravenousPharmacia & Upjohn Company LLC1995-12-28Not applicableUS flag
CorvertSolution0.1 mg / mLIntravenousPfizer Canada Ulc2000-11-28Not applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ibutilide FumarateInjection, solution0.1 mg/1mLIntravenousPaddock Laboratories, Inc.2010-01-132014-07-31US flag
Ibutilide FumarateInjection, solution0.1 mg/1mLIntravenousMylan Institutional LLC2010-01-11Not applicableUS flag
Ibutilide FumarateInjection, solution0.1 mg/1mLIntravenousGenera Medix Inc.2010-01-122017-12-31US flag

Categories

ATC Codes
C01BD05 — Ibutilide
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylbutylamines. These are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylbutylamines
Direct Parent
Phenylbutylamines
Alternative Parents
Sulfanilides / Aralkylamines / Organosulfonamides / Organic sulfonamides / Aminosulfonyl compounds / Trialkylamines / Secondary alcohols / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Alcohol / Amine / Aminosulfonyl compound / Aralkylamine / Aromatic alcohol / Aromatic homomonocyclic compound / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide / Organic oxygen compound
show 14 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
organic amino compound, benzenes (CHEBI:5856)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
2436VX1U9B
CAS number
122647-31-8
InChI Key
ALOBUEHUHMBRLE-UHFFFAOYSA-N
InChI
InChI=1S/C20H36N2O3S/c1-4-6-7-8-9-16-22(5-2)17-10-11-20(23)18-12-14-19(15-13-18)21-26(3,24)25/h12-15,20-21,23H,4-11,16-17H2,1-3H3
IUPAC Name
N-(4-{4-[ethyl(heptyl)amino]-1-hydroxybutyl}phenyl)methanesulfonamide
SMILES
CCCCCCCN(CC)CCCC(O)C1=CC=C(NS(C)(=O)=O)C=C1

References

Synthesis Reference
US5155268A
General References
Not Available
Human Metabolome Database
HMDB0014453
KEGG Drug
D00648
KEGG Compound
C07753
PubChem Compound
60753
PubChem Substance
46507904
ChemSpider
54755
BindingDB
50131432
RxNav
41289
ChEBI
5856
ChEMBL
CHEMBL533
Therapeutic Targets Database
DAP000279
PharmGKB
PA449958
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Ibutilide
FDA label
Download (878 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingPreventionAbnormalities, Drug-Induced / Long QT Syndrome (LQTS)1
4CompletedPreventionLong QT Syndrome (LQTS)1
4CompletedTreatmentAtrial Fibrillation1
4RecruitingTreatmentAbnormalities, Drug-Induced / Long QT Syndrome (LQTS)1
2CompletedPreventionProlonged QT Interval in EKG and Sudden Death1

Pharmacoeconomics

Manufacturers
  • Pharmacia and upjohn co
  • Bioniche pharma usa llc
  • Pharmaforce inc
Packagers
  • Bioniche Pharma
  • Generamedix Inc.
  • Paddock Labs
  • Pharmacia Inc.
Dosage Forms
FormRouteStrength
SolutionIntravenous
SolutionIntravenous0.1 mg / mL
SolutionParenteral87 Mikrogramm/ml
Injection, solutionIntravenous0.1 mg/1mL
Prices
Unit descriptionCostUnit
Corvert 1 mg/10 ml vial54.27USD ml
Ibutilide fum 1 mg/10 ml vial33.6USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5155268No1992-10-132009-12-28US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility100 mg/mLNot Available
logP4.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00473 mg/mLALOGPS
logP4.72ALOGPS
logP2.54Chemaxon
logS-4.9ALOGPS
pKa (Strongest Acidic)9.72Chemaxon
pKa (Strongest Basic)10.4Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area69.64 Å2Chemaxon
Rotatable Bond Count13Chemaxon
Refractivity109.18 m3·mol-1Chemaxon
Polarizability46.45 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9964
Blood Brain Barrier+0.9363
Caco-2 permeable-0.6669
P-glycoprotein substrateSubstrate0.6142
P-glycoprotein inhibitor INon-inhibitor0.7689
P-glycoprotein inhibitor IINon-inhibitor0.8893
Renal organic cation transporterNon-inhibitor0.8738
CYP450 2C9 substrateNon-substrate0.8131
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.5472
CYP450 1A2 substrateNon-inhibitor0.7721
CYP450 2C9 inhibitorNon-inhibitor0.8256
CYP450 2D6 inhibitorNon-inhibitor0.8114
CYP450 2C19 inhibitorNon-inhibitor0.7115
CYP450 3A4 inhibitorNon-inhibitor0.7974
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8467
Ames testNon AMES toxic0.7092
CarcinogenicityNon-carcinogens0.6799
BiodegradationNot ready biodegradable0.9945
Rat acute toxicity2.5314 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.5736
hERG inhibition (predictor II)Inhibitor0.7592
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-MSsplash10-0udi-3494000000-4216adb870d24524f3f8
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kr-0059000000-170d24eab89b19e966d1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000x-3449000000-3bdd60704e7309d32975
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-1029000000-6a02de37bf9f549bf522
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00y0-7697000000-17aa7532d621b4775edb
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ar0-3397000000-c85b44fc752dee994fd1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00b9-3691000000-2a3939f8223953531a66
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-215.7252286
predicted
DarkChem Lite v0.1.0
[M-H]-201.94289
predicted
DeepCCS 1.0 (2019)
[M+H]+215.6951286
predicted
DarkChem Lite v0.1.0
[M+H]+205.27516
predicted
DeepCCS 1.0 (2019)
[M+Na]+216.2254286
predicted
DarkChem Lite v0.1.0
[M+Na]+213.1913
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Activator
General Function
Voltage-gated calcium channel activity
Specific Function
Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hor...
Gene Name
CACNA1C
Uniprot ID
Q13936
Uniprot Name
Voltage-dependent L-type calcium channel subunit alpha-1C
Molecular Weight
248974.1 Da
References
  1. Doggrell SA, Hancox JC: Ibutilide--recent molecular insights and accumulating evidence for use in atrial flutter and fibrillation. Expert Opin Investig Drugs. 2005 May;14(5):655-69. [Article]
  2. Foster RH, Wilde MI, Markham A: Ibutilide. A review of its pharmacological properties and clinical potential in the acute management of atrial flutter and fibrillation. Drugs. 1997 Aug;54(2):312-30. [Article]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Activator
General Function
Voltage-gated calcium channel activity
Specific Function
The beta subunit of voltage-dependent calcium channels contributes to the function of the calcium channel by increasing peak calcium current, shifting the voltage dependencies of activation and ina...
Gene Name
CACNB1
Uniprot ID
Q02641
Uniprot Name
Voltage-dependent L-type calcium channel subunit beta-1
Molecular Weight
65712.995 Da
References
  1. Doggrell SA, Hancox JC: Ibutilide--recent molecular insights and accumulating evidence for use in atrial flutter and fibrillation. Expert Opin Investig Drugs. 2005 May;14(5):655-69. [Article]
  2. Foster RH, Wilde MI, Markham A: Ibutilide. A review of its pharmacological properties and clinical potential in the acute management of atrial flutter and fibrillation. Drugs. 1997 Aug;54(2):312-30. [Article]
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. Perry M, de Groot MJ, Helliwell R, Leishman D, Tristani-Firouzi M, Sanguinetti MC, Mitcheson J: Structural determinants of HERG channel block by clofilium and ibutilide. Mol Pharmacol. 2004 Aug;66(2):240-9. [Article]
  2. Perry M, Stansfeld PJ, Leaney J, Wood C, de Groot MJ, Leishman D, Sutcliffe MJ, Mitcheson JS: Drug binding interactions in the inner cavity of HERG channels: molecular insights from structure-activity relationships of clofilium and ibutilide analogs. Mol Pharmacol. 2006 Feb;69(2):509-19. Epub 2005 Nov 16. [Article]
  3. Wolpert C, Schimpf R, Veltmann C, Borggrefe M: [Short QT syndrome]. Herz. 2007 May;32(3):206-10. [Article]
  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. [Article]
  5. Yang T, Snyders D, Roden DM: Drug block of I(kr): model systems and relevance to human arrhythmias. J Cardiovasc Pharmacol. 2001 Nov;38(5):737-44. [Article]
  6. Doggrell SA, Hancox JC: Ibutilide--recent molecular insights and accumulating evidence for use in atrial flutter and fibrillation. Expert Opin Investig Drugs. 2005 May;14(5):655-69. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
General Function
Voltage-gated calcium channel activity
Specific Function
The alpha-2/delta subunit of voltage-dependent calcium channels regulates calcium current density and activation/inactivation kinetics of the calcium channel. Plays an important role in excitation-...
Gene Name
CACNA2D1
Uniprot ID
P54289
Uniprot Name
Voltage-dependent calcium channel subunit alpha-2/delta-1
Molecular Weight
124566.93 Da
References
  1. Doggrell SA, Hancox JC: Ibutilide--recent molecular insights and accumulating evidence for use in atrial flutter and fibrillation. Expert Opin Investig Drugs. 2005 May;14(5):655-69. [Article]
  2. Foster RH, Wilde MI, Markham A: Ibutilide. A review of its pharmacological properties and clinical potential in the acute management of atrial flutter and fibrillation. Drugs. 1997 Aug;54(2):312-30. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
General Function
Voltage-gated calcium channel activity
Specific Function
This protein is a subunit of the dihydropyridine (DHP) sensitive calcium channel. Plays a role in excitation-contraction coupling. The skeletal muscle DHP-sensitive Ca(2+) channel may function only...
Gene Name
CACNG1
Uniprot ID
Q06432
Uniprot Name
Voltage-dependent calcium channel gamma-1 subunit
Molecular Weight
25028.105 Da
References
  1. Doggrell SA, Hancox JC: Ibutilide--recent molecular insights and accumulating evidence for use in atrial flutter and fibrillation. Expert Opin Investig Drugs. 2005 May;14(5):655-69. [Article]
  2. Foster RH, Wilde MI, Markham A: Ibutilide. A review of its pharmacological properties and clinical potential in the acute management of atrial flutter and fibrillation. Drugs. 1997 Aug;54(2):312-30. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium channel activity
Specific Function
Ion channel that contributes to passive transmembrane potassium transport and to the regulation of the resting membrane potential in brain astrocytes, but also in kidney and in other tissues (PubMe...
Gene Name
KCNK1
Uniprot ID
O00180
Uniprot Name
Potassium channel subfamily K member 1
Molecular Weight
38142.775 Da
References
  1. Doggrell SA, Hancox JC: Ibutilide--recent molecular insights and accumulating evidence for use in atrial flutter and fibrillation. Expert Opin Investig Drugs. 2005 May;14(5):655-69. [Article]
  2. Foster RH, Wilde MI, Markham A: Ibutilide. A review of its pharmacological properties and clinical potential in the acute management of atrial flutter and fibrillation. Drugs. 1997 Aug;54(2):312-30. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Potassium ion leak channel activity
Specific Function
Exhibits outward rectification in a physiological K(+) gradient and mild inward rectification in symmetrical K(+) conditions.
Gene Name
KCNK6
Uniprot ID
Q9Y257
Uniprot Name
Potassium channel subfamily K member 6
Molecular Weight
33746.8 Da
References
  1. Doggrell SA, Hancox JC: Ibutilide--recent molecular insights and accumulating evidence for use in atrial flutter and fibrillation. Expert Opin Investig Drugs. 2005 May;14(5):655-69. [Article]
  2. Foster RH, Wilde MI, Markham A: Ibutilide. A review of its pharmacological properties and clinical potential in the acute management of atrial flutter and fibrillation. Drugs. 1997 Aug;54(2):312-30. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Voltage-gated potassium channel activity
Specific Function
Pore-forming (alpha) subunit of voltage-gated potassium channel. Elicits a slowly activating, rectifying current (By similarity). Channel properties may be modulated by cAMP and subunit assembly.
Gene Name
KCNH6
Uniprot ID
Q9H252
Uniprot Name
Potassium voltage-gated channel subfamily H member 6
Molecular Weight
109923.705 Da
References
  1. Doggrell SA, Hancox JC: Ibutilide--recent molecular insights and accumulating evidence for use in atrial flutter and fibrillation. Expert Opin Investig Drugs. 2005 May;14(5):655-69. [Article]
  2. Foster RH, Wilde MI, Markham A: Ibutilide. A review of its pharmacological properties and clinical potential in the acute management of atrial flutter and fibrillation. Drugs. 1997 Aug;54(2):312-30. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Voltage-gated potassium channel activity
Specific Function
Pore-forming (alpha) subunit of voltage-gated potassium channel. Channel properties may be modulated by cAMP and subunit assembly.
Gene Name
KCNH7
Uniprot ID
Q9NS40
Uniprot Name
Potassium voltage-gated channel subfamily H member 7
Molecular Weight
134998.525 Da
References
  1. Doggrell SA, Hancox JC: Ibutilide--recent molecular insights and accumulating evidence for use in atrial flutter and fibrillation. Expert Opin Investig Drugs. 2005 May;14(5):655-69. [Article]
  2. Foster RH, Wilde MI, Markham A: Ibutilide. A review of its pharmacological properties and clinical potential in the acute management of atrial flutter and fibrillation. Drugs. 1997 Aug;54(2):312-30. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Voltage-gated potassium channel activity
Specific Function
This receptor is controlled by G proteins. Inward rectifier potassium channels are characterized by a greater tendency to allow potassium to flow into the cell rather than out of it. Their voltage ...
Gene Name
KCNJ11
Uniprot ID
Q14654
Uniprot Name
ATP-sensitive inward rectifier potassium channel 11
Molecular Weight
43540.375 Da
References
  1. Doggrell SA, Hancox JC: Ibutilide--recent molecular insights and accumulating evidence for use in atrial flutter and fibrillation. Expert Opin Investig Drugs. 2005 May;14(5):655-69. [Article]
  2. Foster RH, Wilde MI, Markham A: Ibutilide. A review of its pharmacological properties and clinical potential in the acute management of atrial flutter and fibrillation. Drugs. 1997 Aug;54(2):312-30. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 28, 2024 03:23