Ibutilide

Các tên gọi khác (7 ) :

Corvert
Ibutilid
Ibutilida
Ibutilide
Ibutilide Fumarate
Ibutilidum
N-(4-{4-[ethyl(heptyl)amino]-1-hydroxybutyl}phenyl)methanesulfonamide

Thuốc chống loạn nhịp

Thuốc Gốc

Small Molecule

CAS: 122647-32-9

ATC: C01BD05

ĐG : Bioniche Pharma , http://www.bionichepharmausa.com

CTHH: C₂₀H₃₆N₂O₃S

PTK: 384.576

Ibutilide is a Class III antiarrhythmic agent that is indicated for acute cardioconversion of atrial fibrillation and atrial flutter of a recent onset to sinus rhythm. [Wikipedia]

Nhận Dạng Quốc Tế & Đặc Tính Hóa Học

Công thức hóa học

C₂₀H₃₆N₂O₃S

Phân tử khối

384.576

Monoisotopic mass

384.244663718

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

InChI Key

InChIKey=ALOBUEHUHMBRLE-UHFFFAOYSA-N

IUPAC Name

N-(4-{4-[ethyl(heptyl)amino]-1-hydroxybutyl}phenyl)methanesulfonamide

Traditional IUPAC Name

ibutilide

SMILES

CCCCCCCN(CC)CCCC(O)C1=CC=C(NS(C)(=O)=O)C=C1

Độ hòa tan

100 mg/mL

logP

4.6

logS

-4.9

pKa (strongest acidic)

9.72

pKa (Strongest Basic)

10.4

PSA

69.64 Å²

Refractivity

109.18 m³·mol^-1

Polarizability

46.45 Å³

Rotatable Bond Count

H Bond Acceptor Count

H Bond Donor Count

Physiological Charge

Number of Rings

Bioavailability

Rule of Five

true

Ghose Filter

true

Dược Lực Học : 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.

Cơ Chế Tác Dụng : Ibutilide is a Class III antiarrhythmic agent that is indicated for acute cardioconversion of atrial fibrillation and atrial flutter of a recent onset to sinus rhythm. [Wikipedia] 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

Dược Động Học :

▧ 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

Độc Tính : 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.

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

Tương Tác Thuốc :

Artemether Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Cisapride Increased risk of cardiotoxicity and arrhythmias
Fingolimod Pharmacodynamic synergist. Contraindicated. Increased risk of bradycardia, AV block, and torsade de pointes.
Lumefantrine Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Ranolazine Possible additive effect on QT prolongation
Tacrolimus Additive QTc-prolongation may occur increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
Telavancin Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Thiothixene May cause additive QTc-prolonging effects. Increased risk of ventricular arrhythmias. Consider alternate therapy. Thorough risk:benefit assessment is required prior to co-administration.
Toremifene Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Consider alternate therapy. A thorough risk:benefit assessment is required prior to co-administration.
Trimipramine Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
Voriconazole Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Vorinostat Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Ziprasidone Additive QTc-prolonging effects may increase the risk of severe arrhythmias. Concomitant therapy is contraindicated.
Zuclopenthixol Additive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).

Liều Lượng & Cách Dùng : Solution - Intravenous

Dữ Kiện Thương Mại

Giá thị trường

Biệt dược thương mại : Ibutilide fum 1 mg/10 ml vial

Giá bán buôn : USD >33.6

Đơn vị tính : ml
Biệt dược thương mại : Corvert 1 mg/10 ml vial

Giá bán buôn : USD >54.27

Đơn vị tính : ml

Nhà Sản Xuất

Công ty : Pfizer

Sản phẩm biệt dược : Corvert
Công ty : Bioniche

Sản phẩm biệt dược : Ibutilide Fumarate

Đóng gói

Công ty : Bioniche Pharma

Website : http://www.bionichepharmausa.com
Công ty : Generamedix Inc.

Website : http://www.generamedix.com
Công ty : Paddock Labs

Website : http://www.paddocklabs.com
Công ty : Pharmacia Inc.

Website : http://www.pharmaciaupjohn.com

Tài Liệu Tham Khảo Thêm

drugbank

http://www.drugbank.ca/drugs/DB00308

PubChem Compound

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=60753

PubChem Substance

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46507904

KEGG Compound

http://www.genome.jp/dbget-bin/www_bget?cpd:C07753

KEGG Drug

http://www.genome.jp/dbget-bin/www_bget?drug:D00648

ChemSpider

http://www.chemspider.com/Chemical-Structure.54755.html

BindingDB

http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50131432

National Drug Code Directory

http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0574-0840-01

PharmGKB

http://www.pharmgkb.org/drug/PA449958

Wikipedia

http://en.wikipedia.org/wiki/Ibutilide

RxList

http://www.rxlist.com/cgi/generic/ibutilide.htm

Drugs.com

http://www.drugs.com/cdi/ibutilide.html

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