Details
Stereochemistry | RACEMIC |
Molecular Formula | C20H36N2O3S |
Molecular Weight | 384.576 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCN(CC)CCCC(O)C1=CC=C(NS(C)(=O)=O)C=C1
InChI
InChIKey=ALOBUEHUHMBRLE-UHFFFAOYSA-N
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
DescriptionSources: http://www.drugbank.ca/drugs/DB00308Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/cdi/ibutilide.html
Sources: http://www.drugbank.ca/drugs/DB00308
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/cdi/ibutilide.html
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. Ibutilide is indicated for the rapid conversion of atrial fibrillation or atrial flutter of recent onset to sinus rhythm. Ibutilide is marketed as Corvert by Pfizer.
Originator
Sources: http://adisinsight.springer.com/drugs/800001359
Curator's Comment: # Pfizer
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1940 Sources: http://www.drugbank.ca/drugs/DB00308 |
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Target ID: Q02641 Gene ID: 782.0 Gene Symbol: CACNB1 Target Organism: Homo sapiens (Human) Sources: http://www.drugbank.ca/drugs/DB00308 |
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Target ID: CHEMBL240 Sources: http://www.drugbank.ca/drugs/DB00308 |
0.9 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | CORVERT Approved Useindicated for the rapid conversion of atrial fibrillation or atrial flutter of recent onset to sinus rhythm. Launch Date1995 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5.8 μg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19025427 |
1 mg single, intravenous dose: 1 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
IBUTILIDE unknown | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
177 μg × min/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18035195 |
1 mg single, intravenous dose: 1 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
IBUTILIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
13.2 μg × h/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19025427 |
1 mg single, intravenous dose: 1 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
IBUTILIDE unknown | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
9.1 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18035195 |
1 mg single, intravenous dose: 1 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
IBUTILIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
12.4 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19025427 |
1 mg single, intravenous dose: 1 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
IBUTILIDE unknown | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
1 mg single, intravenous Highest studied dose Dose: 1 mg Route: intravenous Route: single Dose: 1 mg Sources: |
healthy, adult n = 8 Health Status: healthy Age Group: adult Sex: M Population Size: 8 Sources: |
|
1 mg 1 times / 10 min multiple, intravenous Recommended Dose: 1 mg, 1 times / 10 min Route: intravenous Route: multiple Dose: 1 mg, 1 times / 10 min Sources: |
unhealthy, adult n = 776 Health Status: unhealthy Condition: atrial flutter or atrial fibrillation Age Group: adult Population Size: 776 Sources: |
Disc. AE: Extrasystoles ventricular, Non-sustained ventricular tachycardia... Other AEs: Chest pain, Bradycardia... AEs leading to discontinuation/dose reduction: Extrasystoles ventricular (3.7%) Other AEs:Non-sustained ventricular tachycardia (3.4%) Non-sustained ventricular tachycardia (3.5%) Polymorphic ventricular tachycardia (1.8%) Chest pain (2.6%) Sources: Bradycardia (1.4%) Hypotension (2.6%) Sinus bradycardia (1.2%) Heart arrest (1%) Headache (4.1%) Procedural complication (1.9%) Nausea (4.8%) Dizziness (1.8%) Diarrhea (1.8%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Heart arrest | 1% | 1 mg 1 times / 10 min multiple, intravenous Recommended Dose: 1 mg, 1 times / 10 min Route: intravenous Route: multiple Dose: 1 mg, 1 times / 10 min Sources: |
unhealthy, adult n = 776 Health Status: unhealthy Condition: atrial flutter or atrial fibrillation Age Group: adult Population Size: 776 Sources: |
Sinus bradycardia | 1.2% | 1 mg 1 times / 10 min multiple, intravenous Recommended Dose: 1 mg, 1 times / 10 min Route: intravenous Route: multiple Dose: 1 mg, 1 times / 10 min Sources: |
unhealthy, adult n = 776 Health Status: unhealthy Condition: atrial flutter or atrial fibrillation Age Group: adult Population Size: 776 Sources: |
Bradycardia | 1.4% | 1 mg 1 times / 10 min multiple, intravenous Recommended Dose: 1 mg, 1 times / 10 min Route: intravenous Route: multiple Dose: 1 mg, 1 times / 10 min Sources: |
unhealthy, adult n = 776 Health Status: unhealthy Condition: atrial flutter or atrial fibrillation Age Group: adult Population Size: 776 Sources: |
Diarrhea | 1.8% | 1 mg 1 times / 10 min multiple, intravenous Recommended Dose: 1 mg, 1 times / 10 min Route: intravenous Route: multiple Dose: 1 mg, 1 times / 10 min Sources: |
unhealthy, adult n = 776 Health Status: unhealthy Condition: atrial flutter or atrial fibrillation Age Group: adult Population Size: 776 Sources: |
Dizziness | 1.8% | 1 mg 1 times / 10 min multiple, intravenous Recommended Dose: 1 mg, 1 times / 10 min Route: intravenous Route: multiple Dose: 1 mg, 1 times / 10 min Sources: |
unhealthy, adult n = 776 Health Status: unhealthy Condition: atrial flutter or atrial fibrillation Age Group: adult Population Size: 776 Sources: |
Polymorphic ventricular tachycardia | 1.8% Disc. AE |
1 mg 1 times / 10 min multiple, intravenous Recommended Dose: 1 mg, 1 times / 10 min Route: intravenous Route: multiple Dose: 1 mg, 1 times / 10 min Sources: |
unhealthy, adult n = 776 Health Status: unhealthy Condition: atrial flutter or atrial fibrillation Age Group: adult Population Size: 776 Sources: |
Procedural complication | 1.9% | 1 mg 1 times / 10 min multiple, intravenous Recommended Dose: 1 mg, 1 times / 10 min Route: intravenous Route: multiple Dose: 1 mg, 1 times / 10 min Sources: |
unhealthy, adult n = 776 Health Status: unhealthy Condition: atrial flutter or atrial fibrillation Age Group: adult Population Size: 776 Sources: |
Chest pain | 2.6% | 1 mg 1 times / 10 min multiple, intravenous Recommended Dose: 1 mg, 1 times / 10 min Route: intravenous Route: multiple Dose: 1 mg, 1 times / 10 min Sources: |
unhealthy, adult n = 776 Health Status: unhealthy Condition: atrial flutter or atrial fibrillation Age Group: adult Population Size: 776 Sources: |
Hypotension | 2.6% | 1 mg 1 times / 10 min multiple, intravenous Recommended Dose: 1 mg, 1 times / 10 min Route: intravenous Route: multiple Dose: 1 mg, 1 times / 10 min Sources: |
unhealthy, adult n = 776 Health Status: unhealthy Condition: atrial flutter or atrial fibrillation Age Group: adult Population Size: 776 Sources: |
Non-sustained ventricular tachycardia | 3.4% Disc. AE |
1 mg 1 times / 10 min multiple, intravenous Recommended Dose: 1 mg, 1 times / 10 min Route: intravenous Route: multiple Dose: 1 mg, 1 times / 10 min Sources: |
unhealthy, adult n = 776 Health Status: unhealthy Condition: atrial flutter or atrial fibrillation Age Group: adult Population Size: 776 Sources: |
Non-sustained ventricular tachycardia | 3.5% Disc. AE |
1 mg 1 times / 10 min multiple, intravenous Recommended Dose: 1 mg, 1 times / 10 min Route: intravenous Route: multiple Dose: 1 mg, 1 times / 10 min Sources: |
unhealthy, adult n = 776 Health Status: unhealthy Condition: atrial flutter or atrial fibrillation Age Group: adult Population Size: 776 Sources: |
Extrasystoles ventricular | 3.7% Disc. AE |
1 mg 1 times / 10 min multiple, intravenous Recommended Dose: 1 mg, 1 times / 10 min Route: intravenous Route: multiple Dose: 1 mg, 1 times / 10 min Sources: |
unhealthy, adult n = 776 Health Status: unhealthy Condition: atrial flutter or atrial fibrillation Age Group: adult Population Size: 776 Sources: |
Headache | 4.1% | 1 mg 1 times / 10 min multiple, intravenous Recommended Dose: 1 mg, 1 times / 10 min Route: intravenous Route: multiple Dose: 1 mg, 1 times / 10 min Sources: |
unhealthy, adult n = 776 Health Status: unhealthy Condition: atrial flutter or atrial fibrillation Age Group: adult Population Size: 776 Sources: |
Nausea | 4.8% | 1 mg 1 times / 10 min multiple, intravenous Recommended Dose: 1 mg, 1 times / 10 min Route: intravenous Route: multiple Dose: 1 mg, 1 times / 10 min Sources: |
unhealthy, adult n = 776 Health Status: unhealthy Condition: atrial flutter or atrial fibrillation Age Group: adult Population Size: 776 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/12688833/ Page: 2.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12688833/ Page: 2.0 |
no |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/ibutilide.html
Usual Adult Dose for Atrial Fibrillation
60 kg or more: 1 mg IV over 10 minutes; if arrhythmia persists 10 minutes after the end of the first infusion, repeat once.
Less than 60 kg: 0.01 mg/kg IV over 10 minutes; if arrhythmia persists 10 minutes after the end of the first infusion, repeat once.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1361444
Ibutilide at the 10(-5) M effective refractory periods at 1 and 3 Hz increased by 18-32 ms, conduction times measured at 3 Hz increased by 27-30% and atrial rate decreased by 19-32% in isolated rabbit myocardium.
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175426
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NCI_THESAURUS |
C47793
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WHO-ATC |
C01BD05
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NCI_THESAURUS |
C93038
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WHO-VATC |
QC01BD05
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Code System | Code | Type | Description | ||
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C72581
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1412
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2436VX1U9B
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IBUTILIDE
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C067192
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DB00308
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CHEMBL533
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41289
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100000083650
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6642
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2436VX1U9B
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7200
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60753
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m6191
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DTXSID20861271
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SUB08102MIG
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7926
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122647-31-8
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)