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Details

Stereochemistry ACHIRAL
Molecular Formula C25H29I2NO3
Molecular Weight 645.3116
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMIODARONE

SMILES

CCCCC1=C(C(=O)C2=CC(I)=C(OCCN(CC)CC)C(I)=C2)C3=C(O1)C=CC=C3

InChI

InChIKey=IYIKLHRQXLHMJQ-UHFFFAOYSA-N
InChI=1S/C25H29I2NO3/c1-4-7-11-22-23(18-10-8-9-12-21(18)31-22)24(29)17-15-19(26)25(20(27)16-17)30-14-13-28(5-2)6-3/h8-10,12,15-16H,4-7,11,13-14H2,1-3H3

HIDE SMILES / InChI

Molecular Formula C25H29I2NO3
Molecular Weight 645.3116
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Amiodarone is an antiarrhythmic with mainly class III properties, but it possesses electrophysiologic characteristics of all four Vaughan Williams classes. Like class I drugs, amiodarone blocks sodium channels at rapid pacing frequencies, and like class II drugs, amiodarone exerts a noncompetitive antisympathetic action. In addition to blocking sodium channels, amiodarone blocks myocardial potassium channels, which contributes to slowing of conduction and prolongation of refractoriness. It is indicated for initiation of treatment and prophylaxis of frequently recurring ventricular fibrillation and hemodynamically unstable ventricular tachycardia in patients refractory to other therapy. The most common adverse reactions (1-2%) leading to discontinuation of intravenous amiodarone therapy are hypotension, asystole/cardiac arrest/pulseless electrical activity, VT, and cardiogenic shock. Other important adverse reactions are, torsade de pointes (TdP), congestive heart failure, and liver function test abnormalities. Fluoroquinolones, macrolide antibiotics, and azoles are known to cause QTc prolongation. There have been reports of QTc prolongation, with or without TdP, in patients taking amiodarone when fluoroquinolones, macrolide antibiotics, or azoles were administered concomitantly. Since amiodarone is a substrate for CYP3A and CYP2C8, drugs/substances that inhibit these isoenzymes may decrease the metabolism and increase serum concentration of amiodarone.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Amiodarone-induced AV block and ventricular standstill. A forme fruste of an idiopathic long QT syndrome.
2000 Aug
[Toxic hepatitis caused by intravenous amiodarone].
2000 Dec 9
Polymorphic ventricular tachycardia after use of intravenous amiodarone for postoperative junctional ectopic tachycardia.
2000 Nov-Dec
Protection against drug- and chemical-induced multiorgan toxicity by a novel IH636 grape seed proanthocyanidin extract.
2001
The effects of amiodarone on the thyroid.
2001 Apr
[Radiofrequency catheter ablation in children with Wolff-Parkinson-White syndrome and sudden cardiac death who had been resuscitated].
2001 Apr
Structure-activity relationships and electrophysiological effects of short-acting amiodarone homologs in guinea pig isolated heart.
2001 Apr
Amiodarone stimulates interleukin-6 production in cultured human thyrocytes, exerting cytotoxic effects on thyroid follicles in suspension culture.
2001 Feb
Oral anticoagulants. Pharmacologic issues for use in the elderly.
2001 Feb
Intravenous amiodarone in cardiac arrest.
2001 Feb
Effects of amiodarone administration during pregnancy on neonatal thyroid function and subsequent neurodevelopment.
2001 Feb
[Acute papilledema. A 69-year-old patient with acute bilateral papilledema].
2001 Feb
Anaesthesia for amiodarone-induced thyrotoxicosis: a case review.
2001 Feb
Inhibitory effects of CYP3A4 substrates and their metabolites on P-glycoprotein-mediated transport.
2001 Feb
Differential effects of dofetilide, amiodarone, and class lc drugs on left and right atrial refractoriness and left atrial vulnerability in pigs.
2001 Feb
Single oral loading dose of propafenone for pharmacological cardioversion of recent-onset atrial fibrillation.
2001 Feb
Coronary artery revascularization in patients with sustained ventricular arrhythmias in the chronic phase of a myocardial infarction: effects on the electrophysiologic substrate and outcome.
2001 Feb
Pharmacologic management of atrial fibrillation: current therapeutic strategies.
2001 Feb
Metabolism of amiodarone (part I): identification of a new hydroxylated metabolite of amiodarone.
2001 Feb
Bioavailability of amiodarone tablets administered with and without food in healthy subjects.
2001 Feb 15
Thyroid hormone and the cardiovascular system.
2001 Feb 15
Impressive amelioration of clinical (NYHA class) and echocardiographic parameters in heart failure patients treated with amiodarone and carvedilol.
2001 Jan
Predictors of failure of transoesophageal cardioversion of common atrial flutter.
2001 Jan
[The best in 2000 on arrhythmia].
2001 Jan
[How I treat...persistent atrial fibrillation, by internal cardioversion, in a patient with exreme obesity].
2001 Jan
[Incidence and timing of thyroid dysfunction with long-term amiodarone therapy].
2001 Jan
Amiodarone-induced thyrotoxicosis.
2001 Jan
Development of heart failure in bradycardic sick sinus syndrome.
2001 Jan
Thyroidectomy for selected patients with thyrotoxicosis.
2001 Jan
The frequency analysis of signal-averaged ECG of P wave as predictor of efficacy of class III antiarrhythmic drugs to maintain sinus rhythm in recurrent idiopathic atrial fibrillation.
2001 Jan
Dofetilide: a new class III antiarrhythmic agent.
2001 Jan
The effect of amiodarone and/or antioxidant treatment on splenocyte blast transformation.
2001 Jan
Chemical cardioversion of atrial fibrillation or flutter with ibutilide in patients receiving amiodarone therapy.
2001 Jan 16
"Stable" ventricular tachycardia is not a benign rhythm : insights from the antiarrhythmics versus implantable defibrillators (AVID) registry.
2001 Jan 16
Amiodarone-induced hyperthyroidism.
2001 Jan 22
[Diagnostic quiz. Increasing dyspnea after bypass operation. Interstitial lung disease].
2001 Jan 25
Efficacy of sequential antiarrhythmic treatment in sinus rhythm maintenance after successful electrocardioversion in patients with chronic non-valvular atrial fibrillation.
2001 Jan-Feb
Torsade de pointes induced by intravenous and long-term oral amiodarone therapy in a patient with dilated cardiomyopathy.
2001 Mar
Does prophylaxis against atrial fibrillation after cardiac surgery reduce length of stay or hospital costs?
2001 Mar
The role of pharmacologic treatment to prevent sudden death in the implantable cardioverter defibrillator era.
2001 Mar
Moxifloxacin: clinical efficacy and safety.
2001 Mar 1
Cost-effectiveness of the implantable cardioverter-defibrillator: results from the Canadian Implantable Defibrillator Study (CIDS).
2001 Mar 13
[Hyperthyroidism and heart].
2001 Mar 15
Visual compatibility of amiodarone hydrochloride injection with various intravenous drugs.
2001 Mar 15
Patients at lower risk of arrhythmia recurrence: a subgroup in whom implantable defibrillators may not offer benefit. Antiarrhythmics Versus Implantable Defibrillator (AVID) Trial Investigators.
2001 Mar 15
Circadian variation of paroxysmal atrial fibrillation. PA3 Investigators. Atrial Pacing Peri-ablation for Prevention of Atrial Fibrillation Trial.
2001 Mar 15
Oral amiodarone for prevention of atrial fibrillation after open heart surgery, the Atrial Fibrillation Suppression Trial (AFIST): a randomised placebo-controlled trial.
2001 Mar 17
Short- and long-term effects of amiodarone on the two components of cardiac delayed rectifier K(+) current.
2001 Mar 6
How to manage atrial fibrillation: an update on recent clinical trials.
2001 Mar-Apr
Prenatal diagnosis of junctional ectopic tachycardia.
2001 Mar-Apr
Patents

Sample Use Guides

In Vivo Use Guide
Intravenous: Initial dose: 1000 mg over the first 24 hours of therapy, delivered by the following infusion regimen: -Loading infusions: 150 mg over the first 10 minutes (15 mg/min), followed by 360 mg over the next 6 hours (1 mg/min) -Maintenance infusion: 540 mg over the remaining 18 hours (0.5 mg/min) Maintenance dose: After the first 24 hours, continue the maintenance infusion rate of 0.5 mg/min; may increase infusion rate to achieve effective arrhythmia suppression. -Supplemental infusions: 150 mg over 10 minutes (15 mg/min) for breakthrough episodes of ventricular fibrillation (VF) or hemodynamically unstable ventricular tachycardia(VT) Maximum dose: Initial infusion rate: 30 mg/min Oral: Loading dose: 800 to 1600 mg orally per day for 1 to 3 weeks (occasionally longer) until adequate arrhythmia control is achieved or if side effects become prominent, then switch to adjustment dose Adjustment dose: 600 to 800 mg orally per day for 1 month, then switch to maintenance dose Maintenance dose: 400 mg orally per day
Route of Administration: Intravenous; Oral
In Vitro Use Guide
At concentrations ranging from 75-200 uM, amiodarone induced a significant and dose-dependent release of 51Cr in FRTL-5 cells. In the same molar concentrations, amiodarone was also cytotoxic in CHO cells. In hTF, the release of 51Cr produced by amiodarone occurred at a lower concentration (37.5 vs. 75 uM) and was significantly greater than that in FRTL-5 cells.
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:37:59 UTC 2019
Edited
by admin
on Tue Oct 22 00:37:59 UTC 2019
Record UNII
N3RQ532IUT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMIODARONE
INN   MART.   MI   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
AMIODARONE [MI]
Common Name English
AMIODARONE [VANDF]
Common Name English
AMIODARONE [USAN]
Common Name English
AMIODARONE [MART.]
Common Name English
2-BUTYL-3-BENZOFURANYL 4-(2-(DIETHYLAMINO)ETHOXY)-3,5-DIIODOPHENYL KETONE
Systematic Name English
AMIODARONE [INN]
Common Name English
AMIODARONE [WHO-DD]
Common Name English
METHANONE, (2-BUTYL-3-BENZOFURANYL)(4-(2-(DIETHYLAMINO)ETHOXY)-3,5-DIIODOPHENYL)-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C47793
Created by admin on Tue Oct 22 00:37:59 UTC 2019 , Edited by admin on Tue Oct 22 00:37:59 UTC 2019
UCSF-FDA TRANSPORTAL AMIODARONE
Created by admin on Tue Oct 22 00:37:59 UTC 2019 , Edited by admin on Tue Oct 22 00:37:59 UTC 2019
WHO-VATC QC01BD01
Created by admin on Tue Oct 22 00:37:59 UTC 2019 , Edited by admin on Tue Oct 22 00:37:59 UTC 2019
FDA ORPHAN DRUG 70292
Created by admin on Tue Oct 22 00:37:59 UTC 2019 , Edited by admin on Tue Oct 22 00:37:59 UTC 2019
NDF-RT N0000175426
Created by admin on Tue Oct 22 00:37:59 UTC 2019 , Edited by admin on Tue Oct 22 00:37:59 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 12.2
Created by admin on Tue Oct 22 00:37:59 UTC 2019 , Edited by admin on Tue Oct 22 00:37:59 UTC 2019
NCI_THESAURUS C93038
Created by admin on Tue Oct 22 00:37:59 UTC 2019 , Edited by admin on Tue Oct 22 00:37:59 UTC 2019
LIVERTOX 43
Created by admin on Tue Oct 22 00:37:59 UTC 2019 , Edited by admin on Tue Oct 22 00:37:59 UTC 2019
WHO-ATC C01BD01
Created by admin on Tue Oct 22 00:37:59 UTC 2019 , Edited by admin on Tue Oct 22 00:37:59 UTC 2019
Code System Code Type Description
EPA CompTox
1951-25-3
Created by admin on Tue Oct 22 00:37:59 UTC 2019 , Edited by admin on Tue Oct 22 00:37:59 UTC 2019
PRIMARY
IUPHAR
2566
Created by admin on Tue Oct 22 00:37:59 UTC 2019 , Edited by admin on Tue Oct 22 00:37:59 UTC 2019
PRIMARY
LACTMED
1951-25-3
Created by admin on Tue Oct 22 00:37:59 UTC 2019 , Edited by admin on Tue Oct 22 00:37:59 UTC 2019
PRIMARY
NDF-RT
N0000182141
Created by admin on Tue Oct 22 00:37:59 UTC 2019 , Edited by admin on Tue Oct 22 00:37:59 UTC 2019
PRIMARY Cytochrome P450 3A4 Inhibitors [MoA]
MESH
D000638
Created by admin on Tue Oct 22 00:37:59 UTC 2019 , Edited by admin on Tue Oct 22 00:37:59 UTC 2019
PRIMARY
DRUG BANK
DB01118
Created by admin on Tue Oct 22 00:37:59 UTC 2019 , Edited by admin on Tue Oct 22 00:37:59 UTC 2019
PRIMARY
RXCUI
703
Created by admin on Tue Oct 22 00:37:59 UTC 2019 , Edited by admin on Tue Oct 22 00:37:59 UTC 2019
PRIMARY RxNorm
ECHA (EC/EINECS)
217-772-1
Created by admin on Tue Oct 22 00:37:59 UTC 2019 , Edited by admin on Tue Oct 22 00:37:59 UTC 2019
PRIMARY
WIKIPEDIA
AMIODARONE
Created by admin on Tue Oct 22 00:37:59 UTC 2019 , Edited by admin on Tue Oct 22 00:37:59 UTC 2019
PRIMARY
NDF-RT
N0000182138
Created by admin on Tue Oct 22 00:37:59 UTC 2019 , Edited by admin on Tue Oct 22 00:37:59 UTC 2019
PRIMARY Cytochrome P450 1A2 Inhibitors [MoA]
CAS
1951-25-3
Created by admin on Tue Oct 22 00:37:59 UTC 2019 , Edited by admin on Tue Oct 22 00:37:59 UTC 2019
PRIMARY
EVMPD
SUB05451MIG
Created by admin on Tue Oct 22 00:37:59 UTC 2019 , Edited by admin on Tue Oct 22 00:37:59 UTC 2019
PRIMARY
PUBCHEM
2157
Created by admin on Tue Oct 22 00:37:59 UTC 2019 , Edited by admin on Tue Oct 22 00:37:59 UTC 2019
PRIMARY
NCI_THESAURUS
C62002
Created by admin on Tue Oct 22 00:37:59 UTC 2019 , Edited by admin on Tue Oct 22 00:37:59 UTC 2019
PRIMARY
NDF-RT
N0000185503
Created by admin on Tue Oct 22 00:37:59 UTC 2019 , Edited by admin on Tue Oct 22 00:37:59 UTC 2019
PRIMARY P-Glycoprotein Inhibitors [MoA]
ChEMBL
CHEMBL633
Created by admin on Tue Oct 22 00:37:59 UTC 2019 , Edited by admin on Tue Oct 22 00:37:59 UTC 2019
PRIMARY
NDF-RT
N0000185504
Created by admin on Tue Oct 22 00:37:59 UTC 2019 , Edited by admin on Tue Oct 22 00:37:59 UTC 2019
PRIMARY Cytochrome P450 2C9 Inhibitors [MoA]
MERCK INDEX
M1748
Created by admin on Tue Oct 22 00:37:59 UTC 2019 , Edited by admin on Tue Oct 22 00:37:59 UTC 2019
PRIMARY Merck Index
NDF-RT
N0000182137
Created by admin on Tue Oct 22 00:37:59 UTC 2019 , Edited by admin on Tue Oct 22 00:37:59 UTC 2019
PRIMARY Cytochrome P450 2D6 Inhibitors [MoA]
INN
2012
Created by admin on Tue Oct 22 00:37:59 UTC 2019 , Edited by admin on Tue Oct 22 00:37:59 UTC 2019
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> INHIBITOR
POTENT
METABOLIC ENZYME -> INHIBITOR
POTENT
TRANSPORTER -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
ACTIVE AT HIGH CONCENTRATIONS; AMIODARONE CONCENTRATES IN THE LIVER
MAJOR
METABOLIC ENZYME -> INHIBITOR
POTENT
BINDER->LIGAND
BINDING
Related Record Type Details
METABOLITE ACTIVE -> PARENT
MAJOR
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC