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QuickView for Amiodarone (compound)


PubChem
Name: Amiodarone
PubChem Compound ID: 2157
Description: An antianginal and antiarrhythmic drug. It increases the duration of ventricular and atrial muscle action by inhibiting Na,K-activated myocardial adenosine triphosphatase. There is a resulting decrease in heart rate and in vascular resistance.
Molecular formula: C25H29I2NO3
Molecular weight: 645.312 g/mol
Synonyms:
NINDS_000079; 2-Butyl-3-(4'-beta-N-diethylaminoethoxy-3',5'-diiodobenzoyl)benzofuran; Ketone, 2-butyl-3-benzofuranyl 4-(2-(diethylamino)ethoxy)-3,5-diiodophenyl; 1951-25-3; (2-Butyl-3-benzofuranyl)(4-(2-(diethylamino)ethoxy)-3,5-diidophenyl)methanone; Amiodarone; CHEBI:2663; AIDS-114337; nchembio732-comp1; 2-Butyl-3-(3,5-diiodo-4-(beta-diethylaminoethoxy)benzoyl)benzofuran.
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DrugBank
Identification
Name: Amiodarone
Name (isomeric): DB01118
Drug Type: small molecule
Description: An antianginal and antiarrhythmic drug. It increases the duration of ventricular and atrial muscle action by inhibiting Na,K-activated myocardial adenosine triphosphatase. There is a resulting decrease in heart rate and in vascular resistance.
Synonyms:
Amiodarona [INN-Spanish]; Amiodarone Base; Amiodaronum [INN-Latin]; Amiodarone HCL; Amiodarone Hydrochloride
Brand: Aratac, Labaz, Amio-Aqueous IV, Aminodarone, Cordarone Intravenous, Cordarone, Amiodarons, pms-Amiodarone, Pacerone, Arycor
Category: Vasodilator Agents, Enzyme Inhibitors, Anti-Arrhythmia Agents
CAS number: 1951-25-3
Pharmacology
Indication: Intravenously, for initiation of treatment and prophylaxis of frequently recurring ventricular fibrillation and hemodynamically unstable ventricular tachycardia in patients refractory to other therapy. Orally, for the treatment of life-threatening recurrent ventricular arrhythmias such as recurrent ventricular fibrillation and recurrent hemodynamically unstable ventricular tachycardia.
Pharmacology:
Amiodarone belongs to a class of drugs called Vaughan-Williams Class III antiarrhythmic agents. It is used in the treatment of a wide range of cardiac tachyarhthmias, including both ventricular and supraventricular (atrial) arrhythmias. After intravenous administration in man, amiodarone relaxes vascular smooth muscle, reduces peripheral vascular r...
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Mechanism of Action: The antiarrhythmic effect of amiodarone may be due to at least two major actions. It prolongs the myocardial cell-action potential (phase 3) duration and refractory period and acts as a noncompetitive a- and b-adrenergic inhibitor.
Absorption: Slow and variable (about 20 to 55% of an oral dose is absorbed).
Protein binding: >96%
Biotransformation: Amiodarone is extensively metabolized in the liver via CYP2C8 (under 1% unchanged in urine), and can effect the metabolism of numerous other drugs. The major metabolite of amiodarone is desethylamiodarone (DEA), which also has antiarrhythmic properties. The metabolism of amiodarone is inhibited by grapefruit juice, leading to elevated serum levels of amiodarone.
Route of elimination: Amiodarone is eliminated primarily by hepatic metabolism and biliary excretion and there is negligible excretion of amiodarone or DEA in urine.
Half Life: 58 days (range 15-142 days)
Clearance: 90-158 mL/h/kg [Healthy with a single dose IV (5 mg/kg over 15 min)] 100 mL/h/kg [Normal subjects > 65 yrs] 150 mL/h/kg [younger subjects] 220 and 440 mL/h/kg [patients with VT and VF]
Toxicity: Intravenous, mouse: LD50 = 178 mg/kg. Some side effects have a significant mortality rate: specifically, hepatitis, exacerbation of asthma and congestive failure, and pneumonitis.
Affected organisms: Humans and other mammals
Interactions
Food interaction:
Grapefruit and grapefruit juice should be avoided throughout treatment.
Grapefruit can significantly increase serum levels of this product.
Take without regard to meals.
Drug interaction:
GrepafloxacinIncreased risk of cardiotoxicity and arrhythmias
ErythromycinIncreased risk of cardiotoxicity and arrhythmias
TipranavirTipranavir, co-administered with Ritonavir, may increase the plasma concentration of Amiodarone. Concomitant therapy is contraindicated.
LevofloxacinIncreased risk of cardiotoxicity and arrhythmias
SparfloxacinIncreased risk of cardiotoxicity and arrhythmias
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