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Amiodarone

Amiodarone Structure
CAS No.
1951-25-3
Chemical Name:
Amiodarone
Synonyms
Ancaron;Atlansil;Sedacoron;AMidorone;Sedacorone;Amiodarons;amiodarona;AMIODARONE;Tranquerone;Amiodarone Base
CBNumber:
CB5310616
Molecular Formula:
C25H29I2NO3
Molecular Weight:
645.31
MOL File:
1951-25-3.mol
MSDS File:
SDS
Modify Date:
2024/7/12 15:32:57

Amiodarone Properties

Melting point 54 - 55°C
Boiling point 635.1±55.0 °C(Predicted)
Density 1.5730 (estimate)
storage temp. 2-8°C
solubility Chloroform (Slightly), Methanol (Slightly)
form Solid
pka 6.56(at 25℃)
color Colourless to Pale Yellow
Water Solubility 716.4mg/L(25 ºC)
Stability Stable. Incompatible with strong oxidizing agents.
CAS DataBase Reference 1951-25-3(CAS DataBase Reference)
EPA Substance Registry System Methanone, (2-butyl-3-benzofuranyl)[4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl]- (1951-25-3)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P264-P270-P301+P312-P330-P501
Hazard Codes  Xn
Risk Statements  20/21/22
Safety Statements  36
WGK Germany  3
RTECS  OB1361000

Amiodarone Chemical Properties,Uses,Production

Description

From the chemical point of view, amiodarone is completely different from other antiarrhythmics. It has two iodide atoms and a diethylaminoethanol group as substituents in the benzoyl part, and overall it is very similar to the structure of thyroxin-like molecules.

Uses

antibacterial

Indications

Clinical use of amiodarone is limited because of its high toxicity, which consists of cardiac block, bradycardia, cardiac insufficiency, damaged thyroid gland function, neuropathology, and increased sensitivity to light, all of which significantly limit use of amiodarona, and it is only used in therapy for extremely serious tachyarrhythmias such as reoccurring ventricular fibrillation and hemodynamic unstable ventricular tachycardia, and only under supervision of a physician in a clinical situation.

Definition

ChEBI: A member of the class of 1-benzofurans that is 1-benzofuran substituted by a butyl group at position 2 and a 4-[2-(diethylamino)ethoxy]-3,5-diiodobenzoyl group at position 3. It is a cardiovascular drug used for the treatment of cardiac dysrhythmias.

Biological Functions

Amiodarone (Cordarone) is an iodine-containing benzofuran derivative identified as a class III agent because it predominantly prolongs action potentials. Amiodarone also blocks sodium and calcium channels and is a noncompetitive β-receptor blocker.Amiodarone is effective for the treatment of most arrhythmias. Toxicity associated with amiodarone has led the U. S. Food and Drug Administration (FDA) to recommend that it be reserved for use in patients with life-threatening arrhythmias.

General Description

Amiodarone, 2-butyl-3-benzofuranyl-4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl ketone (Cordarone),was introduced as an antianginal agent. It has very pronouncedclass III action and is especially effective in maintainingsinus rhythm in patients who have been treated bydirect current shock for atrial fibrillation. Like class IIIantiarrhythmic drugs, amiodarone lengthens the effective refractoryperiod by prolonging the action potential duration inall myocardial tissues. Amiodarone is eliminated very slowlyfrom the body, with a half-life of about 25 to 30 days after oraldoses. Although the drug has a broad spectrum of antiarrhythmicactivity, its main limitation is a slow onset of action.Drug action may not be initiated for several days, and thepeak effect may not be obtained for several weeks.

Mechanism of action

Amiodarone’s antiarrhythmic action is connected to its ability to block K, Na, and Ca2 channels while noncompetitively blocking α- and β-adrenergic receptors of the heart, thus prolonging the action potential and effective refractive period of atrial cells, atrioventricular junctions, and ventricles of the heart, which is accompanied by decreased automatism of sinus node and slowing of atrioventricular conductivity.

Clinical Use

Amiodarone has adverse effects involving many differentorgan systems. It also inhibits metabolism of drugscleared by oxidative microsomal enzymes. It contains iodinein its molecular structure and, as a result, has an effecton thyroid hormones. Hypothyroidism occurs in up to 11%of patients receiving amiodarone. The principal effect isthe inhibition of peripheral conversion of T4 to T3. Serumreverse T3 (rT3) is increased as a function of the dose as wellas the length of amiodarone therapy. As a result, rT3 levelshave been used as a guide for judging adequacy of amiodaronetherapy and predicting toxicity.

Safety Profile

Poison by intravenous and intraperitoneal routes. Human systemic effects by ingestion: photosensitivity of the skin. A flammable liquid. When heated to decomposition it emits very toxic fumes of Iand NO,. A coronary vasoddator

Drug interactions

Amiodarone increases the hypoprothrombinemic response to warfarin (an oral anticoagulant) by reducing its metabolism. Patients receiving digoxin may undergo an increase in serum digoxin concentrations when amiodarone is added to the treatment regimen. Amiodarone interferes with hepatic and renal elimination of flecainide, phenytoin, and quinidine.

Precautions

Amiodarone is contraindicated in patients with sick sinus syndrome and may cause severe bradycardia and secondand third-degree atrioventricular block. Amiodarone crosses the placenta and will affect the fetus, as evidenced by bradycardia and thyroid abnormalities. The drug is secreted in breast milk.

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