19774-82-4 Usage
Description
Amiodarone hydrochloride, marketed under various names such as Pacerone, Cordarone, Aratac, and Atlansil, is a non-selective ion channel blocker and a class III antiarrhythmic agent. It is a white solid that has been used in the medical field for its various properties and applications.
Uses
1. Used in Pharmaceutical Industry:
Amiodarone hydrochloride is used as an antiarrhythmic agent for treating irregular heartbeats. It functions as a Na+ channel blocker, which helps in stabilizing the heart rhythm.
2. Used in Cardiology:
Amiodarone hydrochloride is used as a non-selective ion channel blocker in the treatment of cardiac arrhythmias. Its class III antiarrhythmic properties make it a valuable drug in managing heart rhythm disorders.
3. Used in Fungicidal Applications:
Amiodarone hydrochloride exhibits broad fungicidal activity, making it useful in the treatment of fungal infections. It has been shown to induce an immediate influx of Ca2+ in Saccharomyces cerevisiae, leading to mitochondrial fragmentation and cell death.
4. Used in Environmental Studies:
Amiodarone hydrochloride has been utilized in studies to determine the concentrations of thyroid disrupting substances in effluents from wastewater treatment plants, highlighting its application in environmental research.
5. Used in Autophagy and Cancer Research:
Amiodarone hydrochloride has been found to induce autophagy and suppress hepatocellular carcinoma tumorigenesis via autophagy-mediated MIR224 degradation in vitro and in vivo, making it a potential candidate for cancer research and treatment.
6. Used in Neurodegenerative Disease Research:
Amiodarone hydrochloride acts as an alkalizing agent, stimulating progranulin (GRN) production and preventing GRN-dependent neurodegeneration, which could be beneficial in the study and treatment of neurodegenerative diseases.
Therapeutic Function
Coronary vasodilator
Biochem/physiol Actions
Non-selective ion channel blocker with broad fungicidal activity. Amiodarone induces an immediate influx of Ca2+ in Saccharomyces cerevisiae, followed by mitochondrial fragmentation and cell death.
Clinical Use
Cardiac arrhythmias
Veterinary Drugs and Treatments
Because of its potential toxicity and lack of experience with use in
canine and equine patients, amiodarone is usually used when other
less toxic or commonly used drugs are ineffective. It may be useful
in dogs and horses to convert atrial fib into sinus rhythm and in
dogs for arrhythmias associated with left ventricular dysfunction. In
horses, one horse with Ventricular tachycardia was converted into
sinus rhythm using amiodarone.
As the risk of sudden death is high in Doberman pinschers exhibiting
rapid, wide-complex ventricular tachycardia or syncope with
recurrent VPC’s, amiodarone may be useful when other drug therapies
are ineffective.
Drug interactions
Potentially hazardous interactions with other drugs
Anti-arrhythmics: additive effect and increased
risk of myocardial depression; increased risk
of ventricular arrhythmias with disopyramide
or dronedarone - avoid; increased flecainide
concentration - halve flecainide dose; increased
procainamide concentration - avoid.
Antibacterials: increased risk of ventricular
arrhythmias with parenteral erythromycin, cotrimoxazole levofloxacin and moxifloxacin - avoid;
increased risk of ventricular arrhythmias with
delamanid; avoid with fidaxomicin; possibly
increased risk of ventricular arrhythmias with
telithromycin.
Anticoagulants: metabolism inhibited (increased
anti-coagulant effect); increased dabigatran
concentration (reduce dabigatran dose).
Antidepressants: increased risk of ventricular
arrhythmias with citalopram and escitalopram,
tricyclic antidepressants and venlafaxine - avoid.
Antiepileptics: phenytoin and fosphenytoin
metabolism inhibited (increased concentration).
Antifungals: avoid with fluconazole due to risk of
QT prolongation.
Antihistamines: increased risk of ventricular
arrhythmias with mizolastine - avoid.
Antimalarials: increased risk of ventricular
arrhythmias with chloroquine, hydroxychloroquine,
mefloquine and quinine and possibly with
piperaquine with artenimol and artemether/
lumefantrine - avoid.
Antimuscarinics: increased risk of ventricular
arrhythmias with tolterodine.
Antipsychotics: increased risk of ventricular
arrhythmias with antipsychotics that prolong
the QT interval; increased risk of ventricular
arrhythmias with amisulpride, benperidol,
droperidol, haloperidol, phenothiazines, pimozide or
zuclopenthixol - avoid; increased risk of ventricular
arrhythmias with sulpiride.
Antivirals: increased risk of ventricular arrhythmias
with fosamprenavir ritonavir, saquinavir and
telaprevir - avoid; concentration possibly increased
by atazanavir; possible increased risk of bradycardia
with daclatasvir, ledipasvir, sofosbuvir and
simeprevir; avoid with indinavir, reduce the dose of
the others.
Atomoxetine: increased risk of ventricular
arrhythmias. Beta-blockers, diltiazem, and verapamil: increased
risk of bradycardia, AV block and myocardial
depression; increased risk of ventricular arrhythmias
with sotalol - avoid.
Ciclosporin: increased levels of ciclosporin possible.
Cobicistat: concentration possibly increased by
cobicistat - avoid.
Colchicine: possibly increased colchicine toxicity.
Cytotoxics: possibly increased afatinib concentration
(separate administration by 6-12 hours); possibly
increased risk of ventricular arrhythmias with
panobinostat and vandetanib - avoid; concentration
of ibrutinib possibly increased - reduce dose of
ibrutinib; avoid with idelalisib; increased risk of
ventricular arrhythmias with arsenic trioxide,
bosutinib and ceritinib.
Digoxin: increased concentration (halve digoxin
maintenance dose).
Fingolimod: possible increased risk of bradycardia.
Grapefruit juice: may increase concentration of
amiodarone - avoid.
Ivabradine: increased risk of ventricular arrhythmias
- avoid.
Lipid-lowering drugs: give lomitapide 12 hours
after amiodarone; increased risk of myopathy with
simvastatin - do not exceed 20 mg of simvastatin.1 Lithium: increased risk of ventricular arrhythmias -
avoid.
Pentamidine: increased risk of ventricular
arrhythmias - avoid.
Metabolism
Amiodarone is metabolised in the liver; the major
metabolite, desethylamiodarone, also has antiarrhythmic
properties. There is very little urinary excretion of
amiodarone or its metabolites, the major route of
excretion being in faeces via the bile; some enterohepatic
recycling may occur.
References
1) Yamase et al. (2012), Effectiveness of amiodarone versus bepridil in achieving conversion to sinus rhythm in patients with persistent atrial fibrillation: a randomized trial; Heart, 98 1067
2) Di Matola et al. (2000), Amiodarone induces cytochrome c release and apoptosis through an iodine-independent mechanism; J. Clin. Endocrinol. Metab., 85 4323
3) Capell et al. (2011), Rescue of progranulin deficiency associated with frontotemporal lobar degeneration by alkalizing reagents and inhibition of vacuolar ATPase; J. Neurosci., 31 1885
4) Lan et al. (2014), Autophagy-preferential degradation of MIR224 participates in hepatocellular carcinoma tumorigenesis; Autophagy, 10 1687
Check Digit Verification of cas no
The CAS Registry Mumber 19774-82-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,9,7,7 and 4 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 19774-82:
(7*1)+(6*9)+(5*7)+(4*7)+(3*4)+(2*8)+(1*2)=154
154 % 10 = 4
So 19774-82-4 is a valid CAS Registry Number.
InChI:InChI=1/C25H29I2NO3.ClH/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;1H
19774-82-4Relevant articles and documents
Method for preparing amiodarone hydrochloride
-
, (2021/10/27)
The invention discloses a method for preparing amiodarone hydrochloride, which comprises the following steps: by taking 2-butylbenzofuran and p-acetoxybenzaldehyde as raw materials, carrying out aldol reaction under Lewis acid catalysis and heating conditions, simultaneously carrying out hydroxyl oxidation, deacetylation and iodination reaction on the product in the presence of iodine and alkali, and then reacting the product with N, N-diethyl chloroethylamine, and salifying to obtain amiodarone hydrochloride. According to the method, only a catalytic amount of Lewis acid is needed, strong acidic aluminum chloride is not needed, reaction conditions are milder, byproducts are few, post-treatment is easy, and three wastes are greatly reduced; the whole route is simple to operate, the used reagents are cheap, easy to obtain and non-toxic, and the method is very suitable for industrial production.
Preparation method of amiodarone hydrochloride
-
, (2019/08/12)
The invention relates to a preparation method of amiodarone hydrochloride. According to the preparation method, synthesis of intermediate 2-butylbenzofuran is realized under effect of a catalyst, a cocatalyst, and an acid binding agent, through Sonogashira coupling cyclization reaction of 2-iodo phenol and 1-acetylene in an organic solvent at a 2-iodo phenol to 1-acetylene molar ratio of 1:09-1.3,wherein reaction temperature ranges from 30 to 60 DEG C, and reaction time ranges from 12 to 38h. Compared with the prior art, the advantages are that: operation is simplified; operation convenienceand product stability are improved; controlling of the ratio of the catalyst to the materials is capable of increasing the purities and yields of intermediates; no column chromatography purifying is needed; cost is reduced; production efficiency is increased at the same time; and convenience is provided for industrial large scale production.
