Amiodarone

Base Information

• Chemical Name: Amiodarone
• CAS No.: 1951-25-3
• Molecular Formula: C25H29I2NO3
• Molecular Weight: 645.319
• Hs Code.: 2932999099
• European Community (EC) Number: 217-772-1
• UNII: N3RQ532IUT
• DSSTox Substance ID: DTXSID7022592
• Nikkaji Number: J7.829H
• Wikipedia: Amiodarone
• Wikidata: Q410061
• NCI Thesaurus Code: C62002
• RXCUI: 703
• Pharos Ligand ID: 87DVJ1X9QF62
• Metabolomics Workbench ID: 43343
• ChEMBL ID: CHEMBL633
• Mol file: 1951-25-3.mol

Synonyms:Amiobeta;Amiodarex;Amiodarona;Amiodarone;Amiodarone Hydrochloride;Amiohexal;Aratac;Braxan;Corbionax;Cordarex;Cordarone;Hydrochloride, Amiodarone;Kordaron;L 3428;L-3428;L3428;Ortacrone;Rytmarone;SKF 33134 A;SKF 33134-A;SKF 33134A;Tachydaron;Trangorex

Chemical Property of Amiodarone

Chemical Property:

• Vapor Pressure: 4.95E-16mmHg at 25°C
• Melting Point: 156oC
• Boiling Point: 635.073 °C at 760 mmHg
• PKA: 6.56(at 25℃)
• Flash Point: 337.88 °C
• PSA: 42.68000
• Density: 1.581 g/cm³
• LogP: 6.93620
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: 716.4mg/L(25 oC)
• XLogP3: 7.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 645.02369
• Heavy Atom Count: 31
• Complexity: 547

Purity/Quality:

99% ^*data from raw suppliers

Amiodarone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiarrhythmic Agents
• Canonical SMILES: CCCCC1=C(C2=CC=CC=C2O1)C(=O)C3=CC(=C(C(=C3)I)OCCN(CC)CC)I
• Recent ClinicalTrials: Amiodarone and N-Acetylcysteine or Amiodarone Alone for Preventing Atrial Fibrillation After Thoracic Surgery
• Recent EU Clinical Trials: Amiodarone or Verapamil in COVID-19 hospitalized patients with symptoms: Randomized clinical trial
• Recent NIPH Clinical Trials: Dantrolene VT study
• 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 Amiodarone is a non-selective ion channel blocker. Antiarrhythmic (class III).
• 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.
• Therapeutic Function: Coronary vasodilator
• 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.
• 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.
• 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.

Technology Process of Amiodarone

There total 7 articles about Amiodarone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) + 2-n-butyl-3-(3',5'-diiodo-4'-hydroxybenzoyl)benzofuran (1951-26-4) → Amiodarone (1951-25-3)

Guidance literature:

With potassium carbonate; sodium iodide; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1021/acs.joc.9b00270

Reference yield:

amiodarone decahydrochloride → Amiodarone (1951-25-3)

Guidance literature:

With potassium carbonate; In dichloromethane; water; for 5h;

Reference yield:

2-n-butyl 3-(4-methoxy benzoyl)-benzofuran (83790-87-8) → Amiodarone (1951-25-3)

Guidance literature:

Multi-step reaction with 3 steps

1: boron tribromide / dichloromethane

2: sodium hydroxide; iodine / methanol / 3 h / 0 - 20 °C

3: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 12 h / 20 °C

With iodine; boron tribromide; potassium carbonate; sodium iodide; sodium hydroxide; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/acs.joc.9b00270

upstream raw materials:

2-n-butyl 3-(4-methoxy benzoyl)-benzofuran

2-chloro-N,N-diethylethylamine hydrochloride

2-n-butyl-3-(3',5'-diiodo-4'-hydroxybenzoyl)benzofuran

1-(4-methoxyphenyl)-1,3-heptanedione

Downstream raw materials:

desethylamiodarone

2-n-butyl-3-(3-iodo-4-hydroxybenzoyl)-benzofuran

2-n-butyl-3-(3',5'-diiodo-4'-hydroxybenzoyl)benzofuran

Deiodoamiodarone

Refernces

• 1、 Huang, Wenbo,Xu, Jing,Liu, Changhui,Chen, Zhiyan,Gu, Yanlong. "Lewis Acid-Catalyzed Synthesis of Benzofurans and 4,5,6,7-Tetrahydrobenzofurans from Acrolein Dimer and 1,3-Dicarbonyl Compounds". . p. 2941 - 2950. Retrieved 2019/02/26.