Amiodarone

Title: Amiodarone
CAS Registry Number: 1951-25-3
CAS Name: (2-Butyl-3-benzofuranyl)[4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl]methanone
Additional Names: 2-butyl-3-benzofuranyl-4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl ketone; 2-butyl-3-[3,5-diiodo-4-(b-diethylaminoethoxy)benzoyl]benzofuran
Molecular Formula: C25H29I2NO3
Molecular Weight: 645.31
Percent Composition: C 46.53%, H 4.53%, I 39.33%, N 2.17%, O 7.44%
Literature References: Benzofuran derivative with multiple electrophysiological effects. Prepn: FR 1339389; R. Tondeur, F. Binon, US 3248401 (1963, 1966 to Soc. Belge l'Azote Prod. Chim. Marly). Physicochemical properties: M. Bonati et al., J. Pharm. Sci. 73, 829 (1984). HPLC determn in plasma: M. De Smet, D. L. Massart, J. Pharm. Biomed. Anal. 6, 277 (1988). Comprehensive description: T. A. Plomp, Anal. Profiles Drug Subs. 20, 1-120 (1991). Review of pharmacology, clinical efficacy and safety: M. Chow, Ann. Pharmacother. 30, 637-643 (1996); B. N. Singh, Clin. Cardiol. 20, 608-618 (1997). Clinical trial in cardiac resuscitation: P. J. Kudenchuk et al., N. Engl. J. Med. 341, 871 (1999); to prevent atrial fibrillation: D. Roy et al., ibid. 342, 913 (2000).
Derivative Type: Hydrochloride
CAS Registry Number: 19774-82-4
Manufacturers' Codes: L-3428
Trademarks: Amiodar (Sanofi Winthrop); Ancaron (Taisho); Cordarex (Sanofi Winthrop); Cordarone (Wyeth); Ortacrone (Sanofi Winthrop); Pacerone (Upsher-Smith); Tachydaron (AWD); Trangorex (Sanofi Winthrop)
Molecular Formula: C25H29I2NO3.HCl
Molecular Weight: 681.77
Percent Composition: C 44.04%, H 4.44%, I 37.23%, N 2.05%, O 7.04%, Cl 5.20%
Properties: Crystalline powder, mp 156°. Also reported as crystals from acetone, mp 159 ±2° (Bonati). Soly at 25° (g/100ml): chloroform 44.51; methylene chloride 19.20; methanol 9.98; ethanol 1.28; benzene 0.65; tetrahydrofuran 0.60; acetonitrile 0.32; 1-octanol 0.30; ether 0.17; 1-propanol 0.13; water 0.07; hexane 0.03 petroleum ether 0.001. Sparingly sol in isopropanol; slightly sol in acetone, dioxane, and carbon tetrachloride. pH (5% soln) 3.4-3.9. pKa (25°C) 6.56 ±0.06. uv max (methanol): 208, 242 nm (E1%1cm 662 ±8, 623 ±10).
Melting point: mp 156°; mp 159 ±2° (Bonati)
pKa: pKa (25°C) 6.56 ±0.06
Absorption maximum: uv max (methanol): 208, 242 nm (E1%1cm 662 ±8, 623 ±10)
Therap-Cat: Antiarrhythmic (class III).
Keywords: Antiarrhythmic.
Amiphenazole Amiprilose Amisometradine Amisulpride Amiton

Amiodarone
Amiodarone structure.svg
Amiodarone 3d balls.png
Systematic (IUPAC) name
(2-{4-[(2-butyl-1-benzofuran-3-yl)carbonyl]-2,6-diiodophenoxy}ethyl)diethylamine
Clinical data
Trade names Cordarone, Nexterone
AHFS/Drugs.com monograph
MedlinePlus a687009
Pregnancy cat. D (US)
Legal status Prescription only
Routes oral or intravenous
Pharmacokinetic data
Bioavailability 20–55%
Metabolism Liver
Half-life 58 days (range 15-142 days)
Excretion Primarily Hepatic and Biliary
Identifiers
CAS number 1951-25-3 YesY
ATC code C01BD01
PubChem CID 2157
IUPHAR ligand 2566
DrugBank DB01118
ChemSpider 2072 YesY
UNII N3RQ532IUT YesY
KEGG D02910 YesY
ChEBI CHEBI:2663 YesY
ChEMBL CHEMBL633 YesY
Chemical data
Formula C25H29I2NO3 
Mol. mass 645,31 g/mol
 YesY (what is this?)  (verify)

Amiodarone is an antiarrhythmic agent used for various types of cardiac dysrhythmias, both ventricular and atrial. It was discovered in 1961. Despite relatively common side-effects, it is used in arrhythmias that are otherwise difficult to treat with medication.