482. Amiodarone

Nomenclature

CAS number: 1951-25-3
(2-Butyl-3-benzofuranyl)[4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl]methanone; 2-butyl-3-benzofuranyl-4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl ketone; 2-butyl-3-[3,5-diiodo-4-(β-diethylaminoethoxy)benzoyl]benzofuran.
C25H29I2NO3; mol wt 645.31.
C 46.53%, H 4.53%, I 39.33%, N 2.17%, O 7.44%.

Description and 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 tachyarrythmias: D. Roy et al., ibid. 342, 913 (2000); L. B. Mitchell et al., J. Am. Med. Assoc. 294, 3093 (2005). Review of clinical experience: L. A. Siddoway, Am. Fam. Physician 68, 2189-2196 (2003).

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 19774-82-4
L-3428; Amiodar (Ecosol); Ancaron (Sanofi-Aventis); Cordarex (Sanofi-Aventis); Corbionax (Sanofi-Aventis); Cordarone (Sanofi-Aventis); Cornaron (TAD); Escodarone (Streuli); Pacerone (Upsher-Smith); Tachydaron (AWD); Trangorex (Sanofi-Aventis).
C25H29I2NO3.HCl; mol wt 681.77.
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).

Therapeutic Category

Antiarrhythmic (class III).

Therapeutic Category (Veterinary)

Antiarrhythmic.

Keywords

Antiarrhythmic