Amiodarone
CAS : 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-(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%
In December 1985, amiodarone was approved by the FDA for the treatment of arrhythmias.[6] This makes amiodarone one of the few drugs approved by the FDA without rigorous randomized clinical trials.
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.
A more recent synthesis of amiodarone reports the cyclisation of α-phenoxyhexanal 389 under acidic conditions to yield the substituted benzofuran 390 (Scheme 76). A Friedel–Crafts acylation next introduces the aryl ring at the 3-position. Demethylation, iodination and a final alkylation with a diethylaminoethane fragment yields amiodarone [115-117].
- 115 Witczak, M.; Kwiecień, H. Synth. Commun. 2005, 35, 2223–2230. doi:10.1080/00397910500182747
Return to citation in text: [1] - Wang, Z. J. Synthetic Process for 2-Butyl-3-(hydroxy-3,5-diiodobenzoyl)-benzofuran. Chin. Patent 1,858,042, Nov 8, 2006……….116
Return to citation in text: [1] - Ha, H. R.; Stieger, B.; Grassi, G.; Altorfer, H. R.; Follath, F. Eur. J. Clin. Pharmacol. 2000, 55, 807–814.doi:10.1007/s002280050701….117
![[1860-5397-7-57-i76]](http://www.beilstein-journals.org/bjoc/content/inline/1860-5397-7-57-i76.png?max-width=550&background=EEEEEE)
Scheme 76: Synthesis of amiodarone……….http://www.beilstein-journals.org/bjoc/single/articleFullText.htm?publicId=1860-5397-7-57#S76
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).
External links
- Siddoway LA (December 2003). “Amiodarone: guidelines for use and monitoring”. Am Fam Physician 68 (11): 2189–96. PMID 14677664.
- Amiodarone (MedicineNet.com)
- Amiodarone (FamilyPracticeNotebook.com)
- Amiodarone (The WorldWide Intensivist)
- U.S. National Library of Medicine: Drug Information Portal – Amiodarone
- Amiodarone (FDA MedWatch)
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| 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. |
|
| Legal status |
|
| 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  |
| ATC code | C01BD01 |
| PubChem | CID 2157 |
| IUPHAR ligand | 2566 |
| DrugBank | DB01118 |
| ChemSpider | 2072 |
| UNII | N3RQ532IUT |
| KEGG | D02910 |
| ChEBI | CHEBI:2663 |
| ChEMBL | CHEMBL633 |
| Chemical data | |
| Formula | C25H29I2NO3 |
| Mol. mass | 645,31 g/mol |
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.
Filed under: Uncategorized Tagged: amiodarone
