83409-32-9

Basic information

• Product Name: Desethylamiodarone
• Synonyms: DESETHYL AMIODARONE-D4 HCL;DESETHYL AMIODARONE HCL;(2-butyl-3-benzofuranyl)(4-(2-(ethylamino)ethoxy)-3,5-diiodophenyl)-methanon;(2-butyl-3-benzofuranyl)(4-(2-(ethylamino)ethoxy)-3,5-diiodophenyl)methanone;deethylamiodarone;desethylamiodarone;lb33020;n-deethylamiodarone
• CAS NO: 83409-32-9
• Molecular Formula: C23H25I2NO3
• Molecular Weight: 617.25
• Product Categories: Amiodarone;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 83409-32-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 630.3 °C at 760 mmHg
• Flash Point: 335 °C
• Appearance: /
• Density: 1.638 g/cm³
• Vapor Pressure: 8.51E-16mmHg at 25°C
• Refractive Index: 1.635
• CAS DataBase Reference: Desethylamiodarone(CAS DataBase Reference)
• NIST Chemistry Reference: Desethylamiodarone(83409-32-9)
• EPA Substance Registry System: Desethylamiodarone(83409-32-9)

Safety Data

• Hazardous Substances Data: 83409-32-9(Hazardous Substances Data)

Usage

Chemical Properties

Light-Yellow Syrup

Uses

A metabolite of Amiodarone, a non-selective ion channel blocker

InChI:InChI=1/C23H25I2NO3/c1-3-5-9-20-21(16-8-6-7-10-19(16)29-20)22(27)15-13-17(24)23(18(25)14-15)28-12-11-26-4-2/h6-8,10,13-14,26H,3-5,9,11-12H2,1-2H3

Upstream product

• 1951-25-3 Amiodarone 

Relevant articles and documents

Rapid liquid chromatographic assay for the determination of amiodarone and its N-deethyl metabolite in plasma, urine, and bile

A rapid high-performance liquid chromatographic assay was developed for the determination of amiodarone (1) and its N-deethyl metabolite (desethylamiodarone, 2) in plasma, urine, and bile. Analysis was performed on a C18 reversed-phase column and precolumn using a mobile phase consisting of methanol:water:58% ammonium hydroxide (94:4:2) delivered at a flow rate of 1.5 mL/min. The eluant was monitored at 244 nm. Under these conditions, 1, 2, and the internal standard eluted with retention times of 5.5, 4.6, and 6.8 min, respectively. Samples (100 μL) of plasma were prepared by precipitating the plasma proteins with acetonitrile containing the internal standard and injecting an aliquot of the supernatant directly onto the column. Samples (100 μL) of urine and bile were prepared for injection by acidifying the sample with concentrated HCl and then extracting the mixture with six volumes of 2,2-dimethoxyproprane. The recovery of 1 and 2 from plasma was virtually complete. The recovery from urine and bile was 80-90% for 1 and 60-65% for 2. The limit of sensitivity of both compounds in plasma was 100 ng/mL. For urine and bile, the detection limits were 1 and 5 μg/mL, respectively. Over the plasma concentration range of 0.1-10.0 μg/mL, the within-day CV ranged from 1 to 10% for 1 and from 1 to 8% for 2. The between-day CV ranged from 2 to 12% and from 1 to 17% for 1 and 2, respectively. Of 44 drugs tested for potential assay interference, four interfered with the determination of 2 and one with the analysis of 1. The assay has been used for pharmacokinetic studies in rats and routine monitoring of concentrations of 1 and 2 in human plasma.

Preparation and purification of desethylamiodarone hydrochloride

Reaction of the free base of amiodarone with 1-chloroethyl chloroformate in toluene gives desethylamiodarone, which can be easily purified and converted to the hydrochloride salt. Copyright Taylor & Francis Group, LLC.

Identification of novel substrates for human cytochrome P450 2J2

Several antihistamine drugs including terfenadine, ebastine, and astemizole have been identified as substrates for CYP2J2. The overall importance of this enzyme in drug metabolism has not been fully explored. In this study, 139 marketed therapeutic agents and compounds were screened as potential CYP2J2 substrates. Eight novel substrates were identified that vary in size and overall topology from relatively rigid structures (amiodarone) to larger complex structures (cyclosporine). The substrates displayed in vitro intrinsic clearance values ranging from 0.06 to 3.98 μl/min/pmol CYP2J2. Substrates identified for CYP2J2 are also metabolized by CYP3A4. Extracted ion chromatograms of metabolites observed for albendazole, amiodarone, astemizole, thioridazine, mesoridazine, and danazol showed marked differences in the regioselectivity of CYP2J2 and CYP3A4. CYP3A4 commonly metabolized compounds at multiple sites, whereas CYP2J2 metabolism was more restrictive and limited, in general, to a single site for large compounds. Although the CYP2J2 active site can accommodate large substrates, it may be more narrow than CYP3A4, limiting metabolism to moieties that can extend closer toward the active heme iron. For albendazole, CYP2J2 forms a unique metabolite compared with CYP3A4. Albendazole and amiodarone were evaluated in various in vitro systems including recombinant CYP2J2 and CYP3A4, pooled human liver microsomes (HLM), and human intestinal microsomes (HIM). The Michaelis-Menten-derived intrinsic clearance of N-desethyl amiodarone was 4.6 greater in HLM than in HIM and 17-fold greater in recombinant CYP3A4 than in recombinant CYP2J2. The resulting data suggest that CYP2J2 may be an unrecognized participant in first-pass metabolism, but its contribution is minor relative to that of CYP3A4. Copyright