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Merck

A8423

Amiodarone hydrochloride

≥98% (TLC), powder, ion channel blocker

Sinónimos:

(2-Butyl-3-benzofuranyl)[4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl]methanone hydrochloride, 2-Butyl-3-benzofuranyl-4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl ketone hydrochloride

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About This Item

Fórmula empírica (notación de Hill):
C25H29I2NO3 · HCl
Número CAS:
Peso molecular:
681.77
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
EC Number:
243-293-2
MDL number:

Nombre del producto

Amiodarone hydrochloride, ≥98%

InChI key

ITPDYQOUSLNIHG-UHFFFAOYSA-N

InChI

1S/C25H29I2NO3.ClH/c1-4-7-11-22-23(18-10-8-9-12-21(18)31-22)24(29)17-15-19(26)25(20(27)16-17)30-14-13-28(5-2)6-3;/h8-10,12,15-16H,4-7,11,13-14H2,1-3H3;1H

SMILES string

C(=O)(C=1C=2C(OC1CCCC)=CC=CC2)C3=CC(I)=C(OCCN(CC)CC)C(I)=C3.Cl

assay

≥98%

form

powder

originator

Wyeth

storage temp.

2-8°C

Quality Level

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Application

Amiodarone hydrochloride has been used to study its interaction with cysteamine to stimulate autophagy in cultured biosensor cell lines. It has also been used in larval and adult organ toxicogenomic screening to analyze the transcriptional effects of pharmaceuticals.
Amiodarone hydrochloride is a non-selective ion channel blocker. Amiodarone induces an immediate influx of Ca2+ in Saccharomyces cerevisiae, followed by mitochondrial fragmentation and cell death. Amiodarone hydrochloride has also been used in a study to determine concentrations of thyroid disrupting substances in effluents from wastewater treatment plants.

Biochem/physiol Actions

Non-selective ion channel blocker. Amiodarone induces an immediate influx of Ca2+ in Saccharomyces cerevisiae, followed by mitochondrial fragmentation and cell death.

Features and Benefits

This compound was developed by Wyeth. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

General description

CYP2C8/9 and CYP3A family (minor pathway) inhibitor and substrate; CYP2D6, CYP3A family, CYP2D6, CYP2A6, CYP2B6 desethyl-form inhibitor

signalword

Warning

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 2 - Eye Irrit. 2 - Lact. - Repr. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

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    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

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  4. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  5. What is the solubility of Product A8423, Amiodarone hydrochloride, and in which solvents may it be reconstituted?

    Sigma-Aldrich tests the solubility of Product A8423, Amiodarone hydrochloride in water at a concentration of 50 mg/ml. This requires heating at 105 °C for 10 minutes. This concentration is above the solubility maximum at room temperature. As per the chemicals encyclopedia published by the Royal Society of Chemistry 13th Ed., Entry #482, solubility at 25 °C, (g/100mL):  Water (0.07), Ethanol (1.28), Methanol (9.98), Chloroform (44.51), Methylene Chloride (19.2), and Hexane (0.03).Reportedly, the solubility of the product is 10 mg/ml each in DMSO and in dimethylformamide.

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Na Li et al.
Journal of environmental sciences (China), 23(4), 671-675 (2011-07-29)
It is generally known that there are many endocrine disrupting compounds (EDCs) in the effluents from wastewater treatment plants (WWTPs). Most research has focused on the occurrence of estrogenic or androgenic activities, while ignoring that there are environmental chemicals disrupting
Alex Dexter et al.
Analytical and bioanalytical chemistry, 411(30), 8023-8032 (2019-11-30)
Within drug development and pre-clinical trials, a common, significant and poorly understood event is the development of drug-induced lipidosis in tissues and cells. In this manuscript, we describe a mass spectrometry imaging strategy, involving repeated analysis of tissue sections by
Editor?s Highlight: Transgenic Zebrafish Reporter Lines as Alternative In Vivo Organ Toxicity Models
Poon K, et al.
Toxicological Sciences, 156(1), 133-148 (2017)
Aateka Patel et al.
Pharmaceutics, 11(7) (2019-07-20)
'Foamy' alveolar macrophages (FAM) observed in nonclinical toxicology studies during inhaled drug development may indicate drug-induced phospholipidosis, but can also derive from adaptive non-adverse mechanisms. Orally administered amiodarone is currently used as a model of pulmonary phospholipidosis and it was
Haruka Okamoto et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 1051, 33-40 (2017-03-13)
Cationic amphiphilic drugs (CADs) can induce the hyperaccumulation of phospholipids in cells and tissues. This side effect, which is known as drug-induced phospholipidosis, is sometimes problematic in the development and clinical use of CADs. It is known that CADs generally

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