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A8423

Sigma-Aldrich

Amiodarone hydrochloride

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

Synonym(s):

(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

Empirical Formula (Hill Notation):
C25H29I2NO3 · HCl
CAS Number:
19774-82-4
Molecular Weight:
681.77
EC Number:
243-293-2
MDL number:
MFCD00069204
UNSPSC Code:
12352200
PubChem Substance ID:
24277818
NACRES:
NA.77

product name

Amiodarone hydrochloride, ≥98%

Assay

≥98%

form

powder

originator

Wyeth

storage temp.

2-8°C

SMILES string

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

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

InChI key

ITPDYQOUSLNIHG-UHFFFAOYSA-N

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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.

Substrates

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

Signal Word

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Involvement of CYP3A4/5 and CYP2D6 in the metabolism of aconitine using human liver microsomes and recombinant CYP450 enzymes
Tang, L., et al.
Toxicology Letters, 2022, 47-54 (2011)
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)
Evaluation of autophagy inducers in epithelial cells carrying the DeltaF508 mutation of the cystic fibrosis transmembrane conductance regulator CFTR
Zhang S, et al.
Cell Death & Disease, 9(2), 191-191 (2018)
P Simonen et al.
Journal of internal medicine, 288(5), 560-569 (2020-05-18)
We have earlier reported that amiodarone, a potent and commonly used antiarrhythmic drug increases serum desmosterol, the last precursor of cholesterol, in 20 cardiac patients by an unknown mechanism. Here, we extended our study to a large number of cardiac
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