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Key Documents

A8423

Sigma-Aldrich

Amiodarone hydrochloride

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

Synonyme(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

Formule empirique (notation de Hill):
C25H29I2NO3 · HCl
Numéro CAS:
Poids moléculaire :
681.77
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352200
ID de substance PubChem :
Nomenclature NACRES :
NA.77

product name

Amiodarone hydrochloride, ≥98%

Niveau de qualité

Pureté

≥98%

Forme

powder

Auteur

Wyeth

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

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.

Actions biochimiques/physiologiques

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

Caractéristiques et avantages

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

Substrats

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

Pictogrammes

Health hazardExclamation markEnvironment

Mention d'avertissement

Warning

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves


Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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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