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83409-32-9

83409-32-9 | Desethylamiodarone

CAS No: 83409-32-9 Catalog No: AG00G29K MDL No:

Product Description

Catalog Number:
AG00G29K
Chemical Name:
Desethylamiodarone
CAS Number:
83409-32-9
IUPAC Name:
(2-butyl-1-benzofuran-3-yl)-[4-[2-(ethylamino)ethoxy]-3,5-diiodophenyl]methanone
InChI:
InChI=1S/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
InChI Key:
VXOKDLACQICQFA-UHFFFAOYSA-N
UNII:
M31FU99E3Y

Properties

Complexity:
508  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
616.992g/mol
Formal Charge:
0
Heavy Atom Count:
29  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
617.266g/mol
Monoisotopic Mass:
616.992g/mol
Rotatable Bond Count:
10  
Topological Polar Surface Area:
51.5A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
6.7  

Literature

Title Journal
Humanizing the zebrafish liver shifts drug metabolic profiles and improves pharmacokinetics of CYP3A4 substrates. Archives of toxicology 20170301
Cytotoxic interaction between amiodarone and desethylamiodarone in human peripheral lung epithelial cells. Chemico-biological interactions 20130825
A liquid chromatography-electrospray tandem mass spectrometry method for the determination of antiarrhythmic drugs and their metabolites in forensic whole blood samples. Journal of analytical toxicology 20120301
Amiodarone exposure during modest inflammation induces idiosyncrasy-like liver injury in rats: role of tumor necrosis factor-alpha. Toxicological sciences : an official journal of the Society of Toxicology 20120101
Stimulation of human monocytic THP-1 cells by metabolic activation of hepatotoxic drugs. Drug metabolism and pharmacokinetics 20120101
Preparation and determination of desethylamiodarone in dog lung by HPLC-MS. Die Pharmazie 20111101
Epicardial application of an amiodarone-releasing hydrogel to suppress atrial tachyarrhythmias. International journal of cardiology 20110616
Identification of amiodarone metabolites in human bile by ultraperformance liquid chromatography/quadrupole time-of-flight mass spectrometry. Drug metabolism and disposition: the biological fate of chemicals 20110601
Pharmacokinetics of intravenous amiodarone and its electrocardiographic effects on healthy Japanese subjects. Heart and vessels 20110501
Mechanisms of amiodarone and desethylamiodarone cytotoxicity in nontransformed human peripheral lung epithelial cells. The Journal of pharmacology and experimental therapeutics 20110201
A randomized, controlled study of amiodarone for prevention of atrial fibrillation after transthoracic esophagectomy. The Journal of thoracic and cardiovascular surgery 20100701
The effect of beta-naphthoflavone on the metabolism of amiodarone by hepatic and extra-hepatic microsomes. Toxicology letters 20100602
Simultaneous measurement of amiodarone and desethylamiodarone in human plasma and serum by stable isotope dilution liquid chromatography-tandem mass spectrometry assay. Journal of pharmaceutical and biomedical analysis 20100105
The effect of CYP1A induction on amiodarone disposition in the rat. Journal of pharmaceutical sciences 20100101
Assessment of the inactivation potential of desethylamiodarone on human CYP1A1. Drug metabolism letters 20100101
Characterization of recombinant hERG K(+) channel inhibition by the active metabolite of amiodarone desethyl-amiodarone. Journal of electrocardiology 20100101
Amiodarone and its putative metabolites fail to activate wild type hTAAR1. Bioorganic & medicinal chemistry letters 20091015
Cocktail-substrate assay system for mechanism-based inhibition of CYP2C9, CYP2D6, and CYP3A using human liver microsomes at an early stage of drug development. Xenobiotica; the fate of foreign compounds in biological systems 20090601
Benzofuran derivatives and the thyroid. Clinical endocrinology 20090101
Experimental hyperlipidemia causes an increase in the electrocardiographic changes associated with amiodarone. Journal of cardiovascular pharmacology 20090101
Amiodarone inhibits arterial thrombus formation and tissue factor translation. Arteriosclerosis, thrombosis, and vascular biology 20081201
Effects of intestinal constituents and lipids on intestinal formation and pharmacokinetics of desethylamiodarone formed from amiodarone. The Journal of pharmacy and pharmacology 20081201
Trace amine-associated receptor 1 (TAAR1) is activated by amiodarone metabolites. Bioorganic & medicinal chemistry letters 20081115
The impact of experimental hyperlipidemia on the distribution and metabolism of amiodarone in rat. International journal of pharmaceutics 20080901
Simultaneous determination of amiodarone and its metabolite desethylamiodarone by high-performance liquid chromatography with chemiluminescent detection. Analytica chimica acta 20080808
Amiodarone increases the accumulation of DEA in a human alveolar epithelium-derived cell line. Biological & pharmaceutical bulletin 20080701
Pharmacokinetics of desethylamiodarone in the rat after its administration as the preformed metabolite, and after administration of amiodarone. Biopharmaceutics & drug disposition 20080401
Direct mitochondrial dysfunction precedes reactive oxygen species production in amiodarone-induced toxicity in human peripheral lung epithelial HPL1A cells. Toxicology and applied pharmacology 20080315
Efflux transport of N-monodesethylamiodarone by the human intestinal cell-line Caco-2 cells. Drug metabolism and pharmacokinetics 20070801
The influence of hyperlipoproteinemia on in vitro distribution of amiodarone and desethylamiodarone in human and rat plasma. Pharmaceutical research 20070401
A liquid chromatography-mass spectrometry assay method for simultaneous determination of amiodarone and desethylamiodarone in rat specimens. Biomedical chromatography : BMC 20070301
Amiodarone induces angiotensinogen gene expression in lung alveolar epithelial cells through activation protein-1. Basic & clinical pharmacology & toxicology 20070101
Effect of amiodarone on the serum concentration/dose ratio of metoprolol in patients with cardiac arrhythmia. Drug metabolism and pharmacokinetics 20061201
Amiodarone analog-dependent effects on CYP2C9-mediated metabolism and kinetic profiles. Drug metabolism and disposition: the biological fate of chemicals 20061001
Serum amiodarone and desethylamiodarone concentrations following nasogastric versus oral administration. Journal of clinical pharmacy and therapeutics 20060601
Determination of amiodarone and desethylamiodarone in horse plasma and urine by high-performance liquid chromatography combined with UV detection and electrospray ionization mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20060519
Determination of the enzyme(s) involved in the metabolism of amiodarone in liver and intestine of rat: the contribution of cytochrome P450 3A isoforms. Drug metabolism and disposition: the biological fate of chemicals 20060101
Amiodarone and N-desethylamiodarone enhance endothelial nitric oxide production in human endothelial cells. International heart journal 20060101
Uptake of amiodarone by thyroidal and non-thyroidal cell lines. Journal of endocrinological investigation 20060101
Disruption of hepatic lipid homeostasis in mice after amiodarone treatment is associated with peroxisome proliferator-activated receptor-alpha target gene activation. The Journal of pharmacology and experimental therapeutics 20041201
Long-term amiodarone administration remodels expression of ion channel transcripts in the mouse heart. Circulation 20041109
A pharmacokinetic study of the combined administration of amiodarone and ximelagatran, an oral direct thrombin inhibitor. Journal of clinical pharmacology 20040901
A rapid procedure for the monitoring of amiodarone and N-desethylamiodarone by HPLC-UV detection. Journal of analytical toxicology 20040101
Protective effect of amiodarone but not N-desethylamiodarone on postischemic hearts through the inhibition of mitochondrial permeability transition. The Journal of pharmacology and experimental therapeutics 20031101
Silymarin and vitamin E reduce amiodarone-induced lysosomal phospholipidosis in rats. Toxicology 20030828
[Analysis of increased hepatic density during chronic amiodarone therapy]. Nihon Igaku Hoshasen Gakkai zasshi. Nippon acta radiologica 20030501
Dronerarone acts as a selective inhibitor of 3,5,3'-triiodothyronine binding to thyroid hormone receptor-alpha1: in vitro and in vivo evidence. Endocrinology 20030201
Pharmacological cardioversion of recent onset atrial fibrillation with intravenous amiodarone in patients receiving long-term amiodarone therapy: is it reasonable? Journal of interventional cardiac electrophysiology : an international journal of arrhythmias and pacing 20030201
Attenuation of amiodarone-induced pulmonary fibrosis by vitamin E is associated with suppression of transforming growth factor-beta1 gene expression but not prevention of mitochondrial dysfunction. The Journal of pharmacology and experimental therapeutics 20030101
Amiodarone N-deethylation by CYP2C8 and its variants, CYP2C8*3 and CYP2C8 P404A. Pharmacology & toxicology 20021001
Amiodarone and desethylamiodarone bind to barrier gels in serum separator blood collection tubes. Clinical chemistry and laboratory medicine 20020801
Determination of amiodarone and desethylamiodarone in human plasma by high-performance liquid chromatography-electrospray ionization tandem mass spectrometry with an ion trap detector. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20020125
Amiodarone-Induced thyroid dysfunction and ventricular tachyarrhythmias during long-term therapy in Japan. Japanese circulation journal 20011101
Altered metabolite concentrations with amiodarone generic substitution cannot be observed without monitoring. The Canadian journal of cardiology 20011101
Role of desethylamiodarone in the anticoagulant effect of concurrent amiodarone and warfarin therapy. Journal of cardiovascular pharmacology and therapeutics 20011001
Effects of vitamin E on cytotoxicity of amiodarone and N-desethylamiodarone in isolated hamster lung cells. Toxicology 20010925
Disruption of mitochondrial function and cellular ATP levels by amiodarone and N-desethylamiodarone in initiation of amiodarone-induced pulmonary cytotoxicity. The Journal of pharmacology and experimental therapeutics 20010901
Desethylamiodarone antagonizes the effect of thyroid hormone at the molecular level. European journal of endocrinology 20010701
Electrophysiological effects of dronedarone (SR 33589), a noniodinated amiodarone derivative in the canine heart: comparison with amiodarone. British journal of pharmacology 20010701
Metabolism of amiodarone (Part III): identification of rabbit cytochrome P450 isoforms involved in the hydroxylation of mono-N-desethylamiodarone. Xenobiotica; the fate of foreign compounds in biological systems 20010501
Metabolism of amiodarone (part I): identification of a new hydroxylated metabolite of amiodarone. Drug metabolism and disposition: the biological fate of chemicals 20010201
Inhibitory effects of CYP3A4 substrates and their metabolites on P-glycoprotein-mediated transport. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20010201
Desethylamiodarone interferes with the binding of co-activator GRIP-1 to the beta 1-thyroid hormone receptor. FEBS letters 20000922
Amiodarone induces apoptosis of human and rat alveolar epithelial cells in vitro. American journal of physiology. Lung cellular and molecular physiology 20000501
Effects of triiodothyronine and amiodarone on the promoter of the human LDL receptor gene. Biochemical and biophysical research communications 19980819
Cellular electropharmacology of amiodarone. Cardiovascular research 19970701
Desethylamiodarone is a competitive inhibitor of the binding of thyroid hormone to the thyroid hormone alpha 1-receptor protein. Molecular and cellular endocrinology 19950701
Amiodarone decreases Na,K-ATPase alpha 2 and beta 2 expression specifically in cardiac ventricle. Journal of molecular and cellular cardiology 19940401
Desethylamiodarone is a noncompetitive inhibitor of the binding of thyroid hormone to the thyroid hormone beta 1-receptor protein. Endocrinology 19940401
Amiodarone N-deethylation in human liver microsomes: involvement of cytochrome P450 3A enzymes (first report). Life sciences 19930101
Peripheral neuropathy during longterm high-dose amiodarone therapy. Journal of neurology, neurosurgery, and psychiatry 19850601

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