Amiodarone (CED0001622)

Record Information
Version1.0
Creation Date2014-09-11 05:14:06 UTC
Update Date2026-08-22 05:14:08 UTC
Accession NumberCHEM003694
Identification
Common NameAmiodarone
ClassSmall Molecule
Description
Amiodarone belongs to the carbonyl compounds, a subclass of organooxygen compounds within the organic compounds. With an average molecular weight of 645.31 g/mol, Amiodarone is a heavy molecule. This exogenous compound has the formula C25H29I2NO3 and exists as a solid at room temperature. It is used as a biological drug (PMC10042770). Recorded exposure routes for the compound include oral and intravenous administration. Amiodarone is found in 13 recorded sources, including food preservation, household cleaning and consumer products such as tobacco smoke filters and cigar cigarettes, and electrical and electronic equipment including antennas, electrodes, hybrid capacitors, and electric switches. It is also found in healthcare, pharmaceuticals, and veterinary products specifically within class i and iii antiarrhythmics. The compound acts as a downregulator for the Beta-1 adrenergic receptor (ADRB1), the Voltage-gated inwardly rectifying potassium channel KCNH2, the Voltage-dependent T-type calcium channel subunit alpha-1H (CACNA1H), the Voltage-dependent calcium channel subunit alpha-2/delta-2 (CACNA2D2), and 18 other proteins, functioning as an agonist/antagonist and binder/inhibitor/inhibitor. In terms of health effects, Amiodarone is used as a treatment for ventricular tachycardia (PMC12396106) and atrial fibrillation (PMC5358124). However, it is associated with pulmonary fibrosis (PMC10042770) as well as hypothyroidism and hyperthyroidism (PMC9571437).
Contaminant Type
  • Amine
  • Anti-Arrhythmia Agent
  • Drug
  • Enzyme Inhibitor
  • Ester
  • Ether
  • Human Neurotoxin
  • Organic Compound
  • Synthetic Compound
  • Vasodilator Agent
Chemical Structure
Synonyms
ValueSource
2-Butyl-3-(3,5-diiodo-4-(2-diethylaminoethoxy)benzoyl)benzofuranChEBI
2-Butyl-3-benzofuranyl 4-(2-(diethylamino)ethoxy)-3,5-diiodophenyl ketoneChEBI
2-N-Butyl-3',5'-diiodo-4'-N-diethylaminoethoxy-3-benzoylbenzofuranChEBI
AmiodaronaChEBI
AmiodaronumChEBI
Amiodarone baseHMDB
Alphapharm brand OF amiodarone hydrochlorideHMDB
CorbionaxHMDB
Hexal brand OF amiodarone hydrochlorideHMDB
Leurquin brand OF amiodarone hydrochlorideHMDB
ASTA medica brand OF amiodarone hydrochlorideHMDB
AmiodarexHMDB
Amiodarone hydrochlorideHMDB
AmiohexalHMDB
Berenguer infale brand OF amiodarone hydrochlorideHMDB
Betapharm brand OF amiodarone hydrochlorideHMDB
BraxanHMDB
CordarexHMDB
OrtacroneHMDB
Pharma investi brand OF amiodarone hydrochlorideHMDB
RytmaroneHMDB
Sanofi winthrop brand OF amiodarone hydrochlorideHMDB
TachydaronHMDB
TrangorexHMDB
AmiobetaHMDB
CordaroneHMDB
Hydrochloride, amiodaroneHMDB
KordaronHMDB
SKF 33134 aHMDB
SKF 33134-aHMDB
AratacHMDB
Armstrong brand OF amiodarone hydrochlorideHMDB
g Gam brand OF amiodarone hydrochlorideHMDB
Wyeth brand OF amiodarone hydrochlorideHMDB
Chemical FormulaC25H29I2NO3
Average Molecular Mass645.312 g/mol
Monoisotopic Mass645.024 g/mol
CAS Registry Number1951-25-3
IUPAC Name{2-[4-(2-butyl-1-benzofuran-3-carbonyl)-2,6-diiodophenoxy]ethyl}diethylamine
Traditional Nameamiodarone
SMILESCCCCC1=C(C(=O)C2=CC(I)=C(OCCN(CC)CC)C(I)=C2)C2=CC=CC=C2O1
InChI IdentifierInChI=1S/C25H29I2NO3/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
InChI KeyIYIKLHRQXLHMJQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAryl-phenylketones
Alternative Parents
Substituents
  • Aryl-phenylketone
  • Benzofuran
  • Phenol ether
  • 3-aroylfuran
  • Benzoyl
  • Phenoxy compound
  • Alkyl aryl ether
  • Halobenzene
  • Iodobenzene
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl iodide
  • Aryl halide
  • Heteroaromatic compound
  • Furan
  • Tertiary aliphatic amine
  • Tertiary amine
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organonitrogen compound
  • Organoiodide
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point156°C
Boiling PointNot Available
SolubilityLow
Predicted Properties
PropertyValueSource
Water Solubility0.0048 g/LALOGPS
logP7.24ALOGPS
logP7.64ChemAxon
logS-5.1ALOGPS
pKa (Strongest Basic)8.47ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area42.68 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity145.05 m³·mol⁻¹ChemAxon
Polarizability56.78 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-000i-9000024000-088b6534d1659c5c174dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004r-0690000000-25202a61d19d3dfaed8bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0000009000-8cbab89986761a7a1bc9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0pbj-9300003000-503a542bf1a7678f385eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9110000000-543b8de3c9ba390fa765Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0791000000-77d5d18989052c45b006Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a59-0980000000-a77e32d189cf8e2acdf1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0apl-0940000000-30e016c113387b37ca7cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0000009000-e87a9a6e983c00161bebNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0fb9-0192101000-d4f2f8589987e9dee2fcNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0020009000-bc59c51779e07ba2a4a0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9100000000-cf7a06e18403e76cf41cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0000009000-ec39c036c89b5923fc2cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0pb9-9200000000-5cde40904f838865e7baNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-1000009000-3e4fea6e220ba0a42af4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9100000000-cf88edc5ce5babf0e567Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0000009000-9f22341a9246a58e0df5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0000009000-7304d2b67fba343a8883Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0000009000-fad8f001fba3ffb05e41Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f6t-6400009000-32088cd4966452222ef5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0000009000-3238804f244a68e3f051Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9100000000-a01ab0d8eabf73979e00Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0pbj-9300003000-3ce240944067e565dc77Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0000009000-12770d7be018fc4a7acbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052b-9300007000-99ecd56e4228cfbe38f0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-1000009000-a143e482807e1e2b888bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-1200009000-72e4b7325763a217dd28Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0000009000-5e38aeb8404a27c5807aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9100000000-6db41deda8b2dd34e2d0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9000000000-e17584117bd71437a429Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0000009000-bd6c546b9f51663059f1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9000000000-3cf0550edd2e360fb03eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9000000000-05307725c3008d000724Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-5300009000-6f3506e995c775a9f619Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-1200419000-3080963b2267302d337aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-6920532000-f1048ae0af01f6658877Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-006x-7309200000-46ba6e78349f4d182fe7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-1100029000-9b580022f60608cc2810Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-006x-3202296000-a7445663ea627302ddceNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-7902160000-4817e1c5fca0d177a829Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0000009000-01862e6d48bdfc6ce4f4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-1500289000-6c50b4a34ce5061526f2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0900000000-9527872b814a341cd862Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0000009000-338958536e6103f4fe88Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-2300049000-399067cb05fffb6190ceNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fk9-9502120000-a658e108366f4d1d537dNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityThe antiarrhythmic effect of amiodarone may be due to at least two major actions. It prolongs the myocardial cell-action potential (phase 3) duration and refractory period and acts as a noncompetitive a- and b-adrenergic inhibitor. Intravenous, mouse: LD50 = 178 mg/kg.
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2221.0Log mg/kg[1200:3900]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
hypothyroidismassociated_withNot AvailablePMC9571437
Hyperthyroidismassociated_withNot AvailablePMC9571437
atrial fibrillationis_treatment_forNot AvailablePMC5358124
pulmonary fibrosisassociated_withNot AvailablePMC10042770
ventricular tachycardiais_treatment_forNot AvailablePMC12396106
cardiac arrestassociated_withNot AvailablePMC2676660
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
285Antiarrhythmics, class i and iiiHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
Pathways
3 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase structureClick to view 3D structure3-beta-hydroxysteroid-Delta(8),Delta(7)-isomeraseQ15125HumansPredicted (SEA)0.467095
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)85.0892
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)38.6132
Thyroid hormone receptor beta structureClick to view 3D structureThyroid hormone receptor betaP10828HumansPredicted (SEA)2.17978
Muscarinic acetylcholine receptor M5 structureClick to view 3D structureMuscarinic acetylcholine receptor M5P08912HumansPredicted (SEA)12.1445
Tyrosine-protein kinase Fyn structureClick to view 3D structureTyrosine-protein kinase FynP06241HumansPredicted (SEA)122.068
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)43.0506
Click to view 3D structureC-8 sterol isomerase ERG2P32352Baker's yeastPredicted (SEA)0.389246
Alpha-2B adrenergic receptor structureClick to view 3D structureAlpha-2B adrenergic receptorP18089HumansPredicted (SEA)31.3732
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)88.9038
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)3.97031
Receptor tyrosine-protein kinase erbB-2 structureClick to view 3D structureReceptor tyrosine-protein kinase erbB-2P04626HumansPredicted (SEA)145.344
Click to view 3D structureProtein phosphatase EYA3Q99504HumansPredicted (SEA)0.233548
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)99.1021
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)33.8644
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)43.2842
NAD-dependent protein deacetylase sirtuin-3, mitochondrial structureClick to view 3D structureNAD-dependent protein deacetylase sirtuin-3, mitochondrialQ9NTG7HumansPredicted (SEA)0.155698
Muscarinic acetylcholine receptor M1 structureClick to view 3D structureMuscarinic acetylcholine receptor M1P11229HumansPredicted (SEA)17.5939
Muscarinic acetylcholine receptor M2 structureClick to view 3D structureMuscarinic acetylcholine receptor M2P08172HumansPredicted (SEA)11.1324
Muscarinic acetylcholine receptor M3 structureClick to view 3D structureMuscarinic acetylcholine receptor M3P20309HumansPredicted (SEA)12.3002
Muscarinic acetylcholine receptor M4 structureClick to view 3D structureMuscarinic acetylcholine receptor M4P08173HumansPredicted (SEA)10.2761
Adenosine receptor A3 structureClick to view 3D structureAdenosine receptor A3P0DMS8HumansPredicted (SEA)46.7874
5-hydroxytryptamine receptor 6 structureClick to view 3D structure5-hydroxytryptamine receptor 6P50406HumansPredicted (SEA)50.8355
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)102.294
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)117.397
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansKnownNot Available
Voltage-dependent T-type calcium channel subunit alpha-1H structureClick to view 3D structureVoltage-dependent T-type calcium channel subunit alpha-1HO95180HumansKnownNot Available
Click to view 3D structureVoltage-dependent calcium channel subunit alpha-2/delta-2Q9NY47HumansKnownNot Available
Beta-1 adrenergic receptor structureClick to view 3D structureBeta-1 adrenergic receptorP08588HumansKnownNot Available
Concentrations
Not Available
External Links
DrugBank IDDB01118
HMDB IDHMDB0015250
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAmiodarone
Chemspider ID2072
ChEBI ID2663
PubChem Compound ID2157
Kegg Compound IDC06823
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

DrugSyn.org

MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10188629
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16479044
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18368867
4. Rosenbaum MB, Chiale PA, Halpern MS, Nau GJ, Przybylski J, Levi RJ, Lazzari JO, Elizari MV: Clinical efficacy of amiodarone as an antiarrhythmic agent. Am J Cardiol. 1976 Dec;38(7):934-44.
5. Singh BN, Vaughan Williams EM: The effect of amiodarone, a new anti-anginal drug, on cardiac muscle. Br J Pharmacol. 1970 Aug;39(4):657-67.
6. Rosenbaum MB, Chiale PA, Haedo A, Lazzari JO, Elizari MV: Ten years of experience with amiodarone. Am Heart J. 1983 Oct;106(4 Pt 2):957-64.
7. CHARLIER R, DELTOUR G, TONDEUR R, BINON F: [Studies in the benzofuran series. VII. Preliminary pharmacological study of 2-butyl-3-(3,5-diiodo-4-beta-N-diethylaminoethoxybenzoyl)-benzofuran]. Arch Int Pharmacodyn Ther. 1962 Sep 1;139:255-64.
8. DELTOUR G, BINON F, TONDEUR R, GOLDENBERG C, HENAUX F, SION R, DERAY E, CHARLIER R: [Studies in the benzofuran series. VI. Coronary-dilating activity of alkylated and aminoalkylated derivatives of 3-benzoylbenzofuran]. Arch Int Pharmacodyn Ther. 1962 Sep 1;139:247-54.