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Record Information
Version3.6
Creation Date2012-09-06 15:16:51 UTC
Update Date2016-02-11 01:32:04 UTC
HMDB IDHMDB15250
Secondary Accession NumbersNone
Metabolite Identification
Common NameAmiodarone
DescriptionAmiodarone is only found in individuals that have used or taken this drug. It is an antianginal and antiarrhythmic drug. It increases the duration of ventricular and atrial muscle action by inhibiting Na,K-activated myocardial adenosine triphosphatase. There is a resulting decrease in heart rate and in vascular resistance. [PubChem]The 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.
Structure
Thumb
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 hydrochlorideMeSH
CorbionaxMeSH
Hexal brand OF amiodarone hydrochlorideMeSH
Leurquin brand OF amiodarone hydrochlorideMeSH
ASTA medica brand OF amiodarone hydrochlorideMeSH
AmiodarexMeSH
Amiodarone hydrochlorideMeSH
AmiohexalMeSH
Berenguer infale brand OF amiodarone hydrochlorideMeSH
Betapharm brand OF amiodarone hydrochlorideMeSH
BraxanMeSH
CordarexMeSH
OrtacroneMeSH
Pharma investi brand OF amiodarone hydrochlorideMeSH
RytmaroneMeSH
Sanofi winthrop brand OF amiodarone hydrochlorideMeSH
TachydaronMeSH
TrangorexMeSH
AmiobetaMeSH
CordaroneMeSH
Hydrochloride, amiodaroneMeSH
KordaronMeSH
SKF 33134 aMeSH
SKF 33134-aMeSH
AratacMeSH
Armstrong brand OF amiodarone hydrochlorideMeSH
g Gam brand OF amiodarone hydrochlorideMeSH
Wyeth brand OF amiodarone hydrochlorideMeSH
Chemical FormulaC25H29I2NO3
Average Molecular Weight645.3116
Monoisotopic Molecular Weight645.023680639
IUPAC Name{2-[4-(2-butyl-1-benzofuran-3-carbonyl)-2,6-diiodophenoxy]ethyl}diethylamine
Traditional Nameamiodarone
CAS Registry Number1951-25-3
SMILES
CCCCC1=C(C(=O)C2=CC(I)=C(OCCN(CC)CC)C(I)=C2)C2=CC=CC=C2O1
InChI Identifier
InChI=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 KeyInChIKey=IYIKLHRQXLHMJQ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen 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
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anti-Arrhythmia Agents
  • Enzyme Inhibitors
  • Vasodilator Agents
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.76e-03 g/LNot Available
LogP7.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0048 mg/mLALOGPS
logP7.24ALOGPS
logP7.64ChemAxon
logS-5.1ALOGPS
pKa (Strongest Basic)8.47ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area42.68 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity145.05 m3·mol-1ChemAxon
Polarizability56.78 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Amiodarone Action PathwaySMP00665Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01118
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01118
  • Not Applicable
details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-2 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-1 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01118
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2072
KEGG Compound IDC06823
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAmiodarone
NuGOwiki LinkHMDB15250
Metagene LinkHMDB15250
METLIN IDNot Available
PubChem Compound2157
PDB IDNot Available
ChEBI ID2663
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [793369 ]
  2. 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. [5485142 ]
  3. 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. [6613843 ]
  4. 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. [14020244 ]
  5. 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. [14026835 ]