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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:55 UTC
HMDB IDHMDB0015250
Secondary Accession Numbers
  • HMDB15250
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
Data?1582753275
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 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 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
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0048 g/LNot Available
LogP7.9Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM226.430932474
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+225.59130932474
DeepCCS[M-H]-223.23330932474
DeepCCS[M-2H]-257.41130932474
DeepCCS[M+Na]+233.27230932474
AllCCS[M+H]+225.632859911
AllCCS[M+H-H2O]+224.332859911
AllCCS[M+NH4]+226.832859911
AllCCS[M+Na]+227.132859911
AllCCS[M-H]-224.532859911
AllCCS[M+Na-2H]-226.732859911
AllCCS[M+HCOO]-229.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AmiodaroneCCCCC1=C(C(=O)C2=CC(I)=C(OCCN(CC)CC)C(I)=C2)C2=CC=CC=C2O14395.6Standard polar33892256
AmiodaroneCCCCC1=C(C(=O)C2=CC(I)=C(OCCN(CC)CC)C(I)=C2)C2=CC=CC=C2O13519.4Standard non polar33892256
AmiodaroneCCCCC1=C(C(=O)C2=CC(I)=C(OCCN(CC)CC)C(I)=C2)C2=CC=CC=C2O13714.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Amiodarone GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9000024000-088b6534d1659c5c174d2017-09-01Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Amiodarone LC-ESI-qTof , Positive-QTOFsplash10-004r-0690000000-25202a61d19d3dfaed8b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Amiodarone LC-ESI-QFT , positive-QTOFsplash10-0002-0000009000-8cbab89986761a7a1bc92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Amiodarone LC-ESI-QFT , positive-QTOFsplash10-0pbj-9300003000-503a542bf1a7678f385e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Amiodarone LC-ESI-QFT , positive-QTOFsplash10-0a4i-9110000000-543b8de3c9ba390fa7652017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Amiodarone LC-ESI-QFT , positive-QTOFsplash10-0udi-0791000000-77d5d18989052c45b0062017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Amiodarone LC-ESI-QFT , positive-QTOFsplash10-0a59-0980000000-a77e32d189cf8e2acdf12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Amiodarone LC-ESI-QFT , positive-QTOFsplash10-0apl-0940000000-30e016c113387b37ca7c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Amiodarone , positive-QTOFsplash10-0002-0000009000-e87a9a6e983c00161beb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Amiodarone 50V, Positive-QTOFsplash10-0fb9-0192101000-d4f2f8589987e9dee2fc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Amiodarone 40V, Positive-QTOFsplash10-0002-0020009000-bc59c51779e07ba2a4a02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Amiodarone 40V, Positive-QTOFsplash10-0a4i-9100000000-cf7a06e18403e76cf41c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Amiodarone 15V, Positive-QTOFsplash10-0002-0000009000-ec39c036c89b5923fc2c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Amiodarone 30V, Positive-QTOFsplash10-0pb9-9200000000-5cde40904f838865e7ba2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Amiodarone 20V, Positive-QTOFsplash10-0002-1000009000-3e4fea6e220ba0a42af42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Amiodarone 40V, Positive-QTOFsplash10-0a4i-9100000000-cf88edc5ce5babf0e5672021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Amiodarone 30V, Positive-QTOFsplash10-0002-0000009000-9f22341a9246a58e0df52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Amiodarone 20V, Positive-QTOFsplash10-0002-0000009000-7304d2b67fba343a88832021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Amiodarone 10V, Positive-QTOFsplash10-0002-0000009000-fad8f001fba3ffb05e412021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Amiodarone 35V, Positive-QTOFsplash10-0f6t-6400009000-32088cd4966452222ef52021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amiodarone 10V, Positive-QTOFsplash10-0002-1200419000-3080963b2267302d337a2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amiodarone 20V, Positive-QTOFsplash10-0udi-6920532000-f1048ae0af01f66588772016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amiodarone 40V, Positive-QTOFsplash10-006x-7309200000-46ba6e78349f4d182fe72016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amiodarone 10V, Negative-QTOFsplash10-0006-1100029000-9b580022f60608cc28102016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amiodarone 20V, Negative-QTOFsplash10-006x-3202296000-a7445663ea627302ddce2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Amiodarone 40V, Negative-QTOFsplash10-00di-7902160000-4817e1c5fca0d177a8292016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01118 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01118 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01118
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2072
KEGG Compound IDC06823
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAmiodarone
METLIN IDNot Available
PubChem Compound2157
PDB IDNot Available
ChEBI ID2663
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:14026835 ]