CHEBI:2663 - amiodarone

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ChEBI Name amiodarone
ChEBI ID CHEBI:2663
Definition A member of the class of 1-benzofurans that is 1-benzofuran substituted by a butyl group at position 2 and a 4-[2-(diethylamino)ethoxy]-3,5-diiodobenzoyl group at position 3. It is a cardiovascular drug used for the treatment of cardiac dysrhythmias.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB5310616, eMolecules:901372, ZINC000003830212
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Amiodarone is an antiarrhythmic medication used to treat and prevent a number of types of cardiac dysrhythmias. This includes ventricular tachycardia, ventricular fibrillation, and wide complex tachycardia, atrial fibrillation, and paroxysmal supraventricular tachycardia. Evidence in cardiac arrest, however, is poor. It can be given by mouth, intravenously, or intraosseously. When used by mouth, it can take a few weeks for effects to begin. Common side effects include feeling tired, tremor, nausea, and constipation. As amiodarone can have serious side effects, it is mainly recommended only for significant ventricular arrhythmias. Serious side effects include lung toxicity such as interstitial pneumonitis, liver problems, heart arrhythmias, vision problems, thyroid problems, and death. If taken during pregnancy or breastfeeding it can cause problems in the fetus or the infant. It is a class III antiarrhythmic medication. It works partly by increasing the time before a heart cell can contract again. Amiodarone was first made in 1961 and came into medical use in 1962 for chest pain believed to be related to the heart. It was pulled from the market in 1967 due to side effects. In 1974 it was found to be useful for arrhythmias and reintroduced. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In 2022, it was the 237th most commonly prescribed medication in the United States, with more than 1 million prescriptions.
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Formula C25H29I2NO3
Net Charge 0
Average Mass 645.31160
Monoisotopic Mass 645.02368
InChI 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
InChIKey IYIKLHRQXLHMJQ-UHFFFAOYSA-N
SMILES CCCCc1oc2ccccc2c1C(=O)c1cc(I)c(OCCN(CC)CC)c(I)c1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Application(s): cardiovascular drug
A drug that affects the rate or intensity of cardiac contraction, blood vessel diameter or blood volume.
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ChEBI Ontology
Outgoing amiodarone (CHEBI:2663) has role cardiovascular drug (CHEBI:35554)
amiodarone (CHEBI:2663) is a 1-benzofurans (CHEBI:38830)
amiodarone (CHEBI:2663) is a aromatic ketone (CHEBI:76224)
amiodarone (CHEBI:2663) is a organoiodine compound (CHEBI:37142)
amiodarone (CHEBI:2663) is a tertiary amino compound (CHEBI:50996)
IUPAC Name
(2-butyl-1-benzofuran-3-yl){4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl}methanone
INNs Sources
amiodarona ChemIDplus
amiodaronum ChemIDplus
Synonyms Sources
2-Butyl-3-(3,5-diiodo-4-(2-diethylaminoethoxy)benzoyl)benzofuran ChemIDplus
2-Butyl-3-benzofuranyl 4-(2-(diethylamino)ethoxy)-3,5-diiodophenyl ketone ChemIDplus
2-n-Butyl-3',5'-diiodo-4'-N-diethylaminoethoxy-3-benzoylbenzofuran ChemIDplus
Amiodarone KEGG COMPOUND
Manual Xrefs Databases
176 DrugCentral
Amiodarone Wikipedia
C06823 KEGG COMPOUND
CA2826272 Patent
D02910 KEGG DRUG
DB01118 DrugBank
HMDB0015250 HMDB
LSM-2379 LINCS
TW201400111 Patent
View more database links
Registry Numbers Types Sources
1271711 Beilstein Registry Number Beilstein
1951-25-3 CAS Registry Number KEGG COMPOUND
1951-25-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations
Last Modified
22 February 2017