BBI

(2-butyl-1-benzofuran-3-yl){4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl}methanone

Created: 2014-01-17
Last modified:  2015-04-22

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Chemical Details

Formal Charge0
Atom Count60
Chiral Atom Count0
Bond Count62
Aromatic Bond Count16
2D diagram of BBI

Chemical Component Summary

Name(2-butyl-1-benzofuran-3-yl){4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl}methanone
Systematic Name (OpenEye OEToolkits)(2-butyl-1-benzofuran-3-yl)-[4-[2-(diethylamino)ethoxy]-3,5-bis(iodanyl)phenyl]methanone
FormulaC25 H29 I2 N O3
Molecular Weight645.312
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01Ic1cc(cc(I)c1OCCN(CC)CC)C(=O)c2c3ccccc3oc2CCCC
SMILESCACTVS3.385CCCCc1oc2ccccc2c1C(=O)c3cc(I)c(OCCN(CC)CC)c(I)c3
SMILESOpenEye OEToolkits1.7.6CCCCc1c(c2ccccc2o1)C(=O)c3cc(c(c(c3)I)OCCN(CC)CC)I
Canonical SMILESCACTVS3.385 CCCCc1oc2ccccc2c1C(=O)c3cc(I)c(OCCN(CC)CC)c(I)c3
Canonical SMILESOpenEye OEToolkits1.7.6 CCCCc1c(c2ccccc2o1)C(=O)c3cc(c(c(c3)I)OCCN(CC)CC)I
InChIInChI1.03 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
InChIKeyInChI1.03 IYIKLHRQXLHMJQ-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank IDDB01118 
NameAmiodarone
Groups
  • approved
  • investigational
DescriptionAmiodarone is a benzofuran derivative, anti-arrhythmic drug used commonly in a variety of settings.[A36817] Most known for its approved indication in life-threatening ventricular arrhythmias, it is also used off-label in the outpatient and inpatient setting for atrial fibrillation. Because of its ability to cause serious toxicity and possibly death, amiodarone use should be reserved for its approved indications, according to prescribing information.[L3561,L11265,L11286]
Synonyms
  • 2-Butyl-3-(3,5-diiodo-4-(2-diethylaminoethoxy)benzoyl)benzofuran
  • Amiodarona
  • 2-n-Butyl-3',5'-diiodo-4'-N-diethylaminoethoxy-3-benzoylbenzofuran
  • Amiodarone
  • Amiodarone hydrochloride
Brand Names
  • Amiodarone Hydrochloride Injection
  • PHL-amiodarone
  • Riva-amiodarone
  • Amiodarone Hydrochloride
  • Amiodarone Hydrochloride for Injection, USP
IndicationThe FDA approved indications for amiodarone are recurrent ventricular fibrillation (VF) and recurrent hemodynamically unstable ventricular tachycardia (VT). The FDA emphasizes that this drug should only be given in these conditions when they are clinically documented and have not responded to normal therapeutic doses of other antiarrhythmic agents, or when other drugs are not tolerated by the patient.[L3561] Off-label indications include atrial fibrillation and supraventricular tachycardia.[A189666,A189720,A189723,L11286]
Categories
  • Agents causing hyperkalemia
  • Agents Causing Muscle Toxicity
  • alpha-Galactosidase, antagonists & inhibitors
  • Antiarrhythmic agents
  • Antiarrhythmics, Class III
ATC-CodeC01BD01
CAS number1951-25-3

Drug Targets

NameTarget SequencePharmacological ActionActions
HERG human cardiac K+ channelMPVRRGHVAPQNTFLDTIIRKFEGQSRKFIIANARVENCAVIYCNDGFCE...unknowninhibitor
Beta adrenergic receptorMGAGVLVLGASEPGNLSSAAPLPDGAATAARLLVPASPPASLLPPASESP...unknowninhibitor,downregulator
Voltage-dependent T-type calcium channel subunit alpha-1IMAESASPPSSSAAAPAAEPGVTTEQPGPRSPPSSPPGLEEPLDGADPHVP...unknowninhibitor
Voltage gated L-type calcium channelMVNENTRMYIPEENHQGSNYGSPRPAHANMNANAAAGLAPEHIPTPGAAL...unknowninhibitor
Thyroid hormone receptorMEQKPSKVECGSDPEENSARSPDGKRKRKNGQCSLKTSMSGYIPSYLDKD...unknownantagonist,binder
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL633
PubChem 2157
ChEMBL CHEMBL633
ChEBI CHEBI:2663
CCDC/CSD DUTRUF10