CHEBI:85966 - ivabradine

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ChEBI Name ivabradine
ChEBI ID CHEBI:85966
Definition A member of the class of benzazepines that is 7,8-dimethoxy-1,3,4,5-tetrahydro-3-benzazepin-2-one in which the amide hydrogen is replaced by a [{[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}(methyl)amino]propyl} group. Used (as its hydrochloride salt) to treat patients with angina who have intolerance to beta blockers and/or heart failure.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C27H36N2O5
Net Charge 0
Average Mass 468.58510
Monoisotopic Mass 468.262
InChI InChI=1S/C27H36N2O5/c1-28(17-21-11-20-14-25(33-4)26(34-5)16-22(20)21)8-6-9-29-10-7-18-12-23(31-2)24(32-3)13-19(18)15-27(29)30/h12-14,16,21H,6-11,15,17H2,1-5H3/t21-/m1/s1
InChIKey ACRHBAYQBXXRTO-OAQYLSRUSA-N
SMILES COc1cc2C[C@H](CN(C)CCCN3CCc4cc(OC)c(OC)cc4CC3=O)c2cc1OC
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): cardiotonic drug
A drug that has a strengthening effect on the heart or that can increase cardiac output.
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ChEBI Ontology
Outgoing ivabradine (CHEBI:85966) has role cardiotonic drug (CHEBI:38147)
ivabradine (CHEBI:85966) is a aromatic ether (CHEBI:35618)
ivabradine (CHEBI:85966) is a benzazepine (CHEBI:35676)
ivabradine (CHEBI:85966) is a carbobicyclic compound (CHEBI:36785)
ivabradine (CHEBI:85966) is a tertiary amino compound (CHEBI:50996)
ivabradine (CHEBI:85966) is conjugate base of ivabradine(1+) (CHEBI:85972)
Incoming ivabradine(1+) (CHEBI:85972) is conjugate acid of ivabradine (CHEBI:85966)
IUPAC Name
3-{3-[{[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}(methyl)amino]propyl}-7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one
INN Source
ivabradine KEGG DRUG
Synonyms Sources
S 16257 ChemIDplus
S 16257-2 ChemIDplus
S-16257 ChemIDplus
S-16257-2 ChemIDplus
Manual Xrefs Databases
3312 DrugCentral
D07165 KEGG DRUG
Ivabradine Wikipedia
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Registry Numbers Types Sources
155974-00-8 CAS Registry Number KEGG DRUG
155974-00-8 CAS Registry Number ChemIDplus
8366413 Reaxys Registry Number Reaxys
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Last Modified
22 February 2017