ivabradine (CHEM044237)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 11:54:26 UTC
Update Date2016-11-09 01:23:05 UTC
Accession NumberCHEM044237
Identification
Common Nameivabradine
ClassSmall Molecule
DescriptionA 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.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
S 16257ChEBI
S 16257-2ChEBI
S-16257ChEBI
S-16257-2ChEBI
7,8-Dimethoxy-3-(3-(((4,5-dimethoxybenzocyclobutan-1-yl)methyl)methylamino)propyl)-1,3,4,5-tetrahydro-2H-benzazepin-2-oneMeSH
CorlanorMeSH
Chemical FormulaC27H36N2O5
Average Molecular Mass468.594 g/mol
Monoisotopic Mass468.262 g/mol
CAS Registry Number155974-00-8
IUPAC Name3-[3-({[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}(methyl)amino)propyl]-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one
Traditional Nameivabradine
SMILESCOC1=C(OC)C=C2[C@@H](CN(C)CCCN3CCC4=CC(OC)=C(OC)C=C4CC3=O)CC2=C1
InChI IdentifierInChI=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
InChI KeyACRHBAYQBXXRTO-OAQYLSRUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzazepines
Sub ClassNot Available
Direct ParentBenzazepines
Alternative Parents
Substituents
  • Benzazepine
  • Anisole
  • Alkyl aryl ether
  • Azepine
  • Aralkylamine
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Tertiary amine
  • Lactam
  • Azacycle
  • Carboxylic acid derivative
  • Ether
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP3.17ALOGPS
logP2.72ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)9.37ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area60.47 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity133.51 m³·mol⁻¹ChemAxon
Polarizability54.56 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0320900000-ffd0f55371c521925ff9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0960300000-e78796a6c808ffa3174dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0910000000-4efbb83fe048b558b569Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0010900000-bfb468a787b1a91aa2d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0v4i-0160900000-7d645ce21edc3d5cc8f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-1590100000-7d90d31e314468308b80Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB09083
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkIvabradine
Chemspider IDNot Available
ChEBI ID85966
PubChem Compound ID132999
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=25158669
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=25179314
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=25240447
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=25346368
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=25350985
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=25636072
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=25656911
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=25687888
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=25700807
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=25706659
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=25733317
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=25801408
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=25809454
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=25839989
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=25911606
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=25926678
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=25953938
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=25968495
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=25982136
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=25986146