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148849-67-6 molecular structure
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3-[3-({[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1(6),2,4-trien-7-yl]methyl}(methyl)amino)propyl]-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one hydrochloride

ChemBase ID: 172004
Molecular Formular: C27H37ClN2O5
Molecular Mass: 505.04608
Monoisotopic Mass: 504.23909997
SMILES and InChIs

SMILES:
c1(c(cc2c(c1)CC(=O)N(CC2)CCCN(C[C@H]1Cc2c1cc(c(c2)OC)OC)C)OC)OC.Cl
Canonical SMILES:
COc1cc2C[C@@H](c2cc1OC)CN(CCCN1CCc2c(CC1=O)cc(c(c2)OC)OC)C.Cl
InChI:
InChI=1S/C27H36N2O5.ClH/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;1H/t21-;/m1./s1
InChIKey:
HLUKNZUABFFNQS-ZMBIFBSDSA-N

Cite this record

CBID:172004 http://www.chembase.cn/molecule-172004.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
3-[3-({[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1(6),2,4-trien-7-yl]methyl}(methyl)amino)propyl]-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one hydrochloride
3-[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 hydrochloride
IUPAC Traditional name
3-[3-({[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1(6),2,4-trien-7-yl]methyl}(methyl)amino)propyl]-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one hydrochloride
ivabradine hydrochloride
Synonyms
Coralan
Ivabradine hydrochloride
3-[3-[[[(7S)-3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl]methylamino]propyl]-1,3,4,5-tetrahydro-7,8-dimethoxy-2H-3-benzazepin-2-one Hydrochloride
Corlentor
Procoralan
S-16257
Ivabradine Hydrochloride
Ivabradine HCl (Procoralan)
CAS Number
148849-67-6
PubChem SID
164227914
PubChem CID
3045381

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 3045381 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) -0.6234925  LogD (pH = 7.4) 0.7629721 
Log P 2.7224452  Molar Refractivity 133.5053 cm3
Polarizability 51.369 Å3 Polar Surface Area 60.47 Å2
Rotatable Bonds 10  Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Methanol expand Show data source
Apperance
White to Off-White Solid expand Show data source
Melting Point
193-196°C expand Show data source
Storage Condition
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Target
Adrenergic Receptor expand Show data source
Mechanism of Action
Blocking this channel reduces cardiac pacemaker activity, slowing the heart rate and allowing more time for blood to flow to the myocardium. expand Show data source
Selectively inhibits the pacemaker I(f) current in a dose-dependent manner. expand Show data source
Salt Data
HCl expand Show data source
Certificate of Analysis
Download expand Show data source
Application(s)
Used for the symptomatic management of stable angina pectoris. expand Show data source

DETAILS

DETAILS

TRC TRC
Toronto Research Chemicals - I940500 external link
Selective bradycardic agent with direct effect on the pacemaker If current of the sinoatrial node. Antianginal.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Thollon,C., et al.: Br. J. Pharmacol., 112, 37 (1994)
  • • Ragueneau, I., et al.: Clin. Pharmacol. Ther., 64, 192 (1994)
  • • Borer, J.S., et al.: Circulation, 107, 817 (1994)
  • • DiFrancesco, D., et al.: Drugs, 64, 1757 (1994)
  • • 1. Thollon C, Cambarrat C, Vian J, Prost JF, Peglion JL, Vilaine JP (1994). "Electrophysiological effects of S 16257, a novel sino-atrial node modulator, on rabbit and guinea-pig cardiac preparations:
  • •  comparison with UL-FS 49". Br. J. Pharmacol. 112 (1): 37?2.
  • • 2. Sulfi S, Timmis AD (2006). "Ivabradine -- the first selective sinus node I(f) channel inhibitor in the treatment of stable angina". Int. J. Clin. Pract. 60 (2): 222?.
  • • 3. Tardif JC, Ford I, Tendera M, Bourassa MG, Fox K (2005). "Efficacy of ivabradine, a new selective I(f) inhibitor, compared with atenolol in patients with chronic stable angina".
  • • Eur. Heart J. 26 (23): 2529?6.
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PATENTS

PATENTS

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INTERNET

INTERNET

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