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: 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

NAMES AND DATABASE IDS

Names

• 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)

Database IDs

• CAS Number: 148849-67-6
• PubChem SID: 164227914
• PubChem CID: 3045381

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): -0.6234925
• LogD (pH = 7.4): 0.7629721
• Log P: 2.7224452
• Molar Refractivity: 133.5053 cm^3
• Polarizability: 51.369 Å^3
• Polar Surface Area: 60.47 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 193-196°C

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Target: Adrenergic Receptor
• 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.; Selectively inhibits the pacemaker I(f) current in a dose-dependent manner.

Product Information

• Salt Data: HCl
• Application(s): Used for the symptomatic management of stable angina pectoris.

DETAILS

Toronto Research Chemicals - I940500

Selective bradycardic agent with direct effect on the pacemaker If current of the sinoatrial node. Antianginal.

REFERENCES

• 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.