Ivabradine

Base Information

• Chemical Name: Ivabradine
• CAS No.: 155974-00-8
• Deprecated CAS: 148870-61-5
• Molecular Formula: C27H36N2O5
• Molecular Weight: 468.593
• UNII: 3H48L0LPZQ
• DSSTox Substance ID: DTXSID2048240
• Nikkaji Number: J582.018I
• Wikipedia: Ivabradine
• Wikidata: Q425729
• NCI Thesaurus Code: C65995
• RXCUI: 1649480
• Pharos Ligand ID: 338M8NHVYV2L
• Metabolomics Workbench ID: 152137
• ChEMBL ID: CHEMBL471737
• Mol file: 155974-00-8.mol

Synonyms:7,8-dimethoxy-3-(3-(((4,5-dimethoxybenzocyclobutan-1-yl)methyl)methylamino)propyl)-1,3,4,5-tetrahydro-2H-benzazepin-2-one;Corlanor;ivabradine;S 16257;S 16257 2;S 16257-2;S 162572;S 16260 2;S 16260-2;S 162602;S-16257;S-16257-2;S-16260-2;S16257;S162572;S162602

Chemical Property of Ivabradine

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 1.24E-15mmHg at 25°C
• Refractive Index: 1.56
• Boiling Point: 626.9 °C at 760 mmHg
• PKA: 8.77±0.50(Predicted)
• Flash Point: 332.9 °C
• PSA: 60.47000
• Density: 1.146 g/cm³
• LogP: 3.24790
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 468.26242225
• Heavy Atom Count: 34
• Complexity: 663

Purity/Quality:

99% ^*data from raw suppliers

Ivabradine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiarrhythmic Agents
• Canonical SMILES: CN(CCCN1CCC2=CC(=C(C=C2CC1=O)OC)OC)CC3CC4=CC(=C(C=C34)OC)OC
• Isomeric SMILES: CN(CCCN1CCC2=CC(=C(C=C2CC1=O)OC)OC)C[C@H]3CC4=CC(=C(C=C34)OC)OC
• Recent ClinicalTrials: Ivabradine for Prevention of Myocardial Injury After Noncardiac Surgery Trial (PREVENT-MINS)
• Recent EU Clinical Trials: Empower the Heart of Patients with Terminal Cancer using Cardiac Medicines Trial
• Recent NIPH Clinical Trials: Ivabradine exercise tolerance trial
• Description: Ivabradine is a first selective and specific If inhibitor that was approved by EMEA in November for symptomatic treatment of chronic stable angina pectoris in patients with normal sinus rhythm. This is the first agent to lower heart rate by inhibiting the cardiac pacemaker If current. The compound was discovered and developed by Servier and is currently being marketed in Ireland.

Technology Process of Ivabradine

There total 79 articles about Ivabradine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.1%

[{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine (866783-12-2) + 7,8-dimethoxy-3-(3-chloropropyl)-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one acetate → ivabradine (155974-00-8)

Guidance literature:

With sodium carbonate; In N,N-dimethyl-formamide; at 85 - 88 ℃; for 8h;

Reference yield: 96.0%

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-dihydro-2H-3-benzazepin-2-one (1086026-31-4) → ivabradine (155974-00-8)

Guidance literature:

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-dihydro-2H-3-benzazepin-2-one; With formic acid; palladium 10% on activated carbon; triethylamine; In acetonitrile; at 50 ℃; for 16h;

With hydrogenchloride; In water; acetonitrile; at 0 - 5 ℃; pH=3 - 3.5; Reagent/catalyst;

Reference yield: 95.8%

1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine hydrochloride (866783-13-3) + 7,8-dimethoxy-3-(3-iodopropyl)-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one → ivabradine (155974-00-8)

Guidance literature:

1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine hydrochloride; With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

7,8-dimethoxy-3-(3-iodopropyl)-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one; In N,N-dimethyl-formamide; at 20 ℃; for 6h;

upstream raw materials:

ivabradine hydrochloride

(S)-7,8-dimethoxy-3-(3-(N-[(4,5-dimethoxybenzocyclobut-1-yl)methyl]-N-(methyl)amino)propyl)-1,3,4,5-tetrahydro-2H-3-benzazepine-2-one oxalate

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-dihydro-2H-3-benzazepin-2-one

3-[3-[[[-3,4-dimethoxybicyclo[4.2.0]octane-1,3,5-trien-7-yl]methyl]methylamino]propyl]-1,3,4,5-tetrahydro-7,8-dimethoxy-2H-3-benzazepine-2-one

Downstream raw materials:

ivabradine hydrochloride

[{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine d-camphorsulfonate

Refernces

• 1、 -. "Synthetic method of ivabradine". . . Retrieved 2018/06/21.
• 2、 -. "Ivabradine and preparation method of a pharmaceutically acceptable salt thereof". Paragraph 0011; 0026-0027. . Retrieved 2017/08/25.