Ranolazine

Base Information

• Chemical Name: Ranolazine
• CAS No.: 95635-55-5
• Deprecated CAS: 142387-99-3
• Molecular Formula: C24H33N3O4
• Molecular Weight: 427.544
• Hs Code.: 2933595960
• European Community (EC) Number: 620-450-7
• NSC Number: 759100
• UNII: A6IEZ5M406
• DSSTox Substance ID: DTXSID3045196
• Nikkaji Number: J3.066.456F
• Wikipedia: Ranolazine
• Wikidata: Q907104
• NCI Thesaurus Code: C66507
• RXCUI: 35829
• Pharos Ligand ID: 8W6GWS55J75L
• Metabolomics Workbench ID: 42645
• ChEMBL ID: CHEMBL1404
• Mol file: 95635-55-5.mol

Synonyms:43285, RS;Dihydrochloride, Ranolazine;HCl, Ranolazine;Hydrochloride, Ranolazine;N-(2,6-dimethylphenyl)-4-(2-hydroxy-3-(2-methoxyphenoxy)propyl)-1-piperazineacetamide;Ranexa;ranolazine;Ranolazine Dihydrochloride;Ranolazine HCl;Ranolazine Hydrochloride;renolazine;RS 43285;RS 43285 193;RS 43285-193;RS 43285193;RS-43285;RS43285

Chemical Property of Ranolazine

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 1.94E-16mmHg at 25°C
• Melting Point: 119-1200C
• Refractive Index: 1.585
• Boiling Point: 624.1 °C at 760 mmHg
• PKA: 14.06±0.20(Predicted)
• Flash Point: 331.2 °C
• PSA: 74.27000
• Density: 1.174 g/cm³
• LogP: 2.25680
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 427.24710654
• Heavy Atom Count: 31
• Complexity: 531

Purity/Quality:

99% ^*data from raw suppliers

Ranolazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Antiangina Agents
• Canonical SMILES: CC1=C(C(=CC=C1)C)NC(=O)CN2CCN(CC2)CC(COC3=CC=CC=C3OC)O
• Recent ClinicalTrials: Efficacy of Ranolazine in Patients With Chronic Total Occlusions of Coronary Arteries
• Recent EU Clinical Trials: Comparison of the effectiveness of IntraVenous FLECainide plus oral ranolazine
• Description: Ranolazine ([(+)N-(2,6-dimethylphenyl)-4(2-hydroxy-3-(2-methoxyphenoxy)-propyl)-1-piperazine acetamide dihydrochloride]) is an active piperazine derivative that was patented in 1986 and is available in an oral and intravenous form. Ranolazine is evidenced with anti-ischemic/antianginal properties in patients with chronic angina without clinically significant changes in heart rate or blood pressure. ? Ranolazine is used for the treatment of angina (chronic chest pain). Researches show it also has potential use in cardiovascular conditions such as heart failure, acute and chronic myocardial ischemia, certain types of cardiac sodium channel gene mutations, and ventricular and supraventricular arrhythmias. Ranolazine is an orally available, extended release drug for the treatment of chronic angina in patients who have failed to respond to prior angina therapy. Chronic stable angina (CSA) is a common symptom of coronary artery disease wherein plaques in the coronary vasculature restrict blood flow to the heart, which in turn leads to insufficient oxygenation of the heart, typically during physical exertion or emotional stress. A vast majority of the existing anti-anginal and anti-ischemic therapies aim to correct the imbalance between myocardial oxygen demand and supply through mechanisms that produce reductions in heart rate or blood pressure.
• Uses: antianginal, antiischemic
• Clinical Use: Add on therapy for angina
• Drug interactions: Potentially hazardous interactions with other drugs Anti-arrhythmics: avoid with disopyramide. Antibacterials: concentration possibly increased by clarithromycin and telithromycin - avoid concomitant use; concentration reduced by rifampicin - avoid. Antifungals: concentration increased by ketoconazole and possibly itraconazole, posaconazole and voriconazole - avoid. Antivirals: concentration possibly increased by atazanavir, darunavir, fosamprenavir, indinavir, lopinavir, ritonavir, saquinavir and tipranavir - avoid. Beta-blockers: avoid with sotalol. Ciclosporin: concentration of both drugs possibly increased. Grapefruit juice: concentration of ranolazine possibly increased - avoid. Statins: concentration of simvastatin increased - maximum dose of simvastatin is 20 mg. Tacrolimus: concentration of tacrolimus increased.

Technology Process of Ranolazine

There total 15 articles about Ranolazine 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: 93.0%

(RS)-2-(4-(3-chloro-2-hydroxyphenyl)piperazin-1-yl)-N-(2,6-dimethylphenyl)acetamide (1427177-23-8) + 2-methoxy-phenol (90-05-1) → Ranolazine (95635-55-5,142387-99-3)

Guidance literature:

With potassium carbonate; In water; at 90 ℃; for 5h;

DOI:10.1039/c3gc36997h

Reference yield: 87.4%

N-(2,6-dimethylphenyl)-2-(piperazin-1-yl)acetamide (5294-61-1) + 1-bromo-3-(2-methoxyphenoxy)-2-propyl alcohol → Ranolazine (95635-55-5,142387-99-3)

Guidance literature:

With potassium carbonate; In ethanol; toluene; for 3h; Solvent; Reagent/catalyst; Time; Temperature; Reflux;

Reference yield: 85.0%

2-(2-methoxy-phenoxymethyl)-oxirane (2210-74-4) + N-(2,6-dimethylphenyl)-2-(piperazin-1-yl)acetamide (5294-61-1) → Ranolazine (95635-55-5,142387-99-3)

Guidance literature:

With Sulfated tungstate; at 70 ℃; for 2h; Green chemistry;

DOI:10.1016/j.tetlet.2013.09.065

upstream raw materials:

N-(2,6-dimethylphenyl)-2-(piperazin-1-yl)acetamide

CVT-2513

2-chloro-N-(2,6-dimethylphenyl)acetamide

2-(2-methoxy-phenoxymethyl)-oxirane

Downstream raw materials:

(S)-Ranolazine

(R)-Ranolazine

1-[3-(2-methoxyphenoxy)-2-hydroxypropyl]-4-[(2,6-dimethylphenyl)aminocarbonylmethyl]piperazine besylate

1-[3-(2-methoxyphenoxy)-2-hydroxypropyl]-4-[(2,6-dimethylphenyl)aminocarbonylmethyl]piperazine oxalate

Refernces

• 1、 Sawant, Ganesh,Ghosh, Saptarshi,Banesh, Sooram,Bhaumik, Jayeeta,Chand Banerjee, Uttam. "In silico approach towards lipase mediated chemoenzymatic synthesis of (S)-ranolazine, as an anti-anginal drug". . p. 49150 - 49157. Retrieved 2016/06/09.
• 2、 Kommi, Damodara N.,Kumar, Dinesh,Chakraborti, Asit K.. ""All water chemistry" for a concise total synthesis of the novel class anti-anginal drug (RS), (R), and (S)-ranolazine". . p. 756 - 767. Retrieved 2013/03/29.