95635-56-6

Basic information

• Product Name: Ranolazine dihydrochloride
• Synonyms: (+/-)-4-[2-HYDROXY-3-(O-METHOXYPHENOXY)PROPYL]-1-PIPERAZINEACETO-2',6'-XYLIDIDE DIHYDROCHLORIDE;n-(2,6-dimethylphenyl)-2-[4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl]acetamide dihydrochloride;(+/-)-N-(2,6-DIMETHYLPHENYL)-4-[2-HYDROXY-3-(2-METHOXYPHENOXY)PROPYL]-1-PIPERAZINEACETAMIDE DIHYDROCHLORIDE;RANOLAZINE DIHYDROCHLORIDE;RANOLAZINE HCL;Ranolazine DiHCI;Ranolazine and salt;(±)-N-(2,6-dimethylphenyl)-4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]-1-piperazineacetamide
• CAS NO: 95635-56-6
• Molecular Formula: C24H35Cl2N3O4
• Molecular Weight: 500.46
• Product Categories: Active Pharmaceutical Ingredients;Aromatics Compounds;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Ranolazine;Cardiovascular APIs
• Mol File: 95635-56-6.mol
• Article Data: 0

Chemical Properties

• Melting Point: 222-229.5 °C(lit.)
• Boiling Point: 624.1 °C at 760 mmHg
• Flash Point: 331.2 °C
• Appearance: off-white/solid
• Vapor Pressure: 1.94E-16mmHg at 25°C
• Storage Temp.: Desiccate at RT
• Solubility: H2O: 10 mg/mL, soluble
• Stability: Hygroscopic
• Merck: 14,8111
• CAS DataBase Reference: Ranolazine dihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Ranolazine dihydrochloride(95635-56-6)
• EPA Substance Registry System: Ranolazine dihydrochloride(95635-56-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: TK7845370
• Hazardous Substances Data: 95635-56-6(Hazardous Substances Data)

Usage

Description

Ranolazine dihydrochloride is a piperazine derivative with cardioprotective activity, characterized by its white crystalline powder form. It is known for its ability to reduce the late sodium current (INa) and late potassium current (IKr) in various types of myocytes and cells, as well as inhibit radioligand binding to α1-, β1-, and β2-adrenergic receptors. Ranolazine dihydrochloride also demonstrates in vivo benefits such as reducing clofilium-induced prolongation of the QTc interval and Torsade de Pointes (TdP) in rabbits, and it can decrease interstitial collagen deposition and mRNA levels of atrial natriuretic peptide (ANP), connective tissue growth factor (CTGF), brain natriuretic peptide (BNP), and matrix metalloproteinase-2 (MMP-2), thus preventing left ventricular dilation in a mouse model of cardiotoxicity induced by doxorubicin.

Uses

Used in Pharmaceutical Industry:
Ranolazine dihydrochloride is used as an anti-ischemic agent for the treatment of angina and congestive heart failure. It modulates myocardial metabolism, providing antianginal effects and offering a therapeutic approach to managing ischemic conditions in the heart.
Used in Cardiovascular Medicine:
As a cardioprotective agent, ranolazine dihydrochloride is utilized to reduce the risk of cardiac events in patients with long QT syndrome or other conditions that may lead to arrhythmias. Its ability to modulate myocardial metabolism and reduce late sodium and potassium currents makes it a valuable compound in the management of heart diseases.

Biological Activity

Antianginal agent with antiarrhythmic properties that acts as a partial fatty acid oxidation inhibitor. Activates pyruvate dehydrogenase in ischemic myocytes to promote glucose oxidation, switching substrate utilization from fatty acids to glucose. Also shown to inhibit late I Na and I Kr currents.

Biochem/physiol Actions

Ranolazine is a derivative of anti-ischemic piperazine and acts as sodium (Na+)-current inhibitor. It has the potential to treat diastolic heart failure and helps in ameliorating myocardial diastolic function.

InChI:InChI=1/C24H33N3O4.2ClH/c1-18-7-6-8-19(2)24(18)25-23(29)16-27-13-11-26(12-14-27)15-20(28)17-31-22-10-5-4-9-21(22)30-3;;/h4-10,20,28H,11-17H2,1-3H3,(H,25,29);2*1H