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R6152

Sigma-Aldrich

Ranolazine dihydrochloride

≥98% (HPLC), powder, Na⁺-current blocker

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Synonym(s):
(±) -4-[2-Hydroxy-3-(o-methoxyphenoxy)propyl]-1-piperazineaceto-2′,6′-xylidide dihydrochloride, N-(2,6-Dimethylphenyl)-4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]-1-piperazineacetamide dihydrochloride
Empirical Formula (Hill Notation):
C24H33N3O4 · 2HCl
CAS Number:
95635-56-6
Molecular Weight:
500.46
MDL number:
MFCD03788770
UNSPSC Code:
12352200
PubChem Substance ID:
24278795
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

mp

222-229.5 °C (lit.)

solubility

H2O: soluble ≥10 mg/mL

originator

Gilead

SMILES string

Cl.Cl.COc1ccccc1OCC(O)CN2CCN(CC2)CC(=O)Nc3c(C)cccc3C

InChI

1S/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

InChI key

RJNSNFZXAZXOFX-UHFFFAOYSA-N

Gene Information

human ... SCN4A(6329) , SCN5A(6331)

Application

Ranolazine dihydrochloride has been used:
  • as a low Torsades-de-pointes (TdP) risk drug to study its effects on QTc prolongation, electrocardiographic (PR and QRS) intervals in dog cardiovascular model
  • as a partial fatty acid oxidation (FAO) inhibitor to study its effects on glioblastoma cells
  • as a late sodium(Na+)-current (INaL) inhibitor to study its effects on atrial tachycardia in rabbit heart

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.
pFOX (partial fatty acid oxidation) inhibitor, a new class of anti-anginal drugs, which inhibit fatty acid beta-oxidation and activates pyruvate dehydrogenase, thereby diverting the heart′s energy source from lipids to glucose, which requires less oxygen and helps maintain myocardiac function at times of ischemia

Features and Benefits

This compound was developed by Gilead. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Irene Del-Canto et al.
Frontiers in physiology, 11, 922-922 (2020-08-28)
Mechanical stretch increases Na+ inflow into myocytes, related to mechanisms including stretch-activated channels or Na+/H+ exchanger activation, involving Ca2+ increase that leads to changes in electrophysiological properties favoring arrhythmia induction. Ranolazine is an antianginal drug with confirmed beneficial effects against
Leigh D Plant et al.
Cell reports, 30(7), 2225-2236 (2020-02-23)
Acute cardiac hypoxia produces life-threatening elevations in late sodium current (ILATE) in the human heart. Here, we show the underlying mechanism: hypoxia induces rapid SUMOylation of NaV1.5 channels so they reopen when normally inactive, late in the action potential. NaV1.5
Isaac Aidonidis et al.
The Journal of innovations in cardiac rhythm management, 12(3), 4421-4427 (2021-03-30)
Ranolazine (RAN) has previously been shown to lower the onset of cholinergic atrial fibrillation in intact animals; however, its efficacy in the setting of atrial tachycardia (AT) is unknown. The purpose of this study was to investigate the effects of
G-T Wang et al.
European review for medical and pharmacological sciences, 23(21), 9625-9632 (2019-11-28)
To investigate the effects of ranolazine on the cardiac function and myocardial apoptosis in rats with heart failure and its possible mechanisms. Thirty Wistar rats were randomly divided into sham operation (negative control; NC), chronic heart failure (CHF), and ranolazine
Chung-Chuan Chou et al.
Scientific reports, 10(1), 20032-20032 (2020-11-20)
Studies have demonstrated that diabetic (db/db) mice have increased susceptibility to myocardial ischemia-reperfusion (IR) injury and ventricular tachyarrhythmias (VA). We aimed to investigate the antiarrhythmic and molecular mechanisms of ranolazine in db/db mouse hearts with acute IR injury. Ranolazine was
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