R6152

Ranolazine dihydrochloride

Name: Ranolazine dihydrochloride
Brand: SIGMA

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

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

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About This Item

Empirical Formula (Hill Notation):

C₂₄H₃₃N₃O₄ · 2HCl

CAS Number:

95635-56-6

Molecular Weight:

500.46

UNSPSC Code:

12352200

PubChem Substance ID:

24278795

NACRES:

NA.77

MDL number:

MFCD03788770

Key Documents

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Product Name

Ranolazine dihydrochloride, ≥98% (HPLC), powder

SMILES string

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

InChI key

RJNSNFZXAZXOFX-UHFFFAOYSA-N

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

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

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This Item	R0283	T1330	SML0608
Sigma-Aldrich R6152 Ranolazine dihydrochloride	Sigma-Aldrich R0283 Ropivacaine hydrochloride monohydrate	Sigma-Aldrich T1330 Tamsulosin hydrochloride	Sigma-Aldrich SML0608 A-412997 dihydrochloride
assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)
form powder	form powder	form powder	form powder
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
storage condition desiccated	storage condition desiccated	storage condition desiccated	storage condition desiccated
solubility H₂O: soluble ≥10 mg/mL	solubility H₂O: 5 mg/mL, clear	solubility DMSO: >10 mg/mL	solubility H₂O: 20 mg/mL, clear
originator Gilead	originator AstraZeneca	originator Boehringer Ingelheim	originator -

Biochem/physiol Actions

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

Ranolazine is a derivative of anti-ischemic piperazine[1] and acts as sodium (Na⁺)-current inhibitor.[2] It has the potential to treat diastolic heart failure and helps in ameliorating myocardial diastolic function.[1]

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[3]
as a partial fatty acid oxidation (FAO) inhibitor to study its effects on glioblastoma cells[4]
as a late sodium(Na⁺)-current (INaL) inhibitor to study its effects on atrial tachycardia in rabbit heart[2]

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Effects of Ranolazine and its Combination with Amiodarone on Rapid Pacing-induced Reentrant Atrial Tachycardia in Rabbits.

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

Hypoxia Produces Pro-arrhythmic Late Sodium Current in Cardiac Myocytes by SUMOylation of NaV1.5 Channels.

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

Ranolazine-Mediated Attenuation of Mechanoelectric Feedback in Atrial Myocyte Monolayers.

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

Mechanisms of ranolazine pretreatment in preventing ventricular tachyarrhythmias in diabetic db/db mice with acute regional ischemia-reperfusion injury.

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

Effects of ranolazine on cardiac function in rats with heart failure.

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

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