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R6152

Sigma-Aldrich

Ranolazine dihydrochloride

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

Synonyme(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

Formule empirique (notation de Hill):
C24H33N3O4 · 2HCl
Numéro CAS:
95635-56-6
Poids moléculaire :
500.46
Numéro MDL:
MFCD03788770
Code UNSPSC :
12352200
ID de substance PubChem :
24278795
Nomenclature NACRES :
NA.77

product name

Ranolazine dihydrochloride, ≥98% (HPLC), powder

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Conditions de stockage

desiccated

Couleur

white to beige

Pf

222-229.5 °C (lit.)

Solubilité

H2O: soluble ≥10 mg/mL

Auteur

Gilead

Chaîne SMILES 

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

Clé InChI

RJNSNFZXAZXOFX-UHFFFAOYSA-N

Informations sur le gène

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

Actions biochimiques/physiologiques

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

Caractéristiques et avantages

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
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
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
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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