All Photos(1)

Documents

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

Sign Into View Organizational & Contract Pricing

All Photos(1)

About This Item

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

product name

Ranolazine dihydrochloride, ≥98% (HPLC), powder

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.

Storage Class Code

11 - Combustible Solids

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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

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

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

Regulation of Hyaluronan (HA) Metabolism Mediated by HYBID (Hyaluronan-binding Protein Involved in HA Depolymerization, KIAA1199) and HA Synthases in Growth Factor-stimulated Fibroblasts.

Aya Nagaoka et al.

The Journal of biological chemistry, 290(52), 30910-30923 (2015-11-01)

Regulation of hyaluronan (HA) synthesis and degradation is essential to maintenance of extracellular matrix homeostasis. We recently reported that HYBID (HYaluronan-Binding protein Involved in hyaluronan Depolymerization), also called KIAA1199, plays a key role in HA depolymerization in skin and arthritic

Glycolysis and Fatty Acid Oxidation Inhibition Improves Survival in Glioblastoma.

Kelly J McKelvey et al.

Frontiers in oncology, 11, 633210-633210 (2021-04-16)

Glioblastoma (GBM) is the most aggressive adult glioma with a median survival of 14 months. While standard treatments (safe maximal resection, radiation, and temozolomide chemotherapy) have increased the median survival in favorable O(6)-methylguanine-DNA methyltransferase (MGMT)-methylated GBM (~21 months), a large

View All Related Papers

Articles

Fatty Acid Synthesis and Metabolism in Cancer Cells

Information on fatty acid synthesis and metabolism in cancer cells. Learn how proliferatively active cells require fatty acids for functions such as membrane generation, protein modification, and bioenergetic requirements. These fatty acids are derived either from dietary sources or are synthesized by the cell.