A piperazine derivative with cardioprotective activity
Related Products
Active Metabolite(s)
35003CVT-2738
Metabolite(s)
35002Desmethyl Ranolazine
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Ranolazine (hydrochloride)

Item No. 15604

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(2,6-dimethylphenyl)-4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]-1-piperazineacetamide, dihydrochloride
CAS Number
95635-56-6
Synonyms
  • RS 43285
Molecular Formula
C24H33N3O4 • 2HCl
Formula Weight
500.5
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
272 nm
SMILES
OC(COC1=C(OC)C=CC=C1)CN2CCN(CC(NC3=C(C)C=CC=C3C)=O)CC2.Cl.Cl
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    50 mg

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    Product Description

    Ranolazine is a piperazine derivative with cardioprotective activity.1,2,3,4 It reduces the late sodium current (INa) in mouse myocytes expressing the long QT syndrome 3 mutant sodium channel DKPQ, ventricular myocytes isolated from a canine model of heart failure, guinea pig ventricular myocytes exposed to hydrogen peroxide or anemone toxin-II, and HEK293 cells expressing human Nav1.5 channels (IC50s = 5.9-15 μM) as well as the late potassium current (IKr) in canine ventricular myocytes and HEK293 cells (IC50s = 11.5 and 14.4 μM, respectively).1,2 Ranolazine also inhibits radioligand binding to α1-, β1-, and β2-adrenergic receptors (Kis = 8.2-19.5, 1.4-8.6, and 0.5-14.8 μM, respectively).2 In vivo, ranolazine (480 μg/kg per min) reduces clofilium-induced prolongation of the QTc interval and Torsade de Pointes (TdP) in rabbits.3 Ranolazine also reduces interstitial collagen deposition as well as atrial natriuretic peptide (ANP; Item Nos. 24539 | 24276), connective tissue growth factor (CTGF), brain natriuretic peptide (BNP; Item No. 24541), and matrix metalloproteinase-2 (MMP-2) mRNA levels, and prevents left ventricular dilation in a mouse model of cardiotoxicity induced by doxorubicin (Item No. 15007).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Shryock, J.C., and Belardinelli, L. Inhibition of late sodium current to reduce electrical and mechanical dysfunction of ischaemic myocardium. Br. J. Pharmacol. 153(6), 1128-1132 (2008).

    2. Verrier, R.L., Kumar, K., Nieminen, T., et al. Mechanisms of ranolazine’s dual protection against atrial and ventricular fibrillation. Europace 15(3), 317-324 (2013).

    3. Wang, W.Q., Robertson, C., Dhalla, A.K., et al. Antitorsadogenic effects of (±)-N-(2,6-dimethyl-phenyl)-(4[2-hydroxy-3-(2-methoxyphenoxy)propyl]-1-piperazine (ranolazine) in anesthetized rabbits. J. Pharmacol. Exp. Ther. 325(3), 875-881 (2008).

    4. Tocchetti, C.G., Carpi, A., Coppola, C., et al. Ranolazine protects from doxorubicin-induced oxidative stress and cardiac dysfunction. Eur. J. Heart Fail. 16(4), 358-366 (2014).