Ranolazine

Ranolazine, sold under the brand name Ranexa among others, is a medication used to treat heart related chest pain. Typically it is used together with other medications when those are insufficient. Benefits appear smaller in women than men. It is taken by mouth.

Ranolazine
Clinical data
Trade namesRanexa, Aspruzyo Sprinkle, Corzyna
AHFS/Drugs.comMonograph
MedlinePlusa606015
License data
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability35 to 50%
Protein binding~62%
MetabolismExtensive in liver (CYP3A, CYP2D6) and intestine
Elimination half-life1.4 to 1.9 hours
ExcretionKidney (75%) and fecal (25%)
Identifiers
  • (RS)-N-(2,6-Dimethylphenyl)-2-[4-[2-hydroxy-3-(2-methoxyphenoxy)-propyl]piperazin-1-yl]acetamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.149.259
Chemical and physical data
FormulaC24H33N3O4
Molar mass427.545 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • O=C(Nc1c(cccc1C)C)CN3CCN(CC(O)COc2ccccc2OC)CC3
  • InChI=1S/C24H33N3O4/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) Y
  • Key:XKLMZUWKNUAPSZ-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Common side effects include constipation, headache, nausea, and dizziness. Serious side effects may include QT prolongation. Use is not recommended in those with liver cirrhosis. How it works is not clear but may involve adenosine triphosphate.

Ranolazine was approved for medical use in the United States in 2006. In 2020, it was the 258th most commonly prescribed medication in the United States, with more than 1 million prescriptions.

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