Trimetazidine dihydrochlorideProduct ingredient for Trimetazidine
- Name
- Trimetazidine dihydrochloride
- Drug Entry
- Trimetazidine
Trimetazidine is a piperazine derivative indicated for the symptomatic treatment of stable angina pectoris in patients inadequately controlled or intolerant to first line therapies.9 Trimetazidine has been studied as a treatment for angina pectoris since the late 1960s.7,8
Acidic conditions, caused by anaerobic metabolism and fatty acid oxidation, in response to myocardial ischemia, activate sodium-hydrogen and sodium-calcium antiport systems.5 The increased intracellular calcium decreases contractility.5 It is hypothesized that trimetazidine inhibits 3-ketoacyl coenzyme A thiolase, which decreases fatty acid oxidation but not glucose metabolism, preventing the acidic conditions that exacerbate ischemic injury.1,10 However, evidence for this mechanism is controversial.5
Trimetazidine is not FDA approved. However, it has been approved in France since 1978.10
- Accession Number
- DBSALT001114 (DBSALT001115)
- Structure
Structure for Trimetazidine dihydrochloride (DBSALT001114)
- Synonyms
- Trimetazidine diHCl / Trimetazidine HCl / Trimetazidine hydrochloride
- UNII
- 48V6723Z1P
- CAS Number
- 13171-25-0
- Weight
- Average: 339.26
Monoisotopic: 338.116398 - Chemical Formula
- C14H24Cl2N2O3
- InChI Key
- VYFLPFGUVGMBEP-UHFFFAOYSA-N
- InChI
- InChI=1S/C14H22N2O3.2ClH/c1-17-12-5-4-11(13(18-2)14(12)19-3)10-16-8-6-15-7-9-16;;/h4-5,15H,6-10H2,1-3H3;2*1H
- IUPAC Name
- 1-[(2,3,4-trimethoxyphenyl)methyl]piperazine dihydrochloride
- SMILES
- Cl.Cl.COC1=C(OC)C(OC)=C(CN2CCNCC2)C=C1
- External Links
- ChemSpider
- 75067
- ChEBI
- 32262
- ChEMBL
- CHEMBL3561076
- Predicted Properties
Property Value Source Water Solubility 0.754 mg/mL ALOGPS logP 0.85 ALOGPS logP 0.91 Chemaxon logS -2.6 ALOGPS pKa (Strongest Basic) 9.21 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 42.96 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 74.75 m3·mol-1 Chemaxon Polarizability 29.15 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon