Structure via PubChem · Public domain (PubChem)
trimetazidine
Sign in to saveAlso known as 1-(2,3,4-trimethoxybenzyl)piperazine, 1-[(2,3,4-trimethoxyphenyl)methyl]piperazine
Trimetazidine (IUPAC: 1-(2,3,4-trimethoxybenzyl)piperazine) is a drug used in the treatment of angina pectoris, a condition characterized by chest pain due to reduced blood flow to the heart. Developed and first marketed by Laboratoires Servier (France), it is described as the first cytoprotective anti-ischemic agent. Trimetazidine is an antianginal metabolic drug of the fatty acid oxidation inhibitor class; it shifts cardiac energy metabolism from fatty acid utilization toward glucose oxidation, thereby improving the efficiency of energy production in ischemic conditions.
Key facts
- Drug.C
- 14
- Drug.H
- 22
- Drug.N
- 2
- Drug.O
- 3
- Drug.Verifiedfields
- changed
- Drug.verifiedrevid
- 470615044
- Drug.IUPAC_name
- 1-(2,3,4-trimethoxybenzyl)piperazine
- Drug.image
- Trimetazidine.svg
- Drug.image_class
- skin-invert-image
- Drug.tradename
- Angintriz
- Drug.legal_UK
- CD
- Drug.routes_of_administration
- Oral
- Drug.bioavailability
- completely absorbed at around 5 hours, steady state is reached by 60th hour
- Drug.protein_bound
- low (16%)
- Drug.metabolism
- minimal
- Drug.elimination_half life
- 7 to 12 hours
- Drug.excretion
- mainly renal (unchanged), exposure is increased in renal impairment – on average by four-fold in subjects with severe renal impairment (CrCl <30 ml/min)
- Drug.CAS_number
- 5011-34-7
via Wikipedia infobox
Chemical data
- Formula
- C14H22N2O3
- Molecular weight
- 266.34 g/mol
- IUPAC name
- 1-[(2,3,4-trimethoxyphenyl)methyl]piperazine
- SMILES
- COC1=C(C(=C(C=C1)CN2CCNCC2)OC)OC
- InChIKey
- UHWVSEOVJBQKBE-UHFFFAOYSA-N
- XLogP
- 1
- Polar surface area
- 43 Ų
- H-bond donors
- 1
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Research
1,410 papers- Trimetazidine in Cardiovascular Disease and Beyond: A Comprehensive Review.American journal of cardiovascular drugs : drugs, devices, and other interventions · 2025
- WITHDRAWN: Trimetazidine for stable angina.The Cochrane database of systematic reviews · 2017
- Trimetazidine for stable angina.The Cochrane database of systematic reviews · 2005
- Trimetazidine an emerging paradigm in renal therapeutics: Preclinical and clinical insights.European journal of pharmacology · 2021
- The application of trimetazidine in healthy individuals: a systematic review.European review for medical and pharmacological sciences · 2023
via PubMed
~10 min read
Encyclopedic overview
6 sectionsContents
- Medical uses
- Use as a performance-enhancing drug
- Scientific criticism
- Adverse effects
- Mechanism of action
- References
Trimetazidine (IUPAC: 1-(2,3,4-trimethoxybenzyl)piperazine) is a drug used in the treatment of angina pectoris, a condition characterized by chest pain due to reduced blood flow to the heart. Developed and first marketed by Laboratoires Servier (France), it is described as the first cytoprotective anti-ischemic agent. Trimetazidine is an antianginal metabolic drug of the fatty acid oxidation inhibitor class; it shifts cardiac energy metabolism from fatty acid utilization toward glucose oxidation, thereby improving the efficiency of energy production in ischemic conditions.
The drug has also become controversial as a performance-enhancing drug, with multiple doping scandals linked to its use at successive Olympic Games.
Excerpted from Wikipedia’s “trimetazidine” article, available under the CC BY-SA 4.0 licence.