Trimetazidine

Trimetazidine
Clinical data
Trade names	Angintriz
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	C01EB15 (WHO) ;
Legal status
Legal status	UK: Controlled Drug;
Pharmacokinetic data
Bioavailability	completely absorbed at around 5 hours, steady state is reached by 60th hour
Protein binding	low (16%)
Metabolism	minimal
Elimination half-life	7 to 12 hours
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)
Identifiers
	IUPAC name 1-(2,3,4-trimethoxybenzyl)piperazine;
CAS Number	5011-34-7 ;
PubChem CID	21109;
ChemSpider	19853 ;
UNII	N9A0A0R9S8;
ChEMBL	ChEMBL203266 ;
CompTox Dashboard (EPA)	DTXSID2048531 ;
ECHA InfoCard	100.023.355
Chemical and physical data
Formula	C14H22N2O3
Molar mass	266.341 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O(c1ccc(c(OC)c1OC)CN2CCNCC2)C;
	InChI InChI=1S/C14H22N2O3/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 ; Key:UHWVSEOVJBQKBE-UHFFFAOYSA-N ;
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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.