Trimetazidine dihydrochloride Chemical Properties

Melting point:

231-235 °C(lit.)

storage temp. 

Refrigerator

solubility 

Freely soluble in water, sparingly soluble in alcohol.

form 

Solid

color 

White to Off-White

Merck 

14,9705

Stability:

Hygroscopic

InChIKey

XIRALXKCBGTYSC-UHFFFAOYSA-N

CAS DataBase Reference

13171-25-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

TM2976100

HazardClass 

IRRITANT

HS Code 

29339900

Toxicity

LD50 in male, female mice, rats (mg/kg): 91, 107, 124, 124 i.v.; 264, 245, 327, 288 i.p.; 528, 608, 1147, 987 orally (Harpey)

MSDS

• Language:English Provider:SigmaAldrich

Trimetazidine dihydrochloride Usage And Synthesis

Description

Trimetazidine dihydrochloride is the dihydrochloride salt of Trimetazidine. It is a drug used for the treatment of angina pectoris. It is capable of improving the left ventricular function in diabetic patients suffering coronary heart disease as well as treating the symptoms of patients suffering heart failure of different etiologies. It takes effects through acting as an anti- ischemic metabolic agent being capable of improving the utilization efficiency of myocardial glucose by inhibiting the metabolism of fatty acid (through inhibiting the activity of mitochondrial long- chain 3-ketoacyl coenzyme A Thiolase). The shift from fatty acid oxidation to glucose oxidation optimizes cellular energy process in cells exposed to hypoxia or ischaemia, further maintaining the intracellular ATP levels and ensuring the normal function of ionic pumps and transmembrane sodium-potassium flow to maintain cellular homeostasis.

References

Fragasso, G, et al. "A randomized clinical trial of trimetazidine, a partial free fatty acid oxidation inhibitor, in patients with heart failure. " Journal of the American College of Cardiology 48.5 (2006):992.
Tuunanen, H, et al. "Trimetazidine, a metabolic modulator, has cardiac and extracardiac benefits in idiopathic dilated cardiomyopathy."Circulation 118.12(2008):1250.
Kantor, P. F., et al. "The antianginal drug trimetazidine shifts cardiac energy metabolism from fatty acid oxidation to glucose oxidation by inhibiting mitochondrial long-chain 3-ketoacyl coenzyme A thiolase."Circulation Research 86.5(2000):580.
Stanley, W. C., and M. Marzilli. "Metabolic therapy in the treatment of ischaemic heart disease: the pharmacology of trimetazidine. "Fundamental & Clinical Pharmacology 17.2(2003):133–145.
Kantor, Paul F., et al. "The antianginal drug trimetazidine shifts cardiac energy metabolism from fatty acid oxidation to glucose oxidation by inhibiting mitochondrial long-chain 3-ketoacyl coenzyme A thiolase." Circulation research 86.5 (2000): 580-588.

Description

Trimetazidine (hydrochloride) (Item No. 18165) is an analytical reference standard that is structurally categorized as a piperazine. It decreases fatty acid β-oxidation by reversibly inhibiting mitochondrial long-chain 3-ketoacyl thiolase (IC₅₀ = 75 nM). This, in turn, stimulates glucose oxidation. In ischemic heart, trimetazidine reduces ischemia/reperfusion injury in clinical trials. Compounds that reduce mitochondrial fatty acid β-oxidation, including trimetazidine, have shown clinical efficacy against chronic stable angina in clinical trials. In part because of its ability to ameliorate testosterone cardiotoxicity, trimetazidine has been classified as a prohibited substance by the World Anti-Doping Agency. This product is intended for research and forensic applications.

Chemical Properties

Crystalline Solid

Uses

Antianoxic

Uses

1-(2,3,4-Trimethoxybenzyl)piperazine dihydrochloride or trimetazidine dihydrochloride can be used as a building block to synthesize:

• Phenylpropyl trimetazidine derivatives with potent cerebral vasodilator activity.
• Benzoylguanidine-trimetazidine derivatives for myocardial ischemic-reperfusion activity studies.

Uses

Coronary vasodilator. Antianginal

Definition

ChEBI: Trimetazidine hydrochloride is an aromatic amine.

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