Trimetazidine dihydrochloride

Trimetazidine dihydrochloride
  • CAS No.:13171-25-0
Other grades of this product :
Trimetazidine dihydrochloride Basic information
Description References
Product Name:Trimetazidine dihydrochloride
Synonyms:1-(2,3,4-TRIMETHOXYBENZYL)PIPERAZINE DIHYDROCHLORIDE;1-[(2,3,4-Trimethoxy-phenyl)methyl]piperazine Dihydrochloride;Vastarel F;Yoshimilon;1-(2,3,4-Trimethoxybenzyl)piperazine dihydrochloride,Trimetazidine dihydrochloride;Trimetazidine 3HCl;Takkmint;Youmetazine
CAS:13171-25-0
MF:C14H24Cl2N2O3
MW:339.26
EINECS:236-117-0
Product Categories:Building Blocks;C14 to C15;Intermediates & Fine Chemicals;Chemical Synthesis;Heterocyclic Building Blocks;Piperazines;Pharmaceuticals
Mol File:13171-25-0.mol
Trimetazidine dihydrochloride Chemical Properties
Melting point 231-235 °C(lit.)
storage temp. Refrigerator
solubility Freely soluble in water, sparingly soluble in alcohol.
form neat
color White to Off-White
Merck 14,9705
Stability:Hygroscopic
InChIKeyXIRALXKCBGTYSC-UHFFFAOYSA-N
CAS DataBase Reference13171-25-0(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
ToxicityLD50 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 Information
ProviderLanguage
SigmaAldrich English
Trimetazidine dihydrochloride Usage And Synthesis
DescriptionTrimetazidine 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.
ReferencesFragasso, 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.
DescriptionTrimetazidine (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 PropertiesCrystalline Solid
UsesAntianoxic
Uses1-(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.
UsesCoronary vasodilator. Antianginal
Trimetazidine dihydrochloride Preparation Products And Raw materials

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