Details
Stereochemistry | ACHIRAL |
Molecular Formula | C14H22N2O3 |
Molecular Weight | 266.3361 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC=C(CN2CCNCC2)C(OC)=C1OC
InChI
InChIKey=UHWVSEOVJBQKBE-UHFFFAOYSA-N
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
Molecular Formula | C14H22N2O3 |
Molecular Weight | 266.3361 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Trimetazidine is a medicine, which is used for the treatment of angina pectoris. The drug mechanism of action is explained by its ability to selectively inhibit long-chain 3-ketoacyl coenzyme A thiolase, an enzyme responsible for mitochondrial beta-oxidation of long chain fatty acids. Trimetazidine also increases pyruvate dehydrogenase activity, binds to the mitochondrial membrane, directly inhibits cardiac fibrosis and improves mechanical resistance of the sarcolemma.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P55084 Gene ID: 3032.0 Gene Symbol: HADHB Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24902800 |
75.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | VASTAREL Approved UseTrimetazidine is indicated in adults as add-on therapy for the symptomatic treatment of patients with stable angina pectoris who are inadequately controlled by or intolerant to first-line antianginal therapies. Launch Date1.34023676E12 |
PubMed
Title | Date | PubMed |
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Effects of trimetazidine on the contractile response of chronically dysfunctional myocardium to low-dose dobutamine in ischaemic cardiomyopathy. | 2001 Dec |
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Can metabolic manipulation reverse myocardial dysfunction? | 2001 Dec |
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Combination treatment in stable effort angina using trimetazidine and metoprolol: results of a randomized, double-blind, multicentre study (TRIMPOL II). TRIMetazidine in POLand. | 2001 Dec |
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Metabolic management of coronary heart disease: adjunctive treatment with trimetazidine decreases QT dispersion in patients with a first acute myocardial infarction. | 2001 Jul |
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[Metabolic considerations in the treatment of coronary disease in diabetic patients]. | 2001 Nov |
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[Therapeutic perspectives in the treatment of stable angina]. | 2001 Sep-Oct |
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[Effects of trimetazidine on altered functions of rat kidney induced by cyclosporine]. | 2001 Sep-Oct |
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[The study and comparative evaluation of the actoprotective activity of ATF-LONG in experiment]. | 2002 |
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[Antiischemic efficacy of trimetazidine in patients with ischemic heart disease, stable angina pectoris and disturbances of carbohydrate metabolism]. | 2002 |
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[Trimetazidine in pectoris patients older than 65 years with stable angina]. | 2002 |
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Trimetazidine limits the effects of myocardial ischaemia during percutaneous coronary angioplasty. | 2002 |
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[Decrease in the sensitivity to the anti-ischemic effect of propranolol and prospects for correcting it in patients with stable angina pectoris]. | 2002 |
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[Effect of atenolol and trimetazidine on dispersion of cardiac rhythm in patients with moderately expressed postinfarction left ventricular dysfunction]. | 2002 |
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[Enhancement of antioxidant status of the elderly patients with ischemic heart disease in response to amino acid composition of MP-33 in combined therapy with trimetazidine]. | 2002 |
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Gateways to Clinical Trials. | 2002 Apr |
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Metabolic approaches to the treatment of ischemic heart disease: the clinicians' perspective. | 2002 Apr |
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Energy metabolism in the hypertrophied heart. | 2002 Apr |
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[Oxygen dependent metabolism of neutrophils and monocytes in patients with unstable angina and its correction with preductal]. | 2002 Apr-Jun |
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Trimetazidine: a second look. Still no efficacy in visual disorders. | 2002 Aug |
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Cardioprotective effect of trimetazidine during thrombolytic therapy in patients with acute myocardial infarction. | 2002 Dec |
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Prolonged survival after experimental paraquat intoxication: role of alternative antioxidants. | 2002 Feb |
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Trimetazidine as a potential neuroprotectant in transient global ischemia in gerbils: a behavioral and histological study. | 2002 Feb 22 |
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Acute effects of heparin administration on the ischemic threshold of patients with coronary artery disease: evaluation of the protective role of the metabolic modulator trimetazidine. | 2002 Feb 6 |
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Increase of adenosine plasma levels after oral trimetazidine: a pharmacological preconditioning? | 2002 Jan |
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[The role of endogenous modulators of chemoreactivity in the regulation of coronary blood flow]. | 2002 Jul |
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Last performance with VIAGRA: post-mortem identification of sildenafil and its metabolites in biological specimens including hair sample. | 2002 Mar 28 |
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Cardioprotection of trimetazidine and anthracycline-induced acute cardiotoxic effects. | 2002 Mar 30 |
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New concepts in organ preservation. | 2002 May |
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Oxidative stress-mediated renal dysfunction by cyclosporine A in rats: attenuation by trimetazidine. | 2002 May |
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Partial fatty acid oxidation inhibitors for stable angina. | 2002 May |
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Recognition forces involved in mitochondrial binding to a low-affinity trimetazidine binding site related to anti-ischemic activity. | 2002 May 1 |
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Three-layer guar gum matrix tablet formulations for oral controlled delivery of highly soluble trimetazidine dihydrochloride. | 2002 May 17 |
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[Coronary artery disease observed in general hospitals: ETTIC study. Comparison between trimetazidine and mononitrate isosorbide for patients receiving betablockers]. | 2002 Nov |
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The use of partial fatty acid oxidation inhibitors for metabolic therapy of angina pectoris and heart failure. | 2002 Nov |
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Effects of trimetazidine on tissue damage in kidney after hindlimb ischemia-reperfusion. | 2002 Oct |
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Bioavailability studies on guar gum-based three-layer matrix tablets of trimetazidine dihydrochloride in human volunteers. | 2002 Oct 4 |
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Metabolic plasticity and the promotion of cardiac protection in ischemia and ischemic preconditioning. | 2002 Sep |
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Protective effect of trimetazidine in a model of ischemia-reperfusion in the rat retina. | 2002 Sep-Oct |
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[Effect of treatment with trimethazidine on characteristics of arrhythmia and indicators of heart rhythm in patients with chronic cardiac failure]. | 2003 |
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Efficacy and tolerability of trimetazidine in stable angina: a meta-analysis of randomized, double-blind, controlled trials. | 2003 Apr |
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Insulin therapy as an adjunct to reperfusion after acute coronary ischemia: a proposed direct myocardial cell survival effect independent of metabolic modulation. | 2003 Apr 16 |
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Trimetazidine effect on phospholipid synthesis in ventricular myocytes: consequences in alpha-adrenergic signaling. | 2003 Feb |
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Attenuation of glycerol-induced acute renal failure in rats by trimetazidine and deferoxamine. | 2003 Jan |
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Effects of trimetazidine on acetic acid-induced colitis in female Swiss rats. | 2003 Jan 24 |
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Metabolic modulation and optimization of energy consumption in heart failure. | 2003 Mar |
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Treatment of stable angina with low dose diltiazem in combination with the metabolic agent trimetazidine. | 2003 Mar |
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Prevention of heart failure in rats by trimetazidine treatment: a consequence of accelerated phospholipid turnover? | 2003 Mar |
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Myocardial cytoprotection by trimetazidine against anthracycline-induced cardiotoxicity in anticancer chemotherapy. | 2003 Mar-Apr |
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Trimetazidine reduces basal cytosolic Ca2+ concentration during hypoxia in single Xenopus skeletal myocytes. | 2003 May |
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Pharmacokinetic profile of a modified release formulation of trimetazidine (TMZ MR 35 mg) in the elderly and patients with renal failure. | 2003 May |
Patents
Sample Use Guides
The dose is one tablet of 20 mg of trimetazidine three times a day or 35 mg twice a day during meals.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9342596
Rat cardiomyocytes were treated with trimetazidine (1-5*10(-4) M final concentration) in the bath. Then the cells were submitted either to 150 min normoxia or to 150 min hypoxia followed by 90 min reoxygenation in the absence of oxidizable substrate. The drug (at 5*10(-4) M) was efficient in protecting the isolated cardiac myocytes against the functional alterations induced by substrate-free hypoxia and led thus to a better recovery upon reoxygenation.
Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 22:42:18 UTC 2023
by
admin
on
Thu Jul 06 22:42:18 UTC 2023
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Record UNII |
N9A0A0R9S8
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Record Status |
Validated (UNII)
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Record Version |
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Official Name | English | ||
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C78322
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FDA ORPHAN DRUG |
629618
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WHO-VATC |
QC01EB15
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FDA ORPHAN DRUG |
658318
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FDA ORPHAN DRUG |
642918
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WHO-ATC |
C01EB15
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admin on Thu Jul 06 22:42:19 UTC 2023 , Edited by admin on Thu Jul 06 22:42:19 UTC 2023
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DB09069
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M11144
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D014292
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CHEMBL203266
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N9A0A0R9S8
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225-690-2
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10826
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100000076942
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1544
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SUB11306MIG
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DTXSID2048531
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5011-34-7
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TRIMETAZIDINE
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2750
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C76590
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21109
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Related Record | Type | Details | ||
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TARGET -> INHIBITOR |
Improves myocardial glucose utilization through inhibition of fatty acid metabolism.
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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PARENT -> METABOLITE ACTIVE |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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