TRIMETAZIDINE

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

Structure Search

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

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24902800 | http://www.servier.com/sites/default/files/RCP_Vastarel20.pdf

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
Trifunctional enzyme subunit beta, mitochondrial 2 Target ID: P55084 Gene ID: 3032.0 Gene Symbol: HADHB Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24902800	Inhibitor 8297		75.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Angina pectoris 106 Sources: http://www.servier.com/sites/default/files/RCP_Vastarel20.pdf	Primary		Approved 8429	VASTAREL Approved Use Trimetazidine 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 Date 1.34023676E12

PubMed

Title	Date	PubMed
Management of ischaemic heart disease in diabetic patients--is there a role for cardiac metabolic agents?	2001	11900309
Effects of trimetazidine on the contractile response of chronically dysfunctional myocardium to low-dose dobutamine in ischaemic cardiomyopathy.	2001 Dec	11913478
Can metabolic manipulation reverse myocardial dysfunction?	2001 Dec	11913472
[Metabolic considerations in the treatment of coronary disease in diabetic patients].	2001 Nov	11910982
[The study and comparative evaluation of the actoprotective activity of ATF-LONG in experiment].	2002	12587322
[Antiischemic efficacy of trimetazidine in patients with ischemic heart disease, stable angina pectoris and disturbances of carbohydrate metabolism].	2002	12494204
[Efficacy of trimetazidine in stable angina pectoris refractory to traditional treatment].	2002	12494190
[Trimetazidine in correction of chronic heart failure in patients with ischemic heart disease].	2002	12494179
[Trimetazidine in pectoris patients older than 65 years with stable angina].	2002	12494126
[Use of trimetazidine in the combined therapy of myocardial infarction with left ventricular dysfunction].	2002	12494051
[Significance of trimetazidine for out of hospital physical rehabilitation after myocardial infarction].	2002	12494029
Trimetazidine limits the effects of myocardial ischaemia during percutaneous coronary angioplasty.	2002	12487504
[Decrease in the sensitivity to the anti-ischemic effect of propranolol and prospects for correcting it in patients with stable angina pectoris].	2002	12418118
[Effect of atenolol and trimetazidine on dispersion of cardiac rhythm in patients with moderately expressed postinfarction left ventricular dysfunction].	2002	12360593
[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	12087889
Gateways to Clinical Trials.	2002 Apr	12087878
Metabolic approaches to the treatment of ischemic heart disease: the clinicians' perspective.	2002 Apr	11988642
Energy metabolism in the hypertrophied heart.	2002 Apr	11988640
[Oxygen dependent metabolism of neutrophils and monocytes in patients with unstable angina and its correction with preductal].	2002 Apr-Jun	12152422
Trimetazidine: a second look. Still no efficacy in visual disorders.	2002 Aug	12199261
Cardioprotective effect of trimetazidine during thrombolytic therapy in patients with acute myocardial infarction.	2002 Dec	12660838
[Effects of trimetazidine on serum oxygen free radicals in congestive heart failure].	2002 Dec 28	12658930
Trimetazidine as a potential neuroprotectant in transient global ischemia in gerbils: a behavioral and histological study.	2002 Feb 22	11844466
[The role of endogenous modulators of chemoreactivity in the regulation of coronary blood flow].	2002 Jul	12238353
Last performance with VIAGRA: post-mortem identification of sildenafil and its metabolites in biological specimens including hair sample.	2002 Mar 28	11955836
Cardioprotection of trimetazidine and anthracycline-induced acute cardiotoxic effects.	2002 Mar 30	11943290
New concepts in organ preservation.	2002 May	12180834
Oxidative stress-mediated renal dysfunction by cyclosporine A in rats: attenuation by trimetazidine.	2002 May	12166693
Partial fatty acid oxidation inhibitors for stable angina.	2002 May	11996644
Recognition forces involved in mitochondrial binding to a low-affinity trimetazidine binding site related to anti-ischemic activity.	2002 May 1	12007572
Three-layer guar gum matrix tablet formulations for oral controlled delivery of highly soluble trimetazidine dihydrochloride.	2002 May 17	11992677
[Coronary artery disease observed in general hospitals: ETTIC study. Comparison between trimetazidine and mononitrate isosorbide for patients receiving betablockers].	2002 Nov	12515103
The use of partial fatty acid oxidation inhibitors for metabolic therapy of angina pectoris and heart failure.	2002 Nov	12439634
Effects of trimetazidine on tissue damage in kidney after hindlimb ischemia-reperfusion.	2002 Oct	12361697
Bioavailability studies on guar gum-based three-layer matrix tablets of trimetazidine dihydrochloride in human volunteers.	2002 Oct 4	12363449
Metabolic plasticity and the promotion of cardiac protection in ischemia and ischemic preconditioning.	2002 Sep	12392880
Protective effect of trimetazidine in a model of ischemia-reperfusion in the rat retina.	2002 Sep-Oct	12381891
[Effect of treatment with trimethazidine on characteristics of arrhythmia and indicators of heart rhythm in patients with chronic cardiac failure].	2003	12718225
Metabolic therapy in the treatment of ischaemic heart disease: the pharmacology of trimetazidine.	2003 Apr	12667223
Efficacy and tolerability of trimetazidine in stable angina: a meta-analysis of randomized, double-blind, controlled trials.	2003 Apr	12655281
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	12706939
Trimetazidine effect on phospholipid synthesis in ventricular myocytes: consequences in alpha-adrenergic signaling.	2003 Feb	12588630
Attenuation of glycerol-induced acute renal failure in rats by trimetazidine and deferoxamine.	2003 Jan	12444302
Effects of trimetazidine on acetic acid-induced colitis in female Swiss rats.	2003 Jan 24	12653021
Metabolic modulation and optimization of energy consumption in heart failure.	2003 Mar	12693736
Treatment of stable angina with low dose diltiazem in combination with the metabolic agent trimetazidine.	2003 Mar	12659989
Prevention of heart failure in rats by trimetazidine treatment: a consequence of accelerated phospholipid turnover?	2003 Mar	12604675
Myocardial cytoprotection by trimetazidine against anthracycline-induced cardiotoxicity in anticancer chemotherapy.	2003 Mar-Apr	12678198
Trimetazidine reduces basal cytosolic Ca2+ concentration during hypoxia in single Xenopus skeletal myocytes.	2003 May	12719766
Pharmacokinetic profile of a modified release formulation of trimetazidine (TMZ MR 35 mg) in the elderly and patients with renal failure.	2003 May	12698499

Patents

Sample Use Guides

In Vivo Use Guide

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

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 `Sat Dec 16 17:18:33 UTC 2023` Edited by `admin` on `Sat Dec 16 17:18:33 UTC 2023`
Record UNII	N9A0A0R9S8
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TRIMETAZIDINE

Official Name

English

trimetazidine [INN]

Common Name

English

DILATAN

Brand Name

English

Trimetazidine [WHO-DD]

Common Name

English

TRIMETAZIDINE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C78322