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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 of TRIMETAZIDINE

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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P55084
Gene ID: 3032.0
Gene Symbol: HADHB
Target Organism: Homo sapiens (Human)
75.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

2012
PubMed

PubMed

TitleDatePubMed
The pH-partition profile of the anti-ischemic drug trimetazidine may explain its reduction of intracellular acidosis.
1999 May
Trimetazidine counteracts tacrolimus nephrotoxicity in a hypertensive liver transplant patient.
1999 Oct 27
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.
2000 Mar 17
Management of ischaemic heart disease in diabetic patients--is there a role for cardiac metabolic agents?
2001
[Aspects of diastolic function of the heart in vibration disease].
2001
The efficacy of medication on tinnitus due to acute acoustic trauma.
2001
[Therapy perspectives in subjective tinnitus].
2001
[Use of antioxidants and trimetazidine in preparation of patients with ischemic heart disease for coronary angiography].
2001
The effect of trimetazidine on the survival of rat island skin flaps subjected to ischemia-reperfusion injury.
2001 Aug
Can metabolic manipulation reverse myocardial dysfunction?
2001 Dec
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
S15176 and S16950 interaction with Cyclosporin A antiproliferative effect on cultured human lymphocytes.
2001 Feb
Dobutamine stress echocardiography and the effects of trimetazidine on left ventricular dysfunction in patients with coronary artery disease.
2001 Feb
A randomized double-blind trial of intravenous trimetazidine as adjunctive therapy to primary angioplasty for acute myocardial infarction.
2001 Feb
QT dispersion--what does it mean?
2001 Jul
Mitochondria as target for antiischemic drugs.
2001 Jul 2
Effect of trimetazidine on retinal ischemia/reperfusion injury in rats.
2001 Jul-Aug
About EMIP-FR and reperfusion damage in AMI: a comment to the comment.
2001 Jun
Trimetazidine for stable angina pectoris.
2001 May
[Metabolic considerations in the treatment of coronary disease in diabetic patients].
2001 Nov
Scavenger effect of experimental and clinically used cardiovascular drugs.
2001 Nov
Recipient treatment with trimetazidine improves graft function and protects energy status after lung transplantation.
2001 Oct
[Trimetazidine prevents ischemia-reperfusion injury in hepatic surgery under vascular clamping].
2001 Sep-Oct
[Effect of preservation of the kidney on the long-term function following autotransplantation].
2001 Sep-Oct
[Are sigma receptors implicated in ischemic injury?].
2001 Sep-Oct
[Use of trimetazidine in the combined therapy of myocardial infarction with left ventricular dysfunction].
2002
[Significance of trimetazidine for out of hospital physical rehabilitation after myocardial infarction].
2002
Trimetazidine limits the effects of myocardial ischaemia during percutaneous coronary angioplasty.
2002
[Decrease in the sensitivity to the anti-ischemic effect of propranolol and prospects for correcting it in patients with stable angina pectoris].
2002
[Effect of atenolol and trimetazidine on dispersion of cardiac rhythm in patients with moderately expressed postinfarction left ventricular dysfunction].
2002
[Effects of trimetazidine on serum oxygen free radicals in congestive heart failure].
2002 Dec 28
Prolonged survival after experimental paraquat intoxication: role of alternative antioxidants.
2002 Feb
Trimetazidine as a potential neuroprotectant in transient global ischemia in gerbils: a behavioral and histological study.
2002 Feb 22
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
Increase of adenosine plasma levels after oral trimetazidine: a pharmacological preconditioning?
2002 Jan
Determination of trimetazidine HCl by adsorptive stripping square-wave voltammetry at a glassy carbon electrode.
2002 Jan 1
Cardioprotection of trimetazidine and anthracycline-induced acute cardiotoxic effects.
2002 Mar 30
Oxidative stress-mediated renal dysfunction by cyclosporine A in rats: attenuation by trimetazidine.
2002 May
Partial fatty acid oxidation inhibitors for stable angina.
2002 May
[Coronary artery disease observed in general hospitals: ETTIC study. Comparison between trimetazidine and mononitrate isosorbide for patients receiving betablockers].
2002 Nov
The use of partial fatty acid oxidation inhibitors for metabolic therapy of angina pectoris and heart failure.
2002 Nov
Effects of trimetazidine on tissue damage in kidney after hindlimb ischemia-reperfusion.
2002 Oct
Bioavailability studies on guar gum-based three-layer matrix tablets of trimetazidine dihydrochloride in human volunteers.
2002 Oct 4
Metabolic plasticity and the promotion of cardiac protection in ischemia and ischemic preconditioning.
2002 Sep
Protective effect of trimetazidine in a model of ischemia-reperfusion in the rat retina.
2002 Sep-Oct
[Effect of treatment with trimethazidine on characteristics of arrhythmia and indicators of heart rhythm in patients with chronic cardiac failure].
2003
Metabolic therapy in the treatment of ischaemic heart disease: the pharmacology of trimetazidine.
2003 Apr
Trimetazidine effect on phospholipid synthesis in ventricular myocytes: consequences in alpha-adrenergic signaling.
2003 Feb
Attenuation of glycerol-induced acute renal failure in rats by trimetazidine and deferoxamine.
2003 Jan
Treatment of stable angina with low dose diltiazem in combination with the metabolic agent trimetazidine.
2003 Mar
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
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 GMT 2023
Edited
by admin
on Sat Dec 16 17:18:33 GMT 2023
Record UNII
N9A0A0R9S8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRIMETAZIDINE
INN   MI   WHO-DD  
INN  
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
Created by admin on Sat Dec 16 17:18:34 GMT 2023 , Edited by admin on Sat Dec 16 17:18:34 GMT 2023
FDA ORPHAN DRUG 629618
Created by admin on Sat Dec 16 17:18:34 GMT 2023 , Edited by admin on Sat Dec 16 17:18:34 GMT 2023
WHO-VATC QC01EB15
Created by admin on Sat Dec 16 17:18:34 GMT 2023 , Edited by admin on Sat Dec 16 17:18:34 GMT 2023
FDA ORPHAN DRUG 658318
Created by admin on Sat Dec 16 17:18:34 GMT 2023 , Edited by admin on Sat Dec 16 17:18:34 GMT 2023
FDA ORPHAN DRUG 642918
Created by admin on Sat Dec 16 17:18:34 GMT 2023 , Edited by admin on Sat Dec 16 17:18:34 GMT 2023
WHO-ATC C01EB15
Created by admin on Sat Dec 16 17:18:34 GMT 2023 , Edited by admin on Sat Dec 16 17:18:34 GMT 2023
Code System Code Type Description
DRUG BANK
DB09069
Created by admin on Sat Dec 16 17:18:34 GMT 2023 , Edited by admin on Sat Dec 16 17:18:34 GMT 2023
PRIMARY
MERCK INDEX
m11144
Created by admin on Sat Dec 16 17:18:34 GMT 2023 , Edited by admin on Sat Dec 16 17:18:34 GMT 2023
PRIMARY Merck Index
MESH
D014292
Created by admin on Sat Dec 16 17:18:34 GMT 2023 , Edited by admin on Sat Dec 16 17:18:34 GMT 2023
PRIMARY
ChEMBL
CHEMBL203266
Created by admin on Sat Dec 16 17:18:34 GMT 2023 , Edited by admin on Sat Dec 16 17:18:34 GMT 2023
PRIMARY
FDA UNII
N9A0A0R9S8
Created by admin on Sat Dec 16 17:18:34 GMT 2023 , Edited by admin on Sat Dec 16 17:18:34 GMT 2023
PRIMARY
ECHA (EC/EINECS)
225-690-2
Created by admin on Sat Dec 16 17:18:34 GMT 2023 , Edited by admin on Sat Dec 16 17:18:34 GMT 2023
PRIMARY
RXCUI
10826
Created by admin on Sat Dec 16 17:18:34 GMT 2023 , Edited by admin on Sat Dec 16 17:18:34 GMT 2023
PRIMARY RxNorm
SMS_ID
100000076942
Created by admin on Sat Dec 16 17:18:34 GMT 2023 , Edited by admin on Sat Dec 16 17:18:34 GMT 2023
PRIMARY
INN
1544
Created by admin on Sat Dec 16 17:18:34 GMT 2023 , Edited by admin on Sat Dec 16 17:18:34 GMT 2023
PRIMARY
EVMPD
SUB11306MIG
Created by admin on Sat Dec 16 17:18:34 GMT 2023 , Edited by admin on Sat Dec 16 17:18:34 GMT 2023
PRIMARY
EPA CompTox
DTXSID2048531
Created by admin on Sat Dec 16 17:18:34 GMT 2023 , Edited by admin on Sat Dec 16 17:18:34 GMT 2023
PRIMARY
CAS
5011-34-7
Created by admin on Sat Dec 16 17:18:34 GMT 2023 , Edited by admin on Sat Dec 16 17:18:34 GMT 2023
PRIMARY
WIKIPEDIA
TRIMETAZIDINE
Created by admin on Sat Dec 16 17:18:34 GMT 2023 , Edited by admin on Sat Dec 16 17:18:34 GMT 2023
PRIMARY
DRUG CENTRAL
2750
Created by admin on Sat Dec 16 17:18:34 GMT 2023 , Edited by admin on Sat Dec 16 17:18:34 GMT 2023
PRIMARY
NCI_THESAURUS
C76590
Created by admin on Sat Dec 16 17:18:34 GMT 2023 , Edited by admin on Sat Dec 16 17:18:34 GMT 2023
PRIMARY
PUBCHEM
21109
Created by admin on Sat Dec 16 17:18:34 GMT 2023 , Edited by admin on Sat Dec 16 17:18:34 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Improves myocardial glucose utilization through inhibition of fatty acid metabolism.
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> METABOLITE ACTIVE
Related Record Type Details
ACTIVE MOIETY