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Details

Stereochemistry ACHIRAL
Molecular Formula C14H22N2O3.2ClH
Molecular Weight 339.258
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIMETAZIDINE DIHYDROCHLORIDE

SMILES

Cl.Cl.COC1=CC=C(CN2CCNCC2)C(OC)=C1OC

InChI

InChIKey=VYFLPFGUVGMBEP-UHFFFAOYSA-N
InChI=1S/C14H22N2O3.2ClH/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;2*1H

HIDE SMILES / InChI
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
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

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

Unknown
127998
Targets

Targets

Primary TargetPharmacologyConditionPotency
Trifunctional enzyme subunit beta, mitochondrial
2
Target ID: P55084
Gene ID: 3032.0
Gene Symbol: HADHB
Target Organism: Homo sapiens (Human)
Inhibitor
8146
 75.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8307
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

PubMed

TitleDatePubMed
[Aspects of diastolic function of the heart in vibration disease].
2001
The efficacy of medication on tinnitus due to acute acoustic trauma.
2001
[Use of antioxidants and trimetazidine in preparation of patients with ischemic heart disease for coronary angiography].
2001
Influence of trimetazidine on the synthesis of complex lipids in the heart and other target organs.
2001 Aug
Inhibition of mitochondrial carnitine palmitoyltransferase-1 by a trimetazidine derivative, S-15176.
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
Optimizing cardiac energy metabolism: how can fatty acid and carbohydrate metabolism be manipulated?
2001 Feb
A randomized double-blind trial of intravenous trimetazidine as adjunctive therapy to primary angioplasty for acute myocardial infarction.
2001 Feb
The effects of trimetazidine on heart rate variability and signal-averaged electrocardiography in early period of acute myocardial infarction.
2001 Feb
Mitochondria as target for antiischemic drugs.
2001 Jul 2
Trimetazidine in AMI.
2001 Jun
Trimetazidine and reperfusion injury.
2001 Jun
The EMIP-FR Study: the evolution of scientific background as a non-controlled parameter.
2001 Jun
About EMIP-FR and reperfusion damage in AMI: a comment to the comment.
2001 Jun
Combination therapy in angina: a review of combined haemodynamic treatment and the role for combined haemodynamic and cardiac metabolic agents.
2001 May
Trimetazidine for stable angina pectoris.
2001 May
Trimetazidine: stability indicating RPLC assay method.
2001 May
Recipient treatment with trimetazidine improves graft function and protects energy status after lung transplantation.
2001 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
Metabolic approaches to the treatment of ischemic heart disease: the clinicians' perspective.
2002 Apr
Energy metabolism in the hypertrophied heart.
2002 Apr
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
Last performance with VIAGRA: post-mortem identification of sildenafil and its metabolites in biological specimens including hair sample.
2002 Mar 28
Cardioprotection of trimetazidine and anthracycline-induced acute cardiotoxic effects.
2002 Mar 30
New concepts in organ preservation.
2002 May
Partial fatty acid oxidation inhibitors for stable angina.
2002 May
Three-layer guar gum matrix tablet formulations for oral controlled delivery of highly soluble trimetazidine dihydrochloride.
2002 May 17
The use of partial fatty acid oxidation inhibitors for metabolic therapy of angina pectoris and heart failure.
2002 Nov
Bioavailability studies on guar gum-based three-layer matrix tablets of trimetazidine dihydrochloride in human volunteers.
2002 Oct 4
Metabolic therapy in the treatment of ischaemic heart disease: the pharmacology of trimetazidine.
2003 Apr
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
Metabolic modulation and optimization of energy consumption in heart failure.
2003 Mar
Treatment of stable angina with low dose diltiazem in combination with the metabolic agent trimetazidine.
2003 Mar
Myocardial cytoprotection by trimetazidine against anthracycline-induced cardiotoxicity in anticancer chemotherapy.
2003 Mar-Apr
Patents

Patents

04596803
6
05143921
10
05420132
5
05545645
4
JPS632986A
2

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 17 18:21:03 UTC 2022
Edited
by admin
on Sat Dec 17 18:21:03 UTC 2022
Record UNII
48V6723Z1P
Record Status Validated (UNII)
Record Version
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Name Type Language
TRIMETAZIDINE DIHYDROCHLORIDE
EP   MI  
Common Name English
TRIMETAZIDINE HCL
Common Name English
TRIMETAZIDINE DIHYDROCHLORIDE [EP MONOGRAPH]
Common Name English
TRIMETAZIDINE HYDROCHLORIDE [JAN]
Common Name English
TRIMETAZIDINE DIHYDROCHLORIDE [MI]
Common Name English
TRIMETAZIDINE HYDROCHLORIDE
MART.   WHO-DD  
Common Name English
TRIMETAZIDINE HYDROCHLORIDE [MART.]
Common Name English
TRIMETAZIDINE DI-HCL
Common Name English
NSC-759317
Code English
Trimetazidine hydrochloride [WHO-DD]
Common Name English
TRIMETHAZIDINE DIHYDROCHLORIDE
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
236-117-0
Created by admin on Sat Dec 17 18:21:03 UTC 2022 , Edited by admin on Sat Dec 17 18:21:03 UTC 2022
PRIMARY
MERCK INDEX
M11144
Created by admin on Sat Dec 17 18:21:03 UTC 2022 , Edited by admin on Sat Dec 17 18:21:03 UTC 2022
PRIMARY Merck Index
ChEMBL
CHEMBL203266
Created by admin on Sat Dec 17 18:21:03 UTC 2022 , Edited by admin on Sat Dec 17 18:21:03 UTC 2022
PRIMARY
EVMPD
SUB90444
Created by admin on Sat Dec 17 18:21:03 UTC 2022 , Edited by admin on Sat Dec 17 18:21:03 UTC 2022
PRIMARY
DRUG BANK
DBSALT001114
Created by admin on Sat Dec 17 18:21:03 UTC 2022 , Edited by admin on Sat Dec 17 18:21:03 UTC 2022
PRIMARY
DAILYMED
48V6723Z1P
Created by admin on Sat Dec 17 18:21:03 UTC 2022 , Edited by admin on Sat Dec 17 18:21:03 UTC 2022
PRIMARY
CAS
13171-25-0
Created by admin on Sat Dec 17 18:21:03 UTC 2022 , Edited by admin on Sat Dec 17 18:21:03 UTC 2022
PRIMARY
NSC
759317
Created by admin on Sat Dec 17 18:21:03 UTC 2022 , Edited by admin on Sat Dec 17 18:21:03 UTC 2022
PRIMARY
EVMPD
SUB12374MIG
Created by admin on Sat Dec 17 18:21:03 UTC 2022 , Edited by admin on Sat Dec 17 18:21:03 UTC 2022
PRIMARY
FDA UNII
48V6723Z1P
Created by admin on Sat Dec 17 18:21:03 UTC 2022 , Edited by admin on Sat Dec 17 18:21:03 UTC 2022
PRIMARY
PUBCHEM
83201
Created by admin on Sat Dec 17 18:21:03 UTC 2022 , Edited by admin on Sat Dec 17 18:21:03 UTC 2022
PRIMARY
EPA CompTox
DTXSID1045407
Created by admin on Sat Dec 17 18:21:03 UTC 2022 , Edited by admin on Sat Dec 17 18:21:03 UTC 2022
PRIMARY
RXCUI
235779
Created by admin on Sat Dec 17 18:21:03 UTC 2022 , Edited by admin on Sat Dec 17 18:21:03 UTC 2022
PRIMARY RxNorm
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Structure of TRIMETAZIDINE
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Structure of 1,4-BIS((2,3,4-TRIMETHOXYPHENYL)METHYL)PIPERAZINE
IMPURITY -> PARENT
correction factors: for the calculation of contents, multiply the peak areas of the following impurities by the corresponding correction factor: impurity B = 0.55
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EP
Structure of 1-((3,4,5-TRIMETHOXYPHENYL)METHYL)PIPERAZINE
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EP
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IMPURITY -> PARENT
correction factors: for the calculation of contents, multiply the peak areas of the following impurities by the corresponding correction factor: impurity F = 0.71
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EP
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Structure of 2,3,4-TRIMETHOXYBENZALDEHYDE
IMPURITY -> PARENT
correction factors: for the calculation of contents, multiply the peak areas of the following impurities by the corresponding correction factor: impurity C = 0.37
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 1-PIPERAZINECARBOXYLIC ACID, 4-((2,3,4-TRIMETHOXYPHENYL)METHYL)-, ETHYL ESTER
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of TRIMETAZIDINE
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