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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
139594
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
8297
 75.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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

PubMed

TitleDatePubMed
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
Effects of trimetazidine on the contractile response of chronically dysfunctional myocardium to low-dose dobutamine in ischaemic cardiomyopathy.
2001 Dec
Trimetazidine protects the energy status after ischemia and reduces reperfusion injury in a rat single lung transplant model.
2001 Dec
Trimetazidine and reperfusion injury.
2001 Jun
The EMIP-FR Study: the evolution of scientific background as a non-controlled parameter.
2001 Jun
Trimetazidine for stable angina pectoris.
2001 May
Trimetazidine: stability indicating RPLC assay method.
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
[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
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
[The role of endogenous modulators of chemoreactivity in the regulation of coronary blood flow].
2002 Jul
Last performance with VIAGRA: post-mortem identification of sildenafil and its metabolites in biological specimens including hair sample.
2002 Mar 28
Bioavailability studies on guar gum-based three-layer matrix tablets of trimetazidine dihydrochloride in human volunteers.
2002 Oct 4
[Effect of treatment with trimethazidine on characteristics of arrhythmia and indicators of heart rhythm in patients with chronic cardiac failure].
2003
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 16 05:26:15 UTC 2023
Edited
by admin
on Sat Dec 16 05:26:15 UTC 2023
Record UNII
48V6723Z1P
Record Status Validated (UNII)
Record Version
  • Download
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 16 05:26:15 UTC 2023 , Edited by admin on Sat Dec 16 05:26:15 UTC 2023
PRIMARY
MERCK INDEX
m11144
Created by admin on Sat Dec 16 05:26:15 UTC 2023 , Edited by admin on Sat Dec 16 05:26:15 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL203266
Created by admin on Sat Dec 16 05:26:15 UTC 2023 , Edited by admin on Sat Dec 16 05:26:15 UTC 2023
PRIMARY
EVMPD
SUB90444
Created by admin on Sat Dec 16 05:26:15 UTC 2023 , Edited by admin on Sat Dec 16 05:26:15 UTC 2023
PRIMARY
DRUG BANK
DBSALT001114
Created by admin on Sat Dec 16 05:26:15 UTC 2023 , Edited by admin on Sat Dec 16 05:26:15 UTC 2023
PRIMARY
SMS_ID
100000091242
Created by admin on Sat Dec 16 05:26:15 UTC 2023 , Edited by admin on Sat Dec 16 05:26:15 UTC 2023
PRIMARY
CAS
13171-25-0
Created by admin on Sat Dec 16 05:26:15 UTC 2023 , Edited by admin on Sat Dec 16 05:26:15 UTC 2023
PRIMARY
NSC
759317
Created by admin on Sat Dec 16 05:26:15 UTC 2023 , Edited by admin on Sat Dec 16 05:26:15 UTC 2023
PRIMARY
EVMPD
SUB12374MIG
Created by admin on Sat Dec 16 05:26:15 UTC 2023 , Edited by admin on Sat Dec 16 05:26:15 UTC 2023
PRIMARY
FDA UNII
48V6723Z1P
Created by admin on Sat Dec 16 05:26:15 UTC 2023 , Edited by admin on Sat Dec 16 05:26:15 UTC 2023
PRIMARY
PUBCHEM
83201
Created by admin on Sat Dec 16 05:26:15 UTC 2023 , Edited by admin on Sat Dec 16 05:26:15 UTC 2023
PRIMARY
EPA CompTox
DTXSID1045407
Created by admin on Sat Dec 16 05:26:15 UTC 2023 , Edited by admin on Sat Dec 16 05:26:15 UTC 2023
PRIMARY
RXCUI
235779
Created by admin on Sat Dec 16 05:26:15 UTC 2023 , Edited by admin on Sat Dec 16 05:26:15 UTC 2023
PRIMARY RxNorm
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EP
Structure of 1-PIPERAZINECARBOXYLIC ACID, 4-((2,3,4-TRIMETHOXYPHENYL)METHYL)-, ETHYL ESTER
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Structure of TRIMETAZIDINE
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