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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

2012
PubMed

PubMed

TitleDatePubMed
Trimetazidine. A review of its use in stable angina pectoris and other coronary conditions.
1999 Jul
The pH-partition profile of the anti-ischemic drug trimetazidine may explain its reduction of intracellular acidosis.
1999 May
Management of ischaemic heart disease in diabetic patients--is there a role for cardiac metabolic agents?
2001
The efficacy of medication on tinnitus due to acute acoustic trauma.
2001
Attenuation of liver normothermic ischemia--reperfusion injury by preservation of mitochondrial functions with S-15176, a potent trimetazidine derivative.
2001 Aug 15
Optimizing cardiac energy metabolism: how can fatty acid and carbohydrate metabolism be manipulated?
2001 Feb
Metabolic energy metabolism in diabetes: therapeutic implications.
2001 Feb
Trimetazidine in AMI.
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
Trimetazidine: stability indicating RPLC assay method.
2001 May
[Therapeutic perspectives in the treatment of stable angina].
2001 Sep-Oct
[Are sigma receptors implicated in ischemic injury?].
2001 Sep-Oct
[Efficacy of trimetazidine in stable angina pectoris refractory to traditional treatment].
2002
[Trimetazidine in correction of chronic heart failure in patients with ischemic heart disease].
2002
[Trimetazidine in pectoris patients older than 65 years with stable angina].
2002
[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
[Effect of atenolol and trimetazidine on dispersion of cardiac rhythm in patients with moderately expressed postinfarction left ventricular dysfunction].
2002
[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
Gateways to Clinical Trials.
2002 Apr
Energy metabolism in the hypertrophied heart.
2002 Apr
[Oxygen dependent metabolism of neutrophils and monocytes in patients with unstable angina and its correction with preductal].
2002 Apr-Jun
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
Cardioprotection of trimetazidine and anthracycline-induced acute cardiotoxic effects.
2002 Mar 30
Partial fatty acid oxidation inhibitors for stable angina.
2002 May
Recognition forces involved in mitochondrial binding to a low-affinity trimetazidine binding site related to anti-ischemic activity.
2002 May 1
Three-layer guar gum matrix tablet formulations for oral controlled delivery of highly soluble trimetazidine dihydrochloride.
2002 May 17
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
Protective effect of trimetazidine in a model of ischemia-reperfusion in the rat retina.
2002 Sep-Oct
Efficacy and tolerability of trimetazidine in stable angina: a meta-analysis of randomized, double-blind, controlled trials.
2003 Apr
Trimetazidine effect on phospholipid synthesis in ventricular myocytes: consequences in alpha-adrenergic signaling.
2003 Feb
Effects of trimetazidine on acetic acid-induced colitis in female Swiss rats.
2003 Jan 24
Treatment of stable angina with low dose diltiazem in combination with the metabolic agent trimetazidine.
2003 Mar
Prevention of heart failure in rats by trimetazidine treatment: a consequence of accelerated phospholipid turnover?
2003 Mar
Myocardial cytoprotection by trimetazidine against anthracycline-induced cardiotoxicity in anticancer chemotherapy.
2003 Mar-Apr
Trimetazidine reduces basal cytosolic Ca2+ concentration during hypoxia in single Xenopus skeletal myocytes.
2003 May
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 GMT 2023
Edited
by admin
on Sat Dec 16 05:26:15 GMT 2023
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 16 05:26:15 GMT 2023 , Edited by admin on Sat Dec 16 05:26:15 GMT 2023
PRIMARY
MERCK INDEX
m11144
Created by admin on Sat Dec 16 05:26:15 GMT 2023 , Edited by admin on Sat Dec 16 05:26:15 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL203266
Created by admin on Sat Dec 16 05:26:15 GMT 2023 , Edited by admin on Sat Dec 16 05:26:15 GMT 2023
PRIMARY
EVMPD
SUB90444
Created by admin on Sat Dec 16 05:26:15 GMT 2023 , Edited by admin on Sat Dec 16 05:26:15 GMT 2023
PRIMARY
DRUG BANK
DBSALT001114
Created by admin on Sat Dec 16 05:26:15 GMT 2023 , Edited by admin on Sat Dec 16 05:26:15 GMT 2023
PRIMARY
SMS_ID
100000091242
Created by admin on Sat Dec 16 05:26:15 GMT 2023 , Edited by admin on Sat Dec 16 05:26:15 GMT 2023
PRIMARY
CAS
13171-25-0
Created by admin on Sat Dec 16 05:26:15 GMT 2023 , Edited by admin on Sat Dec 16 05:26:15 GMT 2023
PRIMARY
NSC
759317
Created by admin on Sat Dec 16 05:26:15 GMT 2023 , Edited by admin on Sat Dec 16 05:26:15 GMT 2023
PRIMARY
EVMPD
SUB12374MIG
Created by admin on Sat Dec 16 05:26:15 GMT 2023 , Edited by admin on Sat Dec 16 05:26:15 GMT 2023
PRIMARY
FDA UNII
48V6723Z1P
Created by admin on Sat Dec 16 05:26:15 GMT 2023 , Edited by admin on Sat Dec 16 05:26:15 GMT 2023
PRIMARY
PUBCHEM
83201
Created by admin on Sat Dec 16 05:26:15 GMT 2023 , Edited by admin on Sat Dec 16 05:26:15 GMT 2023
PRIMARY
EPA CompTox
DTXSID1045407
Created by admin on Sat Dec 16 05:26:15 GMT 2023 , Edited by admin on Sat Dec 16 05:26:15 GMT 2023
PRIMARY
RXCUI
235779
Created by admin on Sat Dec 16 05:26:15 GMT 2023 , Edited by admin on Sat Dec 16 05:26:15 GMT 2023
PRIMARY RxNorm
Related Record Type Details
Structure of TRIMETAZIDINE
PARENT -> SALT/SOLVATE
Related Record Type Details
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
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 1-((3,4,5-TRIMETHOXYPHENYL)METHYL)PIPERAZINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of (2,3,4-TRIMETHOXYPHENYL)METHANOL
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 1-((2,4,6-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 F = 0.71
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of Piperazine
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (TLC)
EP
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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