Trimetazidine Dihydrochloride

HCID 83201CAS 13171-25-0

Basic information

Standard SMILES
COc1ccc(CN2CCNCC2)c(OC)c1OC.Cl.Cl
InChIKey
VYFLPFGUVGMBEP-UHFFFAOYSA-N
Molecular formula
C14H24Cl2N2O3
Average molar mass
339.3 g/mol
Monoisotopic mass
338.11639799

Overview

Trimetazidine hydrochloride is an aromatic amine.

Names & identifiers

Preferred name
Trimetazidine Dihydrochloride
IUPAC
1-[(2,3,4-trimethoxyphenyl)methyl]piperazine;dihydrochloride
English name
Trimetazidine dihydrochloride
Molecular formula
C14H24Cl2N2O3
Molecular weight
339.26

Names & synonyms

Trimetazidine dihydrochloride13171-25-01-(2,3,4-Trimethoxybenzyl)piperazine dihydrochlorideTrimetazidine hydrochlorideKyurinettTrimetazidine HClTrimetazidine di-hclDTXSID1045407Trimethazidine dihydrochloride48V6723Z1PNSC-759317DTXCID9025407
Show more names
s4004TakkmintvastarelYoshimilonVastarel FYoumetazineTrimetazidine 3HCl
RefChem:191733Dihydrochloride, Trimetazidine236-117-01-[(2,3,4-trimethoxyphenyl)methyl]piperazine dihydrochlorideTrimetazidine 2HClMFCD00243086Trimetazidine (dihydrochloride)Trimetazidine hydrochloride [JAN]

Database identifiers

CAS
13171-25-0
PubChem CID
83201
DTXSID
DTXSID1045407
ChEMBL
CHEMBL3561076
ChEBI
CHEBI:32262
UNII
48V6723Z1P
EC Number
236-117-0

Properties

Computed structural properties

Topological polar surface area
43 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
5
Rotatable bonds
5
Heavy atoms
21

Experimental & physicochemical properties

Collision Cross Section159.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
231 · 231-235 °C(lit.)
storage temp.
Refrigerator
solubility
Freely soluble in water, sparingly soluble in alcohol.
form
Solid
color
White to Off-White
Merck
14 · 14,9705

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (98.2%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 111 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (98.2%)

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
rtecs
TM2976100
hs_code
29339900
Toxicity
LD50 in male, female mice, rats (mg/kg): 91, 107, 124, 124 i.v.; 264, 245, 327, 288 i.p.; 528, 608, 1147, 987 orally (Harpey)
risk_code
22-36/37/38

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationDrugs used to cause dilation of the blood vessels.
Applications · 5 items

DescriptionTrimetazidine dihydrochloride is the dihydrochloride salt of Trimetazidine. It is a drug used for the treatment of angina pectoris. It is capable of improving the left ventricular function in diabetic patients suffering coronary heart disease as well as treating the symptoms of patients suffering heart failure of different etiologies. It takes effects through acting as an anti- ischemic metabolic agent being capable of improving the utilization efficiency of myocardial glucose by inhibiting the metabolism of fatty acid (through inhibiting the activity of mitochondrial long- chain 3-ketoacyl coenzyme A Thiolase). The shift from fatty acid oxidation to glucose oxidation optimizes cellular energy process in cells exposed to hypoxia or ischaemia, further maintaining the intracellular ATP levels and ensuring the normal function of ionic pumps and transmembrane sodium-potassium flow to maintain cellular homeostasis.

DescriptionTrimetazidine (hydrochloride) (Item No. 18165) is an analytical reference standard that is structurally categorized as a piperazine. It decreases fatty acid β-oxidation by reversibly inhibiting mitochondrial long-chain 3-ketoacyl thiolase (IC50 = 75 nM). This, in turn, stimulates glucose oxidation. In ischemic heart, trimetazidine reduces ischemia/reperfusion injury in clinical trials. Compounds that reduce mitochondrial fatty acid β-oxidation, including trimetazidine, have shown clinical efficacy against chronic stable angina in clinical trials. In part because of its ability to ameliorate testosterone cardiotoxicity, trimetazidine has been classified as a prohibited substance by the World Anti-Doping Agency. This product is intended for research and forensic applications.

UsesAntianoxic

Uses1-(2,3,4-Trimethoxybenzyl)piperazine dihydrochloride or trimetazidine dihydrochloride can be used as a building block to synthesize: Phenylpropyl trimetazidine derivatives with potent cerebral vasodilator activity.Benzoylguanidine-trimetazidine derivatives for myocardial ischemic-reperfusion activity studies.

UsesCoronary vasodilator. Antianginal

Suppliers50 total

北京华美互利生物化工010-56205725 · [email protected]
上海策嵘生物科技有限公司[email protected]
HubeiwidelychemicaltechnologyCo.,Ltd18627774460 · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]
山东雨禾医药科技有限公司15263077727

Additional notes

DefinitionChEBI: Trimetazidine hydrochloride is an aromatic amine.

Related reactions

2 records

Linked notes

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