ContaminantDB: Trimetazidine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-06-03 13:45:49 UTC

Update Date

2016-11-09 01:23:25 UTC

Accession Number

CHEM045856

Identification

Common Name

Trimetazidine

Class

Small Molecule

Description

Trimetazidine is a piperazine derivative indicated for the symptomatic treatment of stable angina pectoris in patients inadequately controlled or intolerant to first line therapies.[L33015] Trimetazidine has been studied as a treatment for angina pectoris since the late 1960s.[A233255,A233260] Acidic conditions, caused by anaerobic metabolism and fatty acid oxidation, in response to myocardial ischemia, activate sodium-hydrogen and sodium-calcium antiport systems.[A233215] The increased intracellular calcium decreases contractility.[A233215] It is hypothesized that trimetazidine inhibits 3-ketoacyl coenzyme A thiolase, which decreases fatty acid oxidation but not glucose metabolism, preventing the acidic conditions that exacerbate ischemic injury.[A7688,L33020] However, evidence for this mechanism is controversial.[A233215] Trimetazidine is not FDA approved. However, it has been approved in France since 1978.[L33020]

Contaminant Sources

STOFF IDENT Compounds

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Dilatan	Kegg
Alpharma brand OF trimetazidine dihydrochloride	MeSH
Biopharma brand OF trimetazidine dihydrochloride	MeSH
Centrophène	MeSH
Danval brand OF trimetazidine dihydrochloride	MeSH
Dihydrochloride, trimetazidine	MeSH
Idaptan	MeSH
Irex brand OF trimetazidine dihydrochloride	MeSH
Trimetazidine dihydrochloride	MeSH
Trimétazidine irex	MeSH
Vasartel	MeSH
Vastarel	MeSH

Chemical Formula

C₁₄H₂₂N₂O₃

Average Molecular Mass

266.341 g/mol

Monoisotopic Mass

266.163 g/mol

CAS Registry Number

5011-34-7

IUPAC Name

1-[(2,3,4-trimethoxyphenyl)methyl]piperazine

Traditional Name

trimetazidine

SMILES

COC1=C(OC)C(OC)=C(CN2CCNCC2)C=C1

InChI Identifier

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

InChI Key

UHWVSEOVJBQKBE-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenylmethylamines. Phenylmethylamines are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylmethylamines

Direct Parent

Phenylmethylamines

Alternative Parents

Substituents

Phenoxy compound
Anisole
Benzylamine
Phenol ether
Phenylmethylamine
Methoxybenzene
Alkyl aryl ether
Aralkylamine
N-alkylpiperazine
1,4-diazinane
Piperazine
Tertiary amine
Tertiary aliphatic amine
Secondary amine
Azacycle
Ether
Secondary aliphatic amine
Organoheterocyclic compound
Amine
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.75 g/L	ALOGPS
logP	0.85	ALOGPS
logP	0.91	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	9.21	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	42.96 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	74.75 m³·mol⁻¹	ChemAxon
Polarizability	29.15 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udr-5290000000-031be15ad33358b71c86	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-014i-2900000000-9af80d4cc6e8d3139dd7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0090000000-3bd53af0cab7221b8595	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-2190000000-1b4544dd267cf6ab4a9f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000b-9840000000-9c903e8f30cbeae9bf0a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-36803fec7c30ad6d4238	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0190000000-4ca7d330826cdb2fed85	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000f-9420000000-68489280e04da881dde0	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB09069

HMDB ID

HMDB0259235

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Trimetazidine

Chemspider ID

19853

ChEBI ID

Not Available

PubChem Compound ID

Not Available

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Trimetazidine (CHEM045856)

Structure for CHEM045856: Trimetazidine