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Details

Stereochemistry ACHIRAL
Molecular Formula C6H14N2O2
Molecular Weight 146.1876
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MELDONIUM

SMILES

C[N+](C)(C)NCCC([O-])=O

InChI

InChIKey=PVBQYTCFVWZSJK-UHFFFAOYSA-N
InChI=1S/C6H14N2O2/c1-8(2,3)7-5-4-6(9)10/h7H,4-5H2,1-3H3

HIDE SMILES / InChI

Molecular Formula C6H14N2O2
Molecular Weight 146.1876
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Meldonium (3-(2,2,2-trimethylhydrazinium)propionate; MET-88; quaterine, trade-named as Mildronate) is an antiischemic drug developed at the Latvian Institute of Organic Synthesis. It is a clinically used in the treatment of heart failure, myocardial infarction, arrhythmia, atherosclerosis, and diabetes. Mechanism of action is based on the regulation of energy metabolism pathways through l-carnitine lowering effect. L-Carnitine biosynthesis enzyme γ-butyrobetaine hydroxylase and carnitine/organic cation transporter type 2 (OCTN2) are the main known drug targets of meldonium, and through inhibition of these activities, meldonium induces adaptive changes in the cellular energy homeostasis. Since L-carnitine is involved in the metabolism of fatty acids, the decline in its levels stimulates glucose metabolism and decreases concentrations of l-carnitine related metabolites, such as long-chain acylcarnitines and trimethylamine-N-oxide. Meldonium is used in neurological clinics for the treatment of brain circulation disorders. It appears to improve patients' mood; they become more active, their motor dysfunction decreases, and asthenia, dizziness, and nausea become less pronounced. CNS effects of Meldonium could be mediated by stimulation of the nitric oxide production in the vascular endothelium by modification of the gamma-butyrobetaine and its esters pools. It is hypothesized that mildronate may increase the formation of the gamma-butyrobetaine esters. Meldonium was on the World Anti-Doping Agency’s (WADA) list of drugs being monitored until September 2015, when it was added to the list of banned substances, effective January 1, 2016.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
16.0 µM [Ki]
41.0 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown
Palliative
Unknown
Palliative
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Cardiovascular disease: myocardial infarction: 0.5-1 g per day intravenous Damage of cerebral circulation: As part of complex therapy in the acute phase of 0.5 g once a day in the / in for 10 days intravenous, switching to oral intake of 0.5-1 g. The general course of treatment is 4-6 weeks Mental and physical overloads: 0.5 g intramuscular or intravenous once a day. The course of treatment is 10-14 days. If necessary, repeat the treatment after 2-3 weeks.
Route of Administration: Other
In Vitro Use Guide
There were investigated the effect of N-trimethyl-hydrazine-3-propionate (THP, meldonium) on butyrobetaine hydroxylase kinetics, and carnitine biosynthesis and body homeostasis in rats fed a casein-based or a vegetarian diet. The K(m )of butyrobetaine hydroxylase purified from rat liver was 41 +/- 9 micromol x L(-1) for butyrobetaine and 37 +/- 5 micromol x L(-1) for THP, and THP was a competitive inhibitor of butyrobetaine hydroxylase (K(i) 16 +/- 2 micromol x L(-1))
Substance Class Chemical
Record UNII
73H7UDN6EC
Record Status Validated (UNII)
Record Version