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Details

Stereochemistry ACHIRAL
Molecular Formula C6H14N2O2.2H2O
Molecular Weight 182.2184
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MELDONIUM DIHYDRATE

SMILES

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

InChI

InChIKey=JFWLFLLRLZSBRA-UHFFFAOYSA-N
InChI=1S/C6H14N2O2.2H2O/c1-8(2,3)7-5-4-6(9)10;;/h7H,4-5H2,1-3H3;2*1H2

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C6H14N2O2
Molecular Weight 146.1878
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: O75936
Gene ID: 8424.0
Gene Symbol: BBOX1
Target Organism: Homo sapiens (Human)
16.0 µM [Ki]
Target ID: O76082
Gene ID: 6584.0
Gene Symbol: SLC22A5
Target Organism: Homo sapiens (Human)
41.0 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Effect of 3-(2,2,2-trimethylhydrazinium) propionate, gamma-butyrobetaine hydroxylase inhibitor, on isoproterenol-induced mitochondrial dysfunction.
1989 Apr
The use of partial fatty acid oxidation inhibitors for metabolic therapy of angina pectoris and heart failure.
2002 Nov
The carnitine transporter SLC22A5 is not a general drug transporter, but it efficiently translocates mildronate.
2009 Feb
Patents

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
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
Created
by admin
on Fri Jun 25 21:08:59 UTC 2021
Edited
by admin
on Fri Jun 25 21:08:59 UTC 2021
Record UNII
22DC15W645
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MELDONIUM DIHYDRATE
WHO-DD  
Common Name English
1,1,1-TRIMETHYL-2-(2-CARBOXYETHYL)HYDRAZINE ZWITTERION DIHYDRATE
Common Name English
MILDRONATE DIHYDRATE
Common Name English
HYDRAZINIUM, 2-(2-CARBOXYETHYL)-1,1,1-TRIMETHYL-, INNER SALT, HYDRATE (1:2)
Systematic Name English
MELDONIUM DIHYDRATE [EP MONOGRAPH]
Common Name English
HYDRAZINIUM, 2-(2-CARBOXYETHYL)-1,1,1-TRIMETHYL-, INNER SALT, DIHYDRATE
Common Name English
3-(2,2,2-TRIMETHYLHYDRAZINIUM)PROPIONATE DIHYDRATE
Common Name English
MELDONIUM DIHYDRATE [WHO-DD]
Common Name English
Code System Code Type Description
CAS
86426-17-7
Created by admin on Fri Jun 25 21:08:59 UTC 2021 , Edited by admin on Fri Jun 25 21:08:59 UTC 2021
PRIMARY
FDA UNII
22DC15W645
Created by admin on Fri Jun 25 21:08:59 UTC 2021 , Edited by admin on Fri Jun 25 21:08:59 UTC 2021
PRIMARY
EVMPD
SUB34941
Created by admin on Fri Jun 25 21:08:59 UTC 2021 , Edited by admin on Fri Jun 25 21:08:59 UTC 2021
PRIMARY
PUBCHEM
6918082
Created by admin on Fri Jun 25 21:08:59 UTC 2021 , Edited by admin on Fri Jun 25 21:08:59 UTC 2021
PRIMARY
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IMPURITY -> PARENT
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ACTIVE MOIETY