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Details

Stereochemistry ACHIRAL
Molecular Formula C6H14N2O2.2H2O
Molecular Weight 182.2181
Optical Activity NONE
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MELDONIUM DIHYDRATE

SMILES

O.O.C[N+](C)(C)NCCC([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 146.1876
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 1
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

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Gamma-butyrobetaine dioxygenase
2
Target ID: O75936
Gene ID: 8424.0
Gene Symbol: BBOX1
Target Organism: Homo sapiens (Human)
Substrate
661
 16.0 µM [Ki]
Solute carrier family 22 member 5
3
Target ID: O76082
Gene ID: 6584.0
Gene Symbol: SLC22A5
Target Organism: Homo sapiens (Human)
Inhibitor
8504
 41.0 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Approved
8583
Unknown

Approved Use

Unknown
Palliative
Not Provided
511
Unknown

Approved Use

Unknown
Palliative
Phase II
1147
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
11 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20116348/
250 mg single, intravenous
dose: 250 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
22.71 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20116348/
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
39.3 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20116348/
1000 mg single, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
25.5 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20116348/
500 mg 2 times / day steady-state, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
5.89 mg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21679246/
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
13.75 mg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21679246/
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
30.38 mg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21679246/
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
35.5 mg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21679246/
1250 mg single, oral
dose: 1250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
46.27 mg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21679246/
1500 mg single, oral
dose: 1500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
23.97 mg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21679246/
500 mg 3 times / day steady-state, oral
dose: 500 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
22.25 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20116348/
250 mg single, intravenous
dose: 250 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
47.85 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20116348/
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
85.4 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20116348/
1000 mg single, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
76.26 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20116348/
500 mg 2 times / day steady-state, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
33.57 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21679246/
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
70.79 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21679246/
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
135.4 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21679246/
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
163.76 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21679246/
1250 mg single, oral
dose: 1250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
206.45 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21679246/
1500 mg single, oral
dose: 1500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
281.12 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21679246/
500 mg 3 times / day steady-state, oral
dose: 500 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5.56 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20116348/
250 mg single, intravenous
dose: 250 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
6.46 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20116348/
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
6.55 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20116348/
1000 mg single, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
15.34 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20116348/
500 mg 2 times / day steady-state, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
3.61 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21679246/
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
5.28 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21679246/
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
6.09 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21679246/
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
6.07 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21679246/
1250 mg single, oral
dose: 1250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
6.58 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21679246/
1500 mg single, oral
dose: 1500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
14.6 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21679246/
500 mg 3 times / day steady-state, oral
dose: 500 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
MELDONIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
2 g 1 times / day steady-state, oral
Highest studied dose
Dose: 2 g, 1 times / day
Route: oral
Route: steady-state
Dose: 2 g, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/30328291/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/30328291/
Sources:
https://pubmed.ncbi.nlm.nih.gov/30328291/
500 mg 2 times / day steady-state, oral
Studied dose
Dose: 500 mg, 2 times / day
Route: oral
Route: steady-state
Dose: 500 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28213178/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/28213178/
Sources:
https://pubmed.ncbi.nlm.nih.gov/28213178/
PubMed

PubMed

TitleDatePubMed
The carnitine transporter SLC22A5 is not a general drug transporter, but it efficiently translocates mildronate.
2009-02
The use of partial fatty acid oxidation inhibitors for metabolic therapy of angina pectoris and heart failure.
2002-11
Effect of 3-(2,2,2-trimethylhydrazinium) propionate, gamma-butyrobetaine hydroxylase inhibitor, on isoproterenol-induced mitochondrial dysfunction.
1989-04
Patents

Patents

8889902
2
WO2010151095A1
2

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
Created
by admin
on Mon Mar 31 23:04:59 GMT 2025
Edited
by admin
on Mon Mar 31 23:04:59 GMT 2025
Record UNII
22DC15W645
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
1,1,1-TRIMETHYL-2-(2-CARBOXYETHYL)HYDRAZINE ZWITTERION DIHYDRATE
Preferred Name English
MELDONIUM DIHYDRATE
WHO-DD  
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 Mon Mar 31 23:04:59 GMT 2025 , Edited by admin on Mon Mar 31 23:04:59 GMT 2025
PRIMARY
SMS_ID
100000128166
Created by admin on Mon Mar 31 23:04:59 GMT 2025 , Edited by admin on Mon Mar 31 23:04:59 GMT 2025
PRIMARY
FDA UNII
22DC15W645
Created by admin on Mon Mar 31 23:04:59 GMT 2025 , Edited by admin on Mon Mar 31 23:04:59 GMT 2025
PRIMARY
EVMPD
SUB34941
Created by admin on Mon Mar 31 23:04:59 GMT 2025 , Edited by admin on Mon Mar 31 23:04:59 GMT 2025
PRIMARY
PUBCHEM
6918082
Created by admin on Mon Mar 31 23:04:59 GMT 2025 , Edited by admin on Mon Mar 31 23:04:59 GMT 2025
PRIMARY
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