MELDONIUM

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H14N2O2
Molecular Weight	146.1876
Optical Activity	NONE
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

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

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28762906 | https://www.ncbi.nlm.nih.gov/pubmed/16007237 | https://www.ncbi.nlm.nih.gov/pubmed/26850121

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 Target	Pharmacology	Condition	Potency
Gamma-butyrobetaine dioxygenase 2 Target ID: O75936 Gene ID: 8424.0 Gene Symbol: BBOX1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/22765904	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) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11248709	Inhibitor 8504		41.0 µM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Chronic heart failure 21 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28762906	Palliative	Approved 8583	Unknown Approved Use Unknown
Type 2 diabetes mellitus 262 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28762906	Palliative	Not Provided 511	Unknown Approved Use Unknown
Acute ischemic stroke 19 Sources: https://clinicaltrials.gov/ct2/show/NCT01831011	Palliative	Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
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

Value	Dose	Analyte	Population
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

T_1/2

Value	Dose	Analyte	Population
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

Dose	Population	Adverse 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

Title	Date	PubMed
The carnitine transporter SLC22A5 is not a general drug transporter, but it efficiently translocates mildronate.	2009-02	18981167
The use of partial fatty acid oxidation inhibitors for metabolic therapy of angina pectoris and heart failure.	2002-11	12439634
Effect of 3-(2,2,2-trimethylhydrazinium) propionate, gamma-butyrobetaine hydroxylase inhibitor, on isoproterenol-induced mitochondrial dysfunction.	1989-04	2546223

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

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 18:22:46 GMT 2025` Edited by `admin` on `Mon Mar 31 18:22:46 GMT 2025`
Record UNII	73H7UDN6EC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MILDRONATE

Preferred Name

English

MELDONIUM

Official Name

English

3-(2,2,2-TRIMETHYLDIAZANIUMYL)PROPANOATE

Common Name

English

MELDONIUM [MART.]

Common Name

English

Meldonium [WHO-DD]

Common Name

English

MET-88

Code

English

QUATERINE

Brand Name

English

meldonium [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2079