Meldonium | CAS#76144-81-5 | Biochemical

MedKoo Cat#: 577100 | Name: Meldonium

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Meldonium is a structural analog of gamma-butyrobetaine used to treat coronary artery disease

Chemical Structure

Meldonium

CAS#76144-81-5 (free)

Theoretical Analysis

MedKoo Cat#: 577100

Name: Meldonium

CAS#: 76144-81-5 (free)

Chemical Formula: C6H18N2O4

Exact Mass: 182.1267

Molecular Weight: 182.22

Elemental Analysis: C, 39.55; H, 9.96; N, 15.37; O, 35.12

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

86426-17-7 (dihydrate) 76144-81-5 (free) 1608503-17-8 (hydrate) 839675-63-7 (phoshate) 839675-65-9 (fumarate)

Synonym

Meldonium dihydrate; MET-88; MET 88; MET88

IUPAC/Chemical Name

Hydrazinium, 2-(2-carboxyethyl)-1,1,1-trimethyl-, inner salt

InChi Key

PVBQYTCFVWZSJK-UHFFFAOYSA-N

InChi Code

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

SMILES Code

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

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Mildronate (Meldonium, MET-88, Quaterin) is an inhibitor of biosynthesis of L-carnitine by gamma-butyrobetaine (GBB) hydroxylase and as a competitive inhibitor of renal carnitine reabsorption.

In vitro activity:

The effect of meldonium was assessed on immortalized striatal cell lines expressing wild-type (STHdhQ7/7) or mutant full-length huntingtin protein. As reported in Figure 1a,b a concentration of meldonium ranging from 25 to 100 µM did not affect cell viability in both striatal cell lines. The mHtt bearing 111 glutamines in the N-terminal domain (Q111/Q111) can promote neuronal cell death depending on the culture conditions. In Figure 1c, we demonstrate that Q111/Q111 expression caused cytotoxicity under serum-deprived conditions, while STHdhQ7/7 cells were resistant to serum deprivation. The effect of meldonium on striatal cells after serum deprivation was examined at different concentrations and time. The STHdhQ111/Q111 cell viability following serum deprivation was improved by meldonium (Figure 1d,e). Since researchers have demonstrated that both soluble forms of mHtt aggregates and insoluble mHtt deposits engender neurotoxicity, experiments were carried out to test the hypothesis that meldonium can affect STHdhQ111/111 cell viability via a reduction of mHtt aggregates. Interestingly, western blot analysis demonstrated that 50 μM meldonium significantly diminished (p < 0.01) the high molecular weight of mHtt aggregates in the STHdhQ111/111 cell line (Figure 2). This supports the idea that meldonium’s protective role could be related to an ability to modulate mHtt aggregation or degradation. Reference: J Cell Physiol. 2019 Jun;234(6):9233-9246. https://doi.org/10.1002/jcp.27602

In vivo activity:

Meldonium is an anti-ischemic agent that shifts energy production from fatty acid oxidation to less oxygen-consuming glycolysis. The effects of a four-week meldonium pre-treatment (300 mg/kg b.m./day) on acute renal I/R was investigated in male rats (Wistar strain). The results showed that meldonium decreased animal body mass gain, food and water intake, and carnitine, glucose, and lactic acid kidney content. In kidneys of animals subjected to I/R, meldonium increased phosphorylation of mitogen-activated protein kinase p38 and protein kinase B, and increased the expression of nuclear factor erythroid 2-related factor 2 and haeme oxygenase 1, causing manganese superoxide dismutase expression and activity to increase, as well as lipid peroxidation, cooper-zinc superoxide dismutase, glutathione peroxidase, and glutathione reductase activities to decrease. By decreasing the kidney Bax/Bcl2 expression ratio and kidney and serum high mobility group box 1 protein content, meldonium reduced apoptotic and necrotic events in I/R, as confirmed by kidney histology. Meldonium increased adrenal noradrenaline content and serum, adrenal, hepatic, and renal ascorbic/dehydroascorbic acid ratio, which caused complex changes in renal lipidomics. Taken together, the results have confirmed that meldonium pre-treatment protects against I/R-induced oxidative stress and apoptosis/necrosis. Reference: Int J Mol Sci. 2019 Nov 15;20(22):5747. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/31731785/

	Solvent	mg/mL	mM
Solubility
	Ethanol	29.0	197.02
	Water	29.0	197.02

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 182.22 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Di Cristo F, Finicelli M, Digilio FA, Paladino S, Valentino A, Scialò F, D'Apolito M, Saturnino C, Galderisi U, Giordano A, Melone MAB, Peluso G. Meldonium improves Huntington's disease mitochondrial dysfunction by restoring peroxisome proliferator-activated receptor γ coactivator 1α expression. J Cell Physiol. 2019 Jun;234(6):9233-9246. doi: 10.1002/jcp.27602. Epub 2018 Oct 26. PMID: 30362565. 2. Đurašević S, Stojković M, Bogdanović L, Pavlović S, Borković-Mitić S, Grigorov I, Bogojević D, Jasnić N, Tosti T, Đurović S, Đorđević J, Todorović Z. The Effects of Meldonium on the Renal Acute Ischemia/Reperfusion Injury in Rats. Int J Mol Sci. 2019 Nov 15;20(22):5747. doi: 10.3390/ijms20225747. PMID: 31731785; PMCID: PMC6888683. 3. Liepinsh E, Vilskersts R, Skapare E, Svalbe B, Kuka J, Cirule H, Pugovics O, Kalvinsh I, Dambrova M. Mildronate decreases carnitine availability and up-regulates glucose uptake and related gene expression in the mouse heart. Life Sci. 2008 Oct 24;83(17-18):613-9. doi: 10.1016/j.lfs.2008.08.008. Epub 2008 Sep 3. PMID: 18801379.

In vitro protocol:

In vivo protocol:

1. Đurašević S, Stojković M, Bogdanović L, Pavlović S, Borković-Mitić S, Grigorov I, Bogojević D, Jasnić N, Tosti T, Đurović S, Đorđević J, Todorović Z. The Effects of Meldonium on the Renal Acute Ischemia/Reperfusion Injury in Rats. Int J Mol Sci. 2019 Nov 15;20(22):5747. doi: 10.3390/ijms20225747. PMID: 31731785; PMCID: PMC6888683. 2. Liepinsh E, Vilskersts R, Skapare E, Svalbe B, Kuka J, Cirule H, Pugovics O, Kalvinsh I, Dambrova M. Mildronate decreases carnitine availability and up-regulates glucose uptake and related gene expression in the mouse heart. Life Sci. 2008 Oct 24;83(17-18):613-9. doi: 10.1016/j.lfs.2008.08.008. Epub 2008 Sep 3. PMID: 18801379.

1: Meneses ES, Arguelho ML, Alves JP. Electroreduction of the antifouling agent TCMTB and its electroanalytical determination in tannery wastewaters. Talanta. 2005 Oct 15;67(4):682-5. doi: 10.1016/j.talanta.2005.01.058. Epub 2005 Jun 22. PubMed PMID: 18970225. 2: Manninen A, Auriola S, Vartiainen M, Liesivuori J, Turunen T, Pasanen M. Determination of urinary 2-mercaptobenzothiazole (2-MBT), the main metabolite of 2-(thiocyanomethylthio)benzothiazole (TCMTB) in humans and rats. Arch Toxicol. 1996;70(9):579-84. PubMed PMID: 8831908. 3: Nawrocki ST, Drake KD, Watson CF, Foster GD, Maier KJ. Comparative aquatic toxicity evaluation of 2-(thiocyanomethylthio)benzothiazole and selected degradation products using Ceriodaphnia dubia. Arch Environ Contam Toxicol. 2005 Apr;48(3):344-50. Epub 2005 Feb 15. PubMed PMID: 15750776. 4: Vyhnalkova R, Eisenberg A, van de Ven TG. Deactivation efficiency of stabilized bactericidal emulsions. Langmuir. 2011 Sep 20;27(18):11296-305. doi: 10.1021/la201112j. Epub 2011 Aug 22. PubMed PMID: 21823610. 5: Hinojosa Reyes L, Wróbel K, Wróbel K. Indirect extraction-spectrophotometric determination of 2-(thiocyanomethylthiol)benzothiazole in chrome tanning liquors after its breakdown to 2-mercaptobenzothiazole. Talanta. 2002 Mar 4;56(3):515-21. PubMed PMID: 18968524.

View History

Aceburic acid

MedKoo CAT#: 571489

CAS#: 26976-72-7