Synonym
Melevodopa hydrochloride; ST 41769; ST-41769; ST41769; Methyl L-DOPA hydrochloride
IUPAC/Chemical Name
Alanine, 3-(3,4-dihydroxyphenyl)-, methyl ester, hydrochloride, l-
InChi Key
WFGNJLMSYIJWII-FJXQXJEOSA-N
InChi Code
InChI=1S/C10H13NO4.ClH/c1-15-10(14)7(11)4-6-2-3-8(12)9(13)5-6;/h2-3,5,7,12-13H,4,11H2,1H3;1H/t7-;/m0./s1
SMILES Code
N[C@@H](CC1=CC=C(O)C(O)=C1)C(OC)=O.[H]Cl
Purity
>97% (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
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Biological target:
Melevodopa hydrochloride is an Anti-Dyskinesia Agent.
In vitro activity:
Methyl-L-DOPA, an antihypertensive agent, has significant in vitro activity against a variety of atypical mycobacteria such as the Mycobacterium avium complex, M. scrofulaceum, M. xenopi and M. marinum, and rare pathogens like M. fortuitum. In the present investigation, the screening of the in vitro activity was further extended by testing the in vitro activity against a total of 53 different strains of mycobacteria, including 34 clinical isolates of both drug-sensitive and drug-resistant Mycobacterium tuberculosis. Most of the strains were inhibited at 10-25 microg/mL concentrations of the drug.
Reference: In Vivo. 2005 May-Jun;19(3):539-45. https://pubmed.ncbi.nlm.nih.gov/15875773/
In vivo activity:
The present study aimed to assess the potential anti-amblyopic effects of L-dopa methyl ester (LDME) on visual cortex area 17 in an amblyopic feline model induced by monocular vision deprivation. These findings suggested that LDME treatment could effectively increase DA and its metabolite contents, and restrain the apoptotic process, as well as elevate the c-fos expression in nerve cells of visual cortex area 17. Taken together, LDME might ameliorate the functional cytoarchitecture in visual cortex area 17 through mechanisms that elevate DA content and increase endogenous c-fos expression, as well as inhibit neuronal lesion in visual cortex tissue.
Reference: Gene. 2013 Sep 15;527(1):115-22. https://pubmed.ncbi.nlm.nih.gov/23774688/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
30.0 |
121.13 |
| DMSO |
20.0 |
80.75 |
| Ethanol |
25.0 |
100.94 |
| PBS (pH 7.2) |
10.0 |
40.38 |
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
247.68
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. Dutta NK, Mazumdar K, Dastidar SG, Chakrabarty AN, Shirataki Y, Motohashi N. In vitro and in vivo antimycobacterial activity of an antihypertensive agent methyl-L-DOPA. In Vivo. 2005 May-Jun;19(3):539-45. Erratum in: In Vivo. 2005 Jul-Aug;19(4):813. PMID: 15875773.
2. Hu M, Borchardt RT. Mechanism of L-alpha-methyldopa transport through a monolayer of polarized human intestinal epithelial cells (Caco-2). Pharm Res. 1990 Dec;7(12):1313-9. doi: 10.1023/a:1015906409585. PMID: 2095572.
3. Li R, Liang T, Chen Z, Zhang S, Lin X, Huang R. L-dopa methyl ester attenuates amblyopia-induced neuronal injury in visual cortex of amblyopic cat. Gene. 2013 Sep 15;527(1):115-22. doi: 10.1016/j.gene.2013.05.072. Epub 2013 Jun 14. Erratum in: Gene. 2021 Apr 20;777:145477. PMID: 23774688.
4. Ren T, Yang X, Wu N, Cai Y, Liu Z, Yuan W. Sustained-release formulation of levodopa methyl ester/benserazide for prolonged suppressing dyskinesia expression in 6-OHDA-leisoned rats. Neurosci Lett. 2011 Sep 15;502(2):117-22. doi: 10.1016/j.neulet.2011.07.042. Epub 2011 Aug 4. PMID: 21835223.
In vitro protocol:
1. Dutta NK, Mazumdar K, Dastidar SG, Chakrabarty AN, Shirataki Y, Motohashi N. In vitro and in vivo antimycobacterial activity of an antihypertensive agent methyl-L-DOPA. In Vivo. 2005 May-Jun;19(3):539-45. Erratum in: In Vivo. 2005 Jul-Aug;19(4):813. PMID: 15875773.
2. Hu M, Borchardt RT. Mechanism of L-alpha-methyldopa transport through a monolayer of polarized human intestinal epithelial cells (Caco-2). Pharm Res. 1990 Dec;7(12):1313-9. doi: 10.1023/a:1015906409585. PMID: 2095572.
In vivo protocol:
1. Li R, Liang T, Chen Z, Zhang S, Lin X, Huang R. L-dopa methyl ester attenuates amblyopia-induced neuronal injury in visual cortex of amblyopic cat. Gene. 2013 Sep 15;527(1):115-22. doi: 10.1016/j.gene.2013.05.072. Epub 2013 Jun 14. Erratum in: Gene. 2021 Apr 20;777:145477. PMID: 23774688.
2. Ren T, Yang X, Wu N, Cai Y, Liu Z, Yuan W. Sustained-release formulation of levodopa methyl ester/benserazide for prolonged suppressing dyskinesia expression in 6-OHDA-leisoned rats. Neurosci Lett. 2011 Sep 15;502(2):117-22. doi: 10.1016/j.neulet.2011.07.042. Epub 2011 Aug 4. PMID: 21835223.
1: Scaturro AL, De Caro V, Campisi G, Giannola LI. Potential transbuccal delivery of l-DOPA methylester prodrug: stability in the environment of the oral cavity and ability to cross the mucosal tissue. Drug Deliv. 2016 Sep;23(7):2355-2362. Epub 2014 Dec 23. PubMed PMID: 25533875.
2: Lee YH, Kim KH, Yoon IK, Lee KE, Chun IK, Rhie JY, Gwak HS. Pharmacokinetic evaluation of formulated levodopa methyl ester nasal delivery systems. Eur J Drug Metab Pharmacokinet. 2014 Dec;39(4):237-42. doi: 10.1007/s13318-013-0171-8. Epub 2013 Dec 21. PubMed PMID: 24363125.
3: Chun IK, Lee YH, Lee KE, Gwak HS. Design and evaluation of levodopa methyl ester intranasal delivery systems. J Parkinsons Dis. 2011;1(1):101-7. doi: 10.3233/JPD-2011-10011. PubMed PMID: 23939261.
4: Stocchi F, Zappia M, Dall'Armi V, Kulisevsky J, Lamberti P, Obeso JA; Melevodopa Plus Carbidopa Study Group. Melevodopa/carbidopa effervescent formulation in the treatment of motor fluctuations in advanced Parkinson's disease. Mov Disord. 2010 Sep 15;25(12):1881-7. doi: 10.1002/mds.23206. PubMed PMID: 20669296.
5: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2006 May;28(4):233-77. PubMed PMID: 16801985.
6: Geurts M, Hermans E, Maloteaux JM. Opposite modulation of regulators of G protein signalling-2 RGS2 and RGS4 expression by dopamine receptors in the rat striatum. Neurosci Lett. 2002 Nov 22;333(2):146-50. PubMed PMID: 12419501.
7: Greenamyre JT, Eller RV, Zhang Z, Ovadia A, Kurlan R, Gash DM. Antiparkinsonian effects of remacemide hydrochloride, a glutamate antagonist, in rodent and primate models of Parkinson's disease. Ann Neurol. 1994 Jun;35(6):655-61. PubMed PMID: 8210221.
8: Tabar J, Hashizume M, Cook CJ, Beart PM, Jackson DM. The effects on central dopamine function of chronic L-dopa (methyl ester hydrochloride) treatment of mice. Pharmacol Biochem Behav. 1989 May;33(1):139-46. PubMed PMID: 2789405.
