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MedKoo Cat#: 596518 | Name: Melevodopa

Description:

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

Melevodopa is an Anti-Dyskinesia Agent.

Chemical Structure

Melevodopa
Melevodopa
CAS#7101-51-1 (free base)

Theoretical Analysis

MedKoo Cat#: 596518

Name: Melevodopa

CAS#: 7101-51-1 (free base)

Chemical Formula: C10H13NO4

Exact Mass: 211.0845

Molecular Weight: 211.22

Elemental Analysis: C, 56.87; H, 6.20; N, 6.63; O, 30.30

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Related CAS #
1421-65-4 (HCl) 7101-51-1 (free base)
Synonym
Melevodopa; L-Dopa methyl ester; Levodopa methyl ester; BRN 3056415; BRN-3056415; BRN3056415;
IUPAC/Chemical Name
methyl (S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate
InChi Key
XBBDACCLCFWBSI-ZETCQYMHSA-N
InChi Code
InChI=1S/C10H13NO4/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/t7-/m0/s1
SMILES Code
N[C@@H](CC1=CC=C(O)C(O)=C1)C(OC)=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
Soluble in DMSO
Shelf Life
>2 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
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Melevodopa 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/

Preparing Stock Solutions

The following data is based on the product molecular weight 211.22 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.

Recalculate based on batch purity %
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: Stocchi F, Vacca L, Grassini P, Pawsey S, Whale H, Marconi S, Torti M. L-Dopa Pharmacokinetic Profile with Effervescent Melevodopa/Carbidopa versus Standard-Release Levodopa/Carbidopa Tablets in Parkinson's Disease: A Randomised Study. Parkinsons Dis. 2015;2015:369465. doi: 10.1155/2015/369465. Epub 2015 Jun 10. PubMed PMID: 26171276; PubMed Central PMCID: PMC4478358. 3: Fasano A, Bove F, Gabrielli M, Ragazzoni E, Fortuna S, Tortora A, Zocco MA, Marconi S, Gasbarrini A, Bentivoglio AR. Liquid melevodopa versus standard levodopa in patients with Parkinson disease and small intestinal bacterial overgrowth. Clin Neuropharmacol. 2014 Jul-Aug;37(4):91-5. doi: 10.1097/WNF.0000000000000034. PubMed PMID: 24992085. 4: Marin C, Bonastre M, Mengod G, Cortés R, Giralt A, Obeso JA, Schapira AH. Early L-dopa, but not pramipexole, restores basal ganglia activity in partially 6-OHDA-lesioned rats. Neurobiol Dis. 2014 Apr;64:36-47. doi: 10.1016/j.nbd.2013.12.009. Epub 2013 Dec 24. PubMed PMID: 24370700. 5: 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. 6: 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. PubMed PMID: 23774688. 7: Yang X, Zheng R, Cai Y, Liao M, Yuan W, Liu Z. Controlled-release levodopa methyl ester/benserazide-loaded nanoparticles ameliorate levodopa-induced dyskinesia in rats. Int J Nanomedicine. 2012;7:2077-86. doi: 10.2147/IJN.S30463. Epub 2012 Apr 19. PubMed PMID: 22619544; PubMed Central PMCID: PMC3356186. 8: Li R, Liang T, Li Y, Jiang W, Huang R. Effects of l-dopa methyl ester on visual cortex injury induced by amblyopia and its underlying mechanism. Neurosci Lett. 2012 Feb 6;508(2):95-100. doi: 10.1016/j.neulet.2011.12.026. Epub 2011 Dec 22. PubMed PMID: 22206838. 9: 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. PubMed PMID: 21835223. 10: Bosco D, Plastino M, Bosco F, Fava A, Rotondo A. Daily motor performance after switching levodopa to melevodopa: an open-label on advanced Parkinson's disease with "delayed-on" and/or"wearing-off". Minerva Med. 2011 Apr;102(2):125-32. PubMed PMID: 21483399. 11: 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. 12: 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. 13: Stocchi F, Marconi S. Factors associated with motor fluctuations and dyskinesia in Parkinson Disease: potential role of a new melevodopa plus carbidopa formulation (Sirio). Clin Neuropharmacol. 2010 Jul;33(4):198-203. doi: 10.1097/WNF.0b013e3181de8924. Review. PubMed PMID: 20414107. 14: Minelli A, Conte C, Prudenzi E, Cacciatore I, Cornacchia C, Taha E, Pinnen F. N-acetyl-L-methionyl-L-Dopa-methyl ester as a dual acting drug that relieves L-Dopa-induced oxidative toxicity. Free Radic Biol Med. 2010 Jul 1;49(1):31-9. doi: 10.1016/j.freeradbiomed.2010.03.011. Epub 2010 Mar 20. PubMed PMID: 20307650. 15: Antonini A, Chaudhuri KR, Martinez-Martin P, Odin P. Oral and infusion levodopa-based strategies for managing motor complications in patients with Parkinson's disease. CNS Drugs. 2010 Feb;24(2):119-29. doi: 10.2165/11310940-000000000-00000. Review. PubMed PMID: 20088619. 16: Singh V, Somvanshi P. Homology modeling of adenosine A2A receptor and molecular docking for exploration of appropriate potent antagonists for treatment of Parkinson's disease. Curr Aging Sci. 2009 Jul;2(2):127-34. PubMed PMID: 20021407. 17: Zangaglia R, Stocchi F, Sciarretta M, Antonini A, Mancini F, Guidi M, Martignoni E, Pacchetti C. Clinical experiences with levodopa methylester (melevodopa) in patients with Parkinson disease experiencing motor fluctuations: an open-label observational study. Clin Neuropharmacol. 2010 Mar-Apr;33(2):61-6. doi: 10.1097/WNF.0b013e3181c5e60c. PubMed PMID: 19935405. 18: Itoh S, Oo C. A feasibility study of differential delivery of levodopa ester and benserazide using site-specific intestinal loops in rats. J Pharm Sci. 2010 Jan;99(1):227-33. doi: 10.1002/jps.21822. PubMed PMID: 19455628. 19: McCairn KW, Turner RS. Deep brain stimulation of the globus pallidus internus in the parkinsonian primate: local entrainment and suppression of low-frequency oscillations. J Neurophysiol. 2009 Apr;101(4):1941-60. doi: 10.1152/jn.91092.2008. Epub 2009 Jan 21. PubMed PMID: 19164104; PubMed Central PMCID: PMC3350155. 20: Domino EF, Ni L. Biperiden enhances L-DOPA methyl ester and dopamine D(l) receptor agonist SKF-82958 but antagonizes D(2)/D(3) receptor agonist rotigotine antihemiparkinsonian actions. Eur J Pharmacol. 2008 Dec 3;599(1-3):81-5. doi: 10.1016/j.ejphar.2008.09.028. Epub 2008 Sep 30. PubMed PMID: 18851961.