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Chemical Compound Review

Dopaflex     (2S)-2-amino-3-(3,4- dihydroxyphenyl)propan...

Synonyms: Larodopa, levodopa, Levopa, Dopar, Dopa, ...
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Disease relevance of L-dopa


Psychiatry related information on L-dopa


High impact information on L-dopa

  • L-Dopa, then, appears to have an action in animals with selective lesions of the substantia nigra pars compacta produced by MPTP that is distinctly different from its effects in the normal monkey [11].
  • We examined the effect of L-Dopa, after peripheral L-amino acid decarboxylase inhibition, on sympathetic nerve activity (SNA) and blood pressure in spontaneously hypertensive rats (SHR) and in normotensive control rats [12].
  • To ascertain the source of the catecholamine, we examined postnatal TH-null albino mice that lack tyrosinase, another enzyme that converts tyrosine to L-Dopa but does so during melanin synthesis [13].
  • L-Dopa therapy reversed the oculomotor symptoms in these monkeys, as well as the decrease of lCMRGlc in the frontal eye fields and the paralamellar mediodorsal thalamus [14].
  • Although the biomarkers L-Dopa decarboxylase, bombesin, carcinoembryonic antigen, and neurotensin were detectable in SCLC-22H, they were undetectable or low in SCLC-21H [15].

Chemical compound and disease context of L-dopa


Biological context of L-dopa

  • CONCLUSIONS: L-Dopa may influence the responsiveness of the parkinsonian brain as assessed by frontal somatosensory evoked potentials [19].
  • The main macrophage nitrating agent was shown to be peroxynitrite derived because parasite nitration occurred in the virtual absence of polymorphonuclear cells (monitored as peroxidase activity) and was accompanied by protein hydroxylation (monitored as 3-hydroxytyrosine levels) [20].
  • Given the likely importance of Arc in the regulation of cytoskeleton during synaptic plasticity, its upregulation supports the hypothesis that a relationship exists between cytoskeletal modifications and the longlasting action of chronically administrated L-Dopa [21].
  • A number of these derivatives effectively prevent the metabolism of L-Dopa prior to and/or during the absorption process, resulting in a significantly better bioavailability of the drug [22].
  • In the blood of rats and mice, 1 functions as a prodrug to release L-Dopa by hydrolysis [23].

Anatomical context of L-dopa


Associations of L-dopa with other chemical compounds

  • Papaverine, 150 mg BID for 2 weeks, a dose which produced marked clinical impairment in Parkinsonian patients taking L-Dopa, failed to alter L-Dopa-stimulated GH secretion or L-Dopa inhibited PRL secretion in 6 normal volunteers [29].
  • This carbamate codrug provides adequate stability [t(1/2) = 12.1 h (pH 1.2); 1.4 h (pH 5.0); 1.1 h (pH 7.4)] against chemical hydrolysis but rapidly hydrolyzes to L-Dopa and entacapone in liver homogenate (t(1/2) = 7 min; pH 7.4) at 37 degrees C. The therapeutical potential of this novel codrug is discussed [30].
  • Simultaneous injection of L-Dopa and metyrapone resulted in a marked increase in plasma ACTH from 93 +/- 18 pg/ml to 432 +/- 80 pg/ml, whereas plasma 11-deoxycortisol increased from 1.5 +/- 0.2 mug/100 ml to 14.6 +/- 1.0 mug/100 ml 90 min after treatment [26].
  • The most striking difference was a rise in 8-OHG in PD substantia nigra (p = 0.0002); rises in other base oxidation/deamination products were not evident, showing that elevation in 8-OHG is unlikely to be due to peroxynitrite (ONOO-) or hydroxyl radicals (OH.), or to be a prooxidant effect of treatment with L-Dopa [31].
  • Catecholamines (CA) were studied in peripheral human lymphocytes, as well as in the supernatants, after incubation with L-tyrosine and L-dihydroxyphenylalanine (L-Dopa) for 1 h [32].

Gene context of L-dopa


Analytical, diagnostic and therapeutic context of L-dopa


  1. L-Dopa methyl ester: prolongation of survival of neuroblastoma-bearing mice after treatment. Wick, M.M. Science (1978) [Pubmed]
  2. Treatment of cirrhotic hepatic encephalopathy with L-dopa. A controlled trial. Michel, H., Solere, M., Granier, P., Cauvet, G., Bali, J.P., Pons, F., Bellet-Hermann, H. Gastroenterology (1980) [Pubmed]
  3. Parkinson's disease: prospects for improved drug therapy. Hagan, J.J., Middlemiss, D.N., Sharpe, P.C., Poste, G.H. Trends Pharmacol. Sci. (1997) [Pubmed]
  4. Activities of L-dopa decarboxylase and diamine oxidase (histaminase) in human lung cancers and decarboxylase as a marker for small (oat) cell cancer in cell culture. Baylin, S.B., Abeloff, M.D., Goodwin, G., Carney, D.N., Gazdar, A.F. Cancer Res. (1980) [Pubmed]
  5. L-Dopa stimulates expression of the antioxidant enzyme NAD(P)H:quinone oxidoreductase (NQO) in cultured astroglial cells. van Muiswinkel, F.L., Riemers, F.M., Peters, G.J., LaFleur, M.V., Siegel, D., Jongenelen, C.A., Drukarch, B. Free Radic. Biol. Med. (2000) [Pubmed]
  6. Dopamine D2 receptor imaging with SPECT: studies in different neuropsychiatric disorders. Brücke, T., Podreka, I., Angelberger, P., Wenger, S., Topitz, A., Küfferle, B., Müller, C., Deecke, L. J. Cereb. Blood Flow Metab. (1991) [Pubmed]
  7. Locomotor stimulation by L-dopa: relative importance of noradrenaline receptor activation. Andén, N.E., Strömbom, U., Svensson, T.H. Psychopharmacology (Berl.) (1977) [Pubmed]
  8. Dementia with Lewy bodies: prevalence, clinical spectrum and natural history. Ransmayr, G. J. Neural Transm. Suppl. (2000) [Pubmed]
  9. The benzamide tiapride: treatment of extrapyramidal motor and other clinical syndromes. Dose, M., Lange, H.W. Pharmacopsychiatry (2000) [Pubmed]
  10. Melatonin in humans physiological and clinical studies. Wetterberg, L. J. Neural Transm. Suppl. (1978) [Pubmed]
  11. Local cerebral metabolic effects of L-dopa therapy in 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced parkinsonism in monkeys. Porrino, L.J., Burns, R.S., Crane, A.M., Palombo, E., Kopin, I.J., Sokoloff, L. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  12. Effect of l-dopa on sympathetic nerve activity and blood pressure in the spontaneously hypertensive rat. Judy, W.V., Watanabe, A.M., Henry, D.P., Besch, H.R., Aprison, B. Circ. Res. (1978) [Pubmed]
  13. Catecholamine synthesis is mediated by tyrosinase in the absence of tyrosine hydroxylase. Rios, M., Habecker, B., Sasaoka, T., Eisenhofer, G., Tian, H., Landis, S., Chikaraishi, D., Roffler-Tarlov, S. J. Neurosci. (1999) [Pubmed]
  14. Metabolic mapping of the oculomotor system in MPTP-induced parkinsonian monkeys. Ho, V.W., Porrino, L.J., Crane, A.M., Burns, R.S., Kopin, I.J., Sokoloff, L. Ann. Neurol. (1988) [Pubmed]
  15. Characterization of two cell lines with distinct phenotypes established from a patient with small cell lung cancer. Bepler, G., Jaques, G., Havemann, K., Koehler, A., Johnson, B.E., Gazdar, A.F. Cancer Res. (1987) [Pubmed]
  16. Iodine-123-iodobenzamide binding in parkinsonism: reduction by dopamine agonists but not L-Dopa. Schwarz, J., Oertel, W.H., Tatsch, K. J. Nucl. Med. (1996) [Pubmed]
  17. Amantadine increases aromatic L-amino acid decarboxylase mRNA in PC12 cells. Li, X.M., Juorio, A.V., Qi, J., Boulton, A.A. J. Neurosci. Res. (1998) [Pubmed]
  18. Pharmacological evidence for cerebral dopamine receptor blockade by metoclopramide in rodents. Dolphin, A., Jenner, P., Marsden, C.D., Pycock, C., Tarsy, D. Psychopharmacologia. (1975) [Pubmed]
  19. Time course of frontal somatosensory evoked potentials. Relation to L-dopa plasma levels and motor performance in PD. Ulivelli, M., Rossi, S., Pasqualetti, P., Rossini, P.M., Ghiglieri, O., Passero, S., Battistini, N. Neurology (1999) [Pubmed]
  20. Role of peroxynitrite in macrophage microbicidal mechanisms in vivo revealed by protein nitration and hydroxylation. Linares, E., Giorgio, S., Mortara, R.A., Santos, C.X., Yamada, A.T., Augusto, O. Free Radic. Biol. Med. (2001) [Pubmed]
  21. Coordinated and spatial upregulation of arc in striatonigral neurons correlates with L-dopa-induced behavioral sensitization in dyskinetic rats. Sgambato-Faure, V., Buggia, V., Gilbert, F., Lévesque, D., Benabid, A.L., Berger, F. J. Neuropathol. Exp. Neurol. (2005) [Pubmed]
  22. Improved delivery through biological membranes. 4. Prodrugs of L-dopa. Bodor, N., Sloan, K.B., Higuchi, T., Sasahara, K. J. Med. Chem. (1977) [Pubmed]
  23. A lymphotropic prodrug of L-dopa: synthesis, pharmacological properties, and pharmacokinetic behavior of 1,3-dihexadecanoyl-2-[(S)-2-amino-3-(3,4-dihydroxyphenyl)prop anoyl] propane-1,2,3-triol. Garzon-Aburbeh, A., Poupaert, J.H., Claesen, M., Dumont, P. J. Med. Chem. (1986) [Pubmed]
  24. Systemic sulpiride modulates striatal blood flow: relationships to spatial working memory and planning. Mehta, M.A., McGowan, S.W., Lawrence, A.D., Aitken, M.R., Montgomery, A.J., Grasby, P.M. Neuroimage (2003) [Pubmed]
  25. New methodology for assessment of the Langerhans cell network. Halliday, G.M., McArdle, J.P., Knight, B.A., Muller, H.K. J. Pathol. (1986) [Pubmed]
  26. Potentiation of the ACTH response to metyrapone by L-dopa in the monkey. Hsu, T.H., Hsu, C.K., Gann, D.S. Endocrinology (1976) [Pubmed]
  27. Use of radiolabeled monofluoromethyl-Dopa to define the subunit structure of human L-Dopa decarboxylase. Maneckjee, R., Baylin, S.B. Biochemistry (1983) [Pubmed]
  28. L-tyrosine and nicotine induce synthesis of L-Dopa and norepinephrine in human lymphocytes. Musso, N.R., Brenci, S., Indiveri, F., Lotti, G. J. Neuroimmunol. (1997) [Pubmed]
  29. Failure of papaverine to alter L-dopa-influenced GH and PRL secretion. Cooper, D.S., Jacobs, L.S. J. Clin. Endocrinol. Metab. (1977) [Pubmed]
  30. Design and synthesis of a novel L-dopa-entacapone codrug. Leppänen, J., Huuskonen, J., Nevalainen, T., Gynther, J., Taipale, H., Järvinen, T. J. Med. Chem. (2002) [Pubmed]
  31. Oxidative DNA damage in the parkinsonian brain: an apparent selective increase in 8-hydroxyguanine levels in substantia nigra. Alam, Z.I., Jenner, A., Daniel, S.E., Lees, A.J., Cairns, N., Marsden, C.D., Jenner, P., Halliwell, B. J. Neurochem. (1997) [Pubmed]
  32. Acetylcholine-induced, calcium-dependent norepinephrine outflow from peripheral human lymphocytes. Musso, N.R., Brenci, S., Indiveri, F., Lotti, G. J. Neuroimmunol. (1998) [Pubmed]
  33. Simultaneous MAO-B and COMT inhibition in L-Dopa-treated patients with Parkinson's disease. Lyytinen, J., Kaakkola, S., Ahtila, S., Tuomainen, P., Teräväinen, H. Mov. Disord. (1997) [Pubmed]
  34. Prolactin response as an index of dopaminergic receptor function in Parkinson's disease. Correlation with clinical findings and therapeutic response. Agnoli, A., Baldassarre, M., Ruggieri, S., Falaschi, P., Urso, R.D., Rocco, A. J. Neural Transm. (1981) [Pubmed]
  35. Dynamic evaluation of growth hormone (GH) and prolactin (hPRL) secretion in active acromegaly with high and low GH output. Tolis, G., Kovacs, L., Friesen, H., Martin, J.B. Acta Endocrinol. (1975) [Pubmed]
  36. Identification and characterization of a novel form of the human L-dopa decarboxylase mRNA. Vassilacopoulou, D., Sideris, D.C., Vassiliou, A.G., Fragoulis, E.G. Neurochem. Res. (2004) [Pubmed]
  37. [125I]EGF binding in basal ganglia of patients with Parkinson's disease and progressive supranuclear palsy and in MPTP-treated monkeys. Villares, J., Faucheux, B., Herrero, M.T., Obeso, J.A., Duyckaerts, C., Hauw, J.J., Agid, Y., Hirsch, E.C. Exp. Neurol. (1998) [Pubmed]
  38. L-Dopa and dopamine-producing gene cassettes for gene therapy approaches to Parkinson's disease. Moffat, M., Harmon, S., Haycock, J., O'Malley, K.L. Exp. Neurol. (1997) [Pubmed]
  39. Alterations of striatal dopamine D2 receptors contribute to deteriorated response to L-dopa in Parkinson's disease: a [123I]-IBZM SPET study. Pizzolato, G., Chierichetti, F., Rossato, A., Cagnin, A., Fabbri, M., Dam, M., Ferlin, G., Battistin, L. J. Neural Transm. Suppl. (1995) [Pubmed]
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