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Chemical Compound Review

Kynurenin     (2S)-2-amino-4-(2- aminophenyl)-4-oxo...

Synonyms: Quinurenine, L-kynurenine, Kynurenine, L-, SureCN20875, CHEMBL498416, ...
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Disease relevance of CCRIS 4425


Psychiatry related information on CCRIS 4425


High impact information on CCRIS 4425


Chemical compound and disease context of CCRIS 4425


Biological context of CCRIS 4425


Anatomical context of CCRIS 4425


Associations of CCRIS 4425 with other chemical compounds

  • After a 1-gm oral dose of LT, untreated EMS patients (n = 4) showed lower peak levels of LT and accentuated synthesis of L-kynurenine and quinolinic acid, compared with these values in corticosteroid-treated EMS patients (n = 2), who responded like normal subjects (n = 5) [15].
  • Neurochemical analysis confirmed that L-kynurenine with or without probenecid markedly increased concentrations of kynurenic acid in cerebral cortex of 7-day-old rats [17].
  • Elevated serum and CSF L-kynurenine concentrations also occurred and are consistent with activation of indoleamine-2,3-dioxygenase and increased substrate flux through the kynurenine pathway [19].
  • The specific activity of L-kynurenine and quinolinate in blood, brain and systemic tissues at equilibrium was then quantified by mass spectrometry and the results applied to a model of metabolism to differentiate the relative contributions of various metabolic precursors [20].
  • The enzyme kynurenine aminotransferase (KAT) catalyses the conversion of L-kynurenine to kynurenic acid [21].

Gene context of CCRIS 4425

  • During IFN-gamma therapy all 3 tumours showed a profound depletion in L-tryptophan and a corresponding rise in L-kynurenine [22].
  • Kynureninase (L-kynurenine hydrolase), a pyridoxal-5'-phosphate-(pyridoxal-P)-dependent enzyme, catalyses the cleavage of L-kynurenine and L-3-hydroxykynurenine into anthranilic and 3-hydroxyanthranilic acids, respectively [23].
  • Intracerebral administration of L-kynurenine decreases N-methyl-D-aspartate receptor-mediated production of cGMP in the cerebellum and hippocampus of unanaesthetized rats subjected to transcerebral microdialysis [24].
  • Untreated EMS patients, who had discontinued LT weeks to months prior to study, had significantly higher plasma levels of L-kynurenine and quinolinic acid than did corticosteroid-treated EMS patients (P less than 0.05), normal subjects (P less than 0.02), and asymptomatic users of LT (P less than 0.05) [15].
  • Mixing kynureninase with 0.5 mM L-kynurenine results in formation of a quinonoid intermediate, with lambdamax = 494 nm, within the dead time (ca. 2 ms) of the stopped-flow mixer [25].

Analytical, diagnostic and therapeutic context of CCRIS 4425


  1. Scleroderma, fasciitis, and eosinophilia associated with the ingestion of tryptophan. Silver, R.M., Heyes, M.P., Maize, J.C., Quearry, B., Vionnet-Fuasset, M., Sternberg, E.M. N. Engl. J. Med. (1990) [Pubmed]
  2. Mechanism of increases in L-kynurenine and quinolinic acid in renal insufficiency. Saito, K., Fujigaki, S., Heyes, M.P., Shibata, K., Takemura, M., Fujii, H., Wada, H., Noma, A., Seishima, M. Am. J. Physiol. Renal Physiol. (2000) [Pubmed]
  3. Reaction of Pseudomonas fluorescens kynureninase with beta-benzoyl-L-alanine: detection of a new reaction intermediate and a change in rate-determining step. Gawandi, V.B., Liskey, D., Lima, S., Phillips, R.S. Biochemistry (2004) [Pubmed]
  4. Mechanism of delayed increases in kynurenine pathway metabolism in damaged brain regions following transient cerebral ischemia. Saito, K., Nowak, T.S., Markey, S.P., Heyes, M.P. J. Neurochem. (1993) [Pubmed]
  5. Quinolinic acid and kynurenine pathway metabolism in inflammatory and non-inflammatory neurological disease. Heyes, M.P., Saito, K., Crowley, J.S., Davis, L.E., Demitrack, M.A., Der, M., Dilling, L.A., Elia, J., Kruesi, M.J., Lackner, A. Brain (1992) [Pubmed]
  6. Tryptophan-derived catabolites are responsible for inhibition of T and natural killer cell proliferation induced by indoleamine 2,3-dioxygenase. Frumento, G., Rotondo, R., Tonetti, M., Damonte, G., Benatti, U., Ferrara, G.B. J. Exp. Med. (2002) [Pubmed]
  7. The tryptophan catabolite L-kynurenine inhibits the surface expression of NKp46- and NKG2D-activating receptors and regulates NK-cell function. Chiesa, M.D., Carlomagno, S., Frumento, G., Balsamo, M., Cantoni, C., Conte, R., Moretta, L., Moretta, A., Vitale, M. Blood (2006) [Pubmed]
  8. High-affinity uptake of L-kynurenine by a Na+-independent transporter of neutral amino acids in astrocytes. Speciale, C., Hares, K., Schwarcz, R., Brookes, N. J. Neurosci. (1989) [Pubmed]
  9. Intraventricular administration of l-kynurenine and kynuramine facilitates lordosis in the female rat. Mendelson, S.D., Lee, N., Gorzalka, B.B. Eur. J. Pharmacol. (1987) [Pubmed]
  10. Taurine selectivity antagonizes L-kynurenine-produced seizures in mice. Lapin, I.P. J. Neural Transm. (1980) [Pubmed]
  11. 4-Chloro-3-hydroxyanthranilate, 6-chlorotryptophan and norharmane attenuate quinolinic acid formation by interferon-gamma-stimulated monocytes (THP-1 cells). Saito, K., Chen, C.Y., Masana, M., Crowley, J.S., Markey, S.P., Heyes, M.P. Biochem. J. (1993) [Pubmed]
  12. Kynureninase-Type enzymes of Penicillum roqueforti, Aspergillus niger, Rhizopus stolonifer, and Pseudomonas fluorescens: further evidence for distinct kynureninase and hydroxykynureninase activities. Shetty, A.S., Gaertner, F.H. J. Bacteriol. (1975) [Pubmed]
  13. Cloning and functional expression of human kynurenine 3-monooxygenase. Alberati-Giani, D., Cesura, A.M., Broger, C., Warren, W.D., Röver, S., Malherbe, P. FEBS Lett. (1997) [Pubmed]
  14. Indoleamine 2,3-dioxygenase protects corneal endothelial cells from UV mediated damage. Serbecic, N., Beutelspacher, S.C. Exp. Eye Res. (2006) [Pubmed]
  15. Tryptophan metabolism via the kynurenine pathway in patients with the eosinophilia-myalgia syndrome. Silver, R.M., McKinley, K., Smith, E.A., Quearry, B., Harati, Y., Sternberg, E.M., Heyes, M.P. Arthritis Rheum. (1992) [Pubmed]
  16. A mechanism for increased quinolinic acid formation following acute systemic immune stimulation. Saito, K., Crowley, J.S., Markey, S.P., Heyes, M.P. J. Biol. Chem. (1993) [Pubmed]
  17. Neuroprotective effects of L-kynurenine on hypoxia-ischemia and NMDA lesions in neonatal rats. Nozaki, K., Beal, M.F. J. Cereb. Blood Flow Metab. (1992) [Pubmed]
  18. Human microglia convert l-tryptophan into the neurotoxin quinolinic acid. Heyes, M.P., Achim, C.L., Wiley, C.A., Major, E.O., Saito, K., Markey, S.P. Biochem. J. (1996) [Pubmed]
  19. Increased cerebrospinal fluid quinolinic acid, kynurenic acid, and L-kynurenine in acute septicemia. Heyes, M.P., Lackner, A. J. Neurochem. (1990) [Pubmed]
  20. Effects of systemic and central nervous system localized inflammation on the contributions of metabolic precursors to the L-kynurenine and quinolinic acid pools in brain. Kita, T., Morrison, P.F., Heyes, M.P., Markey, S.P. J. Neurochem. (2002) [Pubmed]
  21. Molecular cloning of rat kynurenine aminotransferase: identity with glutamine transaminase K. Mosca, M., Cozzi, L., Breton, J., Speciale, C., Okuno, E., Schwarcz, R., Benatti, L. FEBS Lett. (1994) [Pubmed]
  22. The role of indoleamine 2,3-dioxygenase in the anti-tumour activity of human interferon-gamma in vivo. Burke, F., Knowles, R.G., East, N., Balkwill, F.R. Int. J. Cancer (1995) [Pubmed]
  23. Isolation and expression of a cDNA clone encoding human kynureninase. Alberati-Giani, D., Buchli, R., Malherbe, P., Broger, C., Lang, G., Köhler, C., Lahm, H.W., Cesura, A.M. Eur. J. Biochem. (1996) [Pubmed]
  24. Intracerebral administration of L-kynurenine decreases N-methyl-D-aspartate receptor-mediated production of cGMP in the cerebellum and hippocampus of unanaesthetized rats subjected to transcerebral microdialysis. Varnier, G., Fedele, E., Marchi, M., Raiteri, M. Neurosci. Lett. (1999) [Pubmed]
  25. The catalytic mechanism of kynureninase from Pseudomonas fluorescens: evidence for transient quinonoid and ketimine intermediates from rapid-scanning stopped-flow spectrophotometry. Phillips, R.S., Sundararaju, B., Koushik, S.V. Biochemistry (1998) [Pubmed]
  26. Kynurenic acid and kynurenine aminotransferase in heart. Baran, H., Amann, G., Lubec, B., Lubec, G. Pediatr. Res. (1997) [Pubmed]
  27. Determination of extracellular kynurenic acid in the striatum of unanesthetized rats: effect of aminooxyacetic acid. Speciale, C., Wu, H.Q., Gramsbergen, J.B., Turski, W.A., Ungerstedt, U., Schwarcz, R. Neurosci. Lett. (1990) [Pubmed]
  28. Regulation of kynurenic acid synthesis studied by microdialysis in the dorsal hippocampus of unanesthetized rats. Wu, H.Q., Ungerstedt, U., Schwarcz, R. Eur. J. Pharmacol. (1992) [Pubmed]
  29. Purification of L-kynurenine 3-hydroxylase by affinity chromatography. Nishimoto, Y., Takeuchi, F., Shibata, Y. J. Chromatogr. (1979) [Pubmed]
  30. Isolation of L-dynurenine 3-hydroxylase from the mitochondrial outer membrane of rat liver. Nisimoto, Y., Takeuchi, F., Shibata, Y. J. Biochem. (1975) [Pubmed]
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