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Chemical Compound Review

Seromycin     (4R)-4-amino-1,2-oxazolidin- 3-one

Synonyms: Cyclorin, Oxamycin, Closina, Miroseryn, Tisomycin, ...
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Disease relevance of cycloserine

  • We have shown that it is harder to inhibit the catalytic activity of ALR from D-cycloserine (DCS)-producing Streptomyces lavendulae than that from Escherichia coli by DCS [1].
  • In the present study, we cloned a gene, designated bpsA, which encodes a single module type non-ribosomal peptide synthetase (NRPS) from a d-cycloserine (DCS)-producing Streptomyces lavendulae ATCC11924 [2].
  • In agreement with recently published crystallographic data, we also observe similar changes in backbone torsions corresponding to the hinge region between the two lobes for the partial agonist, d-cycloserine [3].
  • Chlamydia growth is inhibited by D-cycloserine (DCS) and in vitro analysis provided evidence for the chlamydial MurC-Ddl as the target for DCS sensitivity [4].
  • Significant synergy was shown to occur between pleurocidin and D-cycloserine targeting Mycobacterium smegmatis [5].

Psychiatry related information on cycloserine

  • Augmentation of exposure therapy with D-cycloserine for social anxiety disorder [6].
  • Fear reduction in exposure therapy is similar to extinction learning, and early clinical data with specific phobias suggest that the treatment effects of exposure therapy for SAD may be enhanced with d-cycloserine, an agonist at the glutamatergic N-methyl-d-aspartate receptor [6].
  • Improved cognition in Alzheimer's disease with short-term D-cycloserine treatment [7].
  • METHOD: Following a 2-week, single-blind placebo lead-in phase, drug-free subjects with autistic disorder were administered three different doses of D-cycloserine during each of three 2-week periods [8].
  • Previous administration of D-serine to schizophrenic patients taking nonclozapine antipsychotics improved positive, negative, and cognitive symptoms, whereas the partial agonist D-cycloserine improved negative symptoms of patients taking conventional antipsychotics but worsened symptoms in clozapine-treated patients [9].

High impact information on cycloserine


Chemical compound and disease context of cycloserine


Biological context of cycloserine


Anatomical context of cycloserine

  • RESULTS: D-Cycloserine at a dose of 50 mg/day produced a significant reduction (mean = 21%, SD = 28%) in negative symptoms and significantly improved reaction time as measured by Sternberg's Item Recognition Paradigm, a test mediated in part by prefrontal cortex [24].
  • In the present work, further characterization of the transport of D-cycloserine in the human intestinal cell line Caco 2 has shown that this occurs in the apical-to-basolateral direction by an active mechanism which is energy dependent but only partially sodium dependent [21].
  • An increased risk of central nervous system effects with concomitant cycloserine has been reported and seen clinically [25].
  • The effect of alanine is observed either in vivo, in rats pretreated with cycloserine to prevent its transamination, or in isolated liver cells under conditions in which its metabolic transformation is fully impeded [26].
  • The adjunction of D-cycloserine enhanced c-fos expression only for clozapine in both regions of the forebrain [27].

Associations of cycloserine with other chemical compounds


Gene context of cycloserine


Analytical, diagnostic and therapeutic context of cycloserine


  1. Structural evidence that alanine racemase from a D-cycloserine-producing microorganism exhibits resistance to its own product. Noda, M., Matoba, Y., Kumagai, T., Sugiyama, M. J. Biol. Chem. (2004) [Pubmed]
  2. Cloning and Characterization of a Streptomyces Single Module Type Non-ribosomal Peptide Synthetase Catalyzing a Blue Pigment Synthesis. Takahashi, H., Kumagai, T., Kitani, K., Mori, M., Matoba, Y., Sugiyama, M. J. Biol. Chem. (2007) [Pubmed]
  3. Molecular Dynamics Simulations of the Ligand-binding Domain of an N-Methyl-D-aspartate Receptor. Kaye, S.L., Sansom, M.S., Biggin, P.C. J. Biol. Chem. (2006) [Pubmed]
  4. Characterization of Chlamydia MurC-Ddl, a fusion protein exhibiting D-alanyl-D-alanine ligase activity involved in peptidoglycan synthesis and D-cycloserine sensitivity. McCoy, A.J., Maurelli, A.T. Mol. Microbiol. (2005) [Pubmed]
  5. Characterization of a fish antimicrobial peptide: gene expression, subcellular localization, and spectrum of activity. Cole, A.M., Darouiche, R.O., Legarda, D., Connell, N., Diamond, G. Antimicrob. Agents Chemother. (2000) [Pubmed]
  6. Augmentation of exposure therapy with D-cycloserine for social anxiety disorder. Hofmann, S.G., Meuret, A.E., Smits, J.A., Simon, N.M., Pollack, M.H., Eisenmenger, K., Shiekh, M., Otto, M.W. Arch. Gen. Psychiatry (2006) [Pubmed]
  7. Improved cognition in Alzheimer's disease with short-term D-cycloserine treatment. Tsai, G.E., Falk, W.E., Gunther, J., Coyle, J.T. The American journal of psychiatry. (1999) [Pubmed]
  8. A pilot study of D-cycloserine in subjects with autistic disorder. Posey, D.J., Kem, D.L., Swiezy, N.B., Sweeten, T.L., Wiegand, R.E., McDougle, C.J. The American journal of psychiatry. (2004) [Pubmed]
  9. D-serine added to clozapine for the treatment of schizophrenia. Tsai, G.E., Yang, P., Chung, L.C., Tsai, I.C., Tsai, C.W., Coyle, J.T. The American journal of psychiatry. (1999) [Pubmed]
  10. Cognitive enhancers as adjuncts to psychotherapy: use of D-cycloserine in phobic individuals to facilitate extinction of fear. Ressler, K.J., Rothbaum, B.O., Tannenbaum, L., Anderson, P., Graap, K., Zimand, E., Hodges, L., Davis, M. Arch. Gen. Psychiatry (2004) [Pubmed]
  11. Mechanism of action of penicillin: triggering of the pneumococcal autolytic enzyme by inhibitors of cell wall synthesis. Tomasz, A., Waks, S. Proc. Natl. Acad. Sci. U.S.A. (1975) [Pubmed]
  12. Different modes of action of inhibitors of bacterial D-amino acid transaminase. A target enzyme for the design of new antibacterial agents. Soper, T.S., Manning, J.M. J. Biol. Chem. (1981) [Pubmed]
  13. Cell wall-inhibitory antibiotics activate the alginate biosynthesis operon in Pseudomonas aeruginosa: roles of sigma (AlgT) and the AlgW and Prc proteases. Wood, L.F., Leech, A.J., Ohman, D.E. Mol. Microbiol. (2006) [Pubmed]
  14. IV glycine and oral D-cycloserine effects on plasma and CSF amino acids in healthy humans. D'Souza, D.C., Gil, R., Cassello, K., Morrissey, K., Abi-Saab, D., White, J., Sturwold, R., Bennett, A., Karper, L.P., Zuzarte, E., Charney, D.S., Krystal, J.H. Biol. Psychiatry (2000) [Pubmed]
  15. A side reaction of alanine racemase: transamination of cycloserine. Fenn, T.D., Stamper, G.F., Morollo, A.A., Ringe, D. Biochemistry (2003) [Pubmed]
  16. Development of a whole-cell assay for peptidoglycan biosynthesis inhibitors. Barbosa, M.D., Yang, G., Fang, J., Kurilla, M.G., Pompliano, D.L. Antimicrob. Agents Chemother. (2002) [Pubmed]
  17. Comparative inhibition of bacterial and microsomal 3-ketodihydrosphingosine synthetases by L-cycloserine and other inhibitors. Sundaram, K.S., Lev, M. Antimicrob. Agents Chemother. (1984) [Pubmed]
  18. Temperature-sensitive mutants of Actinobacillus pleuropneumoniae induce protection in mice. Byrd, W., Hooke, A.M. Infect. Immun. (1997) [Pubmed]
  19. Consolidation of human motor cortical neuroplasticity by D-cycloserine. Nitsche, M.A., Jaussi, W., Liebetanz, D., Lang, N., Tergau, F., Paulus, W. Neuropsychopharmacology (2004) [Pubmed]
  20. Construction and characterization of a Vi-positive variant of the Salmonella typhi live oral vaccine strain Ty21a. Cryz, S.J., Fürer, E., Baron, L.S., Noon, K.F., Rubin, F.A., Kopecko, D.J. Infect. Immun. (1989) [Pubmed]
  21. D-cycloserine uses an active transport mechanism in the human intestinal cell line Caco 2. Ranaldi, G., Islam, K., Sambuy, Y. Antimicrob. Agents Chemother. (1994) [Pubmed]
  22. Panel of Bacillus subtilis reporter strains indicative of various modes of action. Hutter, B., Fischer, C., Jacobi, A., Schaab, C., Loferer, H. Antimicrob. Agents Chemother. (2004) [Pubmed]
  23. Ceramide is a mediator of apoptosis in retina photoreceptors. German, O.L., Miranda, G.E., Abrahan, C.E., Rotstein, N.P. Invest. Ophthalmol. Vis. Sci. (2006) [Pubmed]
  24. Dose-finding trial of D-cycloserine added to neuroleptics for negative symptoms in schizophrenia. Goff, D.C., Tsai, G., Manoach, D.S., Coyle, J.T. The American journal of psychiatry. (1995) [Pubmed]
  25. The role of fluoroquinolones in tuberculosis today. Berning, S.E. Drugs (2001) [Pubmed]
  26. Key role of L-alanine in the control of hepatic protein synthesis. Pérez-Sala, D., Parrilla, R., Ayuso, M.S. Biochem. J. (1987) [Pubmed]
  27. Homer 1a gene expression modulation by antipsychotic drugs: involvement of the glutamate metabotropic system and effects of D-cycloserine. Polese, D., de Serpis, A.A., Ambesi-Impiombato, A., Muscettola, G., de Bartolomeis, A. Neuropsychopharmacology (2002) [Pubmed]
  28. Characterization and modelling of VanT: a novel, membrane-bound, serine racemase from vancomycin-resistant Enterococcus gallinarum BM4174. Arias, C.A., Martín-Martinez, M., Blundell, T.L., Arthur, M., Courvalin, P., Reynolds, P.E. Mol. Microbiol. (1999) [Pubmed]
  29. Behavioral and neuroendocrine effects of the partial NMDA agonist D-cycloserine in healthy subjects. van Berckel, B.N., Lipsch, C., Timp, S., Gispen-de Wied, C., Wynne, H., van Ree, J.M., Kahn, R.S. Neuropsychopharmacology (1997) [Pubmed]
  30. Characterization of a [3H]glycine recognition site as a modulatory site of the N-methyl-D-aspartate receptor complex. Monahan, J.B., Corpus, V.M., Hood, W.F., Thomas, J.W., Compton, R.P. J. Neurochem. (1989) [Pubmed]
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  32. Extinction training in conjunction with a partial agonist of the glycine site on the NMDA receptor erases memory trace. Mao, S.C., Hsiao, Y.H., Gean, P.W. J. Neurosci. (2006) [Pubmed]
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  36. A placebo-controlled crossover trial of D-cycloserine added to clozapine in patients with schizophrenia. Goff, D.C., Henderson, D.C., Evins, A.E., Amico, E. Biol. Psychiatry (1999) [Pubmed]
  37. Interference of modern antibacterials with bacillus Calmette-Guerin viability. Durek, C., Rüsch-Gerdes, S., Jocham, D., Böhle, A. J. Urol. (1999) [Pubmed]
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