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Chemical Compound Review

Sebical     (2,5-dioxoimidazolidin-4- yl)urea

Synonyms: Allantoi, Allantol, Hemocane, Psoralon, Septalan, ...
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Disease relevance of Sebical

  • The allantoin regulon of Escherichia coli, formed by three operons expressed from promoters allA(P), gcl(P) and allD(P), is involved in the anaerobic utilization of allantoin as nitrogen source [1].
  • Isolation of a chromosomal region of Klebsiella pneumoniae associated with allantoin metabolism and liver infection [2].
  • Two homogeneous species were found and tentatively listed as Pseudomonas sp. 1 and Pseudomonas sp. 2, and these were differentiated by gelatin and starch hydrolysis, oxidation of mannitol, and alkalinization of allantoin [3].
  • The results reported here are similar to those reported previously by our laboratory for the effects of Reye's plasma and allantoin + Ca2+, and indicate that, like these agents, salicylate and salicyl compounds can potentiate the Ca2+-induced damage to the mitochondrial inner membrane and may be another factor responsible for Reye's syndrome [4].
  • Metabolism of allantoin in Hyphomicrobium species [5].

High impact information on Sebical


Chemical compound and disease context of Sebical


Biological context of Sebical


Anatomical context of Sebical

  • It was concluded that, under basal conditions, the cytoplasmic 5'-nucleotidase present in the liver cell continuously produces adenosine, which is immediately reconverted into AMP by adenosine kinase, without giving rise to allantoin [20].
  • The concentrations of uric acid and allantoin in human serum and synovial fluid are reported [21].
  • We found that onset of nutrient starvation brought about release of large quantities of arginine and allantoin normally sequestered in the cell vacuole [22].
  • Our data show, therefore, that allantoin, salicylates, and the "toxic" agent in Reye's plasma severely limit the ability of isolated rat liver mitochondria to maintain their structural integrity under conditions of limited Ca2+ loading [23].
  • Factors affecting application of milk allantoin as an estimator of microbial protein flow to the duodenum under commercial conditions [24].

Associations of Sebical with other chemical compounds


Gene context of Sebical


Analytical, diagnostic and therapeutic context of Sebical


  1. Regulation of the Escherichia coli allantoin regulon: coordinated function of the repressor AllR and the activator AllS. Rintoul, M.R., Cusa, E., Baldomà, L., Badia, J., Reitzer, L., Aguilar, J. J. Mol. Biol. (2002) [Pubmed]
  2. Isolation of a chromosomal region of Klebsiella pneumoniae associated with allantoin metabolism and liver infection. Chou, H.C., Lee, C.Z., Ma, L.C., Fang, C.T., Chang, S.C., Wang, J.T. Infect. Immun. (2004) [Pubmed]
  3. Cultural and biochemical characteristics of clinical isolates of unusual colistin-resistant pseudomonads. Oberhofer, T.R. J. Clin. Microbiol. (1980) [Pubmed]
  4. Reye's syndrome: salicylates and mitochondrial functions. Martens, M.E., Lee, C.P. Biochem. Pharmacol. (1984) [Pubmed]
  5. Metabolism of allantoin in Hyphomicrobium species. van der Drift, C., de Windt, F.E., Doddema, H.J. Antonie Van Leeuwenhoek (1981) [Pubmed]
  6. Birth of a metabolic gene cluster in yeast by adaptive gene relocation. Wong, S., Wolfe, K.H. Nat. Genet. (2005) [Pubmed]
  7. The influence of the extracellular fluid volume on the tubular reabsorption of uric acid. Weinman, E.J., Eknoyan, G., Suki, W.N. J. Clin. Invest. (1975) [Pubmed]
  8. A novel superfamily of transporters for allantoin and other oxo derivatives of nitrogen heterocyclic compounds in Arabidopsis. Desimone, M., Catoni, E., Ludewig, U., Hilpert, M., Schneider, A., Kunze, R., Tegeder, M., Frommer, W.B., Schumacher, K. Plant Cell (2002) [Pubmed]
  9. Crystal structure of the protein drug urate oxidase-inhibitor complex at 2.05 A resolution. Colloc'h, N., el Hajji, M., Bachet, B., L'Hermite, G., Schiltz, M., Prangé, T., Castro, B., Mornon, J.P. Nat. Struct. Biol. (1997) [Pubmed]
  10. Genetic analysis of a chromosomal region containing genes required for assimilation of allantoin nitrogen and linked glyoxylate metabolism in Escherichia coli. Cusa, E., Obradors, N., Baldomà, L., Badía, J., Aguilar, J. J. Bacteriol. (1999) [Pubmed]
  11. Glyoxylate conversion by Hyphomicrobium species grown on allantoin as nitrogen source. Van der Drift, C., De Windt, F.E. Antonie Van Leeuwenhoek (1983) [Pubmed]
  12. Oxidation products of uric acid and ascorbic acid in preterm infants with chronic lung disease. Ogihara, T., Kim, H.S., Hirano, K., Imanishi, M., Ogihara, H., Tamai, H., Okamoto, R., Mino, M. Biol. Neonate (1998) [Pubmed]
  13. Emerging therapies in the long-term management of hyperuricaemia and gout. Stamp, L.K., O'Donnell, J.L., Chapman, P.T. Internal medicine journal (2007) [Pubmed]
  14. Hypoxanthine, uric acid and allantoin as indicators of in vivo free radical reactions. Description of a HPLC method and human brain microdialysis data. Marklund, N., Ostman, B., Nalmo, L., Persson, L., Hillered, L. Acta neurochirurgica. (2000) [Pubmed]
  15. Identification of sequences responsible for transcriptional activation of the allantoate permease gene in Saccharomyces cerevisiae. Rai, R., Genbauffe, F.S., Sumrada, R.A., Cooper, T.G. Mol. Cell. Biol. (1989) [Pubmed]
  16. Recombinant urate oxidase for the prophylaxis or treatment of hyperuricemia in patients With leukemia or lymphoma. Pui, C.H., Mahmoud, H.H., Wiley, J.M., Woods, G.M., Leverger, G., Camitta, B., Hastings, C., Blaney, S.M., Relling, M.V., Reaman, G.H. J. Clin. Oncol. (2001) [Pubmed]
  17. Overlapping positive and negative GATA factor binding sites mediate inducible DAL7 gene expression in Saccharomyces cerevisiae. Rai, R., Daugherty, J.R., Cunningham, T.S., Cooper, T.G. J. Biol. Chem. (1999) [Pubmed]
  18. New procedure using a psoralen derivative for analysis of nucleosome associated DNA sequences in chromatin of living cells. Carlson, J.O., Pfenninger, O., Sinden, R.R., Lehman, J.M., Pettijohn, D.E. Nucleic Acids Res. (1982) [Pubmed]
  19. The DAL82 protein of Saccharomyces cerevisiae binds to the DAL upstream induction sequence (UIS). Dorrington, R.A., Cooper, T.G. Nucleic Acids Res. (1993) [Pubmed]
  20. Evidence for a substrate cycle between AMP and adenosine in isolated hepatocytes. Bontemps, F., Van den Berghe, G., Hers, H.G. Proc. Natl. Acad. Sci. U.S.A. (1983) [Pubmed]
  21. Measurement of allantoin and uric acid in human body fluids. A potential index of free-radical reactions in vivo? Grootveld, M., Halliwell, B. Biochem. J. (1987) [Pubmed]
  22. Control of vacuole permeability and protein degradation by the cell cycle arrest signal in Saccharomyces cerevisiae. Sumrada, R., Cooper, T.G. J. Bacteriol. (1978) [Pubmed]
  23. Reye's syndrome: mitochondrial swelling and Ca2+ release induced by Reye's plasma, allantoin, and salicylate. Martens, M.E., Chang, C.H., Lee, C.P. Arch. Biochem. Biophys. (1986) [Pubmed]
  24. Factors affecting application of milk allantoin as an estimator of microbial protein flow to the duodenum under commercial conditions. Schager, W.M., Harrison, J.H., Gaskins, C.T., Davidson, D. J. Dairy Sci. (2003) [Pubmed]
  25. Isolation and characterization of mutants that produce the allantoin-degrading enzymes constitutively in Saccharomyces cerevisiae. Chisholm, G., Cooper, T.G. Mol. Cell. Biol. (1982) [Pubmed]
  26. Oxalurate induction of multiple URA3 transcripts in Saccharomyces cerevisiae. Buckholz, R.G., Cooper, T.G. Mol. Cell. Biol. (1983) [Pubmed]
  27. Characterization of the Transport Mechanism and Permeant Binding Profile of the Uridine Permease Fui1p of Saccharomyces cerevisiae. Zhang, J., Smith, K.M., Tackaberry, T., Sun, X., Carpenter, P., Slugoski, M.D., Robins, M.J., Nielsen, L.P., Nowak, I., Baldwin, S.A., Young, J.D., Cass, C.E. J. Biol. Chem. (2006) [Pubmed]
  28. Purification of allantoinase from soybean seeds and production and characterization of anti-allantoinase antibodies. Webb, M.A., Lindell, J.S. Plant Physiol. (1993) [Pubmed]
  29. Identification of the ureidoglycolate hydrolase gene in the DAL gene cluster of Saccharomyces cerevisiae. Yoo, H.S., Genbauffe, F.S., Cooper, T.G. Mol. Cell. Biol. (1985) [Pubmed]
  30. The GLN3 gene product is required for transcriptional activation of allantoin system gene expression in Saccharomyces cerevisiae. Cooper, T.G., Ferguson, D., Rai, R., Bysani, N. J. Bacteriol. (1990) [Pubmed]
  31. DAL82, a second gene required for induction of allantoin system gene transcription in Saccharomyces cerevisiae. Olive, M.G., Daugherty, J.R., Cooper, T.G. J. Bacteriol. (1991) [Pubmed]
  32. Regulation of the urea active transporter gene (DUR3) in Saccharomyces cerevisiae. ElBerry, H.M., Majumdar, M.L., Cunningham, T.S., Sumrada, R.A., Cooper, T.G. J. Bacteriol. (1993) [Pubmed]
  33. Catabolism of adenine nucleotides and its relation with intracellular phosphorylated metabolite concentration during ethanol oxidation in perfused rat liver. Masson, S., Desmoulin, F., Sciaky, M., Cozzone, P.J. Biochemistry (1993) [Pubmed]
  34. Benzo[a]pyrene diol epoxide I modification of DNA in human skin xenografts. Yohn, J., Lehman, T.A., Kurian, P., Ribovich, M., Milo, G.E. J. Invest. Dermatol. (1988) [Pubmed]
  35. DNA microarray-based typing of an atypical monophasic Salmonella enterica serovar. Garaizar, J., Porwollik, S., Echeita, A., Rementeria, A., Herrera, S., Wong, R.M., Frye, J., Usera, M.A., McClelland, M. J. Clin. Microbiol. (2002) [Pubmed]
  36. Influence of donor pretreatment with N-acetylcysteine on ischemia/reperfusion injury in rat kidney grafts. Fuller, T.F., Serkova, N., Niemann, C.U., Freise, C.E. J. Urol. (2004) [Pubmed]
  37. Metal ion dependence of recombinant Escherichia coli allantoinase. Mulrooney, S.B., Hausinger, R.P. J. Bacteriol. (2003) [Pubmed]
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