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Chemical Compound Review

Barbiturate     1,3-diazinane-2,4,6-trione

Synonyms: Malonylurea, Malonyluree, Barbitursaeure, AC1MMJIY, SureCN38707, ...
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Disease relevance of Barbiturate


Psychiatry related information on Barbiturate


High impact information on Barbiturate


Chemical compound and disease context of Barbiturate


Biological context of Barbiturate


Anatomical context of Barbiturate


Associations of Barbiturate with other chemical compounds


Gene context of Barbiturate

  • Inactivity of 4'-aminophenyl derivatives of imidazolidinedione and pyrimidinetrione indicate that the 4'-aminophenyl moiety alone is insufficient for antagonist activity against aromatase [26].
  • Through the use of computational modeling, a series of pyrimidinetrione-based inhibitors of MMP-13 was designed based on a lead inhibitor identified through file screening [27].
  • Potent pyrimidinetrione-based inhibitors of MMP-13 with enhanced selectivity over MMP-14 [27].
  • In addition we present a simulation of the expected effect in vivo of phosphoribofuranosyl barbituric acid (BMP), a tight-binding inhibitor of OMP decarboxylase [H. L. Levine, R. S. Brody, and F. H. Westheimer (1980) Biochemistry 19, 4993- 4999] [28].
  • Isolation of drugs from post mortem specimens with the automated sample processor. Part I. Barbiturate derivatives [29].

Analytical, diagnostic and therapeutic context of Barbiturate

  • The convulsant barbiturate 5-(2-cyclohexylidene-ethyl)-5-ethyl barbituric acid (CHEB) depolarized most (greater than 90%) mouse spinal cord (SC) neurons in primary dissociated cell culture in a concentration-dependent fashion with threshold effects at 10 to 50 nM [13].
  • Catalymetric - thermometric titration of some derivatives of barbituric acid [30].
  • If the direct barbituric acid assay is in disagreement with self-reported smoking status, this HPLC procedure is a useful method to resolve the discrepancy [31].
  • The Immunoassay demonstrated good cross-reactivity to several commonly prescribed barbiturates; low cross-reactivity with structurally similar compounds; low interference from endogenous substances, dyes, preservatives, and several commonly available adulterants; and good correlation with the TDx Barbiturate Urine assay [32].
  • 5. In 60 h urine of three human volunteers who had taken 150 mg of vinylbital orally, 2.6 +/- 1.7% of the dose was excreted as vinylbitaland 11.0 +/- 4.1% as 5-(1'-methylbutyl) barbituric acid, illustrating that also in humans the epoxide-diol pathway plays a role in the metabolism of vinylbital [33].


  1. Electrophysiological and metabolic effects of a convulsant barbiturate on dissociated mouse primary sensory neurons. Pearce, R.J., Duchen, M.R. J. Physiol. (Lond.) (1995) [Pubmed]
  2. Thiopental-induced apoptosis in lymphocytes is independent of CD95 activation. Keel, M., Mica, L., Stover, J., Stocker, R., Trentz, O., Härter, L. Anesthesiology (2005) [Pubmed]
  3. Depth of EEG suppression and outcome in barbiturate anesthetic treatment for refractory status epilepticus. Krishnamurthy, K.B., Drislane, F.W. Epilepsia (1999) [Pubmed]
  4. Transcranial Doppler ultrasonography to confirm brain death: a meta-analysis. Monteiro, L.M., Bollen, C.W., van Huffelen, A.C., Ackerstaff, R.G., Jansen, N.J., van Vught, A.J. Intensive care medicine (2006) [Pubmed]
  5. 5-(2-Cyclohexylideneethyl)-5-ethyl barbituric acid (CHEB): correlation of hypnotic and convulsant properties with alterations of synaptosomal 45Ca2+ influx. Chandler, L.J., Leslie, S.W., Gonzales, R. Eur. J. Pharmacol. (1986) [Pubmed]
  6. Upper airway function during sleep and wakefulness: experimental studies on normal and anesthetized cats. Orem, J., Lydic, R. Sleep. (1978) [Pubmed]
  7. Mechanism of barbituric-acid protection against inhibition by alloxan of glucose-induced insulin release. Weaver, D.C., McDaniel, M.L., Lacy, P.E. Diabetes (1978) [Pubmed]
  8. The comparative effects of barbituric acid phenobarbital on blood glucose and insulin secretion in mice. Mennear, J.H., Schonwalder, C., Yau, E.T. Diabetologia (1976) [Pubmed]
  9. Transformation of barbituric acid into alloxan by hydroxyl radicals: interaction with melatonin and with other hydroxyl radical scavengers. Brömme, H.J., Mörke, W., Peschke, E. J. Pineal Res. (2002) [Pubmed]
  10. Structural basis for inhibition of Escherichia coli uridine phosphorylase by 5-substituted acyclouridines. Bu, W., Settembre, E.C., el Kouni, M.H., Ealick, S.E. Acta Crystallogr. D Biol. Crystallogr. (2005) [Pubmed]
  11. Synthesis of pyrimidine derivatives possessing an antioxidative property and their inhibitory effects on picryl chloride-induced contact hypersensitivity reaction. Isobe, Y., Hirota, K. Chem. Pharm. Bull. (2003) [Pubmed]
  12. Sarcolemmal and mitochondrial adenosine triphosphate- dependent potassium channels: mechanism of desflurane-induced cardioprotection. Toller, W.G., Gross, E.R., Kersten, J.R., Pagel, P.S., Gross, G.J., Warltier, D.C. Anesthesiology (2000) [Pubmed]
  13. Multiple actions of convulsant barbiturates on mouse neurons in cell culture. Skerritt, J.H., Macdonald, R.L. J. Pharmacol. Exp. Ther. (1984) [Pubmed]
  14. Palladium-catalyzed asymmetric allylic alkylation of barbituric acid derivatives: enantioselective syntheses of cyclopentobarbital and pentobarbital. Trost, B.M., Schroeder, G.M. J. Org. Chem. (2000) [Pubmed]
  15. Differing actions of convulsant and nonconvulsant barbiturates: an electrophysiological study in the isolated spinal cord of the rat. Nicholson, G.M., Spence, I., Johnston, G.A. Neuropharmacology (1988) [Pubmed]
  16. Cardioprotective effects of monophosphoryl lipid A, a novel endotoxin analogue, in the dog. Yao, Z., Auchampach, J.A., Pieper, G.M., Gross, G.J. Cardiovasc. Res. (1993) [Pubmed]
  17. Strychnine-like action of the convulsant barbiturate, CHEB. Nicholson, G.M., Spence, I., Johnston, G.A. Neuropharmacology (1985) [Pubmed]
  18. Inhibitory effects of barbiturates on nicotinic acetylcholine receptors in rat central nervous system neurons. Kamiya, Y., Andoh, T., Watanabe, I., Higashi, T., Itoh, H. Anesthesiology (2001) [Pubmed]
  19. Effects of barbiturates with or without liver-tumor-promoting activity on survival and DNA synthesis of suckling and adult rat hepatocytes in serum-free primary culture. Miyazaki, M., Bai, L., Tsuboi, S., Namba, M. J. Cancer Res. Clin. Oncol. (1992) [Pubmed]
  20. Brbiturate spindle activity in the association cortex of the cat and its relation to spindle activity in the somatosensory system. Ganes, T. Brain Res. (1976) [Pubmed]
  21. Comparison of the effects of a convulsant barbiturate on the release of endogenous and radiolabeled amino acids from slices of mouse hippocampus. Holtman, J.R., Richter, J.A. J. Neurochem. (1983) [Pubmed]
  22. Promotion by sodium barbital of renal cortical and transitional cell tumors, but not intestinal tumors, in F344 rats given methyl(acetoxymethyl)nitrosamine, and lack of effect of phenobarbital, amobarbital, or barbituric acid on development of either renal or intestinal tumors. Diwan, B.A., Ohshima, M., Rice, J.M. Carcinogenesis (1989) [Pubmed]
  23. Crystallization of yeast orotidine 5'-monophosphate decarboxylase complexed with 1-(5'-phospho-beta-D-ribofuranosyl) barbituric acid. Bell, J.B., Jones, M.E., Carter, C.W. Proteins (1991) [Pubmed]
  24. 5-Benzylbarbituric acid derivatives, potent and specific inhibitors of uridine phosphorylase. Naguib, F.N., Levesque, D.L., Wang, E.C., Panzica, R.P., el Kouni, M.H. Biochem. Pharmacol. (1993) [Pubmed]
  25. Effects of anticonvulsants in vivo on high affinity choline uptake in vitro in mouse hippocampal synaptosomes. Miller, J.A., Richter, J.A. Br. J. Pharmacol. (1985) [Pubmed]
  26. Pharmacology of aminoglutethimide: structure/activity relationships and receptor interactions. Nicholls, P.J., Daly, M.J., Smith, H.J. Breast Cancer Res. Treat. (1986) [Pubmed]
  27. Potent pyrimidinetrione-based inhibitors of MMP-13 with enhanced selectivity over MMP-14. Blagg, J.A., Noe, M.C., Wolf-Gouveia, L.A., Reiter, L.A., Laird, E.R., Chang, S.P., Danley, D.E., Downs, J.T., Elliott, N.C., Eskra, J.D., Griffiths, R.J., Hardink, J.R., Haugeto, A.I., Jones, C.S., Liras, J.L., Lopresti-Morrow, L.L., Mitchell, P.G., Pandit, J., Robinson, R.P., Subramanyam, C., Vaughn-Bowser, M.L., Yocum, S.A. Bioorg. Med. Chem. Lett. (2005) [Pubmed]
  28. Metabolic resistance to tight-binding inhibitors of enzymes involved in the de novo pyrimidine pathway. Simulation of time-dependent effects. Duggleby, R.G., Christopherson, R.I. Eur. J. Biochem. (1984) [Pubmed]
  29. Isolation of drugs from post mortem specimens with the automated sample processor. Part I. Barbiturate derivatives. Balkon, J., Prendes, D., Viola, J. Journal of analytical toxicology. (1982) [Pubmed]
  30. Catalymetric - thermometric titration of some derivatives of barbituric acid. Bark, L.S., Ladipo, O. The Analyst. (1976) [Pubmed]
  31. Simple high-performance liquid chromatographic method to verify the direct barbituric acid assay for urinary cotinine. Ubbink, J.B., Lagendijk, J., Vermaak, W.H. J. Chromatogr. (1993) [Pubmed]
  32. A barbiturate screening assay for the Abbott AxSYM analyzer. Adamczyk, M., Douglas, J., Grote, J., Harrington, C.A. Journal of analytical toxicology. (1998) [Pubmed]
  33. The epoxide-diol pathway in the metabolism of vinylbital in rat and man. Vermeulen, N.P., Bakker, B.H., Eylers, D., Breimer, D.D. Xenobiotica (1980) [Pubmed]
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