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Chemical Compound Review

Dormalon     10-nitro-2-phenyl-3,6- diazabicyclo[5.4.0]u...

Synonyms: Nitrazep, Radedorm, Serenade, Alodorm, Imadorm, ...
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Disease relevance of nitrazepam


Psychiatry related information on nitrazepam


High impact information on nitrazepam

  • Gene ablation studies have revealed a requirement for Stat3 in diverse biological processes (Akira, S. 2000. Oncogene. 19: 2607-2611; Levy, D.E., and C.K. Lee. 2002. J. Clin. Invest. 109:1143-1148) [11].
  • We have cloned the ACD2 gene; its predicted product shows significant and extensive similarity to red chlorophyll catabolite reductase, which catalyzes one step in the breakdown of the porphyrin component of chlorophyll [Wüthrich, K. L., Bovet, L., Hunziger, P. E., Donnison, I. S. & Hörtensteiner, S. (2000) Plant J. 21, 189-198] [12].
  • Superoxide and lipid free-radical generation in cultured endothelial cells treated with menadione or nitrazepam were measured using electron paramagnetic resonance spectroscopy [13].
  • The nitro anion free radical of reduced nitrazepam, which cannot cross the plasma membrane, did not generate detectable extracellular superoxide [13].
  • Although the role of the C-terminal Cav1 binding domain is not known, its deletion did not affect localization of TRPC1 (Singh, B. B., Liu, X., and Ambudkar, I. S. (2000) J. Biol. Chem. 275, 36483-36486) [14].

Chemical compound and disease context of nitrazepam


Biological context of nitrazepam

  • Previously, we reported that double-strand DNA breaks can be enzymatically produced from two DNA damages located on opposite DNA strands 18 or 30 base pairs apart in a cell-free double-strand DNA break formation assay (Vispé, S., and Satoh, M. S. (2000) J. Biol. Chem. 275, 27386-27392) [19].
  • Recently it was shown that the NH(2)-terminal domain of the Dfp protein from bacteria catalyzes the next step in CoA biosynthesis, the decarboxylation of (R)-4'-phospho-N-pantothenoylcysteine to form 4'-phosphopantetheine (Kupke, T., Uebele, M., Schmid, D., Jung, G., Blaesse, M., and Steinbacher, S. (2000) J. Biol. Chem. 275, 31838-31846) [20].
  • Previously, we noted that inorganic phosphate (P(i)), a major component of bone extracellular matrix, induced osteoblast apoptosis (Meleti, Z., Shapiro, I. M., and Adams, C. S. (2000) Bone (NY) 27, 359-366) [21].
  • Nitrazepam kinetics were determined from multiple serum concentrations measured during the 72 hr after each dose [22].
  • Polymorphic acetylation of nitrazepam [23].

Anatomical context of nitrazepam

  • In contrast, growth inhibition was observed when high concentrations of gangliosides were continuously present in the culture medium during incubation of fibroblasts with growth factors (Li, R., Manela, J., Kong, Y., and Ladisch, S. (2000) J. Biol. Chem. 275, 34213-34223) [24].
  • DEDMPO was used to determine if hydroxyl radical was produced during the metabolism of menadione or nitrazepam by porcine thoracic aorta endothelial cells [25].
  • 2 Manifestations of unwanted central nervous system (CNS) depression (such as drowsiness or 'hangover') were reported in 49 nitrazepam recipients (2.3%), and signs of unwanted CNS stimulation (such as nightmares, insomnia, agitation, etc.) in 15 (0.7%) [26].
  • The average amount of nitrazepam received by the breast-fed baby in the morning was calculated to increase from 1 to 1.5 micrograms 100 ml-1 breast milk, from days 1 to 5 [27].
  • The efficacy of zaleplon for the competitive inhibition of [(3)H]flunitrazepam binding to the membrane preparation from hippocampus was thus less than that of triazolam and nitrazepam [28].

Associations of nitrazepam with other chemical compounds


Gene context of nitrazepam

  • Although cloxazolam was a potent and specific inhibitor of AKR1C3, diazepam, estazolam, flunitrazepam, medazepam and nitrazepam, that inhibited AKR1C1 and AKR1C2, may influence the neurosteroid metabolism [32].
  • Among the 5 non-conserved residues within this segment, Arg-142 in human and Gln-142 in mouse ADA largely determined the capacity for stable binding to CD26 (Richard, E., Arredondo-Vega, F. X., Santisteban, I., Kelly, S. J., Patel, D. D., and Hershfield, M. S. (2000) J. Exp. Med. 192, 1223-1235) [33].
  • In addition to PAPS, phenol sulfotransferase (PST), a member of the ST family, utilizes other nucleotides as substrates with much less catalytic efficiency [Lin, E. S., and Yang, Y. S. (2000) Biochem. Biophys. Res. Commun. 271, 818-822] [34].
  • We have previously shown (Nuti, S. L., Mehdi, A., and Rao, U. S. (2000) Biochemistry 39, 3424-3432) that tryptic cleavage of Pgp results in the activation of basal and drug-stimulated ATPase functions of Pgp [35].
  • Recently, the propeptide domain of the prototype membrane type matrix metalloproteinase (MT1-MMP) was demonstrated to act as an intramolecular chaperone (Cao, J., Hymowitz, M., Conner, C., Bahou, W. F., and Zucker, S. (2000) J. Biol. Chem. 275, 29648-29653) [36].

Analytical, diagnostic and therapeutic context of nitrazepam


  1. The mechanism of nitrazepam-induced drooling and aspiration. Wyllie, E., Wyllie, R., Cruse, R.P., Rothner, A.D., Erenberg, G. N. Engl. J. Med. (1986) [Pubmed]
  2. The gene ygdP, associated with the invasiveness of Escherichia coli K1, designates a Nudix hydrolase, Orf176, active on adenosine (5')-pentaphospho-(5')-adenosine (Ap5A). Bessman, M.J., Walsh, J.D., Dunn, C.A., Swaminathan, J., Weldon, J.E., Shen, J. J. Biol. Chem. (2001) [Pubmed]
  3. Serum clonazepam concentrations in children with absence seizures. Dreifuss, F.E., Penry, J.K., Rose, S.W., Kupferberg, H.J., Dyken, P., Sato, S. Neurology (1975) [Pubmed]
  4. Infantile spasms. Comparative trial of nitrazepam and corticotropin. Dreifuss, F., Farwell, J., Holmes, G., Joseph, C., Lockman, L., Madsen, J.A., Minarcik, C.J., Rothner, A.D., Shewmon, D.A. Arch. Neurol. (1986) [Pubmed]
  5. Nitrazepam clearance unimpaired in patients with renal insufficiency. Ochs, H.R., Oberem, U., Greenblatt, D.J. Journal of clinical psychopharmacology. (1992) [Pubmed]
  6. Rebound insomnia. A potential hazard following withdrawal of certain benzodiazepines. Kales, A., Scharf, M.B., Kales, J.D., Soldatos, C.R. JAMA (1979) [Pubmed]
  7. Depersonalization following nitrazepam withdrawal. Terao, T., Yoshimura, R., Terao, M., Abe, K. Biol. Psychiatry (1992) [Pubmed]
  8. Paradoxical response to nitrazepam in a patient with hypersomnia secondary to nocturnal myoclonus. Nassr, D.G. Journal of clinical psychopharmacology. (1986) [Pubmed]
  9. Effects of butoctamide hydrogen succinate and nitrazepam on psychomotor function and EEG in healthy volunteers. Tazaki, T., Tada, K., Nogami, Y., Takemura, N., Ishikawa, K. Psychopharmacology (Berl.) (1989) [Pubmed]
  10. Changes in reaction time and drug plasma concentrations after nitrazepam and glutethimide. Curry, S.H., Whelpton, R., Scott, D.F. British journal of clinical pharmacology. (1977) [Pubmed]
  11. Stat3 regulates microtubules by antagonizing the depolymerization activity of stathmin. Ng, D.C., Lin, B.H., Lim, C.P., Huang, G., Zhang, T., Poli, V., Cao, X. J. Cell Biol. (2006) [Pubmed]
  12. The Arabidopsis-accelerated cell death gene ACD2 encodes red chlorophyll catabolite reductase and suppresses the spread of disease symptoms. Mach, J.M., Castillo, A.R., Hoogstraten, R., Greenberg, J.T. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  13. Detection of superoxide generated by endothelial cells. Rosen, G.M., Freeman, B.A. Proc. Natl. Acad. Sci. U.S.A. (1984) [Pubmed]
  14. Caveolin-1 contributes to assembly of store-operated Ca2+ influx channels by regulating plasma membrane localization of TRPC1. Brazer, S.C., Singh, B.B., Liu, X., Swaim, W., Ambudkar, I.S. J. Biol. Chem. (2003) [Pubmed]
  15. Zopiclone and nitrazepam: a multicenter placebo controlled comparative study of efficacy and tolerance in insomniac patients in general practice. Anderson, A.A. Sleep. (1987) [Pubmed]
  16. Kinetic and magnetic resonance studies of the role of metal ions in the mechanism of Escherichia coli GDP-mannose mannosyl hydrolase, an unusual nudix enzyme. Legler, P.M., Lee, H.C., Peisach, J., Mildvan, A.S. Biochemistry (2002) [Pubmed]
  17. Cataleptic and anticataleptic effects of muscimol and gabaculine injected into globus pallidus and substantia nigra, and interactions with haloperidol or benzodiazepines. Matsui, Y., Kamioka, T. Naunyn Schmiedebergs Arch. Pharmacol. (1978) [Pubmed]
  18. A comparison of the effects of chlormezanone and nitrazepam on sleep. Adam, K., Oswald, I. British journal of clinical pharmacology. (1982) [Pubmed]
  19. Double-strand DNA break formation mediated by flap endonuclease-1. Vispé, S., Ho, E.L., Yung, T.M., Satoh, M.S. J. Biol. Chem. (2003) [Pubmed]
  20. Phosphopantothenoylcysteine synthetase from Escherichia coli. Identification and characterization of the last unidentified coenzyme A biosynthetic enzyme in bacteria. Strauss, E., Kinsland, C., Ge, Y., McLafferty, F.W., Begley, T.P. J. Biol. Chem. (2001) [Pubmed]
  21. Matrix regulation of skeletal cell apoptosis. Role of calcium and phosphate ions. Adams, C.S., Mansfield, K., Perlot, R.L., Shapiro, I.M. J. Biol. Chem. (2001) [Pubmed]
  22. Cimetidine impairs nitrazepam clearance. Ochs, H.R., Greenblatt, D.J., Gugler, R., Müntefering, G., Locniskar, A., Abernethy, D.R. Clin. Pharmacol. Ther. (1983) [Pubmed]
  23. Polymorphic acetylation of nitrazepam. Karim, A.K., Evans, D.A. J. Med. Genet. (1976) [Pubmed]
  24. Enhancement of epidermal growth factor signaling and activation of SRC kinase by gangliosides. Li, R., Liu, Y., Ladisch, S. J. Biol. Chem. (2001) [Pubmed]
  25. Synthesis of spin traps specific for hydroxyl radical. Rosen, G.M., Turner, M.J. J. Med. Chem. (1988) [Pubmed]
  26. Toxicity of nitrazepam in the elderly: a report from the Boston Collaborative Drug Surveillance Program. Greenblatt, D.J., Allen, M.D. British journal of clinical pharmacology. (1978) [Pubmed]
  27. Midazolam and nitrazepam in the maternity ward: milk concentrations and clinical effects. Matheson, I., Lunde, P.K., Bredesen, J.E. British journal of clinical pharmacology. (1990) [Pubmed]
  28. Effect of zaleplon on learning and memory in rats. Noguchi, H., Kitazumi, K., Mori, M., Shiba, T. Naunyn Schmiedebergs Arch. Pharmacol. (2002) [Pubmed]
  29. Cloning and functional characterization of a phospholipid:diacylglycerol acyltransferase from Arabidopsis. Ståhl, U., Carlsson, A.S., Lenman, M., Dahlqvist, A., Huang, B., Banas, W., Banas, A., Stymne, S. Plant Physiol. (2004) [Pubmed]
  30. Voltammetric behavior of nitrazepam and its determination in serum using liquid chromatography with redox mode dual-electrode detection. Honeychurch, K.C., Smith, G.C., Hart, J.P. Anal. Chem. (2006) [Pubmed]
  31. Mutational, kinetic, and NMR studies of the mechanism of E. coli GDP-mannose mannosyl hydrolase, an unusual Nudix enzyme. Legler, P.M., Massiah, M.A., Mildvan, A.S. Biochemistry (2002) [Pubmed]
  32. Substrate specificity of human 3(20)alpha-hydroxysteroid dehydrogenase for neurosteroids and its inhibition by benzodiazepines. Usami, N., Yamamoto, T., Shintani, S., Ishikura, S., Higaki, Y., Katagiri, Y., Hara, A. Biol. Pharm. Bull. (2002) [Pubmed]
  33. Clustered charged amino acids of human adenosine deaminase comprise a functional epitope for binding the adenosine deaminase complexing protein CD26/dipeptidyl peptidase IV. Richard, E., Alam, S.M., Arredondo-Vega, F.X., Patel, D.D., Hershfield, M.S. J. Biol. Chem. (2002) [Pubmed]
  34. A single mutation converts the nucleotide specificity of phenol sulfotransferase from PAP to AMP. Hsiao, Y.S., Yang, Y.S. Biochemistry (2002) [Pubmed]
  35. Proteolytic Cleavage of the Linker Region of the Human P-glycoprotein Modulates Its ATPase Function. Nuti, S.L., Rao, U.S. J. Biol. Chem. (2002) [Pubmed]
  36. A conserved sequence within the propeptide domain of membrane type 1 matrix metalloproteinase is critical for function as an intramolecular chaperone. Pavlaki, M., Cao, J., Hymowitz, M., Chen, W.T., Bahou, W., Zucker, S. J. Biol. Chem. (2002) [Pubmed]
  37. Evidence for distinct consecutive steps in the neutral to base transition of human serum albumin. t' Hart, B.J., Wilting, J., de Gier, J.J. Biochem. Pharmacol. (1986) [Pubmed]
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