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Chemical Compound Review

Obidoxim     oxo-[[1-[[4- (oxoazaniumylmethylidene) pyrid...

Synonyms: Obidoxime, Obidoximum, AC1NUNYQ, CHEMBL451635, STL371145, ...
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Disease relevance of 4-(nitrosomethylidene)-1-[[4-(nitrosomethylidene)pyridin-1-yl]methoxymethyl]pyridine

  • One of these reactivators, HI-6, was shown to be significantly more effective in treating soman toxicity than other oximes, such as 2-PAM, TMB4, and obidoxime [1].
  • Six patients with organophosphorus compound intoxications developed an intermediate syndrome (weakness and fasciculations) and obidoxime was given on eight occasions [2].
  • The protocol was based on relatively high doses of obidoxime, relatively low doses of atropine and overriding with a pacemaker in cases of ventricular arrhythmias and prolonged Q-T interval [3].
  • We conclude that each drug should be titrated separately: atropine dosage should be adjusted to the severity of tracheobronchial secretions and bronchospasm, while full doses of obidoxime are justified for the period before "aging" sets in [3].
  • The mean arterial blood pressure (MAP) response to obidoxime, measured in normal rats, was a transient hypotension, but to sarin an immediate hypertension [4].

High impact information on 4-(nitrosomethylidene)-1-[[4-(nitrosomethylidene)pyridin-1-yl]methoxymethyl]pyridine

  • Using obidoxime as an "allosteric antagonist," evidence was found that dimethyl-W84 interacts with the postulated common allosteric site [5].
  • The structural data clearly show analogous coordination of Ortho-7 and obidoxime within the active-site gorge of AChE [6].
  • Crystal structures of the oximes HI-6, Ortho-7 and obidoxime in complex with Mus musculus acetylcholinesterase (mAChE) reveal different roles of the peripheral anionic site (PAS) in the binding of the oximes [6].
  • The low efficiency of HI-6 and the significantly higher efficiency of Ortho-7 and obidoxime may be explained by the differential binding of the oximes in the PAS and active-site gorge of AChE [6].
  • The central chain of Ortho-7 and obidoxime is loosely coordinated in the active-site gorge, whereas the second carboxyimino pyridinium ring is accommodated in the vicinity of the phenol ring of Tyr337 [6].

Chemical compound and disease context of 4-(nitrosomethylidene)-1-[[4-(nitrosomethylidene)pyridin-1-yl]methoxymethyl]pyridine


Biological context of 4-(nitrosomethylidene)-1-[[4-(nitrosomethylidene)pyridin-1-yl]methoxymethyl]pyridine

  • As introduced by Ellis and Seidenberg as a tool to check for a common allosteric site [Mol. Pharmacol. 42:638-641 (1992)], obidoxime was used to antagonize the actions of the test compounds [8].
  • Pharmacokinetics and pharmacodynamics of obidoxime in sarin-poisoned rats [4].
  • The significantly diminished glomerular filtration rate confirmed the retardation of obidoxime excretion in sarin poisoning [4].
  • The serum oxime concentrations (ED50 values) for HI-6, obidoxime, and PAM against a 3 LD50 dose of sarin were 0.72, 9.05, and 2.56 micrograms/ml, respectively [9].
  • Autocatalysis, a mechanism found only rarely in the degradation of pharmaceuticals, has not been reported in previous studies of obidoxime hydrolysis [10].

Anatomical context of 4-(nitrosomethylidene)-1-[[4-(nitrosomethylidene)pyridin-1-yl]methoxymethyl]pyridine


Associations of 4-(nitrosomethylidene)-1-[[4-(nitrosomethylidene)pyridin-1-yl]methoxymethyl]pyridine with other chemical compounds

  • Reactivators (oximes) of inhibited AChE are a mainstay of treatment, however, the commercially available compounds, obidoxime and pralidoxime, are considered to be rather ineffective against various nerve agents [15].
  • The effects of obidoxime, a pyridinium oxime, on the cholinesterase activity and acetylcholine content of the submandibular glands of rats poisoned with armin, an organophosphorus anticholinesterase agent, were studied [11].
  • Atropine and obidoxime in a parenteral injection device are determined by simple HPLC method simultaneously without any pretreatment at 228 nm [16].
  • The pharmacokinetics and pharmacodynamics of the oxime obidoxime (Toxogonin, 50 mg/kg iv) were investigated in anesthetized normal rats and in sarin-poisoned (50 micrograms/kg iv) rats [4].
  • Reactivation of paraoxon-, sarin-, soman- and VX-inhibited AChE by obidoxime was impaired by POX-induced re-inhibition whereas no deviation of pseudo first-order kinetics was observed with tabun, cyclosarin and VR [17].

Gene context of 4-(nitrosomethylidene)-1-[[4-(nitrosomethylidene)pyridin-1-yl]methoxymethyl]pyridine

  • 3. The paraoxon concentrations measured fitted satisfactorily the values calculated from the kinetic constants previously obtained for AChE inhibition and obidoxime-induced reactivation in vitro [18].
  • Obidoxime and 2-PAM were superior to HI 6 and HLö 7 in reactivating butyrylcholinesterase (BChE) [12].
  • At serum concentrations of 3.6, 3.6, and 3.3 micrograms/ml for HI-6, obidoxime, and PAM, respectively, the 24-hr mortality following sarin poisoning was 0, 90, and 20% [9].
  • Thus, the replacement of obidoxime by more effective acetylcholinesterase (AChE) reactivators is necessary to increase the neuroprotective efficacy of antidotal treatment in the case of soman poisonings [19].
  • Only with obidoxime a significant increase in AChE activity was found [20].

Analytical, diagnostic and therapeutic context of 4-(nitrosomethylidene)-1-[[4-(nitrosomethylidene)pyridin-1-yl]methoxymethyl]pyridine

  • The R.S.D. for the HPLC procedure of obidoxime in atropine-obidoxime injectors was 0.82% [21].
  • Perfusion with 10(-3) M obidoxime caused a 19% increase in left ventricular stroke work and a 31% increase in total pressure-volume area [22].
  • Internal standard high-performance liquid chromatography method for the determination of obidoxime in urine of organophosphate-poisoned patients [23].


  1. Two possible orientations of the HI-6 molecule in the reactivation of organophosphate-inhibited acetylcholinesterase. Luo, C., Leader, H., Radic, Z., Maxwell, D.M., Taylor, P., Doctor, B.P., Saxena, A. Biochem. Pharmacol. (2003) [Pubmed]
  2. Efficacy of obidoxime in human organophosphorus poisoning: determination by neuromuscular transmission studies. Besser, R., Weilemann, L.S., Gutmann, L. Muscle Nerve (1995) [Pubmed]
  3. Antidotal therapy of severe acute organophosphate poisoning: a multihospital study. Finkelstein, Y., Kushnir, A., Raikhlin-Eisenkraft, B., Taitelman, U. Neurotoxicology and teratology. (1989) [Pubmed]
  4. Pharmacokinetics and pharmacodynamics of obidoxime in sarin-poisoned rats. Alioth-Streichenberg, C.M., Bodmer, D.M., Waser, P.G. Toxicol. Appl. Pharmacol. (1991) [Pubmed]
  5. Identification of a [3H]Ligand for the common allosteric site of muscarinic acetylcholine M2 receptors. Tränkle, C., Mies-Klomfass, E., Cid, M.H., Holzgrabe, U., Mohr, K. Mol. Pharmacol. (1998) [Pubmed]
  6. Crystal structures of acetylcholinesterase in complex with HI-6, Ortho-7 and obidoxime: structural basis for differences in the ability to reactivate tabun conjugates. Ekström, F., Pang, Y.P., Boman, M., Artursson, E., Akfur, C., Börjegren, S. Biochem. Pharmacol. (2006) [Pubmed]
  7. Acetylcholinesterase inhibition: does it explain the toxicity of organophosphorus compounds? Maxwell, D.M., Brecht, K.M., Koplovitz, I., Sweeney, R.E. Arch. Toxicol. (2006) [Pubmed]
  8. Divergent modes of action among cationic allosteric modulators of muscarinic M2 receptors. Tränkle, C., Mohr, K. Mol. Pharmacol. (1997) [Pubmed]
  9. Comparison of serum concentrations of the acetylcholinesterase oxime reactivators HI-6, obidoxime, and PAM to efficacy against sarin (isopropyl methylphosphonofluoridate) poisoning in rats. Shiloff, J.D., Clement, J.G. Toxicol. Appl. Pharmacol. (1987) [Pubmed]
  10. Autocatalytic degradation and stability of obidoxime. Rubnov, S., Shats, I., Levy, D., Amisar, S., Schneider, H. J. Pharm. Pharmacol. (1999) [Pubmed]
  11. Acetylcholine and cholinesterase in submandibular glands of rats given armin and obidoxime. Vasic, B.V., Milosevic, M.P., Terzic, M.R. J. Dent. Res. (1978) [Pubmed]
  12. Effect of human plasma on the reactivation of sarin-inhibited human erythrocyte acetylcholinesterase. Worek, F., Eyer, P., Kiderlen, D., Thiermann, H., Szinicz, L. Arch. Toxicol. (2000) [Pubmed]
  13. Effect of the bispyridinium compounds HGG12, HGG42, and obidoxime on synaptic transmission and NAD(P)H-fluorescence in the superior cervical ganglion of the rat in vitro. Kirsch, D.M., Weger, N. Arch. Toxicol. (1981) [Pubmed]
  14. Effects of obidoxime chloride on native and sarin-poisoned frog neuromuscular junctions. Caratsch, C.G., Waser, P.G. Pflugers Arch. (1984) [Pubmed]
  15. Kinetic analysis of interactions between human acetylcholinesterase, structurally different organophosphorus compounds and oximes. Worek, F., Thiermann, H., Szinicz, L., Eyer, P. Biochem. Pharmacol. (2004) [Pubmed]
  16. Simple high-performance liquid chromatographic method for determination of atropine and obidoxime in a parenteral injection device. Gören, A.C., Bilsel, G., Bilsel, M., Yenisoy-Karaka, S., Karaka, D. Journal of chromatography. A. (2004) [Pubmed]
  17. Effect of organophosphorus hydrolysing enzymes on obidoxime-induced reactivation of organophosphate-inhibited human acetylcholinesterase. Herkenhoff, S., Szinicz, L., Rastogi, V.K., Cheng, T.C., DeFrank, J.J., Worek, F. Arch. Toxicol. (2004) [Pubmed]
  18. Enzyme-based assay for quantification of paraoxon in blood of parathion poisoned patients. Eyer, F., Eyer, P. Human & experimental toxicology. (1998) [Pubmed]
  19. Neuroprotective effects of currently used antidotes in soman-poisoned rats. Kassa, J., Koupilová, M. Pharmacol. Biochem. Behav. (2000) [Pubmed]
  20. Effects of oximes on muscle force and acetylcholinesterase activity in isolated mouse hemidiaphragms exposed to paraoxon. Thiermann, H., Eyer, P., Worek, F., Szinicz, L. Toxicology (2005) [Pubmed]
  21. Determination of atropine and obidoxime in automatic injection devices used as antidotes against nerve agent intoxication. Pohjola, J., Harpf, M. Journal of chromatography. A. (1994) [Pubmed]
  22. Obidoxime augments the positive inotropic effect of phosphamidon on the isolated working rat heart. Ben-Haim, S.A., Ben-Ami, H., Hayam, G., Taitelman, U., Edoute, Y. Pharmacol. Toxicol. (1992) [Pubmed]
  23. Internal standard high-performance liquid chromatography method for the determination of obidoxime in urine of organophosphate-poisoned patients. Grasshoff, C., Thiermann, H., Gillessen, T., Zilker, T., Szinicz, L. J. Chromatogr. B Biomed. Sci. Appl. (2001) [Pubmed]
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