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Chemical Compound Review

Phenylquinone     2-phenylcyclohexa-2,5-diene- 1,4-dione

Synonyms: SureCN26262, CHEMBL274117, NSC-2806, CCRIS 4280, AG-J-34410, ...
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Disease relevance of NSC 2806

  • The (-)-S isomer of 5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-alpha]pyrrole-1-carboxylic acid is about 60 times more potent than the (+)-R isomer in the carrageenan edema test and ca. 230 times more active than the (+)-R isomer in the mouse phenylquinone writhing assay [1].
  • Administration of phenylbenzoquinone, an agent that stimulated sensory pain receptors, failed to produce a similar decrease in body weight [2].
  • The weight of evidence from the combined database supports the hypothesis that OPP/SOPP-induced DNA damage is a threshold-dependent response associated with target tissue toxicity, most likely induced by their breakdown products phenylhydroquinone and phenylbenzoquinone [3].
  • L-652,343 is an extremely potent analgesic in models of yeast and platelet activating factor induced hyperalgesia in rats and phenylbenzoquinone-induced writhing in mice [4].
  • The analgesic activity of the drug has been evidenced in the phenylquinone-induced writhing and the Randall-Selitto tests, and the antipyretic effects in the yeast-induced hyperthermia in rats [5].

Psychiatry related information on NSC 2806


High impact information on NSC 2806

  • At equimolar oral doses, S-NO-diclofenac derivatives (20a-21b) displayed rat antiinflammatory and analgesic activities comparable to those of diclofenac in the carrageenan-induced paw edema test and the mouse phenylbenzoquinone-induced writhing test, respectively [7].
  • In an in vitro postlabeling experiment with calf thymus DNA, both of the major metabolites of OPP, phenylhydroquinone (PHQ) and phenylbenzoquinone (PBQ), formed adducts, but no adducts were observed with OPP [8].
  • Reactivities of o-phenylphenol and its metabolites (2,5-dihydroxybiphenyl, 2-phenyl-1,4-benzoquinone) with DNA were investigated by a DNA sequencing technique, and the reaction mechanism was studied by UV-visible and ESR spectroscopies [9].
  • Salmon calcitonin (sCT) was tested i.v.t. for its ability to produce antinociception in mice as quantitated by the tail-flick, hot-plate and p-phenylquinone (PPQ) writhing tests. sCT from two sources, Bachem (Torrance, CA) and Armour Pharmaceutical Co [10].
  • CRF administered i.v. in mice did, however, inhibit writhing responses to phenylbenzoquinone (PBQ), suggesting possible peripheral antinociceptive properties [11].

Chemical compound and disease context of NSC 2806

  • The analgesic and anti-inflammatory activities of synthesized compounds were investigated by the phenylquinone-induced writhing syndrome test, carrageenan rat paw oedema test and acetic acid-induced peritonitis assay [12].
  • After acute oral treatment S 19812 exhibited a non-opioid analgesic activity observed in the phenylbenzoquinone-induced writhing model in mice (ED50 = 2.1 mg/kg) and in the carrageenan-induced hyperalgesia model in rats (ED50 = 9.1 mg/kg, preventive treatment; 8.3 mg/kg, curative treatment) [13].
  • A series of methyl 6-substituted-3(2H)-pyridazinone-2-ylacetates 9 were synthesized and their analgesic and anti-inflammatory effects were evaluated in the phenylbenzoquinone-induced writhing test (PBQ test) and carrageenan-induced paw edema method, respectively [14].

Biological context of NSC 2806


Anatomical context of NSC 2806


Associations of NSC 2806 with other chemical compounds


Gene context of NSC 2806


Analytical, diagnostic and therapeutic context of NSC 2806


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  9. DNA damage induced by metabolites of o-phenylphenol in the presence of copper(II) ion. Inoue, S., Yamamoto, K., Kawanishi, S. Chem. Res. Toxicol. (1990) [Pubmed]
  10. Antinociceptive activity of salmon calcitonin injected intraventricularly in mice: modulation of morphine antinociception. Welch, S.P., Cooper, C.W., Dewey, W.L. J. Pharmacol. Exp. Ther. (1986) [Pubmed]
  11. Corticotropin-releasing factor inhibits neurogenic plasma extravasation in the rat paw. Wei, E.T., Kiang, J.G., Buchan, P., Smith, T.W. J. Pharmacol. Exp. Ther. (1986) [Pubmed]
  12. Synthesis of new thieno [2,3-d]pyrimidine-2,4(1H,3H)-diones with analgesic and anti-inflammatory activities. Romeo, G., Russo, F., Caruso, A., Cutuli, V., Amico-Roxas, M. Arzneimittel-Forschung. (1998) [Pubmed]
  13. General pharmacology of the butanamide derivative S 19812, a new dual inhibitor of cyclooxygenase and lipoxygenase pathways. Tordjman, C., Andre, N., Bresson, Y., Bellot, I., Deschamps, C., Pastoureau, P., Wierzbicki, M. Arzneimittel-Forschung. (2003) [Pubmed]
  14. Synthesis and analgesic and antiinflammatory activity of methyl 6-substituted-3(2h)-pyridazinone-2-ylacetate derivatives. Sahina, M.F., Badiçoglu, B., Gökçe, M., Küpeli, E., Yeşilada, E. Arch. Pharm. (Weinheim) (2004) [Pubmed]
  15. DNA damage in urinary bladder epithelium of male F344 rats treated with 2-phenyl-1,4-benzoquinone, one of the non-conjugated urinary metabolites of sodium o-phenylphenate. Morimoto, K., Fukuoka, M., Hasegawa, R., Tanaka, A., Takahashi, A., Hayashi, Y. Jpn. J. Cancer Res. (1987) [Pubmed]
  16. Genotoxic effects of o-phenylphenol metabolites in CHO-K1 cells. Tayama, S., Kamiya, N., Nakagawa, Y. Mutat. Res. (1989) [Pubmed]
  17. The effect of hypophysectomy on acupuncture analgesia in the mouse. Fu, T.C., Halenda, S.P., Dewey, W.L. Brain Res. (1980) [Pubmed]
  18. Sulfhydryl compounds inhibit the cyto- and geno-toxicity of o-phenylphenol metabolites in CHO-K1 cells. Tayama, S., Nakagawa, Y. Mutat. Res. (1991) [Pubmed]
  19. Potentiation of morphine analgesia after pretreatment with probenecid or sulfinpyrazone. Morin, R.A., Lyness, W.H. Pharmacol. Biochem. Behav. (1983) [Pubmed]
  20. Inhibition of prostaglandin-H-synthase by o-phenylphenol and its metabolites. Freyberger, A., Degen, G.H. Arch. Toxicol. (1998) [Pubmed]
  21. The appearance of endogenous opiates in cerebrospinal fluid following opiate injection in various animal species. Dewey, W.L., Bowman, E., Jones, D., Kachur, J., Rosemond, R., Welch, S., Martin, B.R. Life Sci. (1982) [Pubmed]
  22. Nitrous oxide analgesia: reversal by naloxone and development of tolerance. Berkowitz, B.A., Finck, A.D., Ngai, S.H. J. Pharmacol. Exp. Ther. (1977) [Pubmed]
  23. Influence of narcotic antagonist drugs upon nitrous oxide analgesia in mice. Quock, R.M., Graczak, L.M. Brain Res. (1988) [Pubmed]
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  25. A new chloroquinolinyl chalcone derivative as inhibitor of inflammatory and immune response in mice and rats. De León, E.J., Alcaraz, M.J., Dominguez, J.N., Charris, J., Terencio, M.C. J. Pharm. Pharmacol. (2003) [Pubmed]
  26. Production of prostacyclin in mice following intraperitoneal injection of acetic acid, phenylbenzoquinone and zymosan: its role in the writhing response. Berkenkopf, J.W., Weichman, B.M. Prostaglandins (1988) [Pubmed]
  27. Involvement of prostaglandins produced by cyclooxygenase-1 in murine visceronociception induced by phenylquinone. Kusuhara, H., Matsuyuki, H., Okumoto, T. Prostaglandins Other Lipid Mediat. (1998) [Pubmed]
  28. Analgetic activity of SK&F 105809, a dual inhibitor of arachidonic acid metabolism. Griswold, D.E., Marshall, P., Martin, L., Webb, E.F., Zabko-Potapovich, B. Agents Actions Suppl. (1991) [Pubmed]
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  30. Antinociceptive properties of thyrotropin releasing hormone in mice: comparison with morphine. Boschi, G., Desiles, M., Reny, V., Rips, R., Wrigglesworth, S. Br. J. Pharmacol. (1983) [Pubmed]
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