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Chemical Compound Review

Fenidon     1-phenylpyrazolidin-3-one

Synonyms: Phenidone, CHEMBL7660, ARONIS011043, SureCN235192, CCRIS 3624, ...
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Disease relevance of Phenidone


High impact information on Phenidone

  • Phenidone alone did not alter mucosal ornithine decarboxylase activity or [3H]thymidine incorporation into mucosal DNA [6].
  • The fusion of cloned mouse myoblasts was markedly inhibited, in a dose-dependent manner, when cells were cultured in medium supplemented with either phenidone (1-phenyl-3-pyrazolidione) or BW755c (3-amino-1-(3-tri-fluoromethylphenyl)-2-pyrazoline), drugs which have been reported to inhibit lipoxygenase and cyclo-oxygenase activities [7].
  • In contrast, neither the protein kinase A inhibitor H-89 (10(-5) M) nor the cyclooxygenase and lipoxygenase inhibitors indomethacin and phenidone (10(-5) M) affected ET-1 action [8].
  • Phenidone (1-phenyl-3-pyrazolidinone) and 2-(12-hydroxydodeca-5,10-diynyl)3,5,6-trimethyl-1,4-benzoqui none (AA861) also decreased the incidence of tendon lesions [9].
  • Chronic administration of the LO inhibitor phenidone also resulted in an increase of PRC, which was independent of changes in blood pressure [10].

Chemical compound and disease context of Phenidone


Biological context of Phenidone

  • Another member of this series, 4-(2-methoxyethyl)-1-phenyl-3-pyrazolidinone (1f, IC50 = 0.48 microM), although less potent than 1n, was better tolerated in the whole animal relative to phenidone (1a) and also displayed good oral activity in two models of 5-lipoxygenase inhibition [16].
  • Coincident with the inhibition of bronchoconstriction by the SRS-A synthesis inhibitor, phenidone, was a dose-dependent reduction in plasma SRS-A [17].
  • Phenidone (300 microM) decreased staurosporine (100 nM)-induced apoptosis to 30% [18].
  • These results suggest that phenidone may contribute to neuronal survival by modulating oxidative stress, which is involved in the excitotoxic and apoptotic processes occurring under ischemic conditions [18].
  • Phenidone treatment also prevented the declines in body weight and food intake observed in vehicle-treated SHRSP, and maintained urine volume and saline intake [19].

Anatomical context of Phenidone

  • In this experiment, the ability of corticosteroid (dexamethasone sodium phosphate), cyclooxygenase inhibitor (piroxicam), lipoxygenase inhibitor (ferulic acid), and dual cyclo/lipoxygenase inhibitor (phenidone) to inhibit human Tenon's fibroblast proliferation was evaluated in culture [20].
  • Similar inhibition of the melittin response by BPB (10 microM) and phenidone (10 microM) was observed in the epithelium-denuded trachea [21].
  • BW755C was also greater than 10 times more potent at inhibiting cell recruitment and exudate volume than phenidone suggesting that the anti-inflammatory efficacy of the mixed inhibitors reflect their potency against CO rather than LPO activity [22].
  • Cold injury, blood-brain barrier changes, and leukotriene synthesis: inhibition by phenidone [23].
  • We also examined the effect of phenidone on myoneointimal formation in balloon-injured rat carotid arteries [24].

Associations of Phenidone with other chemical compounds


Gene context of Phenidone

  • Synthesis and biological evaluation of new phenidone analogues as potential dual cyclooxygenase (COX-1 and COX-2) and human lipoxygenase (5-LOX) inhibitors [29].
  • The present study examined whether the dual cyclooxygenase/lipoxygenase inhibitor phenidone would protect stroke-prone spontaneously hypertensive rats (SHRSP) from stroke and hypertensive renal disease [19].
  • Thus, the hypotensive effect of phenidone was not due to suppression of renin secretion but presumably due to inhibition of its effects [5].
  • Phenidone is not a substrate for dioxygenation by soybean lipoxygenase-1 (L1) but reduces L1Fe(III) into L1Fe(II), as shown by EPR spectroscopy [30].
  • L1 catalyzes the oxidation of phenidone by 13-HPOD, the hydroperoxide formed by dioxygenation of linoleic acid by L1, with formation of 4,5-dehydrophenidone [30].

Analytical, diagnostic and therapeutic context of Phenidone


  1. Tachyphylaxis in 12-0-tetradecanoylphorbol acetate- and arachidonic acid-induced ear edema. Young, J.M., Wagner, B.M., Spires, D.A. J. Invest. Dermatol. (1983) [Pubmed]
  2. 5-Lipoxygenase inhibitors: synthesis and structure-activity relationships of a series of 1-aryl-2H,4H-tetrahydro-1,2,4-triazin-3-ones. Bhatia, P.A., Brooks, C.D., Basha, A., Ratajczyk, J.D., Gunn, B.P., Bouska, J.B., Lanni, C., Young, P.R., Bell, R.L., Carter, G.W. J. Med. Chem. (1996) [Pubmed]
  3. The effects of drugs on Sephadex-induced eosinophilia and lung hyper-responsiveness in the rat. Spicer, B.A., Baker, R.C., Hatt, P.A., Laycock, S.M., Smith, H. Br. J. Pharmacol. (1990) [Pubmed]
  4. The lipoxygenase inhibitor phenidone is a potent hypotensive agent in the spontaneously hypertensive rat. Stern, N., Nozawa, K., Golub, M., Eggena, P., Knoll, E., Tuck, M.L. Am. J. Hypertens. (1993) [Pubmed]
  5. Hypotensive effects of the lipoxygenase inhibitor phenidone in two-kidney, one clip Goldblatt hypertension. Nozawa, K., Tuck, M.L., Golub, M., Eggena, P., Nadler, J., Stern, N. Am. J. Hypertens. (1989) [Pubmed]
  6. Bile salt stimulation of colonic epithelial proliferation. Evidence for involvement of lipoxygenase products. DeRubertis, F.R., Craven, P.A., Saito, R. J. Clin. Invest. (1984) [Pubmed]
  7. Effect of inhibitors of the lipoxygenase pathway on mouse myoblast fusion. Steiner, S., Manley, G., Adams, T. Exp. Cell Res. (1984) [Pubmed]
  8. Endothelins stimulate deoxyribonucleic acid synthesis and cell proliferation in rat adrenal zona glomerulosa, acting through an endothelin A receptor coupled with protein kinase C- and tyrosine kinase-dependent signaling pathways. Mazzocchi, G., Rossi, G.P., Rebuffat, P., Malendowicz, L.K., Markowska, A., Nussdorfer, G.G. Endocrinology (1997) [Pubmed]
  9. Characterization of fluoroquinolone-induced Achilles tendon toxicity in rats: comparison of toxicities of 10 fluoroquinolones and effects of anti-inflammatory compounds. Kashida, Y., Kato, M. Antimicrob. Agents Chemother. (1997) [Pubmed]
  10. Tonic inhibition of renin secretion by the 12 lipoxygenase pathway: augmentation by high salt intake. Stern, N., Nozawa, K., Kisch, E., Tuck, M.L., Golub, M., Eggena, P., Knoll, E. Endocrinology (1996) [Pubmed]
  11. Antagonism to the actions of platelet activating factor by a nonpsychoactive cannabinoid. Burstein, S.H., Audette, C.A., Doyle, S.A., Hull, K., Hunter, S.A., Latham, V. J. Pharmacol. Exp. Ther. (1989) [Pubmed]
  12. Antiinflammatory effects of free radical scavengers and antioxidants: further support for proinflammatory roles of endogenous hydrogen peroxide and lipid peroxides. Bragt, P.C., Bansberg, J.I., Bonta, I.L. Inflammation (1980) [Pubmed]
  13. Effect of topically applied cyclosporin A on arachidonic acid (AA)- and tetradecanoylphorbol acetate (TPA)-induced dermal inflammation in mouse ear. Puigneró, V., Queralt, J. Inflammation (1997) [Pubmed]
  14. Effects of lipoxygenase inhibitors in a model of lens-induced uveitis in dogs. Dziezyc, J., Millichamp, N.J., Rohde, B.H., Baker, J.S., Chiou, G.C. Am. J. Vet. Res. (1989) [Pubmed]
  15. Anti-inflammatory activity of (E)-1-(3,4-dimethoxyphenyl) butadiene from Zingiber cassumunar Roxb. Jeenapongsa, R., Yoovathaworn, K., Sriwatanakul, K.M., Pongprayoon, U., Sriwatanakul, K. Journal of ethnopharmacology. (2003) [Pubmed]
  16. 5-Lipoxygenase inhibitors: the synthesis and structure-activity relationships of a series of 1-phenyl-3-pyrazolidinones. Hlasta, D.J., Casey, F.B., Ferguson, E.W., Gangell, S.J., Heimann, M.R., Jaeger, E.P., Kullnig, R.K., Gordon, R.J. J. Med. Chem. (1991) [Pubmed]
  17. An in vivo model for measuring antigen-induced SRS-A-mediated bronchoconstriction and plasma SRS-A levels in the guinea-pig. Anderson, W.H., O'Donnell, M., Simko, B.A., Welton, A.F. Br. J. Pharmacol. (1983) [Pubmed]
  18. Phenidone attenuates oxygen/glucose deprivation-induced neurotoxicity by antioxidant and antiapoptotic action in mouse cortical cultures. Wie, M.B., Cho, Y.J., Jhoo, W.K., Kim, H.C. Neurosci. Lett. (1999) [Pubmed]
  19. The lipoxygenase inhibitor phenidone protects against proteinuria and stroke in stroke-prone spontaneously hypertensive rats. Munsiff, A.V., Chander, P.N., Levine, S., Stier, C.T. Am. J. Hypertens. (1992) [Pubmed]
  20. Effect of steroids and nonsteroidal antiinflammatory agents on human ocular fibroblast. Nguyen, K.D., Lee, D.A. Invest. Ophthalmol. Vis. Sci. (1992) [Pubmed]
  21. Influence of epithelium on the inhibition of melittin-induced contraction of guinea-pig isolated trachea by the potassium channel opener NIP-121. Shikada, K., Tanaka, S. Br. J. Pharmacol. (1993) [Pubmed]
  22. Leukocyte recruitment in the subcutaneous sponge implant model of acute inflammation in the rat is not mediated by leukotriene B1. Foster, S.J., McCormick, M.E., Howarth, A., Aked, D. Biochem. Pharmacol. (1986) [Pubmed]
  23. Cold injury, blood-brain barrier changes, and leukotriene synthesis: inhibition by phenidone. Robichaud, L.J., Marcoux, F.W. J. Neurotrauma (1990) [Pubmed]
  24. Lipoxygenase inhibition decreases neointimal formation following vascular injury. Fujita, H., Saito, F., Sawada, T., Kushiro, T., Yagi, H., Kanmatsuse, K. Atherosclerosis (1999) [Pubmed]
  25. Mechanisms of inactivation of lipoxygenases by phenidone and BW755C. Cucurou, C., Battioni, J.P., Thang, D.C., Nam, N.H., Mansuy, D. Biochemistry (1991) [Pubmed]
  26. Inhibition of 12-O-tetradecanoylphorbol-13-acetate-induced epidermal ornithine decarboxylase activity by lipoxygenase inhibitors: possible role of product(s) of lipoxygenase pathway. Nakadate, T., Yamamoto, S., Ishii, M., Kato, R. Carcinogenesis (1982) [Pubmed]
  27. The effects of arachidonic acid and non-steroidal anti-inflammatory drugs on intrapulmonary airways of the guinea-pig. Clay, T.P., Fenske, D.C. Br. J. Pharmacol. (1984) [Pubmed]
  28. The release of a non-prostanoid inhibitory factor from rabbit bronchus detected by co-axial bioassay. Spina, D., Page, C.P. Br. J. Pharmacol. (1991) [Pubmed]
  29. Synthesis and biological evaluation of new phenidone analogues as potential dual cyclooxygenase (COX-1 and COX-2) and human lipoxygenase (5-LOX) inhibitors. Cusan, C., Spalluto, G., Prato, M., Adams, M., Bodensieck, A., Bauer, R., Tubaro, A., Bernardi, P., Da Ros, T. Farmaco (2005) [Pubmed]
  30. Soybean lipoxygenase-catalyzed oxidations by linoleic acid hydroperoxide: different reducing substrates and dehydrogenation of phenidone and BW 755C. Mansuy, D., Cucurou, C., Biatry, B., Battioni, J.P. Biochem. Biophys. Res. Commun. (1988) [Pubmed]
  31. Phenidone, a dual inhibitor of cyclooxygenases and lipoxygenases, ameliorates rat paralysis in experimental autoimmune encephalomyelitis by suppressing its target enzymes. Moon, C., Ahn, M., Wie, M.B., Kim, H.M., Koh, C.S., Hong, S.C., Kim, M.D., Tanuma, N., Matsumoto, Y., Shin, T. Brain Res. (2005) [Pubmed]
  32. Arachidonic acid-induced inflammation: inhibition by dual inhibitor of arachidonic acid metabolism, SK&F 86002. Griswold, D.E., Webb, E., Schwartz, L., Hanna, N. Inflammation (1987) [Pubmed]
  33. 12-lipoxygenase in opioid-induced delayed cardioprotection: gene array, mass spectrometric, and pharmacological analyses. Patel, H.H., Fryer, R.M., Gross, E.R., Bundey, R.A., Hsu, A.K., Isbell, M., Eusebi, L.O., Jensen, R.V., Gullans, S.R., Insel, P.A., Nithipatikom, K., Gross, G.J. Circ. Res. (2003) [Pubmed]
  34. Inhibition of lipoxygenase pathway reduces blood pressure in renovascular hypertensive rats. Nozawa, K., Tuck, M.L., Golub, M., Eggena, P., Nadler, J.L., Stern, N. Am. J. Physiol. (1990) [Pubmed]
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