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Chemical Compound Review

PubChem8558     1-phenylpiperazine

Synonyms: CHEMBL9434, SureCN24889, SureCN55125, CCRIS 4334, P30004_ALDRICH, ...
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Disease relevance of CCRIS 4334

  • Here, we show that KN-62, 1-[N,O-bis(5-isoquinolinesulfonyl)-N-methyl-L-tyrosyl]-4- phenylpiperazine, a specific cell-permeable inhibitor of CamK-II substantially protected neurons from (1) acute NMDA toxicity and (2) hypoxia/hypoglycemia-induced neuronal injury in fetal rat cortical cultures [1].
  • Among them, phenylpiperazine compounds with two-carbon length alkyl chains, 2a and 2b, appeared by high analgesic with little toxicity having neither an antiinflammatory effect nor opioid receptor affinity [2].
  • Cataracts in dogs following subchronic administration of the phenylpiperazine antihypertensive agent PD 78787 [3].
  • All the phenylpiperazine derivatives stimulated the flexor reflex in the spinal rat and evoked hyperthermia in rats at a high ambient temperature (28 degrees C) and in rabbits [4].

High impact information on CCRIS 4334

  • 1-[N, O-bis-(5-isoquinolinesulphonyl)-N-methyl-L-tyrosyl]-4- phenylpiperazine (KN-62), an inhibitor of calcium-dependent camodulin protein kinase II, inhibits both insulin- and hypoxia-stimulated glucose transport in skeletal muscle [5].
  • The highest affinity (IC50 = 0.50 nM) and selectivity for the 5-HT(1A) receptor were showed by 1-phenylpiperazine 2a with a three-membered alkyl chain bearing a 5-methoxytetralin-1-yl ring in the omega position [6].
  • Nefazodone is a phenylpiperazine antidepressant with 5-HT2 antagonism and 5-HT reuptake inhibition [7].
  • Structure-activity relationships for alpha 1-adrenoceptor affinity are presented and indicate that compounds with substitution at the ortho position on the benzene ring of the phenylpiperazine side chain moiety are more potent than those without substitution and/or substitutions at the 3- and 4-positions [8].
  • Autophosphorylation was inhibited by the CaMKII(281-302) peptide, which corresponds to the CaMKII autoinhibitory domain, and by 1-[N,O-bis(5-isoquinolinesulfonyl)-N-methyl-L-tyrosyl]-4- phenylpiperazine (KN-62), a specific CaM kinase antagonist [9].

Biological context of CCRIS 4334


Anatomical context of CCRIS 4334

  • Effects of KN-62 (1-[N,O-bis(5-isoquinolinesulfonyl)-N-methyl-L-tyrosyl]-4- phenylpiperazine), a specific Ca++/calmodulin (CaM)-dependent protein kinase inhibitor, were examined on the rate of spontaneous beating and the intracellular Ca++ transient of cultured myocytes from fetal mouse ventricle [13].

Associations of CCRIS 4334 with other chemical compounds

  • In this study, we examined the influence of the actions of the halogenated phenylpiperazine LY 165,163 at dopamine D1, D2 and D3 receptors on its 5-HT1A agonist properties in vivo [14].
  • Eltoprazine, a phenylpiperazine derivative, selectively reduces offensive aggression in animal models [15].
  • WAY-100635 (N-[2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]-N-(2- pyridinyl)cyclohexanecarboxamide trihydrochloride) is an achiral phenylpiperazine derivative that binds with high affinity and selectivity to the 5-HT1A receptor [16].
  • The in vivo regional distribution and pharmacological profile of a novel iodinated phenylpiperazine derivative, [123I]p-MPPI (4-(2'-methoxy-)phenyl-1-[2'-(N-2"pyridinyl)-p-iodobenzamido-]ethy l- piperazine), in the rat brain were evaluated for use as a potential in vivo imaging agent for 5-HT1A receptors [17].
  • The metabolites in the rat and the dog were 4-hydroxyphenylpiperazine glucuronide (M1), 1,4-dihydroxyphenyl glucuronide (M2), 1,4-dihydroxyphenyl sulfate (M3) and phenylpiperazine (M4) [18].

Gene context of CCRIS 4334


Analytical, diagnostic and therapeutic context of CCRIS 4334


  1. A specific inhibitor of calcium/calmodulin-dependent protein kinase-II provides neuroprotection against NMDA- and hypoxia/hypoglycemia-induced cell death. Hajimohammadreza, I., Probert, A.W., Coughenour, L.L., Borosky, S.A., Marcoux, F.W., Boxer, P.A., Wang, K.K. J. Neurosci. (1995) [Pubmed]
  2. Novel nonopioid non-antiinflammatory analgesics: 3-(aminoalkyl)- and 3-[(4-aryl-1-piperazinyl)alkyl]oxazolo[4,5-b]pyridin-2(3H)-ones. Flouzat, C., Bresson, Y., Mattio, A., Bonnet, J., Guillaumet, G. J. Med. Chem. (1993) [Pubmed]
  3. Cataracts in dogs following subchronic administration of the phenylpiperazine antihypertensive agent PD 78787. Susick, R.L., Jordan, R.A., Watkins, J.R. Fundamental and applied toxicology : official journal of the Society of Toxicology. (1991) [Pubmed]
  4. Central serotoninmimetic action of phenylpiperazines. Maj, J., Lewandowska, A. Polish journal of pharmacology and pharmacy. (1980) [Pubmed]
  5. 1-[N, O-bis-(5-isoquinolinesulphonyl)-N-methyl-L-tyrosyl]-4- phenylpiperazine (KN-62), an inhibitor of calcium-dependent camodulin protein kinase II, inhibits both insulin- and hypoxia-stimulated glucose transport in skeletal muscle. Brozinick, J.T., Reynolds, T.H., Dean, D., Cartee, G., Cushman, S.W. Biochem. J. (1999) [Pubmed]
  6. Structure-activity relationship studies on the 5-HT(1A) receptor affinity of 1-phenyl-4-[omega-(alpha- or beta-tetralinyl)alkyl]piperazines. 4. Perrone, R., Berardi, F., Colabufo, N.A., Leopoldo, M., Tortorella, V., Fornaretto, M.G., Caccia, C., McArthur, R.A. J. Med. Chem. (1996) [Pubmed]
  7. Nefazodone and imipramine in major depression: a placebo-controlled trial. Rickels, K., Schweizer, E., Clary, C., Fox, I., Weise, C. The British journal of psychiatry : the journal of mental science. (1994) [Pubmed]
  8. Studies on quinazolines. 5. 2,3-dihydroimidazo[1,2-c]quinazoline derivatives: a novel class of potent and selective alpha 1-adrenoceptor antagonists and antihypertensive agents. Chern, J.W., Tao, P.L., Yen, M.H., Lu, G.Y., Shiau, C.Y., Lai, Y.J., Chien, S.L., Chan, C.H. J. Med. Chem. (1993) [Pubmed]
  9. Expression of Ca2+/calmodulin-dependent protein kinase types II and IV, and reduced DNA synthesis due to the Ca2+/calmodulin-dependent protein kinase inhibitor KN-62 (1-[N,O-bis(5-isoquinolinesulfonyl)-N-methyl-L-tyrosyl]-4-phenyl piperazine) in small cell lung carcinoma. Williams, C.L., Phelps, S.H., Porter, R.A. Biochem. Pharmacol. (1996) [Pubmed]
  10. 5-Hydroxytryptamine2 (5-HT2) structure-function relationships of the nitro and amino phenylpiperazines on intact human platelets. VandenBerg, S.R., Britt, S.G., Redpath, G.T., Gonias, S.L. Biochem. Pharmacol. (1989) [Pubmed]
  11. Flesinoxan lowers blood pressure and heart rate in cats via 5-HT1A receptors. Wouters, W., Tulp, M.T., Bevan, P. Eur. J. Pharmacol. (1988) [Pubmed]
  12. Pharmacokinetics and tissue distribution of a new heterocyclic N-phenylpiperazine derivative (LASSBio-581) in rats. Tasso, L., Neves, G., Menegatti, R., Fraga, C.A., Barreiro, E., Eifler-Lima, V., Rates, S.M., Costa, T.D. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. (2005) [Pubmed]
  13. KN-62, a specific Ca++/calmodulin-dependent protein kinase inhibitor, reversibly depresses the rate of beating of cultured fetal mouse cardiac myocytes. Okazaki, K., Ishikawa, T., Inui, M., Tada, M., Goshima, K., Okamoto, T., Hidaka, H. J. Pharmacol. Exp. Ther. (1994) [Pubmed]
  14. Antagonist properties of LY 165,163 at pre- and postsynaptic dopamine D2, D3 and D1 receptors: modulation of agonist actions at 5-HT1A receptors in vivo. Millan, M.J., Rivet, J.M., Audinot, V., Gobert, A., Lejeune, F., Brocco, M., Newman-Tancredi, A., Maurel-Remy, S., Bervoets, K. J. Pharmacol. Exp. Ther. (1995) [Pubmed]
  15. Eltoprazine, a drug which reduces aggressive behaviour, binds selectively to 5-HT1 receptor sites in the rat brain: an autoradiographic study. Sijbesma, H., Schipper, J., de Kloet, E.R. Eur. J. Pharmacol. (1990) [Pubmed]
  16. A pharmacological profile of the selective silent 5-HT1A receptor antagonist, WAY-100635. Forster, E.A., Cliffe, I.A., Bill, D.J., Dover, G.M., Jones, D., Reilly, Y., Fletcher, A. Eur. J. Pharmacol. (1995) [Pubmed]
  17. In vivo binding of [123I]4-(2'-methoxyphenyl)-1-[2'-(N-2"-pyridinyl)- p-iodobenzamido-]ethyl-piperazine, p-MPPI, to 5-HT1A receptors in rat brain. Kung, M.P., Zhuang, Z.P., Frederick, D., Kung, H.F. Synapse (1994) [Pubmed]
  18. Characterization of polar urinary metabolites by ionspray tandem mass spectrometry following dansylation. Dalvie, D.K., O'Donnell, J.P. Rapid Commun. Mass Spectrom. (1998) [Pubmed]
  19. Novel phenylpiperazine derivatives as dual cytokine regulators with TNF-alpha suppressing and IL-10 augmenting activity. Hanano, T., Adachi, K., Aoki, Y., Morimoto, H., Naka, Y., Hisadome, M., Fukuda, T., Sumichika, H. Bioorg. Med. Chem. Lett. (2000) [Pubmed]
  20. Novel potent neuropeptide Y Y5 receptor antagonists: Synthesis and structure-activity relationships of phenylpiperazine derivatives. Takahashi, T., Sakuraba, A., Hirohashi, T., Shibata, T., Hirose, M., Haga, Y., Nonoshita, K., Kanno, T., Ito, J., Iwaasa, H., Kanatani, A., Fukami, T., Sato, N. Bioorg. Med. Chem. (2006) [Pubmed]
  21. In vivo SPECT imaging of 5-HT1A receptors with [123I]p-MPPI in nonhuman primates. Kung, H.F., Frederick, D., Kim, H.J., McElgin, W., Kung, M.P., Mu, M., Mozley, P.D., Vessotskie, J.M., Stevenson, D.A., Kushner, S.A., Zhuang, Z.P. Synapse (1996) [Pubmed]
  22. Design and synthesis of an orally active GPIIb/IIIa antagonist based on a phenylpiperazine scaffold. van Maarseveen, J.H., den Hartog, J.A., Tipker, K., Reinders, J.H., Brakkee, J., Schön, U., Kehrbach, W., Kruse, C.G. Bioorg. Med. Chem. Lett. (1998) [Pubmed]
  23. Antagonists of slow-reacting substance of anaphylaxis. 1. Pyrido[2,1-b]quinazolinecarboxylic acid derivatives. Tilley, J.W., Levitan, P., Welton, A.F., Crowley, H.J. J. Med. Chem. (1983) [Pubmed]
  24. Validated HPLC method for determination of LASSBio-581, a new heterocyclic N-phenylpiperazine derivative, in rat plasma. Tasso, L., Neves, G., Menegatti, R., Fraga, C.A., Barreiro, E.J., Eifler-Lima, V.L., Rates, S.M., Dalla Costa, T. Journal of pharmaceutical and biomedical analysis. (2003) [Pubmed]
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