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Chemical Compound Review

Cirazolina     2-[(2- cyclopropylphenoxy)methyl]- 4,5...

Synonyms: cirazoline, Cirazolinum, Lopac-C-223, Tocris-0888, CHEMBL13852, ...
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Disease relevance of cirazoline


Psychiatry related information on cirazoline

  • 4. In rat tail artery, the effects (dose-response and time-response curves) of cirazoline and TL99 on intracellular Ca2+ levels in freshly dispersed single smooth muscle cells were comparable with those obtained with organ bath studies of ring preparations of artery [6].

High impact information on cirazoline

  • In pithed rats (and in isolated canine saphenous vein strips) cirazoline behaved as a preferential alpha 1-adrenoceptor agonist, since its pressor (and contractile) effects were blocked selectively by the alpha 1-adrenoceptor antagonist prazosin and were relatively unaffected by the alpha 2-adrenoceptor antagonist yohimbine [7].
  • The selective alpha1-agonist cirazoline was in itself without effect on cAMP levels or thermogenesis, but when added to forskolin-stimulated cells, potentiated thermogenesis, up to the norepinephrine level, without affecting cAMP [8].
  • In PC-12 membranes, [125I]AZIPI photolabels a major M(r) = approximately 61,000 peptide; the photoincorporation is blocked by cirazoline, guanabenz, and amiloride but not by idazoxan (competing ligands = 10 microM) [9].
  • [125I]AMIPI is structurally related to cirazoline, an imidazoline exhibiting high affinity for IGRS and the family of related imidazoline binding sites [10].
  • Male Sprague-Dawley rats received either cirazoline (0, 10, 25, 50 mug/5 mul), methoxamine (0, 30, 100 mug/5 mul), or phenylephrine (0, 3, 10, 30 mug/5 mul) ICV immediately before testing [11].

Chemical compound and disease context of cirazoline


Biological context of cirazoline


Anatomical context of cirazoline

  • In normotensive Sprague-Dawley rats, repeated treatment with the imidazoline drugs idazoxan and cirazoline also increased (33-37%) the density of imidazoline receptors in the cerebral cortex [17].
  • Muscle strips with the endothelium removed contracted in response to the alpha1-adrenoceptor agonist cirazoline, with half-maximal contraction at 0.23 microM [13].
  • The nonadrenergic inhibition of the twitch response observed in the ileum with cirazoline resulted from weak anticholinergic activity (antimuscarinic) at the level of the postsynaptic effector organ and was observed only at high concentrations [18].
  • The actions of cirazoline on the rat vas deferens [19].
  • Cirazoline did not produce a significant depolarisation in blood vessels of either normotensive or hypertensive rats [20].

Associations of cirazoline with other chemical compounds


Gene context of cirazoline


Analytical, diagnostic and therapeutic context of cirazoline


  1. Functional and biochemical evidence for the lack of cardiac presynaptic alpha-2 adrenoceptor stimulant properties of cirazoline (LD 3098), a potent alpha-1 adrenoceptor agonist in dogs and rats. Cavero, I., Lefèvre-Borg, F., Roach, A.G., Gomeni, R., Scatton, B. J. Pharmacol. Exp. Ther. (1982) [Pubmed]
  2. Effect of pertussis toxin treatment on postjunctional alpha-1 and alpha-2 adrenoceptor function in the cardiovascular system of the pithed rat. Nichols, A.J., Motley, E.D., Ruffolo, R.R. J. Pharmacol. Exp. Ther. (1989) [Pubmed]
  3. Characterization of brain imidazoline receptors in normotensive and hypertensive rats: differential regulation by chronic imidazoline drug treatment. Olmos, G., Miralles, A., Barturen, F., Garcia-Sevilla, J.A. J. Pharmacol. Exp. Ther. (1992) [Pubmed]
  4. Antagonism of the hypothermic effect of clozapine in mice by centrally-active alpha 2-adrenergic antagonists and alpha 1-adrenergic agonists. Menon, M.K., Lloyd, R.L., Fitten, L.J. Psychopharmacology (Berl.) (1990) [Pubmed]
  5. Endotoxin-induced impairment of vasopressor and vasodepressor responses in the pithed rat. Guc, M.O., Furman, B.L., Parratt, J.R. Br. J. Pharmacol. (1990) [Pubmed]
  6. The effects of alpha-adrenoceptor agonists on intracellular Ca2+ levels in freshly dispersed single smooth muscle cells from rat tail artery. Li, X.F., Kargacin, M.E., Triggle, C.R. Br. J. Pharmacol. (1993) [Pubmed]
  7. Differential inhibition of vascular smooth muscle responses to alpha 1- and alpha 2-adrenoceptor agonists by diltiazem and verapamil. Cavero, I., Shepperson, N., Lefèvre-Borg, F., Langer, S.Z. Circ. Res. (1983) [Pubmed]
  8. alpha1-Adrenergic stimulation potentiates the thermogenic action of beta3-adrenoreceptor-generated cAMP in brown fat cells. Zhao, J., Cannon, B., Nedergaard, J. J. Biol. Chem. (1997) [Pubmed]
  9. Visualization of multiple imidazoline/guanidinium-receptive sites. Lanier, S.M., Ivkovic, B., Singh, I., Neumeyer, J.L., Bakthavachalam, V. J. Biol. Chem. (1993) [Pubmed]
  10. Development of a high-affinity radioiodinated ligand for identification of imidazoline/guanidinium receptive sites (IGRS): intratissue distribution of IGRS in liver, forebrain, and kidney. Ivkovic, B., Bakthavachalam, V., Zhang, W., Parini, A., Diz, D., Bosch, S., Neumeyer, J.L., Lanier, S.M. Mol. Pharmacol. (1994) [Pubmed]
  11. Disruption of Prepulse Inhibition after Stimulation of Central but not Peripheral alpha-1 Adrenergic Receptors. Alsene, K.M., Carasso, B.S., Connors, E.E., Bakshi, V.P. Neuropsychopharmacology (2006) [Pubmed]
  12. Single and repeated doses of the vasodilator/beta-adrenergic antagonist, carvedilol, block cirazoline- and isoproterenol-mediated hemodynamic responses in the conscious rat. Smith, E.F., Slivjak, M.J., Gagnon, R. Cardiovascular drugs and therapy / sponsored by the International Society of Cardiovascular Pharmacotherapy. (1992) [Pubmed]
  13. alpha1-Adrenoceptor-mediated phosphorylation of myosin in rat-tail arterial smooth muscle. Mita, M., Walsh, M.P. Biochem. J. (1997) [Pubmed]
  14. Calcium entry blockade by nitrendipine and alpha adrenergic responsiveness in vivo: comparison of systemic vs. local effects. Pedrinelli, R., Tarazi, R.C. J. Pharmacol. Exp. Ther. (1985) [Pubmed]
  15. Inhibitory effect of alpha-1 adrenoceptor stimulation on cardiac sympathetic neurotransmission in pithed normotensive rats. de Jonge, A., van den Berg, G., Qian, J.Q., Wilffert, B., Thoolen, M.J., Timmermans, P.B., van Zwieten, P.A. J. Pharmacol. Exp. Ther. (1986) [Pubmed]
  16. Effects of alpha-adrenoceptor agonists on cardiac output and its regional distribution in the pithed rat. Hiley, C.R., Thomas, G.R. Br. J. Pharmacol. (1987) [Pubmed]
  17. Repeated idazoxan increases brain imidazoline receptors in normotensive (WKY) but not in hypertensive (SHR) rats. Olmos, G., Miralles, A., Barturen, F., García-Sevilla, J.A. J. Neurochem. (1991) [Pubmed]
  18. Receptor interactions of imidazolines. IX. Cirazoline is an alpha-1 adrenergic agonist and an alpha-2 adrenergic antagonist. Ruffolo, R.R., Waddell, J.E. J. Pharmacol. Exp. Ther. (1982) [Pubmed]
  19. The actions of cirazoline on the rat vas deferens. Docherty, J.R., McGrath, J.C. Br. J. Pharmacol. (1984) [Pubmed]
  20. Effects of chloride substitution on electromechanical responses in the pulmonary artery of Dahl normotensive and hypertensive rats. Bieger, D., Duggan, J.A., Tabrizchi, R. Br. J. Pharmacol. (2004) [Pubmed]
  21. Mechanism of neurotransmitter release elicited by the preferential alpha 1-adrenergic receptor agonist phenylephrine in superfused superior cervical ganglion cells in culture. Schwartz, D.D., Malik, K.U. J. Neurochem. (1991) [Pubmed]
  22. Further characterization of the guinea pig cerebral cortex idazoxan receptor: solubilization, distinction from the imidazole site, and demonstration of cirazoline as an idazoxan receptor-selective drug. Wikberg, J.E., Uhlén, S. J. Neurochem. (1990) [Pubmed]
  23. Separable noradrenergic and dopaminergic regulation of prepulse inhibition in rats: implications for predictive validity and Tourette Syndrome. Swerdlow, N.R., Bongiovanni, M.J., Tochen, L., Shoemaker, J.M. Psychopharmacology (Berl.) (2006) [Pubmed]
  24. Effects of basal and acetylcholine-induced release of endothelium-derived relaxing factor on contraction to alpha-adrenoceptor agonists in a rabbit artery and corresponding veins. McGrath, J.C., Monaghan, S., Templeton, A.G., Wilson, V.G. Br. J. Pharmacol. (1990) [Pubmed]
  25. A novel pathway for adrenergic stimulation of cAMP-response-element-binding protein (CREB) phosphorylation: mediation via alpha1-adrenoceptors and protein kinase C activation. Thonberg, H., Fredriksson, J.M., Nedergaard, J., Cannon, B. Biochem. J. (2002) [Pubmed]
  26. alpha1A-adrenoceptors activate glucose uptake in L6 muscle cells through a phospholipase C-, phosphatidylinositol-3 kinase-, and atypical protein kinase C-dependent pathway. Hutchinson, D.S., Bengtsson, T. Endocrinology (2005) [Pubmed]
  27. Inhibition of monoamine oxidase A and B activities by imidazol(ine)/guanidine drugs, nature of the interaction and distinction from I2-imidazoline receptors in rat liver. Ozaita, A., Olmos, G., Boronat, M.A., Lizcano, J.M., Unzeta, M., García-Sevilla, J.A. Br. J. Pharmacol. (1997) [Pubmed]
  28. Alpha 1-adrenoceptor-induced contractility in rat aorta is mediated by the alpha 1D subtype. Buckner, S.A., Oheim, K.W., Morse, P.A., Knepper, S.M., Hancock, A.A. Eur. J. Pharmacol. (1996) [Pubmed]
  29. The effects of perfusion rate and NG-nitro-L-arginine methyl ester on cirazoline- and KCl-induced responses in the perfused mesenteric arterial bed of rats. Adeagbo, A.S., Tabrizchi, R., Triggle, C.R. Br. J. Pharmacol. (1994) [Pubmed]
  30. Changes in EEG spectral power in the prefrontal cortex of conscious rats elicited by drugs interacting with dopaminergic and noradrenergic transmission. Sebban, C., Zhang, X.Q., Tesolin-Decros, B., Millan, M.J., Spedding, M. Br. J. Pharmacol. (1999) [Pubmed]
  31. Effects on ingestive behavior in rats of the alpha 1-adrenoceptor agonist cirazoline. Davies, B.T., Wellman, P.J. Eur. J. Pharmacol. (1992) [Pubmed]
  32. Effects of niflumic acid on alpha1-adrenoceptor-induced vasoconstriction in mesenteric artery in vitro and in vivo in two-kidney one-clip hypertensive rats. He, Y., Tabrizchi, R. Eur. J. Pharmacol. (1997) [Pubmed]
  33. Clonidine and cirazoline inhibit activation of nicotinic channels in PC-12 cells. Musgrave, I.F., Krautwurst, D., Hescheler, J., Schultz, G. Ann. N. Y. Acad. Sci. (1995) [Pubmed]
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