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Chemical Compound Review

Rimcazol     9-[3-[(3S,5R)-3,5- dimethylpiperazin-1...

Synonyms: Rimcazole, Rimcazolum, Tocris-1497, SureCN99084, CHEMBL275707, ...
 
 
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Disease relevance of Rimcazole

  • The inability of the putative sigma receptor antagonists BMY 14802 and rimcazole to antagonize DTG-induced hypothermia suggests that either these compounds at the dose used have little sigma receptor antagonist activity, or that the DTG-induced hypothermia is not due to specific interactions with sigma receptors [1].
  • The potency of sigma ligands on melanoma cells was rimcazole > reduced haloperidol > haloperidol = (+)-pentazocine, whereas DTG and (+)- and (-)-SKF 10,047 and (-)-pentazocine had no effect even at 100 microM [2].
  • The order of potency of protection against hypoxia/hypoglycemia-induced reduction in CA1 presynaptic potential was: NE-100 = haloperidol > rimcazole [3].
  • 1,3-di-o-tolylguanidine and rimcazole act as typical neuroleptics (antagonize the apomorphine-induced aggression and climbing) and at the same time, as dopamine stimulants (antagonize neuroleptic-induced catalepsy) [4].
 

Psychiatry related information on Rimcazole

 

High impact information on Rimcazole

  • The resultant bags were cultured in Eagle's minimum essential medium (EMEM) alone or supplemented with the Sigma receptor antagonists rimcazole (3 microM) and BD1047 (10 microM) [8].
  • To determine the roles of both DAT and sigma(1) receptors in the behavioral actions of rimcazole, a series of analogues was synthesized [9].
  • Structure-activity relationships at the monoamine transporters and sigma receptors for a novel series of 9-[3-(cis-3, 5-dimethyl-1-piperazinyl)propyl]carbazole (rimcazole) analogues [10].
  • Regulation of sigma-receptors: high- and low-affinity agonist states, GTP shifts, and up-regulation by rimcazole and 1,3-Di(2-tolyl)guanidine [11].
  • Carbetapentane and rimcazole, which induced no current response at 100 microM, reversibly suppressed the inward K+ current responses induced by nociceptin in a concentration-dependent manner, and the IC50 values (microM) for these compounds were 9.0 and 12.6, respectively [12].
 

Biological context of Rimcazole

  • The Sigma receptor antagonists BD1047 and rimcazole inhibited lens cell growth and, surprisingly, lens cells accumulated pigment granules in the presence of the antagonists [8].
  • The effects of putative sigma receptor antagonists BMY 14802 and rimcazole on DTG-induced changes in body temperature also were evaluated [1].
  • The effects of subchronic administration of rimcazole and 1,3-di(2-tolyl)guanidine (DTG) on the central R(+)[3H]-3-[3-hydroxyphenyl]-N-(1-propyl)piperidine (R(+)[3H]-3-PPP) binding site were investigated in the rat [13].
  • Addition of the sigma ligands haloperidol, reduced haloperidol, 1,3-di(2-tolyl)guanidine (DTG), (+)- and (-)-N-allylnormetazocine (SKF 10,047), (+)- and (-)-pentazocine and rimcazole at 6.25, 12.5, 25, 50, 100 microM at the beginning of culture or 24 h later, inhibited cell proliferation in a dose-dependent manner [2].
 

Anatomical context of Rimcazole

  • The sigma [corrected] ligand rimcazole antagonises (+)SKF 10,047, but not (+)3-PPP, in the mouse isolated vas deferens [14].
  • The sigma ligand rimcazole activates noradrenergic neurons projecting to the paraventricular nucleus and increases corticosterone secretion in rats [15].
  • Pretreatment with a 'putative' sigma receptor agonist, pentazocine, prevented the rimcazole-induced increase of the concentration of DOPAC in the median eminence, but did not block the ability of rimcazole to decrease plasma concentrations of prolactin [16].
  • The above data suggests a modulatory effect of D1-receptor activation on the inhibitory effect of D2-receptor stimulation in cortex as well as hippocampus and the blockade by rimcazole of the effect of D1-DA receptor agonist in these areas [17].
 

Associations of Rimcazole with other chemical compounds

  • Sulpiride and rimcazole produced significant increases in the concentration of NT in the caudate [18].
  • Fluspirilene, an antipsychotic agent that interacts potently with dopamine receptors, inhibited the binding of [3H]-(+) 3-PPP (IC50 = 380 nM) more potently than rimcazole, a putative sigma antagonist that was tested clinically for antipsychotic activity [19].
  • Despite high-affinity binding at DAT, and structural similarity to GBR 12909, preliminary studies suggest 9b behaves more like rimcazole than GBR 12909 and does not demonstrate cocaine-like psychostimulant behavior in mice [20].
 

Gene context of Rimcazole

  • These results suggest that carbetapentane and rimcazole act as antagonists at the nociceptin/orphanin FQ receptor and may be involved in pain regulation [12].
  • The sigma receptor ligand rimcazole alters secretion of prolactin and alpha-melanocyte stimulating hormone by dopaminergic and non-dopaminergic mechanisms [16].
  • Rimcazole inhibited PCP c-fos induction in the cingulate and parietal cortices and DTG c-fos induction in the cingulate cortex [21].
  • In a continuing effort to identify novel probes with which to study the dopamine transporter (DAT), we discovered that the sigma receptor antagonist, rimcazole, binds with moderate affinity (K(i)=224nM) to the DAT [20].
  • In the presence of 5 X 10(-7) M BW 234U, the apparent KD was 165 +/- 35 nM, but the Bmax (892 +/- 146 fmoles/mg protein) was not affected [22].
 

Analytical, diagnostic and therapeutic context of Rimcazole

  • Intraperitoneal injection of rimcazole, in doses from 1 to 10 mg/kg, significantly and dose dependently antagonized the cough depressant effect of N,N'-di(orthotolyl)guanidine (DTG), a sigma ligand [23].
  • Intravenous injections of Rimcazole did not prevent or reverse the inhibition of firing rates of DA cells produced by DA agonist apomorphine (APO) [24].
  • Amplitude of cortical firing was enhanced but not of hippocampal EEG following administration of rimcazole [17].
  • However, subsequent clinical trials demonstrated that rimcazole lacked efficacy in schizophrenic patients and it is now primarily used as an experimental tool [25].

References

  1. Effects of subcutaneous and intracerebroventricular administration of the sigma receptor ligand 1,3-Di-o-tolylguanidine on body temperature in the rat: interactions with BMY 14802 and rimcazole. Bejanian, M., Pechnick, R.N., Bova, M.P., George, R. J. Pharmacol. Exp. Ther. (1991) [Pubmed]
  2. Sigma binding site ligands inhibit cell proliferation in mammary and colon carcinoma cell lines and melanoma cells in culture. Brent, P.J., Pang, G.T. Eur. J. Pharmacol. (1995) [Pubmed]
  3. A role of sigma receptors on hypoxia/hypoglycemia-induced decrease in CA1 presynaptic fiber spikes in rat hippocampal slices. Shibata, S., Yamamoto, Y., Watanabe, S. Brain Res. (1995) [Pubmed]
  4. Influence of 1,3-di-o-tolylguanidine and rimcazole, selective sigma ligands, on apomorphine and neuroleptic effects. Maj, J., Rogóz, Z., Skuza, G. Polish journal of pharmacology. (1993) [Pubmed]
  5. Behavioral effects of rimcazole analogues alone and in combination with cocaine. Katz, J.L., Libby, T.A., Kopajtic, T., Husbands, S.M., Newman, A.H. Eur. J. Pharmacol. (2003) [Pubmed]
  6. Rimcazole, a sigma receptor ligand, and the anticonvulsive action of conventional antiepileptic drugs. Borowicz, K.K., Wilczyński, P.M., Kleinrok, Z., Czuczwar, S.J. Journal of neural transmission (Vienna, Austria : 1996) (1998) [Pubmed]
  7. A review of evidence for GABergic predominance/glutamatergic deficit as a common etiological factor in both schizophrenia and affective psychoses: more support for a continuum hypothesis of "functional" psychosis. Squires, R.F., Saederup, E. Neurochem. Res. (1991) [Pubmed]
  8. Sigma receptor antagonists inhibit human lens cell growth and induce pigmentation. Wang, L., Prescott, A.R., Spruce, B.A., Sanderson, J., Duncan, G. Invest. Ophthalmol. Vis. Sci. (2005) [Pubmed]
  9. Dual probes for the dopamine transporter and sigma1 receptors: novel piperazinyl alkyl-bis(4'-fluorophenyl)amine analogues as potential cocaine-abuse therapeutic agents. Cao, J., Kulkarni, S.S., Husbands, S.M., Bowen, W.D., Williams, W., Kopajtic, T., Katz, J.L., George, C., Newman, A.H. J. Med. Chem. (2003) [Pubmed]
  10. Structure-activity relationships at the monoamine transporters and sigma receptors for a novel series of 9-[3-(cis-3, 5-dimethyl-1-piperazinyl)propyl]carbazole (rimcazole) analogues. Husbands, S.M., Izenwasser, S., Kopajtic, T., Bowen, W.D., Vilner, B.J., Katz, J.L., Newman, A.H. J. Med. Chem. (1999) [Pubmed]
  11. Regulation of sigma-receptors: high- and low-affinity agonist states, GTP shifts, and up-regulation by rimcazole and 1,3-Di(2-tolyl)guanidine. Beart, P.M., O'Shea, R.D., Manallack, D.T. J. Neurochem. (1989) [Pubmed]
  12. Effects of sigma ligands on the nociceptin/orphanin FQ receptor co-expressed with the G-protein-activated K+ channel in Xenopus oocytes. Kobayashi, T., Ikeda, K., Togashi, S., Itoh, N., Kumanishi, T. Br. J. Pharmacol. (1997) [Pubmed]
  13. Up-regulation of rat cortical sigma receptors after subchronic administration of rimcazole and 1,3-di(2-tolyl)guanidine. Manallack, D.T., Beart, P.M. Neuropharmacology (1988) [Pubmed]
  14. The sigma [corrected] ligand rimcazole antagonises (+)SKF 10,047, but not (+)3-PPP, in the mouse isolated vas deferens. Kennedy, C., Jarvis, G.E., Henderson, G. Eur. J. Pharmacol. (1990) [Pubmed]
  15. The sigma ligand rimcazole activates noradrenergic neurons projecting to the paraventricular nucleus and increases corticosterone secretion in rats. Eaton, M.J., Lookingland, K.J., Moore, K.E. Brain Res. (1996) [Pubmed]
  16. The sigma receptor ligand rimcazole alters secretion of prolactin and alpha-melanocyte stimulating hormone by dopaminergic and non-dopaminergic mechanisms. Eaton, M.J., Lookingland, K.J., Moore, K.E. Eur. J. Pharmacol. (1996) [Pubmed]
  17. Effect of D1- and D2-dopamine agonists on neocortical and hippocampal EEG activity of rat brain: modulation of rimcazole effect. Verma, A., Kulkarni, S.K., Nayar, U. Methods and findings in experimental and clinical pharmacology. (1993) [Pubmed]
  18. Alterations in regional brain neurotensin concentrations produced by atypical antipsychotic drugs. Levant, B., Bissette, G., Widerlöv, E., Nemeroff, C.B. Regul. Pept. (1991) [Pubmed]
  19. GBR-12909 and fluspirilene potently inhibited binding of [3H] (+)3-PPP to sigma receptors in rat brain. Contreras, P.C., Bremer, M.E., Rao, T.S. Life Sci. (1990) [Pubmed]
  20. [3-cis-3,5-Dimethyl-(1-piperazinyl)alkyl]-bis-(4'-fluorophenyl)amine analogues as novel probes for the dopamine transporter. Cao, J., Husbands, S.M., Kopajtic, T., Katz, J.L., Newman, A.H. Bioorg. Med. Chem. Lett. (2001) [Pubmed]
  21. Phencyclidine (PCP) acts at sigma sites to induce c-fos gene expression. Sharp, J.W. Brain Res. (1997) [Pubmed]
  22. Evidence that the potential antipsychotic agent rimcazole (BW 234U) is a specific, competitive antagonist of sigma sites in brain. Ferris, R.M., Tang, F.L., Chang, K.J., Russell, A. Life Sci. (1986) [Pubmed]
  23. Effects of rimcazole, a specific antagonist of sigma sites, on the antitussive effects of non-narcotic antitussive drugs. Kamei, J., Iwamoto, Y., Misawa, M., Kasuya, Y. Eur. J. Pharmacol. (1993) [Pubmed]
  24. Acute and subchronic effects of Rimcazole (BW 234U), a potential antipsychotic drug, on A9 and A10 dopamine neurons in the rat. Piontek, J.A., Wang, R.Y. Life Sci. (1986) [Pubmed]
  25. Review of the pharmacological and clinical profile of rimcazole. Gilmore, D.L., Liu, Y., Matsumoto, R.R. CNS drug reviews. (2004) [Pubmed]
 
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