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Chemical Compound Review

ent-Rotigotine     6-(propyl-(2-thiophen-2- ylethyl)amino)-5,6...

Synonyms: PubChem16422, SureCN50425, CHEBI:268876, AC1Q7ALS, CTK8E7910, ...
 
 
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Disease relevance of N-0924

 

Psychiatry related information on N-0924

  • After repeated administration at doses of 0.05, 0.5, 1, and 5 mg/kg, rotigotine increased spontaneous motor activity at the 5 mg/kg dose after 3-5 days of treatment [4].
  • Rotigotine (0.5, 1, and 5 mg/kg/day for 5 days) reversed the active avoidance deficit of helpless rats in the learned helplessness test, as shown by a significant decrease in escape failures after 3 to 4 days (0.5 mg/kg/day), 5 days (1 mg/kg/day), and 3 to 5 days (5 mg/kg/day) of treatment [4].
  • In this study (+)N-0437 was investigated for its antagonistic activity at postsynaptic DA receptors in four behavioural tests which are commonly used to evaluate potential neuroleptic activity, i.e. d-amphetamine-induced stereotypy, passive avoidance responding, intracranial self-stimulation behaviour, and catalepsy [2].
  • Reinforcement delays exceeding 200 ms largely eliminated the reinforcing efficacy of the D2 agonist N-0437 in CA1 operant conditioning [5].
 

High impact information on N-0924

  • At the D2 receptors in the mouse vas deferens (alpha-2 blocked) the potency order was (+)-propyl-9-hydroxy-naphtoxazine > pergolide > N-0923 = apomorphine > bromocriptine > quinpirole > dopamine [6].
  • N-0923 was therefore the most D2 receptor selective agonist tested.(ABSTRACT TRUNCATED AT 250 WORDS)[6]
  • Experiments were carried out using the D2 dopamine receptor-selective agonist (-)-2-(N-propyl-N-2-thienylethylamino)-5-hydroxytetralin (N-0923) in the rat and the mouse isolated vas deferens to determine whether these tissues contained inhibitory D2 receptors in addition to their inhibitory alpha-2 adrenoceptors [6].
  • Increase of NaCl concentration from 0.07 M to 0.14 M resulted in a decrease of the rotigotine Flux(ss) from 22.7 +/- 5.5 nmol cm(-2) h(-1) to 14.1 +/- 4.9 nmol cm(-2) h(-1) [7].
  • The potencies for in vivo inhibition of substantia nigra pars compacta dopamine single cell firing were determined for apomorphine, BHT 920, N-0923, (+/-)-7-hydroxy-dipropylaminotetralin (7-OH-DPAT), (+)-3-(3-hydroxyphenyl)-N-propylpiperidine (3-PPP), pramipexole, quinelorane, quinpirole, RU 24926, U-86170, and U-91356 [8].
 

Chemical compound and disease context of N-0924

 

Biological context of N-0924

  • N-0437 (1.0 and 3.0 mg/kg) significantly reduced food intake, but had no effect on the duration of feeding, the duration and frequency of feeding bouts, or on the time course of feeding [10].
  • In an attempt to improve its bioavailability, seven ester prodrugs of N-0437 were synthesized, i.e. the acetyl-, propionyl-, isobutyryl-, pivaloyl-, 2-amino-phenyl-, 2-methoxy-phenyl- and 2,4-dimethylphenyl-analogues [11].
  • In order to differentiate between direct dopaminergic activity and metabolic activation, brain and plasma levels of N-0437 after administration of N-0724 and N-0953 were measured [12].
  • In contrast the isobutyryl ester, a prodrug with a relatively rapid hydrolysis rate, gave an improvement of turning behaviour over the whole time course in comparison with N-0437 [13].
  • Furthermore, N-0437 inhibited the calcium-dependent release of [3H]dopamine (IC50: 4 nM) and [3H]acetylcholine (IC50: 6.3 nM) from rabbit striatal slices in the nanomolar range [14].
 

Anatomical context of N-0924

  • Prejunctional adrenoceptor activity of N-0437, 2[N-n-propyl-N-2-(thienylethyl-amino)-5-hydroxytetralin], was investigated by means of the cat nictitating membrane (CNM) preparation [15].
  • N-0923, [-]2-(N-propyl-N-2-thienylethylamino)-5- hydroxytetralin HCl, recognizes the high and low affinity states of the D2 receptor in membranes from bovine caudate with a Klow of 79 nM [16].
  • Intra-arterial (i.a.) administration of N-0437 produced a dose-related inhibition (ED50 = 14 micrograms) of the CNM contractions elicited by electrical stimulation of pre- and postganglionic sympathetic nerves of the superior cervical ganglion [15].
  • In this article we quantified the isotopic separation by reversed-phase HPLC of the unlabeled N-0437, its deuterated and tritiated analogs, and their corresponding glucuronides, synthesized in vitro by rat liver microsomes [17].
 

Associations of N-0924 with other chemical compounds

 

Gene context of N-0924

 

Analytical, diagnostic and therapeutic context of N-0924

  • The maximum Flux(ss) achieved was around 80 nmol cm(-2) h(-1) indicating that by means of iontophoresis, a therapeutic level of rotigotine might be achieved with a reasonable patch size [24].
  • Isotopic separations of the drug N-0437 and its diastereoisomeric glucuronides by high-performance liquid chromatography [17].
  • In vivo activities were assessed by measuring contralateral turning after transdermal administration of N-0437 and its prodrugs to rats with unilateral 6-OHDA lesions of the nigrostriatal pathway [11].
  • The potent and selective D2-agonist N-0437 [2-(N-propyl-N-2-thienylethylamino)-5-hydroxytetralin] undergoes considerable first-pass metabolism after oral administration due to glucuronidation of the phenolic group [11].
  • Microdialysis and striatal dopamine release: stereoselective actions of the enantiomers of N-0437 [25].

References

  1. Rotigotine treatment partially protects from MPTP toxicity in a progressive macaque model of Parkinson's disease. Scheller, D., Chan, P., Li, Q., Wu, T., Zhang, R., Guan, L., Ravenscroft, P., Guigoni, C., Crossman, A.R., Hill, M., Bezard, E. Exp. Neurol. (2007) [Pubmed]
  2. The potential antipsychotic activity of the partial dopamine receptor agonist (+)N-0437. Timmerman, W., Tepper, P.G., Bohus, B.G., Horn, A.S. Eur. J. Pharmacol. (1990) [Pubmed]
  3. Transdermal treatment options for neurological disorders: impact on the elderly. Priano, L., Gasco, M.R., Mauro, A. Drugs & aging. (2006) [Pubmed]
  4. Antidepressant properties of rotigotine in experimental models of depression. Bertaina-Anglade, V., La Rochelle, C.D., Scheller, D.K. Eur. J. Pharmacol. (2006) [Pubmed]
  5. A cellular analogue of operant conditioning. Stein, L., Xue, B.G., Belluzzi, J.D. Journal of the experimental analysis of behavior. (1993) [Pubmed]
  6. (-)-2-(N-propyl-N-2-thienylethylamino)-5-hydroxytetralin (N-0923), a selective D2 dopamine receptor agonist demonstrates the presence of D2 dopamine receptors in the mouse vas deferens but not in the rat vas deferens. Martin, P.L., Kelly, M., Cusack, N.J. J. Pharmacol. Exp. Ther. (1993) [Pubmed]
  7. Transdermal iontophoresis of rotigotine across human stratum corneum in vitro: influence of pH and NaCl concentration. Nugroho, A.K., Li, G.L., Danhof, M., Bouwstra, J.A. Pharm. Res. (2004) [Pubmed]
  8. Dopamine receptor agonist potencies for inhibition of cell firing correlate with dopamine D3 receptor binding affinities. Kreiss, D.S., Bergstrom, D.A., Gonzalez, A.M., Huang, K.X., Sibley, D.R., Walters, J.R. Eur. J. Pharmacol. (1995) [Pubmed]
  9. Determination of the dopamine agonist rotigotine in microdialysates from the rat brain by microbore column liquid chromatography with electrochemical detection. Kehr, J., Hu, X.J., Yoshitake, T., Scheller, D. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. (2007) [Pubmed]
  10. Microstructural analysis of the anorectic effect of N-0437, a highly selective dopamine D2 agonist. Rusk, I.N., Cooper, S.J. Brain Res. (1989) [Pubmed]
  11. Transdermal administration of the dopamine agonist N-0437 and seven ester prodrugs: comparison with oral administration in the 6-OHDA turning model. den Daas, I., Tepper, P.G., Rollema, H., Horn, A.S. Naunyn Schmiedebergs Arch. Pharmacol. (1990) [Pubmed]
  12. Pharmacological profile of non-hydroxylated and ether derivatives of the potent D2-selective agonist N-0437. Jansen, J.M., den Daas, I., Rollema, H., Swart, P.J., Tepper, P.G., de Vries, J.B., Horn, A.S. Naunyn Schmiedebergs Arch. Pharmacol. (1991) [Pubmed]
  13. Improvement of the oral bioavailability of the selective dopamine agonist N-0437 in rats: the in vitro and in vivo activity of eight ester prodrugs. den Daas, I., Tepper, P.G., Horn, A.S. Naunyn Schmiedebergs Arch. Pharmacol. (1990) [Pubmed]
  14. N-0437: a selective D-2 dopamine receptor agonist in in vitro and in vivo models. Van der Weide, J., De Vries, J.B., Tepper, P.G., Krause, D.N., Dubocovich, M.L., Horn, A.S. Eur. J. Pharmacol. (1988) [Pubmed]
  15. Prejunctional adrenoceptor activity of N-0437: a relatively selective DA2 dopamine receptor agonist. Crosson, C.E., Burke, J.A., Chan, M.F., Potter, D.E. Eur. J. Pharmacol. (1990) [Pubmed]
  16. N-0923, a selective dopamine D2 receptor agonist, is efficacious in rat and monkey models of Parkinson's disease. Belluzzi, J.D., Domino, E.F., May, J.M., Bankiewicz, K.S., McAfee, D.A. Mov. Disord. (1994) [Pubmed]
  17. Isotopic separations of the drug N-0437 and its diastereoisomeric glucuronides by high-performance liquid chromatography. Gerding, T.K., Drenth, B.F., de Zeeuw, R.A. Anal. Biochem. (1988) [Pubmed]
  18. Metabolism and disposition of the dopamine agonist 2-(N-propyl-N-2-thienylethylamino)-5-hydroxytetralin in conscious monkeys after subsequent i.v. oral, and ocular administration. Gerding, T.K., Drenth, B.F., de Zeeuw, R.A., Tepper, P.G., Horn, A.S. Drug Metab. Dispos. (1990) [Pubmed]
  19. Pharmacological profiles of three new, potent and selective dopamine receptor agonists: N-0434, N-0437 and N-0734. Van der Weide, J., De Vries, J.B., Tepper, P.G., Horn, A.S. Eur. J. Pharmacol. (1986) [Pubmed]
  20. Pharmacological manipulations of sucrose consumption in the Syrian hamster. Cooper, S.J. Pharmacol. Biochem. Behav. (1989) [Pubmed]
  21. Pharmacokinetic study of (S)-(-)-2-(N-propyl-N-(2-thienylethyl)amino)-5-hydroxytetralin infusion in cynomolgus monkeys. Walters, D.R., McConnell, W.R., Cefali, E.A. Journal of pharmaceutical sciences. (1994) [Pubmed]
  22. Dopamine receptor and adrenoceptor agonists inhibit prolactin release from MMQ cells. Judd, A.M., MacLeod, R.M. Eur. J. Pharmacol. (1991) [Pubmed]
  23. Impact of structural differences on the in vitro glucuronidation kinetics of potentially dopaminergic hydroxy-2-aminotetralins and naphthoxazines using rat and human liver microsomes. Swart, P.J., Jansman, F.G., Drenth, B.F., de Zeeuw, R.A., Dijkstra, D., Horn, A.S. Pharmacol. Toxicol. (1991) [Pubmed]
  24. Transdermal iontophoresis of rotigotine: influence of concentration, temperature and current density in human skin in vitro. Nugroho, A.K., Li, G., Grossklaus, A., Danhof, M., Bouwstra, J.A. Journal of controlled release : official journal of the Controlled Release Society. (2004) [Pubmed]
  25. Microdialysis and striatal dopamine release: stereoselective actions of the enantiomers of N-0437. Timmerman, W., Westerink, B.H., De Vries, J.B., Tepper, P.G., Horn, A.S. Eur. J. Pharmacol. (1989) [Pubmed]
 
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