PRC200

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1	handwiki	Dean Liu	--	1030	2022-10-11 01:43:45

The content is sourced from: https://handwiki.org/wiki/Chemistry:PRC200

PRC200-SS is an arylalkanolamine TRI being developed by the Mayo Clinic. Sympathomimetic PRC200-SS is the PRC050 eutomer, whereas PRC201 is the distomer. These compounds are preceded by venlafaxine, which Wyeth claims is the first SNRI. Venlafaxine was originally developed as an "opioid" although original screening returned negative results. The authors were not satisfied just to drop venlafaxine from development and continued with their study of the compounds biological activity data. Herein, they discovered that venlafaxine exerts its biological actions via interaction with the monoamine receptors. In particular, the actions of the drug on increasing the amount of 5-HT and NE were documented, although with "potentiated" analogs such as the pm-dichlorophenyl ring substituted derivative, it might be expected to behave as a SNDRI also (but no data was available to support this inference). Venlafaxine itself has been said to behave as a SNDRI at very high doses. This would be more likely to be the case in drug naïve subjects than in users that have already built up significant tolerance. Silicon containing analog of venlafaxine was prepared and demonstrated to be an active SNRI.

arylalkanolamine biological activity venlafaxine

References

Shaw, A.; Boules, M.; Zhang, Y.; Williams, K.; Robinson, J.; Carlier, P.; Richelson, E. (2007). "Antidepressant-like effects of novel triple reuptake inhibitors, PRC025 and PRC050". European Journal of Pharmacology 555 (1): 30–36. doi:10.1016/j.ejphar.2006.10.004. PMID 17109850. https://dx.doi.org/10.1016%2Fj.ejphar.2006.10.004
Liang, Y.; Shaw, A.; Boules, M.; Briody, S.; Robinson, J.; Oliveros, A.; Blazar, E.; Williams, K. et al. (2008). "Antidepressant-like pharmacological profile of a novel triple reuptake inhibitor, (1S,2S)-3-(methylamino)-2-(naphthalen-2-yl)-1-phenylpropan-1-ol (PRC200-SS)". The Journal of Pharmacology and Experimental Therapeutics 327 (2): 573–583. doi:10.1124/jpet.108.143610. PMID 18689611. https://dx.doi.org/10.1124%2Fjpet.108.143610
"Assessment of Biomarkers of Drug-induced Kidney Injury in Cynomolgus Monkeys Treated with a Triple Re-uptake Inhibitor". Toxicological Sciences 120 (2): 269–83. January 2011. doi:10.1093/toxsci/kfr013. PMID 21258088. https://dx.doi.org/10.1093%2Ftoxsci%2Fkfr013
Carlier, P. R.; Lo, K. M.; Lo, M. M. C.; Williams, I. D. (1995). "Anti-Selective Aldol Reaction of Benzylic Nitriles and Synthesis of .gamma.-Amino Alcohols". The Journal of Organic Chemistry 60 (23): 7511. doi:10.1021/jo00128a025. https://dx.doi.org/10.1021%2Fjo00128a025
Carlier, P. R.; Lo, K. M. (1994). "2,3-Anti Selective Aldol Reaction of Phenylacetonitrile". The Journal of Organic Chemistry 59 (15): 4053. doi:10.1021/jo00094a011. https://dx.doi.org/10.1021%2Fjo00094a011
Carlier, P. R.; Lo, K. M.; Lo, M. M. -C.; Lo, P. C. -K.; Lo, C. W. -S. (1997). "Synthetic Optimization and Structural Limitations of the Nitrile Aldol Reaction". The Journal of Organic Chemistry 62 (18): 6316. doi:10.1021/jo9702148. https://dx.doi.org/10.1021%2Fjo9702148
Vu, A.; Cohn, S.; Terefenko, E.; Moore, W.; Zhang, P.; Mahaney, P.; Trybulski, E.; Goljer, I. et al. (2009). "3-(Arylamino)-3-phenylpropan-2-olamines as a new series of dual norepinephrine and serotonin reuptake inhibitors". Bioorganic & Medicinal Chemistry Letters 19 (9): 2464–2467. doi:10.1016/j.bmcl.2009.03.054. PMID 19329313. Mahaney, P.; Gavrin, L.; Trybulski, E.; Stack, G.; Vu, T.; Cohn, S.; Ye, F.; Belardi, J. et al. (2008). "Structure-activity relationships of the cycloalkanol ethylamine scaffold: discovery of selective norepinephrine reuptake inhibitors". Journal of Medicinal Chemistry 51 (13): 4038–4049. doi:10.1021/jm8002262. PMID 18557608. https://dx.doi.org/10.1016%2Fj.bmcl.2009.03.054
Valenta, P.; Carroll, P. J.; Walsh, P. J. (2010). "Stereoselective Synthesis of β-Hydroxy Enamines, Aminocyclopropanes, and 1,3-Amino Alcohols via Asymmetric Catalysis". Journal of the American Chemical Society 132 (40): 14179. doi:10.1021/ja105435y. PMID 20853837. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=3014220
http://repository.upenn.edu/cgi/viewcontent.cgi?article=1348&context=edissertations

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