Draft:OPC-14523

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{{Infobox drug

| drug_name = OPC-14523

| image = OPC-14523.svg

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| CAS_number = 145969-30-8

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| PubChem = 9892540

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| IUPAC_name = 1-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-5-methoxy-3,4-dihydroquinolin-2-one

| C=23 | H=28 | Cl=1 | N=3 | O=2

| SMILES = COC1=CC=CC2=C1CCC(=O)N2CCCN3CCN(CC3)C4=CC(=CC=C4)Cl

| StdInChI = 1S/C23H28ClN3O2/c1-29-22-8-3-7-21-20(22)9-10-23(28)27(21)12-4-11-25-13-15-26(16-14-25)19-6-2-5-18(24)17-19/h2-3,5-8,17H,4,9-16H2,1H3

| StdInChIKey = TZZGTNZBLPCBIS-UHFFFAOYSA-N

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OPC-14523 is an invesitgational antidepressant drug developed by Otsuka Pharmaceutical. Its mode of action is mediated by combined sigma receptor agonism and 5-HT1A receptor agonism. It is based on the structure of mCPP and the synthesis shares the same precursor as was used in the synthesis of cloperidone.

Synthesis:{{cite journal | vauthors=((Oshiro, Y.)), ((Sakurai, Y.)), ((Sato, S.)), ((Kurahashi, N.)), ((Tanaka, T.)), ((Kikuchi, T.)), ((Tottori, K.)), ((Uwahodo, Y.)), ((Miwa, T.)), ((Nishi, T.)) | journal=Journal of Medicinal Chemistry | title=3,4-Dihydro-2(1 H )-quinolinone as a Novel Antidepressant Drug: Synthesis and Pharmacology of 1-[3-[4-(3-Chlorophenyl)-1-piperazinyl]propyl]-3,4- dihydro-5-methoxy-2(1 H )-quinolinone and Its Derivatives | volume=43 | issue=2 | pages=177–189 | date=1 January 2000 | doi=10.1021/jm980333v| pmid=10649973 }} Pharmacology: {{cite journal | vauthors=((Tottori, K.)), ((Miwa, T.)), ((Uwahodo, Y.)), ((Yamada, S.)), ((Nakai, M.)), ((Oshiro, Y.)), ((Kikuchi, T.)), ((Altar, C. A.)) | journal=Neuropharmacology | title=Antidepressant-like responses to the combined sigma and 5-HT1A receptor agonist OPC-14523 | volume=41 | issue=8 | pages=976–988 | date= December 2001 | doi=10.1016/S0028-3908(01)00147-2| pmid=11747902 }}{{cite journal | vauthors=((Bermack, J. E.)), ((Haddjeri, N.)), ((Debonnel, G.)) | journal=The Journal of Pharmacology and Experimental Therapeutics | title=Effects of the Potential Antidepressant OPC-14523 [1-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-methoxy-3,4-dihydro-2-quinolinone Monomethanesulfonate] a Combined σ and 5-HT1A Ligand: Modulation of Neuronal Activity in the Dorsal Raphe Nucleus | volume=310 | issue=2 | pages=578–583 | date= August 2004 | doi=10.1124/jpet.104.066472| pmid=15044555 }}{{cite journal | vauthors=((Jordan, S.)), ((Chen, R.)), ((Koprivica, V.)), ((Hamilton, R.)), ((Whitehead, R. E.)), ((Tottori, K.)), ((Kikuchi, T.)) | journal=European Journal of Pharmacology | title=In vitro profile of the antidepressant candidate OPC-14523 at rat and human 5-HT1A receptors | volume=517 | issue=3 | pages=165–173 | date= July 2005 | doi=10.1016/j.ejphar.2005.05.035| pmid=15985260 }}{{cite journal | vauthors=((Bermack, J. E.)), ((Debonnel, G.)) | journal=Journal of Psychopharmacology | title=Effects of OPC-14523, a combined sigma and 5-HT 1a ligand, on pre- and post-synaptic 5-HT 1a receptors | volume=21 | issue=1 | pages=85–92 | date= January 2007 | doi=10.1177/0269881106063996| pmid=16533864 }}

Draft:OPC-14523

References

See also