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Preclinical Characterization of (R)-3-((3S,4S)-3-fluoro-4-(4-hydroxyphenyl)piperidin-1-yl)-1-(4-methylbenzyl)pyrrolidin-2-one (BMS-986169), a Novel, Intravenous, Glutamate N-Methyl-d-Aspartate 2B Receptor Negative Allosteric Modulator with Potential in Major Depressive Disorder.
Bristow, Linda J; Gulia, Jyoti; Weed, Michael R; Srikumar, Bettadapura N; Li, Yu-Wen; Graef, John D; Naidu, Pattipati S; Sanmathi, Charulatha; Aher, Jayant; Bastia, Tanmaya; Paschapur, Mahesh; Kalidindi, Narasimharaju; Kumar, Kuchibhotla Vijaya; Molski, Thaddeus; Pieschl, Rick; Fernandes, Alda; Brown, Jeffrey M; Sivarao, Digavalli V; Newberry, Kimberly; Bookbinder, Mark; Polino, Joseph; Keavy, Deborah; Newton, Amy; Shields, Eric; Simmermacher, Jean; Kempson, James; Li, Jianqing; Zhang, Huiping; Mathur, Arvind; Kallem, Raja Reddy; Sinha, Meenakshee; Ramarao, Manjunath; Vikramadithyan, Reeba K; Thangathirupathy, Srinivasan; Warrier, Jayakumar; Islam, Imadul; Bronson, Joanne J; Olson, Richard E; Macor, John E; Albright, Charlie F; King, Dalton; Thompson, Lorin A; Marcin, Lawrence R; Sinz, Michael.
Affiliation
  • Bristow LJ; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Gulia J; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Weed MR; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Srikumar BN; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Li YW; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Graef JD; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Naidu PS; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Sanmathi C; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Aher J; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Bastia T; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Paschapur M; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Kalidindi N; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Kumar KV; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Molski T; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Pieschl R; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Fernandes A; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Brown JM; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Sivarao DV; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Newberry K; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Bookbinder M; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Polino J; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Keavy D; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Newton A; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Shields E; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Simmermacher J; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Kempson J; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Li J; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Zhang H; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Mathur A; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Kallem RR; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Sinha M; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Ramarao M; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Vikramadithyan RK; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Thangathirupathy S; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Warrier J; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Islam I; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Bronson JJ; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Olson RE; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Macor JE; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Albright CF; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • King D; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Thompson LA; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Marcin LR; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
  • Sinz M; Neuroscience Discovery Biology (L.J.B., M.R.W., Y.-W.L., J.D.G., T.M., R.P., A.F., J.M.B., D.V.S., K.N., M.B., J.P., D.K., A.N., C.F.A.), Neuroscience Discovery Chemistry (J.J.B., R.E.O., J.E.M., D.K., L.A.T., L.R.M.), and Preclinical Candidate Optimization (E.S., J.S., Mi.S.), Bristol-Myers Squibb
J Pharmacol Exp Ther ; 363(3): 377-393, 2017 12.
Article in En | MEDLINE | ID: mdl-28954811
ABSTRACT
(R)-3-((3S,4S)-3-fluoro-4-(4-hydroxyphenyl)piperidin-1-yl)-1-(4-methylbenzyl)pyrrolidin-2-one (BMS-986169) and the phosphate prodrug 4-((3S,4S)-3-fluoro-1-((R)-1-(4-methylbenzyl)-2-oxopyrrolidin-3-yl)piperidin-4-yl)phenyl dihydrogen phosphate (BMS-986163) were identified from a drug discovery effort focused on the development of novel, intravenous glutamate N-methyl-d-aspartate 2B receptor (GluN2B) negative allosteric modulators (NAMs) for treatment-resistant depression (TRD). BMS-986169 showed high binding affinity for the GluN2B subunit allosteric modulatory site (Ki = 4.03-6.3 nM) and selectively inhibited GluN2B receptor function in Xenopus oocytes expressing human N-methyl-d-aspartate receptor subtypes (IC50 = 24.1 nM). BMS-986169 weakly inhibited human ether-a-go-go-related gene channel activity (IC50 = 28.4 µM) and had negligible activity in an assay panel containing 40 additional pharmacological targets. Intravenous administration of BMS-986169 or BMS-986163 dose-dependently increased GluN2B receptor occupancy and inhibited in vivo [3H](+)-5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine ([3H]MK-801) binding, confirming target engagement and effective cleavage of the prodrug. BMS-986169 reduced immobility in the mouse forced swim test, an effect similar to intravenous ketamine treatment. Decreased novelty suppressed feeding latency, and increased ex vivo hippocampal long-term potentiation was also seen 24 hours after acute BMS-986163 or BMS-986169 administration. BMS-986169 did not produce ketamine-like hyperlocomotion or abnormal behaviors in mice or cynomolgus monkeys but did produce a transient working memory impairment in monkeys that was closely related to plasma exposure. Finally, BMS-986163 produced robust changes in the quantitative electroencephalogram power band distribution, a translational measure that can be used to assess pharmacodynamic activity in healthy humans. Due to the poor aqueous solubility of BMS-986169, BMS-986163 was selected as the lead GluN2B NAM candidate for further evaluation as a novel intravenous agent for TRD.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Organophosphates / Piperidines / Pyrrolidinones / Prodrugs / Receptors, N-Methyl-D-Aspartate / Depressive Disorder, Major / Antidepressive Agents Limits: Animals Language: En Journal: J Pharmacol Exp Ther Year: 2017 Type: Article
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Organophosphates / Piperidines / Pyrrolidinones / Prodrugs / Receptors, N-Methyl-D-Aspartate / Depressive Disorder, Major / Antidepressive Agents Limits: Animals Language: En Journal: J Pharmacol Exp Ther Year: 2017 Type: Article