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Literature DB >> 28829612

Synthesis and N-Methyl-d-aspartate (NMDA) Receptor Activity of Ketamine Metabolites.

Patrick J Morris¹, Ruin Moaddel², Panos Zanos³, Curtis E Moore⁴, Todd D Gould⁵, Carlos A Zarate⁶, Craig J Thomas¹.

Abstract

Ketamine is rapidly metabolized in the human body to a variety of metabolites, including the hydroxynorketamines. At least two hydroxynorketamines have significant antidepressant action in rodent models, with limited action against the N-methyl-d-aspartate (NMDA) receptor. The synthesis of 12 hydroxynorketamines and their binding affinity to the NMDA receptor is presented here.

Entities: Chemical Disease Gene Species

Mesh：

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Year: 2017 PMID： 28829612 PMCID： PMC5641405 DOI： 10.1021/acs.orglett.7b02177

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

18 in total

1. Differential effects of ketamine enantiomers on NMDA receptor currents in cultured neurons.

Authors: H U Zeilhofer; D Swandulla; G Geisslinger; K Brune
Journal: Eur J Pharmacol Date: 1992-03-17 Impact factor: 4.432

Review 2. The use of ketamine as an antidepressant: a systematic review and meta-analysis.

Authors: Caoimhe M Coyle; Keith R Laws
Journal: Hum Psychopharmacol Date: 2015-04-07 Impact factor: 1.672

3. Effects of a ketamine metabolite on synaptic NMDAR function.

Authors: Kanzo Suzuki; Elena Nosyreva; Kevin W Hunt; Ege T Kavalali; Lisa M Monteggia
Journal: Nature Date: 2017-06-21 Impact factor: 49.962

4. Emerging mechanisms and treatments for depression beyond SSRIs and SNRIs.

Authors: Elena Dale; Benny Bang-Andersen; Connie Sánchez
Journal: Biochem Pharmacol Date: 2015-03-24 Impact factor: 5.858

5. Replication of ketamine's antidepressant efficacy in bipolar depression: a randomized controlled add-on trial.

Authors: Carlos A Zarate; Nancy E Brutsche; Lobna Ibrahim; Jose Franco-Chaves; Nancy Diazgranados; Anibal Cravchik; Jessica Selter; Craig A Marquardt; Victoria Liberty; David A Luckenbaugh
Journal: Biol Psychiatry Date: 2012-01-31 Impact factor: 13.382

6. Relationship of ketamine's plasma metabolites with response, diagnosis, and side effects in major depression.

Authors: Carlos A Zarate; Nancy Brutsche; Gonzalo Laje; David A Luckenbaugh; Swarajya L Vattem Venkata; Anuradha Ramamoorthy; Ruin Moaddel; Irving W Wainer
Journal: Biol Psychiatry Date: 2012-04-18 Impact factor: 13.382

7. Zanos et al. reply.

Authors: Panos Zanos; Ruin Moaddel; Patrick J Morris; Polymnia Georgiou; Jonathan Fischell; Greg I Elmer; Manickavasagom Alkondon; Peixiong Yuan; Heather J Pribut; Nagendra S Singh; Katina S S Dossou; Yuhong Fang; Xi-Ping Huang; Cheryl L Mayo; Edson X Albuquerque; Scott M Thompson; Craig J Thomas; Carlos A Zarate; Todd D Gould
Journal: Nature Date: 2017-06-21 Impact factor: 49.962

8. Molecular design of the N-methyl-D-aspartate receptor binding site for phencyclidine and dizolcipine.

Authors: A V Ferrer-Montiel; W Sun; M Montal
Journal: Proc Natl Acad Sci U S A Date: 1995-08-15 Impact factor: 11.205

Review 9. Ketamine.

Authors: B Sinner; B M Graf
Journal: Handb Exp Pharmacol Date: 2008

10. Sub-anesthetic concentrations of (R,S)-ketamine metabolites inhibit acetylcholine-evoked currents in α7 nicotinic acetylcholine receptors.

Authors: Ruin Moaddel; Galia Abdrakhmanova; Joanna Kozak; Krzysztof Jozwiak; Lawrence Toll; Lucita Jimenez; Avraham Rosenberg; Thao Tran; Yingxian Xiao; Carlos A Zarate; Irving W Wainer
Journal: Eur J Pharmacol Date: 2012-11-23 Impact factor: 4.432

22 in total

1. Ketamine increases vmPFC activity: Effects of (R)- and (S)-stereoisomers and (2R,6R)-hydroxynorketamine metabolite.

Authors: Brendan D Hare; Santosh Pothula; Ralph J DiLeone; Ronald S Duman
Journal: Neuropharmacology Date: 2020-01-09 Impact factor: 5.250

Review 2. Ketamine and Ketamine Metabolite Pharmacology: Insights into Therapeutic Mechanisms.

Authors: Panos Zanos; Ruin Moaddel; Patrick J Morris; Lace M Riggs; Jaclyn N Highland; Polymnia Georgiou; Edna F R Pereira; Edson X Albuquerque; Craig J Thomas; Carlos A Zarate; Todd D Gould
Journal: Pharmacol Rev Date: 2018-07 Impact factor: 25.468

Review 3. Hydroxynorketamines: Pharmacology and Potential Therapeutic Applications.

Authors: Jaclyn N Highland; Panos Zanos; Lace M Riggs; Polymnia Georgiou; Sarah M Clark; Patrick J Morris; Ruin Moaddel; Craig J Thomas; Carlos A Zarate; Edna F R Pereira; Todd D Gould
Journal: Pharmacol Rev Date: 2021-04 Impact factor: 25.468

Review 4. Convergent Mechanisms Underlying Rapid Antidepressant Action.

Authors: Panos Zanos; Scott M Thompson; Ronald S Duman; Carlos A Zarate; Todd D Gould
Journal: CNS Drugs Date: 2018-03 Impact factor: 5.749

Review 5. Mechanisms of ketamine action as an antidepressant.

Authors: P Zanos; T D Gould
Journal: Mol Psychiatry Date: 2018-03-13 Impact factor: 15.992

6. Prophylactic efficacy of 5-HT₄R agonists against stress.

Authors: Briana K Chen; Indira Mendez-David; Victor M Luna; Charlène Faye; Alain M Gardier; Denis J David; Christine A Denny
Journal: Neuropsychopharmacology Date: 2019-10-10 Impact factor: 7.853

7. (2R,6R)-hydroxynorketamine rapidly potentiates hippocampal glutamatergic transmission through a synapse-specific presynaptic mechanism.

Authors: Lace M Riggs; Yasco Aracava; Panos Zanos; Jonathan Fischell; Edson X Albuquerque; Edna F R Pereira; Scott M Thompson; Todd D Gould
Journal: Neuropsychopharmacology Date: 2019-06-19 Impact factor: 7.853