Literature DB >> 24936922

(R,S)-Ketamine metabolites (R,S)-norketamine and (2S,6S)-hydroxynorketamine increase the mammalian target of rapamycin function.

Rajib K Paul1, Nagendra S Singh, Mohammed Khadeer, Ruin Moaddel, Mitesh Sanghvi, Carol E Green, Kathleen O'Loughlin, Marc C Torjman, Michel Bernier, Irving W Wainer.   

Abstract

BACKGROUND: Subanesthetic doses of (R,S)-ketamine are used in the treatment of neuropathic pain and depression. In the rat, the antidepressant effects of (R,S)-ketamine are associated with increased activity and function of mammalian target of rapamycin (mTOR); however, (R,S)-ketamine is extensively metabolized and the contribution of its metabolites to increased mTOR signaling is unknown.
METHODS: Rats (n = 3 per time point) were given (R,S)-ketamine, (R,S)-norketamine, and (2S,6S)-hydroxynorketamine and their effect on the mTOR pathway determined after 20, 30, and 60 min. PC-12 pheochromocytoma cells (n = 3 per experiment) were treated with escalating concentrations of each compound and the impact on the mTOR pathway was determined.
RESULTS: The phosphorylation of mTOR and its downstream targets was significantly increased in rat prefrontal cortex tissue by more than ~2.5-, ~25-, and ~2-fold, respectively, in response to a 60-min postadministration of (R,S)-ketamine, (R,S)-norketamine, and (2S,6S)-hydroxynorketamine (P < 0.05, ANOVA analysis). In PC-12 pheochromocytoma cells, the test compounds activated the mTOR pathway in a concentration-dependent manner, which resulted in a significantly higher expression of serine racemase with ~2-fold increases at 0.05 nM (2S,6S)-hydroxynorketamine, 10 nM (R,S)-norketamine, and 1,000 nM (R,S)-ketamine. The potency of the effect reflected antagonistic activity of the test compounds at the α7-nicotinic acetylcholine receptor.
CONCLUSIONS: The data demonstrate that (R,S)-norketamine and (2S,6S)-hydroxynorketamine have potent pharmacological activity both in vitro and in vivo and contribute to the molecular effects produced by subanesthetic doses of (R,S)-ketamine. The results suggest that the determination of the mechanisms underlying the antidepressant and analgesic effects of (R,S)-ketamine requires a full study of the parent compound and its metabolites.

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Year:  2014        PMID: 24936922      PMCID: PMC4061505          DOI: 10.1097/ALN.0000000000000285

Source DB:  PubMed          Journal:  Anesthesiology        ISSN: 0003-3022            Impact factor:   7.892


  23 in total

1.  Norketamine, the main metabolite of ketamine, is a non-competitive NMDA receptor antagonist in the rat cortex and spinal cord.

Authors:  B Ebert; S Mikkelsen; C Thorkildsen; F M Borgbjerg
Journal:  Eur J Pharmacol       Date:  1997-08-20       Impact factor: 4.432

Review 2.  TOR signaling in growth and metabolism.

Authors:  Stephan Wullschleger; Robbie Loewith; Michael N Hall
Journal:  Cell       Date:  2006-02-10       Impact factor: 41.582

3.  Nicotinic acetylcholine receptor antagonists alter the function and expression of serine racemase in PC-12 and 1321N1 cells.

Authors:  Nagendra S Singh; Rajib K Paul; Anuradha Ramamoorthy; Marc C Torjman; Ruin Moaddel; Michel Bernier; Irving W Wainer
Journal:  Cell Signal       Date:  2013-09-04       Impact factor: 4.315

4.  mSin1 is necessary for Akt/PKB phosphorylation, and its isoforms define three distinct mTORC2s.

Authors:  Maria A Frias; Carson C Thoreen; Jacob D Jaffe; Wayne Schroder; Tom Sculley; Steven A Carr; David M Sabatini
Journal:  Curr Biol       Date:  2006-08-17       Impact factor: 10.834

5.  Distribution in the brain and metabolism of ketamine in the rat after intravenous administration.

Authors:  M L Cohen; S L Chan; W L Way; A J Trevor
Journal:  Anesthesiology       Date:  1973-10       Impact factor: 7.892

6.  Nonstereoselective inhibition of neuronal nicotinic acetylcholine receptors by ketamine isomers.

Authors:  T Sasaki; T Andoh; I Watanabe; Y Kamiya; H Itoh; T Higashi; T Matsuura
Journal:  Anesth Analg       Date:  2000-09       Impact factor: 5.108

7.  Ketamine and its preservative, benzethonium chloride, both inhibit human recombinant alpha7 and alpha4beta2 neuronal nicotinic acetylcholine receptors in Xenopus oocytes.

Authors:  K M Coates; P Flood
Journal:  Br J Pharmacol       Date:  2001-10       Impact factor: 8.739

8.  Comparative pharmacology in the rat of ketamine and its two principal metabolites, norketamine and (Z)-6-hydroxynorketamine.

Authors:  L Y Leung; T A Baillie
Journal:  J Med Chem       Date:  1986-11       Impact factor: 7.446

9.  Biotransformation of ketamine, (Z)-6-hydroxyketamine, and (E)-6-hydroxyketamine by rat, rabbit, and human liver microsomal preparations.

Authors:  T F Woolf; J D Adams
Journal:  Xenobiotica       Date:  1987-07       Impact factor: 1.908

10.  Studies on the biotransformation of ketamine. 1-Identification of metabolites produced in vitro from rat liver microsomal preparations.

Authors:  J D Adams; T A Baillie; A J Trevor; N Castagnoli
Journal:  Biomed Mass Spectrom       Date:  1981-11
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  45 in total

1.  A chronobiological perspective on ketamine's antidepressant efficacy.

Authors:  Giandomenico Schiena; Edoardo Giuseppe Ostinelli; Orsola Gambini; Armando D'Agostino
Journal:  Psychopharmacology (Berl)       Date:  2015-08-06       Impact factor: 4.530

Review 2.  Antidepressant Actions of Ketamine Mediated by the Mechanistic Target of Rapamycin, Nitric Oxide, and Rheb.

Authors:  Maged M Harraz; Solomon H Snyder
Journal:  Neurotherapeutics       Date:  2017-07       Impact factor: 7.620

3.  GLYX-13 Produces Rapid Antidepressant Responses with Key Synaptic and Behavioral Effects Distinct from Ketamine.

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4.  What is hydroxynorketamine and what can it bring to neurotherapeutics?

Authors:  Nagendra S Singh; Carlos A Zarate; Ruin Moaddel; Michel Bernier; Irving W Wainer
Journal:  Expert Rev Neurother       Date:  2014-11       Impact factor: 4.618

5.  Ketamine: NMDA Receptors and Beyond.

Authors:  Charles F Zorumski; Yukitoshi Izumi; Steven Mennerick
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6.  Are basal D-serine plasma levels a predictive biomarker for the rapid antidepressant effects of ketamine and ketamine metabolites?

Authors:  Irving W Wainer
Journal:  Psychopharmacology (Berl)       Date:  2014-09-11       Impact factor: 4.530

Review 7.  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

8.  Mouse, rat, and dog bioavailability and mouse oral antidepressant efficacy of (2R,6R)-hydroxynorketamine.

Authors:  Jaclyn N Highland; Patrick J Morris; Panos Zanos; Jacqueline Lovett; Soumita Ghosh; Amy Q Wang; Carlos A Zarate; Craig J Thomas; Ruin Moaddel; Todd D Gould
Journal:  J Psychopharmacol       Date:  2018-11-29       Impact factor: 4.153

9.  Influence of formulation and route of administration on ketamine's safety and tolerability: systematic review.

Authors:  Paul Glue; Bruce Russell; Natalie J Medlicott
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10.  Effects of Ketamine and Ketamine Metabolites on Evoked Striatal Dopamine Release, Dopamine Receptors, and Monoamine Transporters.

Authors:  Adem Can; Panos Zanos; Ruin Moaddel; Hye Jin Kang; Katinia S S Dossou; Irving W Wainer; Joseph F Cheer; Douglas O Frost; Xi-Ping Huang; Todd D Gould
Journal:  J Pharmacol Exp Ther       Date:  2016-07-28       Impact factor: 4.030

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