A Phase 1 Assessment of the Safety, Tolerability, Pharmacokinetics and Pharmacodynamics of (2R,6R)-Hydroxynorketamine in Healthy Volunteers.

(R,S)-Ketamine (ketamine) is a dissociative anesthetic that also possesses analgesic and antidepressant activity. Undesirable dissociative side effects and misuse potential limit expanded use of ketamine in several mental health disorders despite promising clinical activity and intensifying medical need. (2R,6R)-Hydroxynorketamine (RR-HNK) is a metabolite of ketamine that lacks anesthetic and dissociative activity but maintains antidepressant and analgesic activity in multiple preclinical models. To enable future assessments in selected human indications, we report the safety, tolerability, pharmacokinetics (PK), and pharmacodynamics (PD) of RR-HNK in a Phase 1 study in healthy volunteers (NCT04711005). A six-level single-ascending dose (SAD) (0.1-4 mg/kg) and a two-level multiple ascending dose (MAD) (1 and 2 mg/kg) study was performed using a 40-minute IV administration emulating the common practice for ketamine administration for depression. Safety assessments showed RR-HNK possessed a minimal adverse event profile and no serious adverse events at all doses examined. Evaluations of dissociation and sedation demonstrated that RR-HNK did not possess anesthetic or dissociative characteristics in the doses examined. RR-HNK PK parameters were measured in both the SAD and MAD studies and exhibited dose-proportional increases in exposure. Quantitative electroencephalography (EEG) measurements collected as a PD parameter based on preclinical findings and ketamine's established effect on gamma-power oscillations demonstrated increases of gamma power in some participants at the lower/mid-range doses examined. Cerebrospinal fluid examination confirmed RR-HNK exposure within the central nervous system (CNS). Collectively, these data demonstrate RR-HNK is well tolerated with an acceptable PK profile and promising PD outcomes to support the progression into Phase 2.

[1]  C. Mazucanti,et al.  Cerebrospinal fluid exploratory proteomics and ketamine metabolite pharmacokinetics in human volunteers after ketamine infusion , 2023, iScience.

[2]  I. Lucki,et al.  Antinociceptive and Analgesic Effects of (2R,6R)-Hydroxynorketamine , 2022, The Journal of Pharmacology and Experimental Therapeutics.

[3]  S. Thompson,et al.  (2R,6R)-hydroxynorketamine rapidly potentiates optically-evoked Schaffer collateral synaptic activity , 2022, Neuropharmacology.

[4]  C. Zarate,et al.  Ketamine treatment for depression: a review , 2022, Discover Mental Health.

[5]  Jiao-jiao Yang,et al.  BDNF-TrkB signaling-mediated upregulation of Narp is involved in the antidepressant-like effects of (2R,6R)-hydroxynorketamine in a chronic restraint stress mouse model , 2022, BMC Psychiatry.

[6]  T. Gould,et al.  A comparison of the pharmacokinetics and NMDAR antagonism-associated neurotoxicity of ketamine, (2R,6R)-hydroxynorketamine and MK-801. , 2021, Neurotoxicology and teratology.

[7]  T. Gould,et al.  Hydroxynorketamines: Pharmacology and Potential Therapeutic Applications , 2021, Pharmacological Reviews.

[8]  T. Cooper,et al.  Sex-specific neurobiological actions of prophylactic (R,S)-ketamine, (2R,6R)-hydroxynorketamine, and (2S,6S)-hydroxynorketamine , 2020, Neuropsychopharmacology.

[9]  C. Zarate,et al.  Electrophysiological biomarkers of antidepressant response to ketamine in treatment-resistant depression: Gamma power and long-term potentiation , 2020, Pharmacology Biochemistry and Behavior.

[10]  D. Buhl,et al.  Pharmacological evaluation of clinically relevant concentrations of (2R,6R)-hydroxynorketamine , 2019, Neuropharmacology.

[11]  S. Thompson,et al.  (R)‐Ketamine exerts antidepressant actions partly via conversion to (2R,6R)‐hydroxynorketamine, while causing adverse effects at sub‐anaesthetic doses , 2019, British journal of pharmacology.

[12]  S. Thompson,et al.  (2R,6R)-hydroxynorketamine rapidly potentiates hippocampal glutamatergic transmission through a synapse-specific presynaptic mechanism , 2019, Neuropsychopharmacology.

[13]  S. Kasper,et al.  Prognosis and improved outcomes in major depression: a review , 2019, Translational Psychiatry.

[14]  T. Gould,et al.  (2R,6R)-hydroxynorketamine exerts mGlu2 receptor-dependent antidepressant actions , 2019, Proceedings of the National Academy of Sciences.

[15]  J. Kehr,et al.  Antidepressant-relevant concentrations of the ketamine metabolite (2R,6R)-hydroxynorketamine do not block NMDA receptor function , 2019, Proceedings of the National Academy of Sciences.

[16]  J. Kroin,et al.  Efficacy of the ketamine metabolite (2R,6R)-hydroxynorketamine in mice models of pain , 2018, Regional Anesthesia & Pain Medicine.

[17]  R. Duman,et al.  Activity-dependent brain-derived neurotrophic factor signaling is required for the antidepressant actions of (2R,6R)-hydroxynorketamine , 2018, Proceedings of the National Academy of Sciences.

[18]  K. Chergui,et al.  Ketamine and its metabolite (2R,6R)-hydroxynorketamine induce lasting alterations in glutamatergic synaptic plasticity in the mesolimbic circuit , 2018, Molecular Psychiatry.

[19]  M. Hsieh,et al.  (2R,6R)-hydroxynorketamine rescues chronic stress-induced depression-like behavior through its actions in the midbrain periaqueductal gray , 2018, Neuropharmacology.

[20]  T. Gould,et al.  Ketamine and Ketamine Metabolite Pharmacology: Insights into Therapeutic Mechanisms , 2018, Pharmacological Reviews.

[21]  C. Chiamulera,et al.  Ketamine enhances structural plasticity in mouse mesencephalic and human iPSC-derived dopaminergic neurons via AMPAR-driven BDNF and mTOR signaling , 2018, Molecular Psychiatry.

[22]  T. Gould,et al.  Synthesis and N-Methyl-d-aspartate (NMDA) Receptor Activity of Ketamine Metabolites. , 2017, Organic letters.

[23]  Xi-Ping Huang,et al.  NMDAR inhibition-independent antidepressant actions of ketamine metabolites , 2016, Nature.

[24]  G. Aghajanian,et al.  Synaptic plasticity and depression: new insights from stress and rapid-acting antidepressants , 2016, Nature Medicine.

[25]  Allison C. Nugent,et al.  Ketamine and other N-methyl-D-aspartate receptor antagonists in the treatment of depression: a perspective review , 2015, Therapeutic advances in chronic disease.

[26]  T. Hillhouse,et al.  A brief history of the development of antidepressant drugs: from monoamines to glutamate. , 2015, Experimental and clinical psychopharmacology.

[27]  G. Mion,et al.  Ketamine Pharmacology: An Update (Pharmacodynamics and Molecular Aspects, Recent Findings) , 2013, CNS neuroscience & therapeutics.

[28]  G. Laje,et al.  Relationship of Ketamine's Plasma Metabolites with Response, Diagnosis, and Side Effects in Major Depression , 2012, Biological Psychiatry.

[29]  D. Luckenbaugh,et al.  Simultaneous population pharmacokinetic modelling of ketamine and three major metabolites in patients with treatment-resistant bipolar depression. , 2012, British journal of clinical pharmacology.

[30]  P. O’Donnell,et al.  Gamma and Delta Neural Oscillations and Association with Clinical Symptoms under Subanesthetic Ketamine , 2010, Neuropsychopharmacology.

[31]  L. H. Finkel,et al.  N-methyl-d-aspartic acid receptor antagonist–induced frequency oscillations in mice recreate pattern of electrophysiological deficits in schizophrenia , 2009, Neuroscience.

[32]  Paul J Carlson,et al.  A randomized trial of an N-methyl-D-aspartate antagonist in treatment-resistant major depression. , 2006, Archives of general psychiatry.

[33]  T. Baillie,et al.  Comparative pharmacology in the rat of ketamine and its two principal metabolites, norketamine and (Z)-6-hydroxynorketamine. , 1986, Journal of medicinal chemistry.

[34]  D. Lodge,et al.  The dissociative anaesthetics, ketamine and phencyclidine, selectively reduce excitation of central mammalian neurones by N‐methyl‐aspartate , 1983, British journal of pharmacology.

[35]  D. Lodge,et al.  Effects of optical isomers of ketamine on excitation of cat and rat spinal neurones by amino acids and acetylcholine , 1982, Neuroscience Letters.

[36]  I. Ahlgren,et al.  Ketamine infusions: pharmacokinetics and clinical effects. , 1979, British journal of anaesthesia.