Ketamine Metabolite Salt Formulation for Stable Solid Dosage

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Solution Overview

Problem

Developing stable and processable solid oral dosage forms of ketamine metabolites like 2R,6R-hydroxynorketamine and 2S,6S-hydroxynorketamine is challenging due to their chemical instability and tendency to form viscous oils or gums at ambient conditions, which complicates their formulation into effective pharmaceutical forms.

Innovation Solution

Formulating a solid oral dosage form comprising a low molecular weight salt of ketamine metabolites, specifically reacting them with organic acids to achieve a crystalline form that is stable, processable, and has high oral bioavailability, with a bioavailability of 60% or more, and suitable for delivering high doses effectively.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If ketamine metabolites are used in free base form, then they show promise in treatment efficacy, but they form viscous oil or gum and are chemically unstable at ambient conditions

Engineering Contradiction:
Improvetreatment efficacyVSAvoidchemical stability
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent applies parameter changes by converting the ketamine metabolite from free base form to salt form through reaction with organic acids. This chemical parameter change transforms the physical state from viscous oil/gum to stable crystalline solid, while preserving the therapeutic efficacy. The salt formation modifies the molecular properties to achieve both stability and effectiveness.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent uses organic acids as intermediaries to convert the unstable free base form into stable salt forms. The organic acid acts as a mediator that facilitates the transformation, creating a new chemical form (salt) that combines the therapeutic benefits of the original compound with improved stability and processability.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Ease of operation

If ketamine metabolites are formulated as solid oral dosage forms, then outpatient treatment is enabled, but the compounds are difficult to process unless in liquid state

Engineering Contradiction:
Improveoutpatient treatment capabilityVSAvoidformulation processing
Core Design Contradiction:
Ease of operationVSEase of manufacture

Solution Approach 1:

The patent changes the physical parameter of the ketamine metabolite from liquid/viscous state to solid crystalline state through salt formation. This parameter change enables the compound to be processed using standard solid-state pharmaceutical manufacturing techniques, facilitating tablet or capsule formulation for outpatient treatment.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent induces a phase transition from liquid/viscous phase to solid crystalline phase by forming salts with organic acids. This phase transition is critical for enabling solid oral dosage form manufacturing, as the crystalline salt form can be milled, compressed, and encapsulated using conventional pharmaceutical processing equipment.

Inventive Principle:
Principle #36Phase transitions

3Reliability

If high doses of ketamine metabolites are administered to achieve high oral bioavailability, then cognitive enhancement is observed, but the dosage form size increases

Engineering Contradiction:
Improveoral bioavailabilityVSAvoiddosage form size
Core Design Contradiction:
ReliabilityVSVolume of moving object

Solution Approach 1:

The patent changes the chemical parameters of the ketamine metabolite through salt formation, which improves oral bioavailability by enhancing solubility and stability. This parameter change allows high doses to be delivered in a form that maintains acceptable dosage form dimensions, as the salt form has superior dissolution characteristics compared to the free base.

Inventive Principle:
Principle #35Parameter changes

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The solid oral dosage form achieves high oral bioavailability and effective cognitive enhancement, including improved executive function, perceptual function, learning ability, memory, and attention, while being stable and easily administrable, overcoming the challenges of chemical instability and formulation issues.

Implementation Method 1

reacting them with organic acids to achieve a crystalline form

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Data Source

PatentEP3687515B1Solid oral dosage forms of ketamine derivatives
Publication Date: 2022.07.06 CYBIN UK LTD
  • EP3687515B1 patent drawingFigure 1
  • EP3687515B1 patent drawingFigure 2
  • EP3687515B1 patent drawingFigure 3

AI summary

This invention relates to high concentration solid oral dosage forms of a ketamine metabolite selected from 2R,6R-hydroxynorketamine, 2S,6S-hydroxynorketamine, R-5,6- dehydronorketamine and S-5,6-dehydronorketamine.