Lyophilized Tripeptide Formulation Stability via Buffering

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Solution Overview

Problem

Lysyl-Prolyl-Threonine is highly hygroscopic and degrades easily, leading to reduced storage stability in medicaments, posing safety and efficacy concerns due to its conversion into lysine-proline diketopiperazine, especially in aqueous solutions.

Innovation Solution

A lyophilized formulation of Lysyl-Prolyl-Threonine with bulking agents like mannitol, sucrose, and trehalose, and buffering agents such as citric acid, sodium dihydrogenphosphate, is developed, which increases storage stability by maintaining the active ingredient in a non-crystalline form and controlling pH between 3.0 and 5.0.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If Lysyl-Prolyl-Threonine is formulated as a solid by lyophilization, then storage stability is improved, but surface area increases which would normally reduce stability

Engineering Contradiction:
Improvestorage stabilityVSAvoidsurface area
Core Design Contradiction:
ReliabilityVSArea of moving object

Solution Approach 1:

The patent changes the physical state parameters of the formulation by controlling the lyophilization process to create a specific non-crystalline matrix structure. This parameter change allows the formulation to achieve both high surface area from lyophilization and enhanced stability through the amorphous state, resolving the contradiction between increased surface area and reduced stability

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite lyophilized formulation containing Lysyl-Prolyl-Threonine combined with excipients in a non-crystalline matrix. This composite structure provides protective effects that stabilize the active ingredient despite the high surface area, transforming the normally destabilizing effect of high surface area into a stabilizing feature through the composite matrix structure

Inventive Principle:
Principle #40Composite materials

2Ease of operation

If Lysyl-Prolyl-Threonine is stored in aqueous solution, then ease of administration is improved, but degradation into lysine-proline diketopiperazine increases

Engineering Contradiction:
Improveease of administrationVSAvoidstorage stability
Core Design Contradiction:
Ease of operationVSReliability

Solution Approach 1:

The patent segments the formulation into two distinct states: a stable lyophilized solid form for storage and a reconstituted aqueous solution form for administration. This segmentation allows the formulation to maintain stability during storage as a solid while providing ease of administration when reconstituted, resolving the contradiction between storage stability and ease of administration

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent performs preliminary lyophilization to create a stable solid formulation before administration is needed. This preliminary action of freeze-drying preserves the active ingredient in a stable state during storage, and only when administration is required is the formulation reconstituted with water, preventing degradation during the storage period

Inventive Principle:
Principle #10Preliminary action

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 lyophilized formulation exhibits significantly improved storage stability with minimal degradation into lysine-proline diketopiperazine, ensuring the safety and efficacy of medicaments over an extended period.

Implementation Method 1

Lysyl-Prolyl-Threonine in lyophilized formulations (i.e. as a lyophilisate) shows an increased storage stability as compared to Lysyl-Prolyl-Threonine alone

Methodology Applied
Scientific EffectLyophilization (Freeze-drying): Freeze Drying

Implementation Method 2

wherein the buffering agent is selected from the group consisting of citric acid, sodium dihydrogenphosphate, acetic acid, succinic acid, glutamate, Tris and histidine

Methodology Applied
Scientific EffectBuffering:

Data Source

PatentEP3065756B1Storage stable lyophilized tripeptide formulations
Publication Date: 2019.02.20 DR AUGUST WOLFF GMBH & CO KG ARZNEIMITTEL
  • EP3065756B1 patent drawingFigure 1
  • EP3065756B1 patent drawingFigure 2
  • EP3065756B1 patent drawing

AI summary

The invention relates to Lysyl-Prolyl- Threonine lyophilized formulations, in particular to L-Lysyl-D-Prolyl-L-Threonine lyophilized formulations, that are stable in storage, and to a process for preparing the lyophilized formulations. Moreover, the invention relates to pharmaceutical and cosmetic compositions comprising the lyophilized formulations, that are used in the therapeutic and/or prophylactic treatment, diagnosis and/or therapy of pain-related diseases, pruritus-related diseases, inflammatory diseases, and/or other diseases in a mammal.