GLP-1 Agonist Solid Compositions with Histidine for Storage Stability

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Human GLP-1 and its analogues have low oral bioavailability and stability issues, necessitating improved formulations to enhance absorption and maintain efficacy during storage.

Innovation Solution

A solid pharmaceutical composition comprising a GLP-1 agonist, such as semaglutide, combined with a salt of N-(8-(2-hydroxybenzoyl)amino)caprylic acid (NAC) and histidine, where the moles of histidine are at least equal to half the moles of the GLP-1 agonist, to enhance stability and absorption.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If GLP-1 agonist is formulated with absorption enhancers for oral administration, then oral bioavailability is improved, but stability during storage deteriorates

Engineering Contradiction:
Improveoral bioavailabilityVSAvoidstability during storage
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

Histidine acts as an intermediary substance that mediates between the GLP-1 agonist and the absorption enhancer SNAC. It reduces the harmful interaction between SNAC and the peptide while maintaining the absorption-enhancing effect, thereby improving both stability and bioavailability simultaneously

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The invention converts the potentially harmful effect of SNAC (which can cause degradation of the peptide) into a beneficial outcome by adding histidine. The histidine protects the peptide from SNAC-induced degradation while allowing SNAC to continue enhancing absorption, thus turning a harmful interaction into a beneficial formulation strategy

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

2Ease of operation

If GLP-1 agonist is stored at ambient temperature, then ease of storage is improved, but shelf-life deteriorates

Engineering Contradiction:
Improveease of storageVSAvoidshelf-life
Core Design Contradiction:
Ease of operationVSDuration of action of stationary object

Solution Approach 1:

The invention changes the chemical environment parameters by introducing histidine, which alters the pH and chemical stability profile of the formulation. This enables the product to maintain stability at ambient temperature conditions without requiring refrigeration, thereby extending shelf-life while improving ease of storage

Inventive Principle:
Principle #35Parameter changes

3Reliability

If higher amount of absorption enhancer is used, then oral bioavailability is improved, but formulation complexity increases

Engineering Contradiction:
Improveoral bioavailabilityVSAvoidformulation complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

Histidine serves as a mediator that allows the use of SNAC at optimized concentrations without requiring excessive amounts. It facilitates effective interaction between the enhancer and the peptide, achieving high bioavailability with a balanced formulation rather than requiring large excesses of any single component

Inventive Principle:
Principle #24Intermediary (Mediator)

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 composition achieves increased stability and improved oral bioavailability of GLP-1 agonists, allowing for therapeutically relevant plasma concentrations and extended shelf-life.

Implementation Method 1

The inventors have surprisingly found that an increased stability of GLP-1 agonists is observed when compositions are prepared with a relatively small amount of histidine

Methodology Applied
Scientific EffectStability enhancement:

Implementation Method 2

Human GLP-1 and analogues thereof have a low oral bioavailability. Exposure and bioavailability of human GLP-1 and analogues thereof is very low following oral administration

Methodology Applied
Scientific EffectAbsorption enhancement:

Data Source

PatentEP4142695B1Solid compositions comprising a GLP-1 agonist and histidine
Publication Date: 2025.11.05 NOVO NORDISK AS
  • EP4142695B1 patent drawingFigure 1
  • EP4142695B1 patent drawingFigure 2
  • EP4142695B1 patent drawing

AI summary

The invention relates to stabilised solid pharmaceutical compositions comprising a GLP-1 agonist. The invention further relates to processes for the preparation of such compositions, and their use in medicine.