Amorphous Bardoxolone Methyl Solid Dispersion for Bioavailability

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Solution Overview

Problem

Bardoxolone methyl, a potent anti-inflammatory and anti-tumor agent, has low oral bioavailability due to its crystalline form, which limits its therapeutic effectiveness and increases the risk of adverse events by fluctuating plasma concentrations.

Innovation Solution

A solid dosage form comprising amorphous bardoxolone methyl and a glass-forming excipient, admixed with hydrophilic binders like hydroxypropyl methyl cellulose, which modulates the dissolution rate and maintains therapeutic plasma levels, enhancing oral bioavailability while reducing peak concentrations.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If amorphous bardoxolone methyl is used to improve oral bioavailability, then solubility and bioavailability are enhanced, but the formulation becomes inherently unstable and may return to crystalline state

Engineering Contradiction:
Improveoral bioavailabilityVSAvoidformulation stability
Core Design Contradiction:
Quantity of substanceVSStability of the object's composition

Solution Approach 1:

The patent combines amorphous bardoxolone methyl with a glass-forming excipient to create a composite amorphous solid dispersion. This composite structure maintains the high solubility and bioavailability of the amorphous drug form while the glass-forming excipient provides structural stability and prevents crystallization, resolving the contradiction between improved bioavailability and formulation stability.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent changes the physical state of the drug from crystalline to amorphous, which fundamentally alters the molecular arrangement from ordered to disordered. This parameter change increases solubility and bioavailability while the subsequent incorporation into a glass-forming matrix stabilizes this high-energy state, preventing return to the crystalline form.

Inventive Principle:
Principle #35Parameter changes

2Quantity of substance

If amorphous drug formulation is used to enhance bioavailability, then area-under-curve values increase several-fold, but the time to maximal plasma concentration and maximal concentration observed are altered markedly

Engineering Contradiction:
Improvearea-under-curve valueVSAvoidtime to maximal plasma concentration
Core Design Contradiction:
Quantity of substanceVSDuration of action of moving object

Solution Approach 1:

The patent creates a dynamic dissolution profile by using amorphous solid dispersion, which allows the formulation to adapt its release characteristics. The amorphous form provides rapid initial dissolution for enhanced AUC, while the glass-forming excipient matrix controls the release kinetics to moderate the rate of absorption, thereby adjusting Tmax and Cmax to therapeutic ranges.

Inventive Principle:
Principle #15Dynamics

3Stability of the object's composition

If crystalline form is used to ensure stability, then formulation stability is maintained, but oral bioavailability is relatively low

Engineering Contradiction:
Improveformulation stabilityVSAvoidoral bioavailability
Core Design Contradiction:
Stability of the object's compositionVSQuantity of substance

Solution Approach 1:

The patent exploits the phase transition from crystalline to amorphous state to resolve the contradiction. By transforming the drug from the stable crystalline phase to the metastable amorphous phase and then stabilizing it in a glass-forming matrix, the formulation achieves both improved bioavailability (characteristic of amorphous form) and long-term stability (characteristic of crystalline form).

Inventive Principle:
Principle #36Phase transitions

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 formulation achieves significantly higher oral bioavailability and a modified plasma concentration curve that resembles the crystalline form, ensuring safer and more effective chronic administration with reduced peak concentrations.

Implementation Method 1

particles consisting of amorphous bardoxolone methyl and a glass-forming excipient, whereby the dosage form is characterized by a single glass transition temperature

Methodology Applied
Scientific EffectGlass transition:

Implementation Method 2

admixed with particles of at least one hydrophilic binder selected from the group consisting of: (1) naturally occurring carbohydrate polymers selected from starch and pregelatinized starch; (2) gelatin or modified gelatins; (3) chitosan; (4) anionic polymers selected from acrylic acid homopolymers cross-linked with allyl sucrose or allyl pentaerythritol, and (5) cellulose-based excipients

Methodology Applied
Scientific EffectDissolution:

Data Source

PatentEP3254675B1Delayed release, oral dosage compositions that contain amorphous CDDO-me
Publication Date: 2019.05.15 1 REATA PHARMA INC 2 TRUSTEES OF DARTMOUTH COLLEGE
  • EP3254675B1 patent drawingFigure 1
  • EP3254675B1 patent drawingFigure 2

AI summary

Pharmaceutical formulations exhibit a desirably low Cmax, among other properties, that contain particles of amorphous bardoxolone methyl, either in pure form or in the form of a solid dispersion, admixed with particles of a hydrophilic binding agent. Such formulations possess the advantage of higher oral bioavailability, relative to formulations based on the crystalline form of bardoxolone methyl.