Rigosertib Formulation Stability via Alkaline PEG pH Adjustment

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Solution Overview

Problem

Rigosertib formulations with water-soluble polymers like PEG 400 suffer from stability issues, leading to unacceptable impurity levels and degradation, especially when stored at room temperature, and result in urothelial toxicity upon oral administration, necessitating improved stability and bioavailability.

Innovation Solution

Pharmaceutical compositions of Rigosertib with basic pre-treated low molecular weight polyethylene glycol at a pH of 11.0 to 14.0 and less than 5% water or aqueous solution, which enhance stability and bioavailability, and an oral dosage regimen to reduce urotoxicity by administering Rigosertib in specific doses before and after breakfast.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of operation

If Rigosertib is formulated with water-soluble polymers like PEG 400 and stored at room temperature, then ease of operation is improved, but stability deteriorates leading to unacceptable impurity levels

Engineering Contradiction:
Improvestorage convenienceVSAvoiddrug stability
Core Design Contradiction:
Ease of operationVSStability of the object's composition

Solution Approach 1:

The patent applies parameter changes by adjusting the pH of the PEG 400 formulation to alkaline conditions (pH 10-14) through the addition of bases such as sodium hydroxide, potassium hydroxide, or ammonium hydroxide. This pH modification fundamentally changes the chemical environment to prevent degradation reactions, allowing the formulation to maintain stability at room temperature while retaining ease of operation.

Inventive Principle:
Principle #35Parameter changes

2Reliability

If Rigosertib is administered orally to treat cancer, then treatment effectiveness is improved, but harmful factors increase due to urothelial toxicity

Engineering Contradiction:
Improvetreatment effectivenessVSAvoidurothelial toxicity
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent employs parameter changes by modifying the pH of the oral formulation to alkaline conditions. This pH adjustment alters the drug's solubility and absorption characteristics, enabling effective cancer treatment while reducing urothelial toxicity. The alkaline environment appears to modify the drug's interaction with urothelial tissues, thereby mitigating harmful effects while preserving therapeutic efficacy.

Inventive Principle:
Principle #35Parameter changes

3Stability of the object's composition

If Rigosertib is stored in PEG 400 with phosphate buffer at high pH, then stability is improved, but harmful factors increase due to crystal formation

Engineering Contradiction:
Improvedrug stabilityVSAvoidcrystal formation
Core Design Contradiction:
Stability of the object's compositionVSObject-generated harmful factors

Solution Approach 1:

The patent applies the extraction principle by removing phosphate buffer from the formulation entirely. Instead of using phosphate buffer to maintain high pH, the patent uses simple bases (sodium hydroxide, potassium hydroxide, or ammonium hydroxide) directly in PEG 400. This elimination of phosphate buffer prevents the crystal formation issue while maintaining the necessary alkaline pH for stability.

Inventive Principle:
Principle #2Taking out (Extraction)

4Ease of operation

If Rigosertib is administered via infusion bags with PEG 400, then ease of operation is improved, but stability deteriorates during long infusion periods

Engineering Contradiction:
Improveadministration convenienceVSAvoiddrug stability during infusion
Core Design Contradiction:
Ease of operationVSStability of the object's composition

Solution Approach 1:

The patent applies parameter changes by adjusting the pH of the PEG 400 formulation to alkaline conditions (pH 10-14). This pH modification creates a chemically stable environment that prevents degradation during long infusion periods, while the formulation remains compatible with infusion bag administration, maintaining ease of operation.

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentEP4193988B1(e)-2,4,6-trimethoxystyryl-3-[(carboxymethyl)amino]-4- methoxybenzylsulphone, sodium salt for use in a method of treating a solid tumor cancer
Publication Date: 2024.06.05 ONCONOVA THERAPEUTICS INC
  • EP4193988B1 patent drawingFigure 1
  • EP4193988B1 patent drawingFigure 2

AI summary

Pharmaceutical compositions of (E)-2,4,6-trimethoxystyryl-3-[(carboxymethyl)amino]-4-methoxybenzylsulphone and pharmaceutically acceptable salts thereof are described as well as their use, and a dose regimen of (E)-2,4,6-trimethoxystyryl-3-[(carboxymethyl)amino]-4-methoxybenzylsulphone, sodium salt to reduce the incidence of urothelial toxicity.