Nimesulide Salts Ionization Solubility

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Solution Overview

Problem

Nimesulide, a non-steroidal anti-inflammatory drug (NSAID), suffers from poor water solubility, which limits its bioavailability and effectiveness in pharmaceutical preparations.

Innovation Solution

The development of new nimesulide salts, specifically tetramethylammonium and tetraethylammonium salts, which are crystallized in an ionized form, significantly enhancing their water solubility and bioavailability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If nimesulide is used in its pure form, then the drug structure is simple, but water solubility is poor (0.01 mg/mL)

Engineering Contradiction:
Improvewater solubilityVSAvoiddrug structure complexity
Core Design Contradiction:
Quantity of substanceVSDevice complexity

Solution Approach 1:

The patent applies parameter changes by transforming nimesulide from its neutral molecular form to ionized salt forms (tetramethylammonium and tetraethylammonium salts). This chemical parameter transformation fundamentally alters the solubility characteristics, increasing water solubility from 0.01 mg/mL to at least 1.5 mg/mL while maintaining the core nimesulide therapeutic structure.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite crystalline structures by combining nimesulide anions with tetramethylammonium or tetraethylammonium cations. These composite salt crystals integrate two different chemical components into a single crystalline phase, achieving enhanced solubility through the synergistic interaction between the nimesulide anion and the quaternary ammonium cation.

Inventive Principle:
Principle #40Composite materials

2Quantity of substance

If nimesulide poor water solubility is addressed by using solvents, then solubility improves, but bioavailability remains limited

Engineering Contradiction:
Improvewater solubilityVSAvoidbioavailability
Core Design Contradiction:
Quantity of substanceVSReliability

Solution Approach 1:

The patent changes the chemical parameter of nimesulide from neutral to ionized form through salt formation. This parameter transformation not only improves water solubility but also enhances bioavailability by creating a more favorable pharmacokinetic profile, allowing the drug to be effectively absorbed and distributed in the body.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The quaternary ammonium cations (tetramethylammonium or tetraethylammonium) act as intermediaries that facilitate the interaction between nimesulide and the aqueous environment. These cationic intermediaries form stable salt complexes with nimesulide anions, enabling improved solubility and bioavailability without requiring external solvents.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Reliability

If nimesulide is used in conventional formulations, then the formulation is simple, but therapeutic effectiveness is reduced due to poor solubility

Engineering Contradiction:
Improvetherapeutic effectivenessVSAvoidformulation complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The invention transforms the chemical parameter of nimesulide into ionized salt forms, which directly addresses the solubility limitation and thereby improves therapeutic effectiveness. This parameter change enables the drug to achieve adequate concentrations in biological fluids for effective anti-inflammatory, analgesic, and antipyretic activity.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates multi-functional nimesulide salts that simultaneously provide anti-inflammatory, analgesic, and antipyretic effects while overcoming the solubility barrier. The tetramethylammonium and tetraethylammonium salts serve multiple purposes: maintaining the therapeutic activity of nimesulide while providing enhanced solubility and bioavailability properties.

Inventive Principle:
Principle #6Universality (Multi-functionality)

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

These new salts exhibit water solubility at least 100 times higher than pure nimesulide, leading to improved bioavailability and potential therapeutic benefits in analgesic, anti-inflammatory, and antipyretic applications.

Implementation Method 1

crystals of tetramethylammonium salt of nimesulide shown as formula 1 and tetraethylammonium salt of nimesulide, formula 2, in which nimesulide is present in an ionized form

Methodology Applied
Scientific EffectIonization: Ionisation

Implementation Method 2

a method for producing a tetramethylammonium salt of nimesulide and a tetraethylammonium salt of nimesulide in the form of crystals

Methodology Applied
Scientific EffectCrystallization: Crystallisation

Data Source

PatentEP4198016B1Nimesulide salts and method of obtaining nimesulide salt crystals
Publication Date: 2025.06.04 UNIV GDANSKI
  • EP4198016B1 patent drawingFigure 1~2
  • EP4198016B1 patent drawingFigure 3~4
  • EP4198016B1 patent drawingFigure 5~6

AI summary

The invention referes to the tetramethylammonium salt of nimesulide of formula 1: where nimesulide occurs in the ionised form, and the tetraethylammonium salt of nimesulide of formula 2: where nimesulide occurs in ionised form and how to obtain them.