Zoledronic Acid Cocrystals for Oral Bioavailability

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Solution Overview

Problem

Zoledronic acid, a poorly water-soluble drug, faces challenges in oral bioavailability due to poor gastrointestinal tract membrane permeability, leading to low oral bioavailability and severe gastric and intestinal irritations, with existing methods failing to effectively improve its aqueous solubility and permeability.

Innovation Solution

The development of novel molecular complexes, including cocrystals, salts, and solvates of zoledronic acid with coformers like sodium, ammonium, L-lysine, DL-lysine, nicotinamide, adenine, and glycine, which enhance its aqueous solubility and permeability, forming stable crystalline structures that improve bioavailability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of operation

If zoledronic acid is administered orally, then it can avoid invasive IV injection, but its poor aqueous solubility and membrane permeability result in low oral bioavailability

Engineering Contradiction:
Improveadministration routeVSAvoidoral bioavailability
Core Design Contradiction:
Ease of operationVSReliability

Solution Approach 1:

The patent creates composite molecular complexes of zoledronic acid with amino acids (lysine, glycine, nicotinamide, adenine) forming cocrystals, salts, and solvates. These composite structures combine the drug with coformers to produce a new crystalline material that maintains therapeutic efficacy while dramatically improving aqueous solubility and membrane permeability, enabling effective oral delivery

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent alters the physicochemical parameters of zoledronic acid by forming it into different molecular complexes (cocrystals, salts, solvates) with varying solubility and permeability characteristics. By changing the molecular form while maintaining the active drug component, the patent achieves improved bioavailability without losing therapeutic effect

Inventive Principle:
Principle #35Parameter changes

2Ease of operation

If zoledronic acid is administered orally, then convenience is improved, but severe gastric and intestinal irritations occur

Engineering Contradiction:
Improveadministration routeVSAvoidgastrointestinal irritation
Core Design Contradiction:
Ease of operationVSObject-affected harmful factors

Solution Approach 1:

The patent uses amino acids (lysine, glycine, nicotinamide, adenine) as intermediary substances that form molecular complexes with zoledronic acid. These coformers act as mediators that reduce the direct contact between zoledronic acid and the gastrointestinal mucosa, thereby minimizing gastric and intestinal irritations while still allowing the drug to be absorbed systemically

Inventive Principle:
Principle #24Intermediary (Mediator)

3Quantity of substance

If existing formulation methods are used to improve solubility, then some aqueous solubility enhancement is achieved, but they fail to effectively improve permeability and bioavailability

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

Solution Approach 1:

The patent systematically changes the physicochemical parameters of zoledronic acid by forming it into different molecular complexes (cocrystals, salts, solvates) with varying solubility and permeability characteristics. By changing the molecular form while maintaining the active drug component, the patent achieves simultaneous improvement in both solubility and permeability, unlike previous formulations that only addressed solubility

Inventive Principle:
Principle #35Parameter changes

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 novel molecular complexes significantly enhance the oral bioavailability of zoledronic acid by improving its aqueous solubility and permeability, potentially allowing for an oral dosage form where only IV administration was previously possible, offering improved therapeutic efficacy and reduced gastrointestinal irritation.

Implementation Method 1

generating a crystalline form of a drug material... The novel forms include but are not limited to cocrystals, salts, hydrates, solvates

Methodology Applied
Scientific EffectCrystallization: Crystallisation

Implementation Method 2

novel molecular complexes of zoledronic acid that includes cocrystals, salts, and solvates (e.g. hydrates and mixed solvates)

Methodology Applied
Scientific EffectSolvation: Solvation

Data Source

PatentEP3295935B1Crystallization method and bioavailability
Publication Date: 2020.07.22 THAR PHARMA INC
  • EP3295935B1 patent drawingFigure 1
  • EP3295935B1 patent drawingFigure 2
  • EP3295935B1 patent drawingFigure 3

AI summary

Preparation, in -vitro and in vivo characterization of novel forms of (1 -hydroxy- 2-imida/ol-1-yl-1 -phosphono-cthyl) phosphonic acid, suitable for pharmaceutical compositions in drug delivery systems for humans.