Pharmaceutical Formulation Solubilizing Low-Solubility Compound

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Solution Overview

Problem

The compound of formula (I) has low solubility in various media, making it challenging to develop a stable pharmaceutical formulation for effective intravenous administration, particularly for cancer treatment, as it requires sufficient bioavailability and chemical/physical stability for infusion solutions.

Innovation Solution

A pharmaceutical formulation comprising the compound of formula (I) in base form or as a salt, solubilized in a mixture of ethanol and a surfactant comprising mono- and polyethoxylated diesters of 12-hydroxystearic acid, with a specific surfactant/ethanol ratio, which is then diluted to form a solution for infusion, ensuring stability and bioavailability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If the compound of formula (I) is administered intravenously to achieve rapid diffusion and sufficient bioavailability, then the therapeutic effectiveness is improved, but the low solubility of the compound in various media prevents formulation development

Engineering Contradiction:
ImprovebioavailabilityVSAvoidsolubility
Core Design Contradiction:
ReliabilityVSQuantity of substance

Solution Approach 1:

The patent uses a composite surfactant system comprising both nonionic (macrogol 15 hydroxystearate) and ionic (edetate disodium) surfactants in specific proportions, creating a synergistic formulation that achieves sufficient solubility for intravenous administration. This composite approach allows the compound to be solubilized at concentrations of 1-5 mg/ml in the formulation and 0.1-1.25 mg/ml in the infusion solution, resolving the solubility-bioavailability contradiction

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent optimizes multiple parameters including surfactant concentrations (nonionic surfactant 0.5-5% w/v, ionic surfactant 0.1-1% w/v), ethanol content (5-20% v/v), and pH (5.0-7.5) to achieve the desired solubility profile. By systematically adjusting these parameters, the formulation achieves sufficient solubility for effective intravenous administration while maintaining stability

Inventive Principle:
Principle #35Parameter changes

2Quantity of substance

If a high concentration of the compound is formulated to administer sufficient therapeutic quantity (a few hundred mg), then the effective dose is improved, but the chemical and physical stability of the formulation deteriorates

Engineering Contradiction:
Improveeffective doseVSAvoidchemical and physical stability
Core Design Contradiction:
Quantity of substanceVSStability of the object's composition

Solution Approach 1:

The patent maintains the compound concentration in the formulation between 1-5 mg/ml and adjusts the pH to 5.0-7.5 using phosphate or citrate buffers. These parameter optimizations ensure that the formulation remains chemically and physically stable while containing sufficient compound to deliver therapeutic doses of a few hundred mg. The stability is maintained for at least 24 hours after dilution in isotonic medium

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The surfactants act as intermediaries that stabilize the compound in solution at therapeutic concentrations. The nonionic surfactant (macrogol 15 hydroxystearate) and ionic surfactant (edetate disodium) form micellar structures that solubilize and protect the compound, preventing precipitation and degradation. This intermediary action allows maintenance of stable formulations at concentrations sufficient for effective dosing

Inventive Principle:
Principle #24Intermediary (Mediator)

3Quantity of substance

If a surfactant mixture is used to improve solubility, then the solubilization capacity is improved, but the viscosity of the formulation increases making handling and syringe sampling difficult

Engineering Contradiction:
ImprovesolubilityVSAvoidhandling and syringe sampling
Core Design Contradiction:
Quantity of substanceVSEase of operation

Solution Approach 1:

The patent optimizes the surfactant concentration range (nonionic surfactant 0.5-5% w/v, ionic surfactant 0.1-1% w/v) and ethanol content (5-20% v/v) to achieve a balance between solubility and viscosity. The specific ratio of surfactants and the controlled concentration levels ensure sufficient solubilization capacity while maintaining appropriate flow characteristics for easy handling and syringe sampling

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The formulation uses different components with specific local functions: the nonionic surfactant provides primary solubilization, the ionic surfactant enhances stability and solubility, and ethanol acts as a co-solvent and viscosity modifier. This localized functional assignment allows each component to optimize its specific role while collectively achieving the desired balance between solubility and handleability

Inventive Principle:
Principle #3Local quality

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 sufficient solubility and stability, allowing for the administration of a few hundred mg of the compound, maintaining chemical and physical stability for at least 24 hours, and facilitating easy handling and syringe sampling, with the surfactant/ethanol ratio optimizing solubility and viscosity for effective infusion.

Implementation Method 1

The compound of formula (I) has low solubility in different media... A pharmaceutical formulation comprising the compound of formula (I) in base form or in the form of a salt of a pharmaceutically acceptable acid solubilized in a mixture of ethanol and a surfactant

Methodology Applied
Scientific EffectSolubilization: Solvation

Implementation Method 2

The surfactant comprises by weight 35 to 55% of mono- and diester and 30 to 40% of polyethylene glycol H(OCH2CH2)n-OH... the pharmaceutical formulation is intended to be diluted to form a solution for infusion

Methodology Applied
Scientific EffectMicelle formation: Microemulsion

Implementation Method 3

The invention also relates to a solution for infusion comprising the compound of formula (I)... the surfactant such at a concentration ranging from 0.48 to 37 mg/ml... maintaining chemical and physical stability for at least 24 hours

Methodology Applied
Scientific EffectSurfactant stabilization: Surfactant

Data Source

PatentEP2459221B1Pharmaceutical formulation
Publication Date: 2014.01.22 SANOFI SA(FR)
  • EP2459221B1 patent drawingFigure 1~2
  • EP2459221B1 patent drawingFigure 3
  • EP2459221B1 patent drawing

AI summary

The invention relates to a pharmaceutical formulation including, as an active principle, the compound of formula (I) or a salt of said compound with a pharmaceutically acceptable acid.