Sebacoyl Dinalbuphine Ester Formulation for Extended Release

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Solution Overview

Problem

Current extended release opioid formulations, such as those for nalbuphine ester prodrugs, face challenges in achieving controlled and prolonged release periods, particularly for nalbuphine, which has a short duration of action and requires frequent dosing, and existing methods are complex, costly, and not suitable for large-scale manufacturing.

Innovation Solution

A pharmaceutical formulation comprising sebacoyl dinalbuphine ester (SDE) dissolved in a pharmaceutically acceptable oil with an oil-miscible retaining solvent like benzyl benzoate, adjusting the weight ratio of the solvent to oil to extend the release period, allowing for a homogenous solution suitable for intramuscular or subcutaneous administration.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Duration of action of moving object

If nalbuphine ester prodrugs are mixed with therapeutically injectable oils and excipients to create extended release formulations, then the duration of action can be extended to 4-5 days, but the injection volume increases to 7.15 mL which exceeds the maximum recommended volume of 5 mL for intramuscular injection and causes injection site irritation

Engineering Contradiction:
Improveduration of actionVSAvoidinjection volume
Core Design Contradiction:
Duration of action of moving objectVSVolume of moving object

Solution Approach 1:

The patent changes the concentration parameter of the active ingredient in the formulation. By increasing the concentration of nalbuphine ester prodrug from previous formulations to approximately 7.15 mg/mL, the total injection volume is reduced to 5 mL while maintaining the same total dose. This parameter change resolves the contradiction by allowing extended duration of action (4-5 days) without exceeding the maximum safe injection volume, thereby preventing injection site irritation.

Inventive Principle:
Principle #35Parameter changes

2Duration of action of moving object

If microparticles with average particle size of 5-25 microns are used for controlled release suspension formulations, then the release period can be extended to 12-24 hours, but the particle sizes are too large to be suitable for intramuscular injection or sterilization by filtration

Engineering Contradiction:
Improverelease periodVSAvoidsuitability for injection and sterilization
Core Design Contradiction:
Duration of action of moving objectVSEase of operation

Solution Approach 1:

The patent changes the physical state parameter from particulate suspension to clear solution by dissolving the nalbuphine ester prodrug in therapeutically injectable oil. This eliminates the particle size issue entirely, making the formulation suitable for intramuscular injection and sterilization by filtration while achieving extended release through the oil vehicle rather than particle size control.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent uses a composite formulation system combining nalbuphine ester prodrug with therapeutically injectable oil and small amounts of excipients. This composite approach achieves controlled release without requiring large microparticles, resolving the contradiction between extended release period and suitability for injection/sterilization.

Inventive Principle:
Principle #40Composite materials

3Duration of action of moving object

If emulsion or oil-based vehicles are used to prepare extended release formulations, then prolonged release can be achieved, but the complexity of sterilization increases and the solubility of nalbuphine ester prodrugs in oily substances is limited

Engineering Contradiction:
Improverelease periodVSAvoidsterilization complexity
Core Design Contradiction:
Duration of action of moving objectVSDevice complexity

Solution Approach 1:

The patent optimizes the concentration of nalbuphine ester prodrug in the oil-based vehicle to achieve complete dissolution, creating a clear solution rather than a suspension or emulsion. This parameter change simplifies sterilization by filtration while maintaining the extended release properties of the oil-based formulation.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite formulation using nalbuphine ester prodrug dissolved in therapeutically injectable oil with small amounts of specific excipients. This composite material system achieves both prolonged release and simplified sterilization by ensuring complete solubility and using a formulation that can be sterilized by standard filtration methods.

Inventive Principle:
Principle #40Composite materials

4Quantity of substance

If oral formulations with solubility-assisting agents are used, then bioavailability and half-life can be improved, but the apparent half-life is only about 24 hours requiring dosing every 8-12 hours which is not practical for long-term or severe pain

Engineering Contradiction:
ImprovebioavailabilityVSAvoidhalf-life
Core Design Contradiction:
Quantity of substanceVSDuration of action of moving object

Solution Approach 1:

The patent changes the formulation route from oral to parenteral (intramuscular injection) and modifies the chemical structure by using nalbuphine ester prodrugs. These changes result in significantly extended half-life (4-5 days compared to 24 hours for oral formulations) while maintaining adequate bioavailability through parenteral administration, resolving the contradiction between bioavailability and duration of action.

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 formulation achieves a prolonged release period of SDE, with durations of action exceeding 5 to 14 days, providing a controlled and sustained analgesic effect with reduced dosing frequency and simplified manufacturing, while maintaining stability and bioavailability.

Implementation Method 1

sebacoyl dinalbuphine ester (SDE) dissolved in a pharmaceutically acceptable oil and an oil-miscible retaining solvent wherein the oil-miscible retaining solvent is benzyl benzoate

Methodology Applied
Scientific EffectSolvation: Solvation

Data Source

PatentEP3302477B1Pharmaceutical formulations for sustained release of sebacoyl dinalbuphine ester
Publication Date: 2024.02.07 SHANGHAI LUMOSA THERAPEUTICS
  • EP3302477B1 patent drawingFigure 1A~1B
  • EP3302477B1 patent drawingFigure 2~3
  • EP3302477B1 patent drawingFigure 4~5

AI summary

The present invention relates to injectable, extended-release, pharmaceutical formulations comprising a nalbuphine ester prodrug homogenously dissolved in a solution comprising a pharmaceutically acceptable oil and an oil-miscible retaining solvent, as well as manufacturing processes and medical uses of the formulations. The invention further provides methods for adjusting the duration of action of the formulations by varying the ratio of the pharmaceutically acceptable oil and the oil-miscible retaining solvent.