Oxycodone Granule Subcoat Prevents Oxidation

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Solution Overview

Problem

Oxycodone in orally disintegrating tablets degrades due to oxidation, and its combination with acetaminophen leads to stability issues and delayed release, affecting the efficacy and stability of pain relief in patients, especially in moist conditions or during storage.

Innovation Solution

Formulating oxycodone as coated granules with a neutral core, a subcoat soluble in gastric fluids, and a taste-masking coating with dialkylaminoalkyl(meth)acrylate units, and separating oxycodone from acetaminophen to prevent degradation and ensure stable release, using a hydroalcoholic medium for coating and incorporating crospovidone as a disintegrant to maintain oxycodone stability and facilitate rapid dissolution.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If oxycodone is formulated in conventional coated granules using dimethylaminoethyl methacrylate copolymer (Eudragit E100), then taste-masking is achieved and immediate release in stomach is obtained, but oxycodone degrades into oxidation by-products over time

Engineering Contradiction:
Improvetaste-masking capabilityVSAvoidoxycodone stability
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

A subcoat comprising a compound soluble in gastric fluid is introduced as an intermediary layer between the oxycodone coating and the taste-masking coating. This subcoat acts as a protective barrier that prevents direct contact between oxycodone and the dimethylaminoethyl methacrylate copolymer, thereby eliminating the hydrogen bonding interaction that facilitates oxidation while still allowing immediate release in gastric fluid.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The granule structure is segmented into three distinct layers: a neutral core, an oxycodone coating layer, and a subcoat layer with gastric fluid solubility, and a taste-masking coating layer. This segmentation isolates the active ingredient from degrading agents while maintaining the desired release profile and taste-masking properties.

Inventive Principle:
Principle #1Segmentation

2Ease of operation

If oxycodone and acetaminophen are combined in the same granules for orally disintegrating tablets, then convenient co-administration is achieved, but oxycodone degradation is accelerated and acetaminophen release is delayed

Engineering Contradiction:
Improveco-administration convenienceVSAvoidoxycodone stability and release profile
Core Design Contradiction:
Ease of operationVSReliability

Solution Approach 1:

The tablet is segmented into two separate granule populations: oxycodone-containing granules with the protective subcoat structure, and acetaminophen-containing granules. This physical separation prevents the harmful interaction between the two active ingredients while maintaining the convenience of co-administration in a single tablet.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The subcoat soluble in gastric fluid serves as a protective intermediary that specifically protects oxycodone from degradation by acetaminophen and other oxidation catalysts, while allowing rapid dissolution and release of both active ingredients when the tablet disintegrates in the mouth.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Ease of manufacture

If oxycodone is stored under ambient conditions, then ease of storage is maintained, but oxycodone content decreases due to oxidation over time

Engineering Contradiction:
Improvestorage convenienceVSAvoidoxycodone content
Core Design Contradiction:
Ease of manufactureVSStability of the object's composition

Solution Approach 1:

The subcoat comprising a compound soluble in gastric fluid acts as a protective intermediary barrier that prevents direct contact between oxycodone and oxidation catalysts such as peroxides and other contaminants. This protective layer maintains oxycodone stability during storage under ambient conditions without requiring special storage conditions.

Inventive Principle:
Principle #24Intermediary (Mediator)

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 solution maintains at least 90% oxycodone stability after 21 days at 80°C, ensures rapid release of acetaminophen, and provides effective pain relief with improved stability and dissolution profiles, ensuring consistent medication efficacy.

Implementation Method 1

a subcoat comprising a compound soluble in gastric fluid; wherein said subcoat is further coated with a taste-masking coating

Methodology Applied
Scientific EffectSolubility: Solvation

Implementation Method 2

This coating is insoluble at a pH above 5.5, thus remains intact in contact with saliva but is readily soluble in gastric juice, due to the protonation of the amine functions

Methodology Applied
Scientific EffectProtonation:

Implementation Method 3

This coating is insoluble at a pH above 5.5, thus remains intact in contact with saliva but is readily soluble in gastric juice

Methodology Applied
Scientific EffectpH-dependent solubility: Solvation

Implementation Method 4

the nitrogen atom of the tertiary amines of the dimethylaminoethyl methacrylate units of Eudragit® E100 may form hydrogen bonding with the hydrogen atom of the ammonium function of oxycodone hydrochloride

Methodology Applied
Scientific EffectHydrogen bonding:

Implementation Method 5

the nitrogen atom of the tertiary amines of the dimethylaminoethyl methacrylate units of Eudragit® E100 may form hydrogen bonding with the hydrogen atom of the ammonium function of oxycodone hydrochloride

Methodology Applied
Scientific EffectHydrogen bonding interaction:

Data Source

PatentEP2046285B1Granule and orally disintegrating tablet comprising oxycodone
Publication Date: 2018.02.21 ETHYPHARM SA

AI summary

The present invention relates to granules comprising oxycodone, as well as to orally disintegrating tablets including same and optionally acetaminophen.