CBD Ester Prodrugs for Poor Oral Bioavailability
Find Innovative SolutionsGenerate Solutions
Solution Overview
Problem
Cannabidiol (CBD) and CBD-type phytocannabinoids exhibit poor oral bioavailability, high plasma protein binding, and high first-pass metabolism, limiting their therapeutic effectiveness.
Innovation Solution
The development of prodrugs of CBD-type phytocannabinoids, where one or both hydroxyl groups are attached through ester bonds with polar moieties such as 2-morpholinylacetic acid, 2-(4-phenylpiperidin-1-yl)acetic acid, and others, to enhance plasma exposure and bioavailability.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If CBD and CBD-type phytocannabinoids are administered orally, then therapeutic treatment can be provided, but oral bioavailability is very poor
Solution Approach 1:
The patent changes the chemical parameters of CBD by converting hydroxyl groups into ester prodrugs with polar moieties. This chemical modification alters the pharmacokinetic properties, specifically improving oral bioavailability while maintaining therapeutic effectiveness. The ester prodrug formulation allows for better absorption and reduced first-pass metabolism.
Solution Approach 2:
The patent introduces ester prodrug intermediaries that facilitate the delivery of CBD to the bloodstream. These prodrugs act as carriers that improve plasma exposure and bioavailability, serving as intermediaries between the oral administration route and the active CBD molecule.
2Reliability
If CBD is administered, then therapeutic effects are achieved, but plasma protein binding is very high (>94%)
Solution Approach 1:
The patent modifies the chemical parameters of CBD through ester prodrug formation, which changes how the molecule interacts with plasma proteins. This modification reduces plasma protein binding while maintaining the therapeutic effects, allowing more free drug to be available for action.
3Ease of operation
If CBD undergoes first pass metabolism, then oral administration is possible, but metabolism is very high
Solution Approach 1:
The ester prodrug acts as an intermediary that protects CBD from extensive first-pass metabolism. The prodrug structure allows the molecule to survive the first pass through the liver more effectively, reducing metabolic loss while maintaining the ability to be administered orally.
Solution Approach 2:
The chemical modification through ester prodrug formation changes the metabolic parameters of CBD, reducing its susceptibility to first-pass metabolism and improving the amount of active drug that reaches systemic circulation.
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 prodrugs improve the oral bioavailability and plasma exposure of CBD and CBD-type phytocannabinoids, facilitating their therapeutic delivery and efficacy.
Implementation Method 1
prodrugs of CBD-type phytocannabinoids, where one or both hydroxyl groups are attached through ester bonds with polar moieties
Data Source
AI summary
The present invention provides the novel prodrugs of cannabidio-type phytocannabinoids having the general Formula A and its process thereof, where one or both the hydroxyl groups are attached to the other counter parts through ester bond. The present invention also studies the drug release studies in Ex-vivo and In-vivo systems.