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Phase II Reactions: Acetylation Reactions

Phase II Reactions: Acetylation Reactions

Acetylation, a phase II biotransformation reaction, introduces an acetyl group to drugs or their metabolites. Acetyltransferase enzymes facilitate this reaction, which resembles α-amino acid conjugation due to the addition of a functional group to the drug molecule.
The substrates for acetylation are typically drugs or their metabolites with an amino, sulfonamide, or hydrazine functional group. Acetylation can occur at several points in the drug molecule, including primary, secondary, and...

Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones

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Acetals are formed by reacting two equivalents of alcohol with carbonyl compounds like aldehydes or ketones. Acetals are unaffected by bases, nucleophiles, oxidizing agents, and reducing agents. They serve as protecting groups for aldehydes and ketones. Acetals can be easily formed and also easily removed via mild acid hydrolysis.
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...

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Sulfation and α-amino acid conjugation are two critical biotransformation reactions in drug metabolism. Sulfation, a phase II biotransformation reaction, involves adding a polar sulfate group to a drug, enhancing its water solubility and promoting excretion. This process can either co-occur with or occur independently of glucuronidation. Nonmicrosomal sulfotransferase enzymes catalyze the process. The reaction involves 3'-phosphoadenosine-5'-phosphosulfate or PAPS coenzyme...

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Spontaneous Formation and Rearrangement of Artificial Lipid Nanotube Networks as a Bottom-Up Model for Endoplasmic Reticulum

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Surface modification of acetaminophen particles by atomic layer deposition.

Tommi O Kääriäinen¹, Marianna Kemell², Marko Vehkamäki²

¹Laboratory of Inorganic Chemistry, University of Helsinki, P.O. Box 55 (A.I.Virtasen aukio 1), FI-00014 Helsinki, Finland; Department of Chemistry and Biochemistry and Department of Mechanical Engineering, University of Colorado, Boulder, CO 80309, United States; NovaldMedical Ltd Oy, Telkäntie 5, 82500 Kitee, Finland.

International Journal of Pharmaceutics

|April 23, 2017

Summary

Atomic Layer Deposition (ALD) coats acetaminophen powders with nanometer-scale films, improving properties without degradation. ALD coatings show potential for pharmaceutical manufacturing, with varying biocompatibility observed.

Keywords:

Acetaminophen Atomic layer deposition Cytocombatibility Drug delivery system Drug release

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Area of Science:

Materials Science
Pharmaceutical Technology
Nanotechnology

Background:

Active pharmaceutical ingredients (APIs) are often organic solid powders requiring processing for improved formulation and manufacturing.
Enhancing powder flow and API protection are critical in pharmaceutical production for various drug dosage forms.

Purpose of the Study:

To investigate the modification of acetaminophen particles using Atomic Layer Deposition (ALD) for pharmaceutical applications.
To evaluate the impact of ALD coatings on acetaminophen's properties, including stability, drug release, and cytocompatibility.

Main Methods:

Acetaminophen particles were coated using ALD with nanometer-scale conformal films of Al₂O₃, TiO₂, and ZnO in a single step.
Characterization of ALD-coated acetaminophen included assessment of degradation, polymorphic structure, drug release kinetics, and in vitro cytocompatibility using Caco-2 cells.

Main Results:

ALD is a promising method for coating pharmaceutical powders, with acetaminophen showing no degradation and maintaining its polymorphic structure.
Nanometer-scale ALD coatings resulted in slowed drug release from acetaminophen particles.
ALD TiO₂ coated particles demonstrated cytocompatibility, while thicker ZnO coatings exhibited significant cytotoxicity in vitro.

Conclusions:

ALD offers a viable one-step coating process for modifying pharmaceutical powders like acetaminophen.
ALD coatings can modulate drug release profiles and influence particle properties.
The choice of ALD material and coating thickness is crucial for achieving desired biocompatibility, with TiO₂ showing promise and ZnO requiring careful consideration.