Intratablet S-nitrosation: A New Approach for the Oral Administration of S-nitrosothiols as Nitric Oxide Donors

The primary S-nitrosothiol, S-nitroso-N-acetylcysteine (SNAC) is a nitric oxide donor with potential pharmaceutical applications for the oral treatment of hepatic steatosis and cirrhosis and for protection against gastric acid–peptic disorders. However, its low thermal stability precludes the prepar...

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Bibliographic Details
Published in:Journal of pharmaceutical sciences 2016-01, Vol.105 (1), p.359-361
Main Authors: de Souza, Gabriela Freitas Pereira, de Oliveira, Marcelo Ganzarolli
Format: Article
Language:English
Subjects:
Acetylcysteine - chemistry
Acetylcysteine - pharmacology
Administration, Oral
Chemistry, Pharmaceutical
Delayed-Action Preparations
hydroxymethylpropylcellulose
N-acetyl-L-cysteine
nitric oxide
Nitric Oxide Donors - administration & dosage
Nitric Oxide Donors - chemistry
Nitrosation
Nitroso Compounds - chemistry
Nitrous Acid - chemistry
S-nitroso-N-acetylcysteine
S-nitrosothiols
S-Nitrosothiols - administration & dosage
S-Nitrosothiols - chemistry
tablets
Tablets - chemistry
Water - chemistry
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Summary:The primary S-nitrosothiol, S-nitroso-N-acetylcysteine (SNAC) is a nitric oxide donor with potential pharmaceutical applications for the oral treatment of hepatic steatosis and cirrhosis and for protection against gastric acid–peptic disorders. However, its low thermal stability precludes the preparation of stable dosage forms based on presynthesized SNAC. In this study, we describe an innovative strategy for the oral administration of SNAC based on its intratablet formation via the S-nitrosation reaction of its parent stable thiol, N-acetyl-L-cysteine by nitrous acid during the absorption of water by the tablet. The proposed strategy allows for the manufacturing of thermally stable oral dosage forms for the controlled release of SNAC in the enteric medium.
ISSN:0022-3549
1520-6017
DOI:10.1016/j.xphs.2015.10.011