Characterization of the Solution Degradation Products of Etintidine, An H2-Receptor Antagonist

The primary solution degradation products of the antiulcer drug etintidine (1,N″-cyano-N-[2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio]ethyl]-N′-2-propynylguanidine) were determined to be the guanyl urea 2, the guanidine 3, the amine 4a, and the cyanoamine 4b. These products resulted from nitrile hydr...

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Bibliographic Details
Published in:Journal of pharmaceutical sciences 1989-01, Vol.78 (1), p.21-24
Main Authors: Oyler, Alan R., Naldi, Roxanne E., Stefanick, Stephen M., Lloyd, John R., Graden, David A., Cotter, Mary Lou
Format: Article
Language:English
Subjects:
Biological and medical sciences
Chromatography, High Pressure Liquid
Cyclization
Drug Residues - analysis
General pharmacology
Histamine H2 Antagonists - analysis
Hydrogen-Ion Concentration
Hydrolysis
Imidazoles - analysis
Medical sciences
Oxidation-Reduction
Pharmaceutical technology. Pharmaceutical industry
Pharmacology. Drug treatments
Spectrophotometry, Ultraviolet
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Summary:The primary solution degradation products of the antiulcer drug etintidine (1,N″-cyano-N-[2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio]ethyl]-N′-2-propynylguanidine) were determined to be the guanyl urea 2, the guanidine 3, the amine 4a, and the cyanoamine 4b. These products resulted from nitrile hydrolysis and/or intramolecular cyclization of the guanidino and propargyl groups. The amine 4a was found to be a predominant degradation product in aqueous media of pH 4–7 at 70 ± 0.2°C.
ISSN:0022-3549
1520-6017
DOI:10.1002/jps.2600780107