Structural characterization of sulfoaildenafil, an analog of sildenafil.

Samuel R Gratz, Matthias Zeller, Daryl W Mincey, Cheryl L Flurer

U.S. Food and Drug Administration, Forensic Chemistry Center, 6751 Steger Drive, Cincinnati, OH 45237, USA.

Journal of pharmaceutical and biomedical analysis 2009 Sep 8

filter terms:

Phosphodiesterase type 5 (PDE-5) inhibitors represent a class of drugs used primarily in the treatment of erectile dysfunction. Currently, three PDE-5 inhibitors have been approved by the U.S. Food and Drug Administration (FDA) for use in the United States: sildenafil citrate, tadalafil, and vardenafil hydrochloride trihydrate. A bulk material, labeled as an ingredient for a dietary supplement, was analyzed for the presence of PDE-5 inhibitors. The compound that was detected displayed structural similarities to sildenafil, and was characterized further using LC-MS(n), FTICRMS, X-ray crystallography and NMR. The compound was given the name sulfoaildenafil. When compared to sildenafil, sulfoaildenafil contains a sulfur atom substitution for the oxygen atom in the pyrazolopyrimidine portion of the molecule, and a 3,5-dimethyl substitution on the piperazine ring, rather than the 4-methyl moiety. The X-ray crystallographic data indicate that the material in this sample is comprised of two polymorphs, which may affect the chemical and/or biological properties of any product formulated with this compound.

Citation

Samuel R Gratz, Matthias Zeller, Daryl W Mincey, Cheryl L Flurer. Structural characterization of sulfoaildenafil, an analog of sildenafil. Journal of pharmaceutical and biomedical analysis. 2009 Sep 8;50(2):228-31