Structural characterization of sulfoaildenafil, an analog of sildenafil

J Pharm Biomed Anal. 2009 Sep 8;50(2):228-31. doi: 10.1016/j.jpba.2009.04.003. Epub 2009 Apr 10.

Abstract

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.

MeSH terms

  • Chromatography, Liquid
  • Crystallography, X-Ray
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Models, Molecular
  • Molecular Structure
  • Phosphodiesterase Inhibitors / chemistry*
  • Piperazines / chemistry*
  • Purines / chemistry
  • Sildenafil Citrate
  • Sulfones / chemistry*

Substances

  • Phosphodiesterase Inhibitors
  • Piperazines
  • Purines
  • Sulfones
  • sulfoaildenafil
  • Sildenafil Citrate