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Isolation and Identification of an Unauthorized Sildenafil Analogue in a Commercial Functional Food

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초록

HPLC analysis of a commercial herb drink marketed as a functional food revealed to contain an unauthorized substance similar to sildenafil, the active ingredient of the prescription drug Viagra® approved for the treatment of male erectile dysfunction. In order to identify the illegal additive, the herb drink was extracted with methylene chloride, and the extract was purified further using semipreparative HPLC. The chemical structure of the isolated substance was elucidated based on IR, LC/MS-ESI, and NMR spectroscopy, which showed the characteristics similar to sildenafil with minor modification. The only difference was the substitution of the methylpiperazine moiety of sildenafil to the hydroxyethylpiperazine group of the illegal additive.

Abstract

HPLC analysis of a commercial herb drink marketed as a functional food revealed to contain an unauthorized substance similar to sildenafil, the active ingredient of the prescription drug Viagra® approved for the treatment of male erectile dysfunction. In order to identify the illegal additive, the herb drink was extracted with methylene chloride, and the extract was purified further using semipreparative HPLC. The chemical structure of the isolated substance was elucidated based on IR, LC/MS-ESI, and NMR spectroscopy, which showed the characteristics similar to sildenafil with minor modification. The only difference was the substitution of the methylpiperazine moiety of sildenafil to the hydroxyethylpiperazine group of the illegal additive.

참고문헌 (8)

  1. Food Sanitation Act (Republic of Korea), "Article 6 (Prohibition of Sale, etc. of Chemical Synthetic Compounds, etc. without Notice of Criteria and Standards)", ~
  2. Terrett, N. K, , Bioorg. Med. Chem. Lett., pp.1819~ (1996)
  3. Boolell, M., , Int. J. of Impotence Res., 8, pp.47~ (1996)
  4. Webb, D. J., , Am. J. Cardiol., 83, pp.21C~ (1999)
  5. Jang, J., , Fd. Hyg. Safety, 18, pp.195~ (2003)
  6. Graz, S. R., , J. Pharm. Biomed. Anal., 36, pp.525~ (2004)
  7. "Manual for the Determination of Illegal Compounds in Foods (Publication Number 11-1470000-00839-14)" (2005), Korea Food and Drug Administration
  8. Bell, A. S., "Pyrazolopyrimidinone antianginal agents", Eur. Pat. Appl., pp.463756~ (1992)

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