Isolation and identification of a new sildenafil analogue adulterated in energy drink: Propoxyphenyl sildenafil

Journal of Pharmaceutical and Biomedical Analysis

Volumn 72, Issue , 2013, Pages 155-158

  Alp, Mehmet ^a   Coşkun, Maksut ^a   Göker, Hakan ^a  

^a ANKARA UNIVERSITY   (Turkey)

Author keywords

Adulterants; Homosildenafil; PDE 5 inhibitors; Propoxyphenyl sildenafil; Sildenafil analogues

Indexed keywords

PHOSPHODIESTERASE V INHIBITOR; PROPOXYPHENYL SILDENAFIL; SILDENAFIL; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; DRUG ISOLATION; ELECTROSPRAY MASS SPECTROMETRY; ENERGY DRINK; EXTRACTION; INFRARED SPECTROSCOPY; LIQUID CHROMATOGRAPHY; MOLECULAR WEIGHT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SEXUAL HEALTH; ULTRAVIOLET SPECTROSCOPY;

CHROMATOGRAPHY, LIQUID; ENERGY DRINKS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; PIPERAZINES; PURINES; SPECTROPHOTOMETRY, INFRARED; SPECTROPHOTOMETRY, ULTRAVIOLET; SULFONES;

EID: 84869068033     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2012.09.017     Document Type: Article

References (16)

1. Venhuis B.J., Kaste D. Towards a decade of detecting new analogues of sildenafil, tadalafil and vardenafil in food supplements: a history, analytical aspects and health risks. J. Pharm. Biomed. Anal. 2012, 69:196-208.
2. Göker H., Coşkun M., Ki{dotless}lci{dotless}gil G.A. Chromatographic Separation and Identification of Sildenafil and Yohimbine Analogues Illegaly Added in Herbal Supplement, Chromatography and its Applications 2012, 51-68. Available from:. http://www.intechopen.com/books/chromatography-and-its-applications/chromatographic-seperation-and-identification-of-a-sildenafil-and-yohimbine-analogue-illegally-added, S. Dhanarasu (Ed.).
3. Kloner R.A. Cardiovascular effects of the 3 phosphodiesterase-5 inhibitors approved for the treatment of erectile dysfunction. Circulation 2004, 110:3149-3155.
4. Pissarnitski D. Phosphodiesterase 5 (PDE 5) inhibitors for the treatment of male erectile disorder: attaining selectivity versus PDE6. Med. Res. Rev. 2006, 26:369-395.
5. Pomeranz H.D., Bhavsar A.R. Nonarteritic ischemic optic neuropathy developing soon after use of sildenafil (viagra): a report of seven new cases. J. Neuro-Ophthalmol. 2005, 25:9-13.
6. Maddox P.T., Saunders J., Chandrasekhar S.S. Sudden hearing loss from PDE-5 inhibitors: a possible cellular stress etiology. Laryngoscope 2009, 119:1586-1589.
7. B.J. Venhuis, M.E. Zwaagstra, J.D.J. van den Berg, A.J.H.P. van Riel, H.W.G. Wagenaar, K. van Grootheest, D.M. Barends, D. Kaste, Illicit erectile dysfunction products in the Netherlands. A decade of trends and a 2007-2010 product update. RIVM Report 370030003/2010 National Institute for Public Health and the Environment, Available from: http://www.rivm.nl/bibliotheek/rapporten/370030003.pdf.
8. Vaysse J., Gilard V., Balayssac S., Zedde C., Martino R., Martino M.M. Identification of a novel sildenafil analogue in an adulterated herbal supplement. J. Pharm. Biomed. Anal. 2012, 59:58-66.
9. Lee H.M., Kim C.S., Jang Y.M., Kwon S.W., Lee B.J. Separation and structural elucidation of a novel analogue of vardenafil included as an adulterant in a dietary supplement by liquid chromatography-electrospray ionization mass spectrometry, infrared spectroscopy and nuclear magnetic resonance spectroscopy. J. Pharm. Biomed. Anal. 2011, 54:491-496.
10. Kesting J.R., Huang J., Sørensen D. Identification of adulterants in a Chinese herbal medicine by LC-HRMS and LC-MS-SPE/NMR and comparative in vivo study with standards in a hypertensive rat model. J. Pharm. Biomed. Anal. 2010, 51:705-711.
11. Shin M.H., Hong M.K., Kim W.S., Lee Y.J., Jeoung Y.C. Identification of a new analogue of sildenafil added illegally to a functional food marketed for penile erectile dysfunction. Food Addit. Contam. 2003, 20:793-796.
12. Göker H., Coskun M., Alp M. Isolation and identification of a new acetildenafil analogue used to adulterate a dietary supplement: dimethylacetildenafil. Turk. J. Chem. 2010, 34:157-163. http://journals.tubitak.gov.tr/chem/issues/kim-10-34-2/kim-34-2-1-1002-25.pdf.
13. Zou P., Hou P., Oh S.S.Y., Chong Y.M., Bloodworth B.C., Low M.Y., Koh H.L. Isolation and identification of thiohomosildenafil and thiosildenafil in health supplements. J. Pharm. Biomed. Anal. 2008, 47:279-284.
14. Blok-Tip L., Zomer B., Bakker F., Hartog K.D., Hamzink M., Ten Hove J., Vredenbregt M., de Kaste D. Structure elucidation of sildenafil analogues in herbal products. Food Addit. Contam. 2004, 21:737-748.
15. Balayssac S., Gilard V., Zedde C., Martino R., Martino M.M. Analysis of herbal dietary supplements for sexual performance enhancement: first characterization of propoxyphenyl-thiohydroxyhomosildenafil and identification of sildenafil, thiosildenafil, phentolamine and tetrahydropalmatine as adulterants. J. Pharm. Biomed. Anal. 2012, 63:135-150.
16. Kee C.L., Ge X., Koh H.L., Low M.Y. Isolation and characterization of propoxyphenyl linked sildenafil and thiosildenafil analogues in health supplements. J. Pharm. Biomed. Anal. 2012, 70:265-272.