Isolation and characterization of propoxyphenyl linked sildenafil and thiosildenafil analogues in health supplements

Journal of Pharmaceutical and Biomedical Analysis

Volumn 70, Issue , 2012, Pages 265-272

  Kee, Chee Leong ^a   Ge, Xiaowei ^a   Koh, Hwee Ling ^b   Low, Min Yong ^a  

^a HEALTH SCIENCES AUTHORITY   (Singapore)

^b NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

Health supplement; MS; NMR; Propoxyphenyl aildenafil; Propoxyphenyl thioaildenafil

Indexed keywords

MEN PEPTIDE IV; PEPTIDE; PHENYL GROUP; PROPOXYPHENYL; PROPOXYPHENYL AILDENAFIL; PROPOXYPHENYL METHISOSILDENAFIL; PROPOXYPHENYL THIOAILDENAFIL; PROPOXYPHENYL THIOMETHISOSILDENAFIL; SILDENAFIL; THIOSILDENAFIL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DIET SUPPLEMENTATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; ISOLATION AND PURIFICATION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; ULTRAVIOLET SPECTROSCOPY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIETARY SUPPLEMENTS; DRUG CONTAMINATION; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PHOSPHODIESTERASE 5 INHIBITORS; PIPERAZINES; PURINES; PYRIMIDINES; SPECTROPHOTOMETRY, ULTRAVIOLET; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; SULFONES; TANDEM MASS SPECTROMETRY;

EID: 84866243856     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2012.07.008     Document Type: Article

References (21)

1. Shin M.N., Hong K.M., 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.
2. Venhuis B.J., Zomer G., de Kaste D. Structure elucidation of a novel synthetic thiono analogue of sildenafil detected in an alleged herbal aphrodisiac. J. Pharm. Biomed. Anal. 2008, 46:814-817.
3. Oh S.S., Zou P., Low M.Y., Koh H.L. Detection of sildenafil analogues in herbal products for erectile dysfunction. J. Toxicol. Environ. Health A 2006, 69:1951-1958.
4. Reepmeyer J.C., Avignon D.A. Structure elucidation of thioketone analogues of sildenafil detected as adulterants in herbal aphrodisiacs. J. Pharm. Biomed. Anal. 2009, 49:145-150.
5. Reepmeyer J.C., Woodruff J.T., Avignon D.A. Structure elucidation of a novel analogue of sildenafil detected as an adulterant in an herbal dietary supplement. J. Pharm. Biomed. Anal. 2007, 43:1615-1621.
6. Ge X., Li L., Koh H.L., Low M.Y. Structure of a new sildenafil analogue in a health supplement. J. Pharm. Biomed. Anal. 2011, 56:491-496.
7. Venhuis B.J., Zomer G., Hamzink M., Meiring H.D., Aubin Y., de Kaste D. The identification of a nitrosated prodrug of the PDE-5 inhibitor aildenafil in a dietary supplement: a Viagra with a pop. J. Pharm. Biomed. Anal. 2011, 54:735-741.
8. 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.
9. Reepmeyer J.C., Woodruff J.T. Use of liquid chromatography-mass spectrometry and a hydrolytic technique for the detection and structure elucidation of a novel synthetic vardenafil designer drug added illegally to a natural herbal dietary supplement. J. Chromatogr. A 2006, 1125:67-75.
10. 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 bi liquid chromatography-eletrospray ionisation mass spectrometry, infrared spectroscopy and nuclear magnetic resonance spectroscopy. J. Pharm. Biomed. Anal. 2011, 54:491-496.
11. Zou P., Hou P., Low M.Y., Koh H.L. Structural elucidation of a tadalafil analogue found as an adulterant of a herbal product. Food Addit. Contam. 2006, 23:446-451.
12. B.J. Venhuis, D. de Kaste, 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., , in press. doi:10.1016/j.jpba.2012.02.014.
13. Balayssac S., Gilard V., Zedde C., Martino R., Malet-Martino 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.
14. D.H. Kim, J.H. Choi, K.I. Choi, Y. Kim, G. Nam, J.H. Seo, Novel pyrazolopyrimidinethione derivatives. Preparation methods thereof and their use as therapeutics for erectile dysfunction, USP 2004/0176371 (2004).
15. Food and Drug Administration, Department of Health, Taiwan. (accessed 17.04.12). http://www.fda.gov.tw/gradation.aspx%3Fsite_content_sn=2708.
16. Sikoska-Tomicka H. Spectrophotometric extraction determination of thiolactam with picric acid and silver. Mikrochim. Acta 1985, 86:479-486.
17. Socrates G. Infrared and Raman Characteristic Group Frequencies 2001, John Wiley & Sons, Chichester. third ed.
18. B. Liu, 1,6,Dihydro-7H-pyrazolo[3,4,d]pyrimidin-7-one compound for the treatment of impotence, US Patent 6960592 B2 10/736,732 (2005).
19. M. Yoo, W. Kim, M.S. Chang, J.I. Lim, D.S. Kim, I.K. Kim, T.K. Lim, B.O. Ahn, K.K. Kang, M. Son, H. Doh, S. Kim, H. Shim, T. Oh, H. Kim, D.J. Kim, Pyrazolopyrimidione derivatives for the treatment of impotence, EP 1129093 B1 (2003).
20. Jesberger M., Davis T.P., Barner L. Application of Lawesson's reagent in organic and organometallic syntheses. Synthesis 2003, 12:1929-1958.
21. Gratz S.R., Gamble B.M., Flurer R.A. Rapid Commun. Mass Spectrom. 2006, 20:2317-2327.