Rapid-screening detection of acetildenafils, sildenafils and avanafil by ion mobility spectrometry

Journal of Pharmaceutical and Biomedical Analysis

Volumn 75, Issue , 2013, Pages 153-157

  Mans, Daniel J ^a   Callahan, Rebecca J ^a   Dunn, Jamie D ^a   Gryniewicz Ruzicka, Connie M ^a  

^a CENTER FOR DRUG EVALUATION AND RESEARCH   (United States)

Author keywords

Acetildenafils; Avanafil; Ion mobility spectrometry; Sildenafils

Indexed keywords

ACETILDENAFIL; ACETILDENAFIL DERIVATIVE; AVANAFIL; CYCLOPENTYNAFIL; DIMETHYLACETILDENAFIL; HYDROXYACETILDENAFIL; HYDROXYHOMOSILDENAFIL; N DESETHYLACETILDENAFIL; NOR ACETILDENAFIL; PHOSPHODIESTERASE V INHIBITOR; SILDENAFIL; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; COVALENT BOND; DRUG DETERMINATION; DRUG SCREENING; ION MOBILITY SPECTROMETRY; PRIORITY JOURNAL; SPECTROMETER;

CARBOLINES; CHEMISTRY TECHNIQUES, ANALYTICAL; DIETARY SUPPLEMENTS; FOOD CONTAMINATION; FOOD INSPECTION; IMIDAZOLES; ISOMERISM; PHOSPHODIESTERASE 5 INHIBITORS; PIPERAZINES; PURINES; PYRIMIDINES; SULFONES; TANDEM MASS SPECTROMETRY; TRIAZINES; VASODILATOR AGENTS;

EID: 84871811024     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2012.11.031     Document Type: Article

References (44)

1. Feldman H.A., Goldstein I., Hatzichristou D.G., Krane R.J., McKinlay J.B. Impotence and its medical and psychosocial correlates: results of the Massachusetts Male Aging Study. J. Urol. 1994, 151:54-61.
2. Benet A.E., Melman A. The epidemiology of erectile dysfunction. Urol. Clin. North Am. 1995, 22:699-709.
3. Lue T.F. Erectile dysfunction. N. Engl. J. Med. 2000, 342:1802-1813.
4. Ahn S., Hong J.Y., Hong M.K., Jang Y.P., Oh M.S., Jung J.H., Hong J. Structural determination of sildenafil and its analogues in dietary supplements by fast-atom bombardment collision-induced dissociation tandem mass spectrometry. Rapid Commun. Mass Spectrom. 2009, 23:3158-3166.
5. 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.
6. Bogusz M.J., Hassan H., Ai-Enazi E., Ibrahim Z., Al-Tufail M. Application of LC-ESI-MS-MS for detection of synthetic adulterants in herbal remedies. J. Pharm. Biomed. Anal. 2006, 41:554-564.
7. Goker 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.
8. Gratz S.R., Flurer C.L., Wolnik K.A. Analysis of undeclared synthetic phosphodiesterase-5 inhibitors in dietary supplements and herbal matrices by LC-ESI-MS and LC-UV. J. Pharm. Biomed. Anal. 2004, 36:525-533.
9. Gratz S.R., Gamble B.M., Flurer R.A. Accurate mass measurement using Fourier transform ion cyclotron resonance mass spectrometry for structure elucidation of designer drug analogs of tadalafil, vardenafil and sildenafil in herbal and pharmaceutical matrices. Rapid Commun. Mass Spectrom. 2006, 20:2317-2327.
10. Gryniewicz C.M., Reepmeyer J.C., Kauffman J.F., Buhse L.F. Detection of undeclared erectile dysfunction drugs and analogues in dietary supplements by ion mobility spectrometry. J. Pharm. Biomed. Anal. 2009, 49:601-606.
11. Haberli A., Girard P., Low M.Y., Ge X.W. Isolation and structure elucidation of an interaction product of aminotadalafil found in an illegal health food product. J. Pharm. Biomed. Anal. 2010, 53:24-28.
12. Hasegawa T., Saijo M., Ishii T., Nagata T., Haishima Y., Kawahara N., Goda Y. Structural elucidation of a tadalafil analogue found in a dietary supplement. J. Food Hyg. Soc. Jpn. 2008, 49:311-315.
13. Hasegawa T., Takahashi K., Saijo M., Ishii T., Nagata T., Kurihara M., Haishima Y., Goda Y., Kawahara N. Isolation and structural elucidation of cyclopentynafil and N-octylnortadalafil found in a dietary supplement. Chem. Pharm. Bull. 2009, 57:185-189.
14. Hou P.L., Zou P., Low M.Y., Chan E.L., Koh H.L. Structural identification of a new acetildenafil analogue from pre-mixed bulk powder intended as a dietary supplement. Food Addit. Contam. 2006, 23:870-875.
15. Lai K.C., Liu Y.C., Liao Y.C., Lin Y.L., Tsai L.Y., Lin J.H., Lo C.F. Isolation and identification of three thio-sildenafil analogues in dietary supplements. J. Food Drug Anal. 2010, 18:269-278.
16. Li L., Low M.Y., Aliwarga F., Teo J., Ge X.W., Zeng Y., Bloodworth B.C., Koh H.L. Isolation and identification of hydroxythiohomosildenafil in herbal dietary supplements sold as sexual performance enhancement products. Food Addit. Contam. Part A: Chem. Anal. Control Expos. Risk Assess. 2009, 26:145-151.
17. Liang Q.L., Qu J., Luo G.A., Wang Y.M. Rapid and reliable determination of illegal adulterant in herbal medicines and dietary supplements by LC/MS/MS. J. Pharm. Biomed. Anal. 2006, 40:305-311.
18. Lin M.C., Liu Y.C., Lin Y.L., Lin J.H. Isolation and identification of a novel sildenafil analogue adulterated in dietary supplements. J. Food Drug Anal. 2008, 16:15-20.
19. Lin M.C., Liu Y.C., Lin Y.L., Lin J.H. Identification of a tadalafil analogue adulterated in a dietary supplement. J. Food Drug Anal. 2009, 17:451-458.
20. Low M.Y., Zeng Y., Li L., Ge X.W., Lee R., Bloodworth B.C., Koh H.L. Safety and quality assessment of 175 illegal sexual enhancement products seized in red-light Districts in Singapore. Drug Saf. 2009, 32:1141-1146.
21. Mikami E., Ohno T., Matsumoto F. Simultaneous identification/determination system for phentolamine and sildenafil as adulterants in soft drinks advertising roborant nutrition. Forensic Sci. Int. 2002, 130:140-146.
22. Oh S.S.Y., Zou P., Low M.Y., Koh H.L. Detection of sildenafil analogues in herbal products for erectile dysfunction. J. Toxicol. Environ. Health Part A: Curr. Issues 2006, 69:1951-1958.
23. Park H.J., Jeong H.K., Chang M.I., Im M.H., Jeong J.Y., Choi D.M., Park K., Hong M.K., Youm J., Han S.B., Kim D.J., Park J.H., Kwon S.W. Structure determination of new analogues of vardenafil and sildenafil in dietary supplements. Food Addit. Contam. 2007, 24:122-129.
24. Reepmeyer J.C., d'Avignon D.A. Structure elucidation of thioketone analogues of sildenafil detected as adulterants in herbal aphrodisiacs. J. Pharm. Biomed. Anal. 2009, 49:145-150.
25. 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.
26. Reepmeyer J.C., Woodruff J.T. Use of liquid chromatography-mass spectrometry and a chemical cleavage reaction for the structure elucidation of a new sildenafil analogue detected as an adulterant in an herbal dietary supplement. J. Pharm. Biomed. Anal. 2007, 44:887-893.
27. Reepmeyer J.C., Woodruff J.T., d'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.
28. Shin C., Hong M.K., Kim D., Lim Y. Structure determination of a sildenafil analogue contained in commercial herb drinks. Magn. Reson. Chem. 2004, 42:1060-1062.
29. 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.
30. Venhuis B.J., Blok-Tip L., de Kaste D. Designer drugs in herbal aphrodisiacs. Forensic Sci. Int. 2008, 177:E25-E27.
31. Zhu X.L., Xiao S., Chen B., Zhang F., Yao S.Z., Wan Z.T., Yang D.J., Han H.W. Simultaneous determination of sildenafil, vardenafil and tadalafil as forbidden components in natural dietary supplements for male sexual potency by high-performance liquid chromatography-electrospray ionization mass spectrometry. J. Chromatogr. A 2005, 1066:89-95.
32. 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.
33. Zou P., Hou P., Oh S.S.Y., Ge X., Bloodworth B.C., Low M.Y., Koh H.L. Identification of benzamidenafil, a new class of phosphodiesterase-5 inhibitor, as an adulterant in a dietary supplement. J. Pharm. Biomed. Anal. 2008, 47:255-259.
34. Zou P., Hou P.L., 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.
35. Zou P., Hou P.L., Oh S.S.Y., Low M.Y., Koh H.L. Electrospray tandem mass spectrometric investigations of tadalafil and its analogue. Rapid Commun. Mass Spectrom. 2006, 20:3488-3490.
36. Zou P., Oh S.S.Y., Hou P.L., Low M.Y., Koh H.L. Simultaneous determination of synthetic phosphodiesterase-5 inhibitors found in a dietary supplement and pre-mixed bulk powders for dietary supplements using high-performance liquid chromatography with diode array detection and liquid chromatography-electrospray ionization tandem mass spectrometry. J. Chromatogr. A 2006, 1104:113-122.
37. Everts S. Fake pharmaceuticals. C&E News 2010, 88:27-29.
38. http://www.hhs.gov/news/press/2012pres/07/20120709b.html.
39. A.S. Bell, N.K. Terrett, Preparation of pyrazolopyrimidinones as cGMP phosphodiesterase inhibitors, Eur. Pat. Appl. EP 526004 A1 (1993).
40. A.S. Bell, D., Brown, N.K. Terrett, Preparation of pyrazolo[4,3-d]pyrimidin-7-ones as cardiovascular agents, Eur. Pat. Appl. EP 463756 A1, 1992.
41. G.A. Piazza, R. Pamukcu, Preparation of phenyl purinone derivatives for the treatment of precancerous lesions, US 6200980 B1 (2001).
42. J.H. Kim, Y. Kim, K.I. Choi, D.H. Kim, G. Nam, J.H. Seo, Preparation of novel pyrazolopyrimidinethiones as phosphodiesterase V inhibitors for treating erectile dysfunction, PCT Int. Appl. WO 2002102802 A1 (2002).
43. Inman E.L., Tenbarge H.J. High-low chromatography: estimating impurities in HPLC using a pair of sample injections. J. Chromatogr. Sci. 1988, 26:89-94.
44. Dunn J.D., Gryniewicz-Ruzicka C.M., Mans D.J., Mecker-Pogue L.C., Kauffman J.F., Westenberger B.J., Buhse L.F. Qualitative screening for adulterants in weight-loss supplements by ion-mobility spectrometry. J. Pharm. Biomed. Anal. 2012, 71:18-26.