Identification of a tadalafil analogue adulterated in a dietary supplement

Journal of Food and Drug Analysis

Volumn 17, Issue 6, 2009, Pages 451-458

  Lin, Mei Chih ^a   Liu, Yi Chu ^a   Lin, Yun Lian ^c   Lin, Jer Huei ^a,b  

^a Ministry of Health and Welfare   (Taiwan)

^b TAIPEI MEDICAL UNIVERSITY   (Taiwan)

^c NATIONAL RESEARCH INSTITUTE OF CHINESE MEDICINE   (Taiwan)

Author keywords

Aminotadalafil; Dietary supplements; LC MS MS; NMR; Tadalafil; Tadalafil analogue

Indexed keywords

AMINOTADALAFIL; TADALAFIL; UNCLASSIFIED DRUG;

ADULTERATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CIRCULAR DICHROISM; CRIME; CRYSTALLIZATION; DIET SUPPLEMENTATION; DRUG PURIFICATION; DRUG SCREENING; DRUG STRUCTURE; ERECTILE DYSFUNCTION; HETERONUCLEAR MULTIPLE QUANTUM COHERENCE; LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POWDER; PROTON NUCLEAR MAGNETIC RESONANCE; SOLVENT EXTRACTION; STANDARD; STRUCTURE ACTIVITY RELATION; TANDEM MASS SPECTROMETRY; THIN LAYER CHROMATOGRAPHY; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 77949577274     PISSN: 10219498     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (21)

1. 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., Hanm S. B., Kim, D. J., Park, J. H. and Kwon, S. W. 2007. Structure determination of new analogues of vardenafil and sildenafil in dietary supplements. Food Addit. Contam. 24: 122-129.
2. Reepmeyer, J. C. and Woodruff, J. T. 2006. 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 1125: 67-75.
3. Zou, P., Oh, S. S, Hou, P., Lowb, M. Y. and Koh H. L. 2006. 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 1104: 113-122.
4. Zhu, X., Xiao, S., Chen, B., Zhang, F., Yao, S., Wan, Z., Yang, D. and Han, H. 2005. 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 1066: 89-95.
5. Lai, K. C., Liu, Y. C., Tseng, M. C. and Lin, J. H. 2006. Isolation and identification of a sildenafil analogue illegally added in dietary supplements. J. Food Drug Anal. 14: 19-23.
6. Lin, M. C., Liu, Y. C. and Lin, J. H. 2006. Identification of a sildenafil analogue adulterated in two herbal food supplements. J. Food Drug Anal. 14: 260-264.
7. Fleshner, N., Harvey, M., Adomat, H., Wood, C., Eberding, A., Hersey, K. and Guns, E. 2005. Evidence for contamination of herbal erectile dysfunction products with phosphodiesterase type 5 inhibitors. J. Urol. 174: 636-641.
8. Gratz, S. R., Flurer, C. L. and Wolnik, K. A. 2004. Analysis of undeclared synthetic phosphodiesterase-5 inhibitors in dietary supplements and herbal matrices by LC-ESI-MS and LC-UV. J. Pharm. Biomed. Anal. 36: 525-533.
9. Shin, C. S., Hong, M. K., Kim, D. Y. and Lim, Y. G. 2004. Structure determination of a sildenafil analogue contained in commercial herb drinks. Magn. Reson. Chem. 42: 1060-1062.
10. Blok-Tip, L., Zomer, B., Bakker, F., Hartog, K. D., Hamzink, M., Ten Hove, J., Vredenbregt, M. and De Kaste, D. 2004. Structure elucidation of sildenafil analogues in herbal products. Food Addit. Contam. 21: 737-748.
11. Shin, M. H., Hong, M. K., Kim, W. S., Lee, Y. J. and Jeoung, Y. C. 2003. Identification of a new analogue of sildenafil added illegally to a functional food marketed for penile erectile dysfunction. Food Addit. Contam. 20: 793-796.
12. Mikami, E., Ohno, T. and Matsumoto, H. 2002. Simultaneous identification/determination system for phentolamine and sildenafil as adulterants in soft drinks advertising roborant nutrition. Forensic Sci. Int. 130: 140-146.
13. Moriyasu, T., Shigeoka, S., Kishmoto, K., Ishikawa, F., Nakajima, J., Kamimura, H. and Yasuda, I. 2001. Identification system for sildenafil in health foods. Yakugaku Zasshi 121: 765-769.
14. Tseng, M. C. and Lin, J. H. 2002. Determination of sildenafil citrate adulterated in a dietary supplement capsule by LC/MS/MS. J. Food Drug Anal. 10: 112-119.
15. Kuan, J. and Brock, G. 2002. Selective phosphodiesterase type 5 inhibition using tadalafil for the treatment of erectile dysfunction. Export Opin. Investig. Drugs. 11: 1605-1613.
16. Carson, C. C., Rajfer, J., Eardley, I, Barbien, L., Zanni, G., Suardi, N., Cestari, A., Montorsi, P. and Rigatti, P. 2004. The efficacy and safety of tadalafil: an update. BJU Int. 93: 1276-1281.
17. Rosen, R. C. and Kostis, J. B. 2003. Overview of phosphodiesterase 5 inhibition in erectile dysfunction. Am. J. Cardiol. 92: 9M-18M.
18. Daugan, A., Grondin, P., Ruault, C., Le Monnier de Gouville A.- C., Coste, H., Linget, J. M., Kirilovsky, J., Hyafil, F. and Labaudinière, R. 2003. The discovery of tadalafil: a novel and highly selective PDE5 inhibitor. 2:2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1, 4-dione analogues. J. Med. Chem. 46: 4533-4542.
19. Zou, P., Hou, P., Low, M. Y. and Koh, H. L. 2006. Structural elucidation of a tadalafil analogue found as an adulterant of a herbal product. Food Addit. Contam. 23: 446-451.
20. Division of Safety Information on Drug, Food and Chemicals, National Institute of Health Sciences, Japan. 2004. Detection of a new synthetic analogue for the treatment of erectile dysfunction (Japanese edition). Food Safety Information. No. 18, pp 23, 27.
21. Gratz, S. R., Gamble, B. M. and flurer, R. A. 2006. 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. 20: 2317-2327.