Determination of a new type of phosphodiesterase-5 inhibitor, thioquinapiperifil, in a dietary supplement promoted for sexual enhancement

Chemical and Pharmaceutical Bulletin

Volumn 56, Issue 9, 2008, Pages 1331-1334

  Uchiyama, Nahoko ^a   Saisho, Kazuhiro ^a   Kikura Hanajiri, Ruri ^a   Haishima, Yuji ^a   Goda, Yukihiro ^a  

^a NATIONAL INSTITUTE OF HEALTH SCIENCES   (Japan)

Author keywords

Erectile dysfunction; LC MS; NMR; Phosphodiesterase 5 inhibitor; Thioquinapiperifil

Indexed keywords

3 ETHYL 1,3 DIHYDRO 8 [[[2 [4 (HYDROXYMETHYL) 1 PIPERIDINYL]PHENYL]METHYL]AMINO] 2H IMIDAZO[4,5 G]QUINAZOLINE 2 THIONE; FR 226807; IMIDAZOQUINAZOLINE DERIVATIVE; KF 31327; KJH 1002; PHOSPHODIESTERASE V INHIBITOR; QUINAZOLINE DERIVATIVE; SILDENAFIL; TADALAFIL; THIODENAFIL; THIOQUINAPIPERIFIL; UNCLASSIFIED DRUG; VARDENAFIL;

ARTICLE; CHEMICAL COMPOSITION; DIET SUPPLEMENTATION; DRUG DETERMINATION; DRUG STRUCTURE; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; QUANTITATIVE ANALYSIS; SEXUAL FUNCTION;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLIC NUCLEOTIDE PHOSPHODIESTERASES, TYPE 5; DIETARY SUPPLEMENTS; ERECTILE DYSFUNCTION; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MALE; PHOSPHODIESTERASE INHIBITORS; PIPERAZINES; REFERENCE STANDARDS; SOLUTIONS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, ULTRAVIOLET; SULFONES; TABLETS;

EID: 51349126437     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.56.1331     Document Type: Article

References (31)

1. Japan, Ministry of Health, Labour and Welfare, websites: listed in (http://www.mhlw.go.jp/kinkyu/diet/other/050623-l.html) [in Japanese].
2. Moriyasu T., Shigeoka S., Kishimoto K., Ishikawa E, Nakajima J., Kamimura H., Yasuda I., Yakugaku Zasshi, 121, 765-769 (2001).
3. Zhu X., Xiao S., Chen B., Zhang E, Yao S., Wan Z., Yang D., Han H., J. Chromatogr. A, 1066, 89-95 (2005).
4. Venhuis B. J., Barends D. M., Zwaagstra M. E., De Kaste D., "RIVM Report 370030001/2007," National Institute for Public Health and the Environment, the Netherlands, 2007.
5. Shin M. H., Hong M. K., Kim, W S., Lee Y. J., Jeoung Y. C., Food Addit. Contain., 20, 793-796 (2003).
6. Shin C., Hong M., Kim D., Lim Y., Magn. Reson. Chem., 42, 1060-1062 (2004).
7. Park H. J., Jeong H. K, Chang M. I., Ira M. H, Jeong X Y., Choi D. M., Park K, Hong M. K, Youm X, Han S. B., Food Addit. Contain., 24, 122-129 (2007).
8. Blok-Tip L., Zomer B., Bakker F., Hartog K. D., Hamzuink M., ten Hove J., Vredenbregt M., de Kaste D., Food Addit. Contam., 21, 737-748 (2004).
9. Hou P., Zou P., Low M. Y., Chan E., Koh H L., Food Addit. Contam., 23, 870-875 (2006).
10. Zou P., Hou P., Low M.-Y., Koh H. L., Food Addit. Contam., 23, 446-451 (2006).
11. Zou P., Hou P., Oh S. S., Low M. Y., Koh H. L., Rapid Commun. Mass Spectrom., 20, 3488-3490 (2006).
12. Gratz S. R., Flurer, C. L., Wolnik K A., J. Pharm. Biomed. Anal., 36, 525-533 (2004).
13. Gratz S. R., Gamble B. M., Flurer R. A., Rapid Commun. Mass Spectrom., 20, 2317-2327 (2006).
14. Lai K C., Liu Y. C., Tseng M. C., Lin X H., J. Food Drug Anal., 14, 19-23 (2006).
15. Reepmeyer X C., Woodruff X T., J. Chromatogr. A, 1125, 67-75 (2006).
16. Reepmeyer X C., Woodruff X T., d'Avignon D. A., J. Pharm. Biomed. Anal., 43, 1615-1621 (2007).
17. Reepmeyer X C., Woodruff X T., J. Pharm. Biomed. Anal., 44, 887-893 (2007).
18. Lam Y. H., Poon W T., Lai C. K., Chan AY. W., Mak T. W L., J. Pharm. Biomed. Anal., 46, 804-807 (2008).
19. Cho E. Y., Chung S. H., Kim X H., Kim D K., Jin C., J. Appl. Phar-macol., 11, 232-237 (2003).
20. Kim J. H., Kim Y., Choi K., Kim D. H., Nam G., Seo J. H., WO 2002102802 (2002) [PCT Int. Appl., (2002)].
21. Zou P., Hou P., Oh S. S., Chong Y. M., Bloodworth B. C., Low M. Y., Koh H. L., J. Pharm. Biomed. Anal., 47, 279-284 (2008).
22. Kumasaka K, Doi K., Kojima T., Kawahara N., Goda Y., Proceedings of the 127th Annual Meeting of the Pharmaceutical Society of Japan, Toyama, Japan, 28-30 March, 2007.
23. Kumasaka K., Kawahara N., Doi K, Kojima T., Goda Y., Chem. Pharm. Bull., 56, 227-230 (2008).
24. Hosogai N., Hamada K., Tomita M., Nagashima A., Takahashi T., Sekizawa T., Mizutani T., Urano Y., Kuroda A., Sawada K, Ozaki T., Seki J., Goto T., Eur. J. Pharm., 428, 295-302 (2001).
25. Fujino K., Takami H., Atsumi T., Ogasa T., Mohri S., Kasai M., Org. Process Res. Dev., 5, 426-433 (2001).
26. Onoda Y., Nomoto Y., Ohno T., Yamada K, Ichimura M., WO9808848 (1998) [PCTIni. Appl., (1998)].
27. Hirose R., Okumura H., Yoshimatsu A., Irie J., Onoda Y., Nomoto Y., Takai H., Ohno T., Ichimura M., Eur. J. Pharmacol., 431, 17-24 (2001).
28. Kamakura H., Hirama Y., Hayashi T., Kanetoshi A., Goda Y., Proceedings of the 128th Annual Meeting of the Pharmaceutical Society of Japan, Yokohama, Japan, 26-28 March, 2008.
29. Thomsen I., Clausen K., Scheibye S., Lawesson S. O., "Org. Synth.," Vol. 62, ed. by Danheiser R. L., Organic Syntheses Inc., New York, 1984, pp. 158-161.
30. Zou P., Oh S. S., Hou P., Low M. Y., Koh H. L., J. Chromatogr. A, 1104, 113-122 (2006).
31. Detailed NMR data with assignments are available from the corresponding author upon request.