Isolation and structural elucidation of cyclopentynafil and n-octylnortadalafil found in a dietary supplement

Chemical and Pharmaceutical Bulletin

Volumn 57, Issue 2, 2009, Pages 185-189

  Hasegawa, Takashi ^a   Takahashi, Kazunaga ^a   Saijo, Masaaki ^a   Ishii, Toshiyasu ^a   Nagata, Tomoko ^a   Kurihara, Masaaki ^b   Haishima, Yuji ^b   Goda, Yukihiro ^b   Kawahara, Nobuo ^b  

^a CHIBA PREFECTURAL INSTITUTE OF PUBLIC HEALTH   (Japan)

^b NATIONAL INSTITUTE OF HEALTH SCIENCES   (Japan)

Author keywords

Cyclopentynafil; Erectile dysfunction; LC MS; N octylnortadalafil; NMR; Phosphodiesterase 5 inhibitor

Indexed keywords

CYCLOPENTYNAFIL; N OCTYLNORTADALAFIL; SILDENAFIL; TADALAFIL; UNCLASSIFIED DRUG;

ARTICLE; DIET SUPPLEMENTATION; DRUG DETERMINATION; DRUG STRUCTURE; MOLECULAR DOCKING; QUANTITATIVE ASSAY; STRUCTURE ANALYSIS;

CARBOLINES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CIRCULAR DICHROISM; DIETARY SUPPLEMENTS; ERECTILE DYSFUNCTION; HUMANS; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MALE; PHOSPHODIESTERASE INHIBITORS; PIPERAZINES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STREET DRUGS; SULFONES;

EID: 61449169037     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.57.185     Document Type: Article

References (30)

1. Ministry of Health, Labour and Welfare of Japan, websites: (http://www.mhlw.go.jp/kinkyu/diet/other/050623-1.html)
2. Moriyasu T., Shigeoka S., Kishimoto K., Ishikawa F., Nakajima J., Kamgimura H., Yasguda I., Yakugaku Zasshi, 121, 765-769 (2001).
3. Zhu X., Xiao S., Chen B., Zhang F., Yao S., Wan Z., Yang D., Han H., J. Chromatogr. A, 1066, 89-95 (2005).
4. Hasegawa T., Saijo M., Ishii T., Nagata T., Haishima, Y., Kawahara N., Goda Y., J. Food Hyg. Soc. Jpn., 49, 311-315 (2008).
5. Jefferson D. R., Natarajan S., Ganesan A., Synlett, 1004, 1428-1430 (2004).
6. 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.
7. Shin M. H., Hong M. K., Kim W. S., Lee Y. J., Jeoung Y. C., Food Addit. Contam., 20, 793-796 (2003).
8. Shin C., Hong M., Kim D., Lim Y., Magn. Reson. Chem., 41, 1060-1062 (2004).
9. 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., Food Addit. Contam., 24, 122-129 (2007).
10. Blok-Tip L., Zomer B., Bakker F., Hartog K. D., Hamzink M., ten Hove J., Vredenbregt M., de Kaste D., Food Addit. Contam., 21, 737-748 (2004).
11. Hou P., Zou P., Low M. Y., Chan E., Koh H. L., Food Addit. Contam., 23, 870-875 (2006).
12. Zou P., Hou P., Low M.-Y., Koh H. L., Food Addit. Contam., 23, 446-451 (2006).
13. Zou P., Hou P., Oh S. S., Low M. Y., Koh H. L., Rapid Commun. Mass Spectrom., 20, 3488-3490 (2006).
14. Gratz S. R., Flurer, C. L., Wolnik K. A., J. Pharm. Biomed. Anal., 36, 525-533 (2004).
15. Gratz S. R., Gamble B. M., Flurer R. A., Rapid Commun. Mass Spectrom., 20, 2317-2327 (2006).
16. Lai K. C., Liu Y. C., Tseng M. C., Lin J. H., J. Food Drug Anal., 14, 19-23 (2006).
17. Reepmeyer J. C., Woodruff J. T., J. Chromatogr. A, 1115, 67-75 (2006).
18. Reepmeyer J. C., Woodruff J. T., d'Avignon D. A., J. Pharm. Biomed. Anal., 43, 1615-1621 (2007).
19. Reepmeyer J. C., Woodruff J. T., J. Pharm. Biomed. Anal., 44, 887-893 (2007).
20. Lam Y. H., Poon W. T., Lai C. K., Chan A.Y. W., Mak T. W. L., J. Pharm. Biomed. Anal., 46, 804-807 (2008).
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. Cho E. Y., Chung S. H., Kim J. H., Kim D. K., Jin C., J. Appl. Pharmacol., 11, 232-237 (2003).
23. Kim J. H., Kim Y., Choi K., Kim D. H., Nam G., Seo J. H., WO2002102802 (2002).
24. Kumasaka K., Kawahara N., Doi K., Kojima T., Goda Y., Chem. Pharm. Bull., 56, 227-230 (2008).
25. 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., 418, 295-302 (2001).
26. Uchiyama N., Saisho K., Kikura-Hanajiri R., Haishima Y., Goda Y., Chem. Pharm. Bull., 56, 1331-1334 (2008).
27. Fujino K., Takami H., Atsumi T., Ogasa T., Mohri S., Kasai M., Org. Process Res. Dev., 5, 426-433 (2001).
28. Onoda Y., Nomoto Y., Ohno T., Yamada K., Ichimura M., WO9808848 (1998).
29. Hirose R., Okumura H., Yoshimatsu A., Irie J, Onoda Y., Nomoto Y., Takai H., Ohno T., Ichimura M., Eur. J. Pharm., 431, 17-24 (2001).
30. Toque F. H. A., Priviero F. B. M., Teixeira C. E., Perissutti E., Fiorino F., Severino B., Frecentese F., Lorenzetti R., Baracat J., Santagada V., Caliendo G., Antunes E., De Nucci G., J. Med. Chem., 51, 2807-2815 (2008).