2004
DOI: 10.1080/02652030412331272467
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Structure elucidation of sildenafil analogues in herbal products

Abstract: The structure of unknown compounds present in herbal products was elucidated using liquid chromatography-electrospray ionization-mass spectrometry, direct-infusion electrospray ionization-mass spectrometry, and nuclear magnetic resonance. Compounds 1-3 were identified as sildenafil analogues, 1 bearing an N-ethylpiperazine moiety instead of an Nmethylpiperazine, and an acetyl group instead of the sulfonyl group, named acetildenafil, 2 bearing an N-ethylpiperazine moiety instead of an N-methylpiperazine (homosi… Show more

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Cited by 103 publications
(59 citation statements)
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“…Thus far, a large number of analogues of sildenafil, tadarafil and vardenafil have been reported, [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23] while a new type of phosphodiesterase-5 (PDE-5) inhibitor, (R)-xanthoanthrafil, an anthranilic acid derivative, has been found in a dietary supplement advertising sexual enhancement for men. 24) (R)-Xanthoanthrafil was first synthesized as a candidate compound for the treatment of ED by Fujisawa Pharmaceutical Co., Ltd. (currently Astellas Pharma Inc., Tokyo, Japan), 25) and was reported as a PDE-5 inhibitor, FR226807, after the manufacturer discontinued the process of developing the drug for approval.…”
mentioning
confidence: 99%
“…Thus far, a large number of analogues of sildenafil, tadarafil and vardenafil have been reported, [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23] while a new type of phosphodiesterase-5 (PDE-5) inhibitor, (R)-xanthoanthrafil, an anthranilic acid derivative, has been found in a dietary supplement advertising sexual enhancement for men. 24) (R)-Xanthoanthrafil was first synthesized as a candidate compound for the treatment of ED by Fujisawa Pharmaceutical Co., Ltd. (currently Astellas Pharma Inc., Tokyo, Japan), 25) and was reported as a PDE-5 inhibitor, FR226807, after the manufacturer discontinued the process of developing the drug for approval.…”
mentioning
confidence: 99%
“…It is potentially dangerous for consumers to take adulterated dietary supplements. Moreover, not only prescription drugs but also their analogues such as N-nitroso-fenfluramine 5) , homosildenafil 6) , acetildenafil 7) , hydroxyhomosildenafil 7) and aminotadalafil 8) have been detected. We have already established a HPLC screening method for synthetic drugs in dietary supplements, such as tonic medicines, anorexic agents, hypoglycemic agents, and so on῍ 2 .…”
Section: Introductionmentioning
confidence: 99%
“…Structural analogs that have a partly modified structure of pharmaceuticals have been detected in some cases. [1][2][3] Although such analogs are considered to possess the same activities as their original compounds, little is known about their actual * To whom correspondence should be addressed: Department of Drug and Food Science, Shizuoka Institute of Environment and Hygiene, 4-27-2 Kita-ando, Aoi-ku, Shizuoka, Shizuoka, 420-8637, Japan. Tel.…”
Section: Introductionmentioning
confidence: 99%