Determination of analogs of sildenafil and vardenafil in foods by column liquid chromatography with a photodiode array detector, mass spectrometry, and nuclear magnetic resonance spectrometry.
Two analogs of sildenafil and vardenafil in food were detected by column liquid chromatography (LC) with a photodiode array detector. They were isolated by preparative LC; their structures were established by mass spectrometry and nuclear magnetic resonance spectrometry. One analog was found to be methisosildenafil (compound A), 5-(5-(3,5-dimethylpiperazin-1-ylsulfonyl)-2-ethoxy-phenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]-pyrimidin-7(6H)-one. It is a sildenafil analog with a dimethylpiperazine ring substituted for the methylpiperazine group. The second analog, hydroxyvardenafil (compound B) is reported for the first time in this study. Hydroxyvardenafil's International Union of Pure and Applied Chemistry name is 2-(2-ethoxy-5-(4-(2-hydroxyethyl)-piperazin-1-ylsulfonyl)phenyl)-5-methyl-7-propyl-imidazo[1,5-f][1,2,4]triazin-4(3H)-one. The novel vardenafil analog has a hydroxyl group added to the ethylpiperazine group.
Choi
Dong Mi
DM
Korea Food and Drug Administration, 194 Tongilro, Eunpyeong-gu, Seoul 122704, Korea.
Park
Sangaeh
S
Yoon
Tae Hyung
TH
Jeong
Hye Kyoung
HK
Pyo
Jae Sung
JS
Park
Janghyun
J
Kim
Deukjoon
D
Kwon
Sung Won
SW
D002853:Chromatography, Liquid / Q000379:methods* / Q000592:standards; D005506:Food Contamination / Q000032:analysis*; D007093:Imidazoles / Q000032:analysis* / Q000737:chemistry / Q000592:standards; D009682:Magnetic Resonance Spectroscopy / Q000379:methods* / Q000592:standards; D013058:Mass Spectrometry / Q000379:methods* / Q000592:standards; D015394:Molecular Structure; D010726:Phosphodiesterase Inhibitors / Q000032:analysis / Q000737:chemistry / Q000592:standards; D010879:Piperazines / Q000032:analysis* / Q000737:chemistry / Q000592:standards; D011687:Purines / Q000032:analysis / Q000737:chemistry / Q000592:standards; D012015:Reference Standards; D000068677:Sildenafil Citrate; D013450:Sulfones / Q000032:analysis* / Q000737:chemistry / Q000592:standards; D014227:Triazines / Q000032:analysis / Q000737:chemistry / Q000592:standards; D000069058:Vardenafil Dihydrochloride
D007093:Imidazoles; D010726:Phosphodiesterase Inhibitors; D010879:Piperazines; D011687:Purines; D013450:Sulfones; D014227:Triazines; D000069058:Vardenafil Dihydrochloride; D000068677:Sildenafil Citrate