Identification of a new tadalafil analogue, dipropylaminopretadalafil, in a dietary supplement

作者: Yen-Chun Huang , Hui-Chun Lee , Yun-Lian Lin , Chia-Fen Tsai , Hwei-Fang Cheng

DOI: 10.1080/19440049.2016.1184530

关键词: High-performance liquid chromatographyChromatographyTadalafilDietary supplementColumn chromatographyChemistryStereochemistry

摘要: A novel tadalafil analogue in a dietary supplement was found by drug-adulteration screening and isolated column chromatography HPLC. Based on extensive 1D- 2D-NMR mass spectral analyses, the structure of this new compound determined as 2-(N,N-dipropyl acetyl) 3-methyl 1-(benzo[d][1,3]dioxol-5-yl)-3,4-dihydro-1H-pyrido[3,4-b]indole-3-carboxylate - its common name is dipropylaminopretadalafil.

参考文章(8)
M.-C. Lin, Y.-C. Liu, Y.-L. Lin, J.-H. Lin, Identification of a Tadalafil Analogue Adulterated in a Dietary Supplement Journal of Food and Drug Analysis. ,vol. 17, pp. 451- 458 ,(2020) , 10.38212/2224-6614.2584
Takashi HASEGAWA, Masaaki SAIJO, Toshiyasu ISHII, Tomoko NAGATA, Yuji HAISHIMA, Nobuo KAWAHARA, Yukihiro GODA, Structural elucidation of a tadalafil analogue found in a dietary supplement. Journal of The Food Hygienic Society of Japan (shokuhin Eiseigaku Zasshi). ,vol. 49, pp. 311- 315 ,(2008) , 10.3358/SHOKUEISHI.49.311
Dhavalkumar Narendrabhai Patel, Lin Li, Chee-Leong Kee, Xiaowei Ge, Min-Yong Low, Hwee-Ling Koh, Screening of synthetic PDE-5 inhibitors and their analogues as adulterants: Analytical techniques and challenges Journal of Pharmaceutical and Biomedical Analysis. ,vol. 87, pp. 176- 190 ,(2014) , 10.1016/J.JPBA.2013.04.037
Alain Daugan, Pascal Grondin, Cécile Ruault, Anne-Charlotte Le Monnier de Gouville, Hervé Coste, Jean Michel Linget, Jorge Kirilovsky, François Hyafil, Richard Labaudinière, 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. Journal of Medicinal Chemistry. ,vol. 46, pp. 4533- 4542 ,(2003) , 10.1021/JM0300577
Gaofei Zhang, Yue Yu, Xiaoou Wu, Jun Li, Separation and structural elucidation of a new tadalafil analogue diethylaminopretadalafil included as an adulterant in a dietary supplement. Journal of Pharmaceutical and Biomedical Analysis. ,vol. 94, pp. 210- 214 ,(2014) , 10.1016/J.JPBA.2014.01.043
Valerie M. Toomey, Jonathan J. Litzau, Cheryl L. Flurer, Isolation and structural characterization of two tadalafil analogs found in dietary supplements Journal of Pharmaceutical and Biomedical Analysis. ,vol. 59, pp. 50- 57 ,(2012) , 10.1016/J.JPBA.2011.09.038
Yen-Chun Huang, Hui-Chun Lee, Yun-Lian Lin, Chia-Ying Li, Chia-Fen Tsai, Hwei-Fang Cheng, Separation and identification of a novel tadalafil analogue adulterant in a dietary supplement Food Additives and Contaminants Part A-chemistry Analysis Control Exposure & Risk Assessment. ,vol. 33, pp. 179- 185 ,(2015) , 10.1080/19440049.2015.1125531
Alaa A.-M. Abdel-Aziz, Yousif A. Asiri, Adel S. El-Azab, Mohamed A. Al-Omar, Takehisa Kunieda, Chapter 8 - Tadalafil Profiles of Drug Substances, Excipients and Related Methodology. ,vol. 36, pp. 287- 329 ,(2011) , 10.1016/B978-0-12-387667-6.00008-7