Isolation and structural characterization of a new tadalafil analog (2-hydroxyethylnortadalafil) found in a dietary supplement.

Autor: Kern SE; United States Food and Drug Administration, Forensic Chemistry Center, 6751 Steger Drive, Cincinnati, OH, 45237, USA. Electronic address: sara.kern@fda.hhs.gov., Nickum EA; United States Food and Drug Administration, Forensic Chemistry Center, 6751 Steger Drive, Cincinnati, OH, 45237, USA., Flurer RA; United States Food and Drug Administration, Forensic Chemistry Center, 6751 Steger Drive, Cincinnati, OH, 45237, USA., Toomey VM; United States Food and Drug Administration, Forensic Chemistry Center, 6751 Steger Drive, Cincinnati, OH, 45237, USA., Litzau JJ; United States Food and Drug Administration, Forensic Chemistry Center, 6751 Steger Drive, Cincinnati, OH, 45237, USA.
Jazyk: angličtina
Zdroj: Journal of pharmaceutical and biomedical analysis [J Pharm Biomed Anal] 2015 Jan 25; Vol. 103, pp. 99-103. Date of Electronic Publication: 2014 Nov 05.
DOI: 10.1016/j.jpba.2014.10.021
Abstrakt: A screen for known PDE-5 inhibitors in a dietary supplement product marketed for "enhanced sexual performance" detected a compound that structurally resembled tadalafil. The compound was isolated from the supplement matrix using high-performance liquid chromatography with ultraviolet detection (HPLC-UV) and a fraction collector, and was further characterized using nuclear magnetic resonance (NMR), liquid chromatography-mass spectrometry (LC-MS), as well as high-resolution accurate mass mass spectrometry (HRAM-MS). The analog had an accurate mass of m/z 420.15614 (error is 1.77235ppm) for the protonated species [M+H](+), corresponding to a molecular formula of C23H22N3O5. Mass spectral fragmentation data suggested that the modification occurred in place of the CH3 located on the pyrazinopyridoindole-1,4-dione of tadalafil. NMR was utilized to further elucidate the configuration of the substitution. The analysis indicated that the moiety is a CH2CH2OH, hydroxyethyl group. The new analog has been named 2-hydroxyethylnortadalafil.
(Published by Elsevier B.V.)
Databáze: MEDLINE
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