title: Detection and structure elucidation of hydroxythiovardenafil as an adulterant in a herbal dietary supplement.
abstract: A new derivative of vardenafil was detected in an alleged herbal dietary supplement and identified as 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)-thione. Structure elucidation was carried out by LC-UV-MS/MS and NMR. Results obtained with high resolution MS and IR spectroscopy confirmed the proposed chemical structure. The compound was distinguished from hydroxyvardenafil, a second active substance identified in the same product, by the conversion of the oxo group to a thio group on the imidazo-triazin moiety. Hydroxythiovardenafil was therefore suggested as a proprietary name for the new molecule. This is the first paper to describe a thio-analog of vardenafil in a commercially available product.
authors.affiliation: National Institute of Pharmacy, Zrínyi u. 3., PO Box 450, H-1051 Budapest, Hungary. jankovics.peter@gyemszi.hu
authors.forename: Péter
authors.initials: P
authors.lastname: Jankovics
authors.forename: Szilvia
authors.initials: S
authors.lastname: Lohner
authors.forename: András
authors.initials: A
authors.lastname: Darcsi
authors.forename: Júlia
authors.initials: J
authors.lastname: Németh-Palotás
authors.forename: Szabolcs
authors.initials: S
authors.lastname: Béni
mesh_terms: D002853:Chromatography, Liquid / Q000379:methods; D019587:Dietary Supplements / Q000032:analysis* / Q000592:standards; D004340:Drug Contamination; D007093:Imidazoles / Q000032:analysis* / Q000737:chemistry / Q000592:standards; D010879:Piperazines / Q000032:analysis* / Q000737:chemistry / Q000592:standards; D028321:Plant Preparations / Q000032:analysis* / Q000737:chemistry / Q000592:standards; D013450:Sulfones / Q000032:analysis / Q000737:chemistry / Q000592:standards; D053719:Tandem Mass Spectrometry / Q000379:methods; D014227:Triazines / Q000032:analysis / Q000737:chemistry / Q000592:standards; D000069058:Vardenafil Dihydrochloride
chemical_list: D007093:Imidazoles; D010879:Piperazines; D028321:Plant Preparations; D013450:Sulfones; D014227:Triazines; D000069058:Vardenafil Dihydrochloride