The identification of a nitrosated prodrug of the PDE-5 inhibitor aildenafil in a dietary supplement: A Viagra with a pop

Towards a decade of detecting new analogues of sildenafil, tadalafil and vardenafil in food supplements: A history, analytical aspects and health risks

“…Examples are dithio-desmethylcarbodenafil [53], two dihydro-derivatives of acetildenafil [54] and nitroso-prodenafil [55]. Out of these four analogues, only 22-dihydro-acetildenafil had already been disclosed in patent literature [30].…”

“…Hydroxy-acetildenafil Hydroxy-hongdenafil [18,19,111] Homosildenafil [11,24,109] Nitroso-prodenafil (top) Muta-prodenafil (below) [55,56] [75] increased sensitivity and specificity [8]. In searching for unknowns MS/MS screening techniques are very suitable.…”

Identification and evaluation of fragmentation pathways of PDE-5 inhibitor analogues using LC-QTOF-MS

“…[1][2][3][4][5] Some products have been found to be adulterated with approved PDE-5 inhibitors as well as their unapproved synthetic analogues, which contain minor structural modifications compared to the approved compounds. The presence of PDE-5 inhibitors or their analogues in herbal supplements could pose a significant risk to the public health.…”

Identification of Mutaprodenafil in a Dietary Supplement and Its Subsequent Synthesis

“…It was reported that the compound is converted to aildenafil, a structural analogue of sildenafil, 15) under physiological acidic conditions. 16) Recently, Venhuis's group reported its structural determination, mainly based on a detailed discussion of the results of MS analyses, and concluded that it was a nitrosated prodrug (A) of aildenafil (Fig. 1A).…”

“…1A). 16) We have also independently isolated the same compound from a dietary supplement and analyzed its structure. Most of our analytical data (1D-, 1 H-, 13 C-NMR, and LC-MS spectra) matched Venhuis's data, and we predicted the structure to be an aildenafil derivative (Table 1).…”