Isolation and identification of a new sildenafil analogue adulterated in energy drink: Propoxyphenyl sildenafil

Alp, Mehmet; Coşkun, Maksut; Göker, Hakan

doi:10.1016/j.jpba.2012.09.017

Cited by 25 publications

(11 citation statements)

References 13 publications

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“…As a result, foods and dietary supplements illegally adulterated with ED drugs and their analogues are becoming increasingly diversified and sophisticated in terms of their products and processes. In a recent report, about 48 or more PDE-5 inhibitors and their analogues were illegally added to foods, dietary supplements, medicinal herbs and other products, and detected or isolated from those products (Kee et al 2012;Alp et al 2013;Lee et al 2013;Lee et al 2013). Consequently, the use of these products represents a sufficient threat to public health, especially considering the widely known side effects of ED drugs.…”

Section: Introductionmentioning

confidence: 99%

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LC-ESI-MS/MS analysis of phosphodiesterase-5 inhibitors and their analogues in foods and dietary supplements in Korea

Jeong

Lee

Kim

et al. 2016

Food Additives & Contaminants: Part B

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A number of 188 food and dietary supplement samples were collected from 2009 to the first half of 2013 in Korean online and offline stores. A method to identify phosphodiesterase-5 (PDE-5) inhibitors and their analogues using liquid chromatography-electrospray ionisation-mass spectrometry/mass spectrometry (LC-ESI-MS/MS) was validated. Limit of detection and limit of quantitation of liquid-type and solid-type negative samples ranged from 0.05 to 3.33 ng/mL or ng/g and from 0.15 to 10.00 ng/mL or ng/g, respectively. Recoveries ranged from 83% to 112%. Nineteen PDE-5 inhibitors and their analogues were detected, with tadalafil group compounds being the most frequently observed (53.0%), followed by the sildenafil group (42.5%). Tadalafil concentrations ranged from 0.08 to 138.69 mg/g. Compounds were most frequently detected in capsules (in 40 of 80 adulterated samples). To protect public health and food safety, appropriate monitoring of PDE-5 inhibitors and their analogues in foods and dietary supplements is recommended.

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Section: Introductionmentioning

confidence: 99%

“…According to Alp et al (2013), the major side effects of ED drugs are headache, face flushing, cardiovascular disorder, dyspepsia, back pain and vision disturbance. Therefore, ED drugs are only available by prescription.…”

Section: Introductionmentioning

confidence: 99%

LC-ESI-MS/MS analysis of phosphodiesterase-5 inhibitors and their analogues in foods and dietary supplements in Korea

Jeong

Lee

Kim

et al. 2016

Food Additives & Contaminants: Part B

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show abstract

“…2C and 2D). The former analogue has been found as an adulterant in one energy drink (Alp et al 2013). The first two ions can be referred as Nmethylated piperazynyl moieties, see Table 3.…”

Section: Resultsmentioning

confidence: 99%

Application of Orbitrap-mass spectrometry to differentiate isomeric sildenafil- and thiosildenafil-like analogues used for the adulteration of dietary supplements

Kee

Low

2015

Food Additives & Contaminants: Part A

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Two groups of isomeric phosphodiestrase-type 5 inhibitors (PDE-5), consisting of four sildenafil- and three thiosildenafil-like analogues, have been successfully differentiated using high-resolution MS/MS. The optimised MS/MS data obtained from each compound were used to build a database with the aid of mass processing software. Isomeric compounds with very close chromatographic separation like dimethylsildenafil and homosildenafil could be distinguished by their unique fingerprint fragment ions in the MS/MS database. All fragment ions were within the mass tolerance of 5 ppm. One case study using an adulterated dietary supplement is included to provide more insights into this application.

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“…A characteristic example is a review paper summarizing the literature before 2009 [63],in which 11 sildenafil analogues were said to have been illegally administered in herbal drugs and herbal dietary supplements (i.e., homosildenafil, hydroxyhomosildenafil, piperidinosildenafil, aildenafil, thiosildenafil, thiohomosildenafil, thioaildenafil, acetildenafil, noracetildenafil, hydroxyacetildenafil, piperidinoacetildenafil). Since the publication of this review [63], further illegal derivatives were identified in herbal drugs [i.e., propoxyphenyl-sildenafil [64], propoxyphenyl-aildenafil, propoxyphenylthioaildenafil, propoxyphenyl-hydroxyethyl-thiosildenafil [65], dithiodesethylcarbodenafil, norcarbodenafil [66] and propoxyphenyl-isobutyl-aildenafil [67]}. Fig.…”

Section: Counterfeit Productsmentioning

confidence: 99%

Identification in drug quality control and drug research

Gǒrög

2015

TrAC Trends in Analytical Chemistry

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Isolation and identification of a new sildenafil analogue adulterated in energy drink: Propoxyphenyl sildenafil

Cited by 25 publications

References 13 publications

LC-ESI-MS/MS analysis of phosphodiesterase-5 inhibitors and their analogues in foods and dietary supplements in Korea

LC-ESI-MS/MS analysis of phosphodiesterase-5 inhibitors and their analogues in foods and dietary supplements in Korea

Application of Orbitrap-mass spectrometry to differentiate isomeric sildenafil- and thiosildenafil-like analogues used for the adulteration of dietary supplements

Identification in drug quality control and drug research

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