Sildenafil and analogous phosphodiesterase type 5 (PDE-5) inhibitors in herbal food supplements sampled on the Dutch market

References

• Bell AS, Brown D, Terrett NK, inventors; Pfizer-Research-and-Development-Company, assignee. 1992 Feb 2. Pyralozopyrimidone antianginal agents. Patent 0463756 A1.
   Google Scholar
• Blok-Tip L, Zomer B, Bakker F, Hartog KD, Hamzink M, ten Hove J, Vredenbregt M, de Kaste D. 2004. Structure elucidation of sildenafil analogues in herbal products. Food Add Contam. 21:737–748.
   PubMed Web of Science ®Google Scholar
• Boden WE, Aloke AV, Finn V, Patel D, Peacock WF, Thadani U, Zimmerman FH. 2012. Nitrates as an integral part of optimal medical therapy and cardiac rehabilitation for stable angina: review of current concepts and therapeutics. Clin Cardiol. 35:263–271.
   PubMed Web of Science ®Google Scholar
• Cho EY, Chung S-H, Kim JH, Kim D-H, Jin C. 2003. Effects of a new selective phosphodiesterase type 5 inhibitor, KJH-1002, on the relaxation of rabbit corpus cavernosum tissue. J Appl Pharmacol. 11:232–237.
   Google Scholar
• Codevilla CF, Machado Lemos A, Shreiner Delgado L, Bueno Rolim CM, Horn Adams AI, Bergold AM. 2011. Development and validation of a stability-indicating LC method for the assay of lodenafil carbonate in tablets. J Chromatogr Sci. 49:502–507.
   PubMedGoogle Scholar
• Corbin JD, Francis SH. 2002. Pharmacology of phosphodiesterease-5 inhibitors. Int J Clin Pract. 56:453–459.
   PubMed Web of Science ®Google Scholar
• Corbin JD, Francis SH, Webb DJ. 2002. Phosphodiesterase type 5 as a pharmacologic target in erectile dysfunction. Urology. 60:4–11.
   PubMed Web of Science ®Google Scholar
• Dale DJ, Dunn PJ, Golightly C, Hughes ML, Levett PC, Pearce AK, Searle PM, Ward G, Wood AS. 2000. The chemical development of the commercial route to sildenafil: a case history. Org Process Res Dev. 4:17–22.
   Web of Science ®Google Scholar
• Daugan AC, Gellibert F, Orme MW, Sawyer JS, Schultze LM; inventors. 2001 May 15. Pirazino. [1',2':1,6] Pyrido [3,4b] Indole derivatives. Patent WO2002/00656 A2.
   Google Scholar
• EFSA. 2009. Guidance on safety assessment of botanicals and botanical preparations intended for use as ingredients in food supplements EFSA J. 7:1249.
   Google Scholar
• Elder DP, Snodin D, Teasdale A. 2011. Control and analysis of hydrazine, hydrazides and hydrazone-genotoxic impurities in active pharmaceutical ingredients (APIs) and drug products. J Pharmaceut Biomed. 54:900–910.
   PubMed Web of Science ®Google Scholar
• Ellis P, Terrett NK, inventors; Pfizer, assignee. 1994. Pfizer-Research-and-Development-Company, Pyralozopyrimidones for the treatment of impotence. Patent WO94/28902.
   Google Scholar
• EMA. 2013a. European public assessment report (APA) on Viagra [Internet]. Last updated on 09/2008. London: European Medicines Agency; [cited 2013 May 3]. Available from: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Summary_for_the_public/human /00 0202/WC500049824.pdf
   Google Scholar
• EMA. 2013b. EPAR summary for the public on Revatio [Internet]. Last updated on 02/2012. London: European Medicines Agency; [cited 2013 May 2]. Available from: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Summary_for_the_public/human/000638/WC500055835.pdf
   Google Scholar
• EMA. 2013c. EPAR summary for the public on Levitra [Internet]. Last updated on 03/2012. London: European Medicines Agency; [cited 2013 May 3]. Available from: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Summary_for_the_public/human/000475/WC500039993.pdf
   Google Scholar
• EMA. 2013d. EPAR summary for the public on Cialis [Internet]. Last updated on 11/2012. London: European Medicines Agency; [cited 2013 May 3]. Available from: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Summary_for_the_public/human/000436/WC500026312.pdf
   Google Scholar
• EMA. 2013e. EPAR summary for the public on Adcirca [Internet]. Last updated on 08/2012. London: European Medicines Agency; [cited 2013 May 2]. Available from: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Summary_for_the_public/human/001021/WC500032786.pdf
   Google Scholar
• European Court of Justice [Internet]. 2009. Hecht-Pharma GmbH v Staatliches Gewerbeaufsichtsamt Lüneburg. Case C 140/07. European Court reports 2009. Page I–0004. Available from: http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=CELEX:62007CJ0140:EN:HTML
   Google Scholar
• FDA. 2013. Tainted sexual enhancement products [Internet]. Silver Spring (MD): Food and Drug Administration; [cited 2013 May 2]. Available from: http://www.fda.gov/Drugs/ResourcesForYou/Consumers/BuyingUsingMedicineSafely/MedicationHealthFraud/ucm234539.htm
   Google Scholar
• Flores Toque HA, Priviero FBM, Teixeira CE, Perissutti E, Fiorino F, Severino B, Frecentese F, Lorenzetti R, Baracat JS, Santagada V, et al. 2008. Synthesis and pharmacological evaluations of sildenafil analogues for treatment of erectile dysfunction. J Med Chem. 51:2807–2815.
   PubMed Web of Science ®Google Scholar
• Göker H, Coşkun M, Ayhan-Kılcıgil G. 2012. Chromatographic separation and identification of sildenafil and yohimbine analogues illegally added in herbal supplements. In: Sasikumar D, editor. Chromatography and its applications. Croatia: InTech; [cited 2013 Sep 16]. Available from: http://www.intechopen.com/books/chromatography-and-its-applications/chromatographic-seperation-and-identification-of-a-sildenafil-and-yohimbine-analogue-illegally-added
   Google Scholar
• Guo J, Li S, Ren J, Zhao Y, inventors; Institue of Radiation Medicine Academy of Military Medical Sciences, assignee; 2006 Aug 30; Pyrazolopyrimidinethione derivatives, salts and solvates thereof, preparation methods and use thereof. Patent US 2007/0219220 A1.
   Google Scholar
• Gresser U, Gleiter CH. 2002. Erectile dysfunction: comparison of efficacy and side effects of the PDE-5 inhibitors sildenafil, vardenafil and tadalafil. Review of the literature. Eur J Med Res. 7:435–446.
   PubMed Web of Science ®Google Scholar
• Häberli A, Girard P, Low M-Y GeX. 2010. Isolation and structure elucidation of an interaction product of aminotadalafil found in an illegal health food product. J Pharmaceut Biomed Anal. 53:24–28.
   PubMed Web of Science ®Google Scholar
• Hasegawa T, Saijo M, Ishii T, Nagata T, Haishima Y, Kawahara N, Goda Y. 2008. Structural elucidation of a tadalafil analogue found in a dietary supplement. J Food Hyg Soc Japan. 49:311–315.
   PubMed Web of Science ®Google Scholar
• He ZJ, Zhang K, Jin J, Li NC, Na YQ, Bai WJ, Wang XF, Zhu JC, Jiang H, Yuan RP, et al. 2006. Aildenafil citrate: a new potent and highly selective phosphodiesterase type 5 inhibitor for the treatment of erectile dysfunction (abstract). Zhonghua Nan Ke Xue. 12:1080–1083. Chinese.
   PubMedGoogle Scholar
• Kee C-L, Ge X, Koh H-L, Low M-Y. 2012. Isolation and characterization of propoxyphenyl linked sildenafil and thiosildenafil analogues in health supplements. J Pharmaceut Biomed Anal. 70:265–271.
   PubMed Web of Science ®Google Scholar
• Kloner R. 2007. Erectile dysfunction and hypertension; review. Int J Impot Res. 19:296–302.
   PubMed Web of Science ®Google Scholar
• Lee JH, Kim NS, Han KM, Kim SH, Cho S, Kim WS. 2013. Monitoring by LC-MS/MS of 48 compounds of sildenafil, tadalafil, vardenafil and their analogues in illicit health food products in the Korean market advertised as enhancing male sexual performance. Food Addit Contam. 30:1849–1857.
   Google Scholar
• Li L, Low M-Y, Ge X, Bloodworth BC, Koh H-L. 2009. Isolation and structural elucidation of dapoxetine as an adulterant in a health supplement used for sexual performance enhancement. J Pharmaceut Biomed Anal. 50:724–728.
   PubMed Web of Science ®Google Scholar
• Lin M-C, Liu Y-C, Lin J-H. 2006. Identification of a sildenafil analogue adulterated in two herbal food supplements. J Food Drug Anal. 14:260–264.
   Web of Science ®Google Scholar
• Liu B, inventor; 2005 Nov 1. 1,6,dihydro-7H-pyrazolo[3,4-D]pyrimidin-7-one compound for the treatment of impotence. Patent US6960592 B2 10/736,732.
   Google Scholar
• Mayrhofer A, Hackl A, Urban E. 2012. Vom SPICE-Problem zum NPSG –Legal Highs-. ÖAZ. 26:44–47.
   Google Scholar
• McMahon CG. 2012. Dapoxetine: a new option in the medical management of premature ejaculation. Ther Adv Urol. 4:233–251.
   PubMedGoogle Scholar
• NIH. 1993. Consensus development panel on impotence. NIH Consensus Conference. J Am Med Assoc. 270:83–90.
   Web of Science ®Google Scholar
• Niewöhner U, Es-Sayed M, Haning H, Schenke T, Schlemmer K-H, Keldenich J, Bischoff Erwin, Perzborn E, Dembowsky K, Serno P, Nowakowski M, inventors; 1999 May 20. 2-Phenylsubstituted imidazotriazinones as phosphodiesterase inhibitors. WO/1999/024433
   Google Scholar
• Oh SS-Y, Zou P, Low M-Y, Koh H-L. 2006. Detection of sildenafil analogues in herbal products for erectile dysfunction. J Toxicol Environ Health. 69:1951–1958.
   PubMed Web of Science ®Google Scholar
• Pissarnitski D. 2006. Phosphodiesterase 5 (PDE 5) inhibitors for the treatment of male erectile disorder: attaining selectivity versus PDE-6. Med Res Rev. 26:369–395.
   PubMed Web of Science ®Google Scholar
• Reepmeyer JC, Woodruff JT. 2007. Use of liquid chromatography–mass spectrometry and a chemical cleavage reaction for the structure elucidation of a new sildenafil analogue detected as an adulterant in an herbal dietary supplement. J Pharmaceut Biomed. 4:887–893.
   Web of Science ®Google Scholar
• Reepmeyer JC, Woodruff JT, d’Avignon A. 2007. Structure elucidation of a novel analogue of sildenafil detected as an adulterant in a herbal dietary supplement. J Pharm Biomed Anal. 43:1615–1621.
   PubMed Web of Science ®Google Scholar
• RIVM. 2007. Recent developments in counterfeits and imitations of Viagra, Cialis and Levitra. A 2005–2007 update [Internet]. RIVM Report 370020001/2007. Bilthoven: RIVM; [cited 2013 Mar 4]. Available from: http://www.rivm.nl/bibliotheek/rapporten/370030001.pdf
   Google Scholar
• RIVM. 2010. Illicit erectile dysfunction products in the Netherlands. A decade of trends and a 2007–2010 product update [Internet]. RIVM Report 370030003/2010. Bilthoven: RIVM; [cited 2013 Mar 4]. Available from: http://www.rivm.nl/bibliotheek/rapporten/370030003.pdf
   Google Scholar
• Savaliya AA, Shah RP, Prasad B, Singh S. 2010. Screening of Indian aphrodisiac ayurvedic/herbal healthcare products for adulteration with sildanafil, tadalafil and/or vardenafil using LC/PDA and extracted ion LC-MS/TOF. J Pharm Biomed Anal. 52:406–409.
   PubMed Web of Science ®Google Scholar
• Shin C, Hong M, Kim D, Lim Y. 2004. Structure determination of a sildenafil analogue contained in commercial herb drinks. Magn Reson Chem. 42:1060–1062.
   PubMed Web of Science ®Google Scholar
• Singh S, Prasad B, Savaliya AA, Shah RP, Gohil VM, Kaur A. 2009. Strategies for characterizing sildenafil, vardenafil, tadalafil and their analogues in herbal dietary supplements, and detecting counterfeit products containing these drugs. Trends Anal Chem. 28:13–28.
   Web of Science ®Google Scholar
• Toque HA, Teixeira CE, Lorenzetti R, Okuyama CE, Antures E, De Nucci G. 2008. Pharmacological characterization of a novel phosphodiesterase type 5 (PDE5) inhibitor lodenafil carbonate on human and rabbit corpus cavernosum. Eur J Pharmacol. 591:189–195.
   PubMed Web of Science ®Google Scholar
• Venhuis BJ, Blok-Tip L, de Kaste D. 2008a. Designer drugs in herbal aphrodisiacs. Forensic Sci Int. 177:e25–e27.
   PubMedGoogle Scholar
• Venhuis BJ, de Kaste D. 2012. Towards a decade of detecting new analogues of sildenafil, tadalafil and vardenafil in food supplements: a history, analytical aspects and health risks. J Pharm Biomed Anal. 69:196–208.
   PubMed Web of Science ®Google Scholar
• Venhuis BJ, Zomer G, de Kaste D. 2008b. Structure elucidation of a novel synthetic thiono analogue of sildenafil detected in an alleged herbal aphrodisiac. J Pharm Biomed Anal. 46:814–817.
   PubMed Web of Science ®Google Scholar
• Venhuis BJ, Zomer G, Hamzink M, Meiring HD, Aubin Y, de Kaste D. 2011. The identification of a nitrosated prodrug of the PDE-5 inhibitor aildenafil in a dietary supplement: a Viagra with a pop. J Pharm Biomed Anal. 54:735–741.
   PubMed Web of Science ®Google Scholar
• Venhuis BJ, Zomer G, Vredenbregt MJ, de Kaste D. 2010. The identification of (-)-trans-tadalafil, tadalafil, and sildenafil in counterfeit Cialis® and the optical purity of tadalafil stereoisomers. J Pharm Biomed Anal. 51:723–727.
   PubMed Web of Science ®Google Scholar
• Wang J, Jiang Y, Wang Y, Zhao X, Cui Y, Gu J. 2007. Liquid chromatography tandem mass spectrometry assay to determine the pharmacokinetics of aildenafil in human plasma. J Pharm Biomed Anal. 44:231–235.
   PubMed Web of Science ®Google Scholar
• Wollein U, Eisenreich W, Schramek N. 2011. Identification of novel sildenafil-analogues in an adulterated herbal food supplement. J Pharm Biomed Anal. 56:705–712.
   PubMed Web of Science ®Google Scholar
• Yee S-K, Chu S-S, Xu Y-M, Choo P-L. 2005. Regulatory control of Chinese proprietary medicines in Singapore. Health Pol. 71:133–149.
   PubMed Web of Science ®Google Scholar
• Zou P, Hou P, Low M-Y, Kou H-L. 2006. Structural elucidation of a tadalafil analogue found as an adulterant of a herbal product. Food Add Contam. 23:446–451.
   PubMed Web of Science ®Google Scholar