348
Views
9
CrossRef citations to date
0
Altmetric
Original Articles

Pyrazolopyrimidines in ‘all-natural’ products for erectile dysfunction treatment: the unreliable quality of dietary supplements

, &
Pages 127-140 | Received 08 Sep 2014, Accepted 24 Nov 2014, Published online: 17 Dec 2014

References

  • Abdel-Jalil RJ, Khanfar M, Abu-Safieh K, Al-Gharabli S, El-Abadelah M, Voelter W. 2005. An efficient one-pot synthesis of pyrazolopyrimidines, intermediates for potential phosphodiesterase inhibitors. Monatsh Chem. 136:619–624.
  • Abdel-Jalil RJ, Khanfar M, Al-Gharabli S, El-Abadelah MM, Eichele K, Anwar MU, Voelter W. 2005. High throughput synthesis of pyrazolopyrimidines via copper-catalysed cyclization and x-ray study. Heterocycles. 65:1821–1827.
  • 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 Addit Contam. 21:737–748.
  • Chan Lee J, Park C, Choi Y. 1997. A New Procedure for α-Hydroxylation of Ketones Using Thallium(III) p-Nitrobenzenesulfonate (TNS). Synth Commun. 27:4079–4084.
  • Crowley R, FitzGerald LH. 2006. The impact of cGMP compliance on consumer confidence in dietary supplement products. Toxicology. 221:9–16.
  • Deisingh AK. 2005. Pharmaceutical counterfeiting. Analyst. 130:271–279.
  • Ellis P, Terrett NK, inventors. 1994. Pyrazolopyrimidinones for the treatment of impotence WO 1994028902 A1.
  • Ham M. 2003. Health RISKS OF COUNTERFEIT PHARMACEUTICALS. Drug Saf. 26:991–997.
  • Hou P, Zou P, Low M-Y, Chan E, Koh H-L. 2006. Structural identification of a new acetildenafil analogue from pre-mixed bulk powder intended as a dietary supplement. Food Addit Contam. 23:870–875.
  • ICH Q3A (R2) Impurities in New Drug Substances O. 2006.
  • Instrumental Analysis Data of Illegal Compounds in Food [Internet]. 2010. Korean National Institute for Food and Drug Safety Evaluation. [cited 2013 Nov 13]. Available from: http://nifds.go.kr
  • Jones AB, editor. 1991. Chapter 2.3: oxidation adjacent to C=X bonds by hydroxylation methods. Oxford: Pergamon Press.
  • Kagan J, Arora SK, Bryzgis M, Dhawan SN, Reid K, Singh SP, Tow L. 1983. Reaction of phosphorus pentachloride with 2-acetylthiophene and acetophenone. J Org Chem. 48:703–706.
  • Khazan M, Hedayati M, Askari S, Azizi F. 2013. Adulteration of products sold as Chinese Herbal medicines for weight loss with thyroid hormones and PCP. J Herbal Med. 3:39–43.
  • Kim D-K, Lee JY, Lee N, Ryu DH, Kim J-S, Lee S, Choi J-Y, Ryu J-H, Kim N-H, Im G-J, et al. 2001. Synthesis and phosphodiesterase inhibitory activity of new sildenafil analogues containing a carboxylic acid group in the 5′-sulfonamide moiety of a phenyl ring. Bioorg Med Chem. 9:3013–3021.
  • Kim J-H, Kim Y, Choi KI, Kim DH, Nam G, Seo JH, inventors. 2002. Preparation of novel pyrazolopyrimidinethiones as phosphodiesterase V inhibitors for treating erectile dysfunction WO2002102802A1.
  • Kim JY, Hwang IG, Oh JH, Kang IH, Kwon SW, Kim D. 2013. Efficient synthesis of dichlorodenafil, an unapproved sildenafil analogue appearing in non-prescription supplements. Chem Pharm Bull (Tokyo). 61:572–575.
  • Ley SV, Baxendale IR, Brusotti G, Caldarelli M, Massi A, Nesi M. 2002. Solid-supported reagents for multi-step organic synthesis: preparation and application. Il Farmaco. 57:321–330.
  • Li J-J, Johnson DS, Sliskovic DR, Roth BD, editors. 2004. Chapter 13, PDE 5 inhibitors for erectile dysfunction: sildenafil (Viagra), vardenafil (Levitra), and tadalafil (Cialis). In: Contemporary drug synthesis. Hoboken, NJ: John Wiley & Sons, Inc.; p. 189–199.
  • Lin M-C, Liu Y-C, Lin Y-L, Lin J-H. 2008. Isolation and identification of a novel sildenafil analogue adulterated in dietary supplements. J Food Drug Anal. 16:15–20.
  • Marik PE, Flemmer M. 2012. Do dietary supplements have beneficial health effects in industrialized nations: what is the evidence? J Parenter Enteral Nutr. 36:159–168.
  • Maughan RJ. 2005. Contamination of dietary supplements and positive drug tests in sport. J Sports Sci. 23:883–889.
  • Medrasi HY, Al-Sheikh MA, Salaheldin AM. 2013. Enaminonitriles in heterocyclic synthesis: a route to 1,3-diaryl-4-aminopyrazole derivatives. Molecules. 18:535–544.
  • Patel DN, Li L, Kee C-L., Ge X, Low M-Y., Koh H-L. 2014. Screening of synthetic PDE-5 inhibitors and their analogues as adulterants: analytical techniques and challenges. J Pharm Biomed Anal. 87:176–190.
  • Roy J. 2002. Pharmaceutical impurities–a mini-review. AAPS PharmSciTech. 3:1–8.
  • Slifman NR, Obermeyer WR, Aloi BK, Musser SM, Correll WA, Cichowicz SM, Betz JM, Love LA. 1998. Contamination of botanical dietary supplements by digitalis lanata. N Engl J Med. 339:806–811.
  • Stelzer U, inventor. 1995. Preparation of phenylacetic acids EP665212A1.
  • Tang MHY, Chen SPL, Ng SW, Chan AYW, Mak TWL. 2011. Case series on a diversity of illicit weight-reducing agents: from the well known to the unexpected. Br J Clin Pharmacol. 71:250–253.
  • 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.
  • Venhuis BJ, Zomer G, De Kaste D. 2008. Structure elucidation of a novel synthetic thiono analogue of sildenafil detected in an alleged herbal aphrodisiac. J Pharm Biomed Anal. 46:814–817.
  • Venhuis BJ, Zwaagstra ME, Keizers PH, De Kaste D. 2014. Dose-to-dose variations with single packages of counterfeit medicines and adulterated dietary supplements as a potential source of false negatives and inaccurate health risk assessments. J Pharm Biomed Anal. 89:158–165.
  • 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.
  • Xia GX, Li JF, Lai SA, Peng AM, Zhang SJ, Wei XH, Chen XJ, Shen JS, Ji RY. 2005. Design and synthesis of pyrido[1,2-e]purin-4(3H)-one derivatives as potential PDE 5 inhibitors. Chin Chem Lett. 16:1283–1286.
  • Yu G, Mason H, Wu X, Wang J, Chong S, Beyer B, Henwood A, Pongrac R, Seliger L, He B, et al. 2003. Substituted pyrazolopyridopyridazines as orally bioavailable potent and selective PDE5 inhibitors: potential agents for treatment of erectile dysfunction. J Med Chem. 46:457–460.
  • Yuen YP, Lai CK, Poon WT, Ng SW, Chan AY, Mak TW. 2007. Adulteration of over-the-counter slimming products with pharmaceutical analogue–an emerging threat. Hong Kong Med J. 13:216–220.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.