Chemistry:Acetildenafil

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Short description: Chemical compound
Acetildenafil
Acetildenafil.svg
Clinical data
MedlinePlusa699015
Routes of
administration
By mouth
ATC code
  • None
Legal status
Legal status
  • US: Unapproved and unscheduled
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
Chemical and physical data
FormulaC25H34N6O3
Molar mass466.586 g·mol−1
3D model (JSmol)
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Acetildenafil (hongdenafil) is a synthetic drug which acts as a phosphodiesterase inhibitor.[1] It is an analog of sildenafil (Viagra)[2] which has been detected in numerous different brands of "herbal aphrodisiac" products sold in convenience stores that claim to boost libido and alleviate erectile dysfunction.[3]

A range of designer analogs of licensed PDE5 inhibitors such as sildenafil and vardenafil have been detected in recent years in over-the-counter herbal aphrodisiac products,[4][5][6][7] in an apparent attempt to circumvent both the legal restrictions on sale of erectile dysfunction drugs, which are prescription-only medicines in most Western countries, and the patent protection which allows sale of these drugs by competitors only with permission from the patent holders (typically, under a license from the inventors) and to introduce efficacy into otherwise ineffective herbal products. These compounds have been demonstrated to display PDE5 inhibitory activity in vitro and presumably have similar effects when consumed, but have undergone no formal testing in either humans or animals, and as such may represent significant health risks to consumers of these products due to their unknown safety profile.[3][8] Attempts to ban such ingredients have not been successful for the most part, many jurisdictions having laws restricting chemical analogs but only those of narcotics and doping agents. However, at least one court case has resulted in a product being taken off the market.[9]

See also

References

  1. "Acetildenafil". https://www.caymanchem.com/product/12049. 
  2. "Structure elucidation of sildenafil analogues in herbal products". Food Additives and Contaminants 21 (8): 737–48. August 2004. doi:10.1080/02652030412331272467. PMID 15370823. 
  3. 3.0 3.1 "Analogues of erectile dysfunction drugs: an under-recognised threat". Hong Kong Medical Journal = Xianggang Yi Xue Za Zhi 13 (5): 359–63. October 2007. PMID 17914141. 
  4. "Towards a decade of detecting new analogues of sildenafil, tadalafil and vardenafil in food supplements: a history, analytical aspects and health risks". Journal of Pharmaceutical and Biomedical Analysis 69: 196–208. October 2012. doi:10.1016/j.jpba.2012.02.014. PMID 22464558. 
  5. "Simultaneous determination of synthetic phosphodiesterase-5 inhibitors found in a dietary supplement and pre-mixed bulk powders for dietary supplements using high-performance liquid chromatography with diode array detection and liquid chromatography-electrospray ionization tandem mass spectrometry". Journal of Chromatography A 1104 (1–2): 113–22. February 2006. doi:10.1016/j.chroma.2005.11.103. PMID 16364350. 
  6. "Accurate mass measurement using Fourier transform ion cyclotron resonance mass spectrometry for structure elucidation of designer drug analogs of tadalafil, vardenafil and sildenafil in herbal and pharmaceutical matrices". Rapid Communications in Mass Spectrometry 20 (15): 2317–27. 2006. doi:10.1002/rcm.2594. PMID 16817245. Bibcode2006RCMS...20.2317G. 
  7. "Structural identification of a new acetildenafil analogue from pre-mixed bulk powder intended as a dietary supplement". Food Additives and Contaminants 23 (9): 870–5. September 2006. doi:10.1080/02652030600803856. PMID 16901855. 
  8. "Detection of sildenafil analogues in herbal products for erectile dysfunction". Journal of Toxicology and Environmental Health. Part A 69 (21): 1951–8. November 2006. doi:10.1080/15287390600751355. PMID 16982533. 
  9. "Designer drugs in herbal aphrodisiacs". Forensic Science International 177 (2–3): e25-7. May 2008. doi:10.1016/j.forsciint.2007.11.007. PMID 18178354.