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Thiomethisosildenafil
Systematic (IUPAC) name
5-{5-[(3R,5S)-3,5-dimethylpiperazin-1-ylsulfonyl]-2-ethoxyphenyl}-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidine-7(6H)-thione
Identifiers
ATC code none
PubChem 23139635
Chemical data
Formula C23H34N6O3S2 
Mol. mass 506.683 g/mol
SMILES eMolecules & PubChem
Therapeutic considerations
Pregnancy cat.  ?
Legal status

Thiomethisosildenafil is a drug which acts as a phosphodiesterase inhibitor. It is a synthetic structural analogue of sildenafil (Viagra) which has been detected in several different brands of supposedly "herbal" aphrodisiac products sold to boost libido and alleviate erectile dysfunction.[1][2][3]

A range of designer analogues of legitimate inhibitors of type-5 cGMP-specific phosphodiesterase (PDE5), such as sildenafil and vardenafil, have been detected in recent years as adulturants in over-the-counter herbal aphrodisiac products and dietary supplements,[4][5][6] 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 prevents sale of these drugs by competitors except under license to their inventors. 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 represent a significant health risk to consumers of these products due to their unknown safety profile.[7] Some attempts have been made to ban these drugs as unlicensed medicines, but progress has been slow so far, as even in those jurisdictions which have laws targeting designer drugs, the laws are drafted to ban analogues of illegal drugs of abuse, rather than analogues of prescription medicines. However at least one court case has resulted in a product being taken off the market.[8]

See also

References

  1. ^ Reepmeyer JC, d'Avignon DA (January 2009). "Structure elucidation of thioketone analogues of sildenafil detected as adulterants in herbal aphrodisiacs". Journal of Pharmaceutical and Biomedical Analysis 49 (1): 145–50. doi:10.1016/j.jpba.2008.10.007. PMID 19042103. 
  2. ^ Balayssac S, Trefi S, Gilard V, Malet-Martino M, Martino R, Delsuc MA (November 2008). "2D and 3D DOSY (1)H NMR, a useful tool for analysis of complex mixtures: Application to herbal drugs or dietary supplements for erectile dysfunction". Journal of Pharmaceutical and Biomedical Analysis. doi:10.1016/j.jpba.2008.10.034. PMID 19108978. 
  3. ^ Gryniewicz CM, Reepmeyer JC, Kauffman JF, Buhse LF (April 2009). "Detection of undeclared erectile dysfunction drugs and analogues in dietary supplements by ion mobility spectrometry". Journal of Pharmaceutical and Biomedical Analysis 49 (3): 601–6. doi:10.1016/j.jpba.2008.12.002. PMID 19150190. 
  4. ^ Zou P, Oh SS, Hou P, Low MY, Koh HL. 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. 2006 Feb 3;1104(1-2):113-22. PMID 16364350
  5. ^ Gratz SR, Gamble BM, Flurer RA. 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. 2006;20(15):2317-27. PMID 16817245
  6. ^ Hou P, Zou P, Low MY, Chan E, Koh HL. Structural identification of a new acetildenafil analogue from pre-mixed bulk powder intended as a dietary supplement. Food Additives and Contaminants. 2006 Sep;23(9):870-5. PMID 16901855
  7. ^ Oh SS, Zou P, Low MY, Koh HL. Detection of sildenafil analogues in herbal products for erectile dysfunction. Journal of Toxicology and Environmental Health Part A. 2006 Nov;69(21):1951-8. PMID 16982533
  8. ^ Venhuis BJ, Blok-Tip L, de Kaste D. Designer drugs in herbal aphrodisiacs. Forensic Science International. 2008 May 20;177(2-3):e25-7. PMID 18178354







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