Sulfoaildenafil Explained

Drug Name:	Sulfoaildenafil
Legal Status:	Unapproved and unscheduled
Cas Number:	856190-47-1
Pubchem:	56841591
Chemspiderid:	24751855
Unii:	33DX49E09G
Synonyms:	Thiomethisosildenafil; Sildenafil thione; Thioaildenafil
Iupac Name:	5-[5-[(3S,5R)-3,5-dimethylpiperazin-1-yl]sulfonyl-2-ethoxyphenyl]-1-methyl-3-propyl-4H-pyrazolo[4,3-d]pyrimidine-7-thione
C:	23
H:	32
N:	6
O:	3
S:	2
Smiles:	CCCC1=NN(C2=C1NC(=NC2=S)C3=C(C=CC(=C3)S(=O)(=O)N4C[C@H](N[C@H](C4)C)C)OCC)C
Stdinchi:	1S/C23H32N6O3S2/c1-6-8-18-20-21(28(5)27-18)23(33)26-22(25-20)17-11-16(9-10-19(17)32-7-2)34(30,31)29-12-14(3)24-15(4)13-29/h9-11,14-15,24H,6-8,12-13H2,1-5H3,(H,25,26,33)/t14-,15+
Stdinchikey:	SCLUKEPFXXPARW-GASCZTMLSA-N

Sulfoaildenafil (thioaildenafil) is a synthetic drug that is a structural analog of sildenafil (Viagra).^[1] It was first reported in 2005,^[2] and it is not approved by any health regulation agency. Like sildenafil, sulfoaildenafil is a phosphodiesterase type 5 inhibitor.

Sulfoaildenafil has been found as an adulterant in a variety of supplements which are sold as "natural" or "herbal" sexual enhancement products.^{[3] [4] [5] [6]} A range of designer analogues of USA FDA-approved inhibitors of type-5 cGMP-specific phosphodiesterase (PDE₅), such as sildenafil and vardenafil, have been detected in recent years as adulterants in over-the-counter herbal aphrodisiac products and dietary supplements,^{[7] [8] [9]} 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.^[10] 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.^[11]

In December 2010, the United States Food and Drug Administration (FDA) issued a warning to consumers about such products stating, "The FDA has found many products marketed as dietary supplements for sexual enhancement during the past several years that can be harmful because they contain active ingredients in FDA-approved drugs or variations of these ingredients."^[12]

See also

• Aildenafil
• Acetildenafil
• Nitrosoprodenafil

Notes and References

1. Gratz SR, Zeller M, Mincey DW, Flurer CL . Structural characterization of sulfoaildenafil, an analog of sildenafil . . 50 . 2 . 228–231 . September 2009 . 19427155 . 10.1016/j.jpba.2009.04.003 .
2. WO. 2005058899 . Pyrazolopyrimidinethione Derivatives, Salts and Solvates thereof, Preparation Methods and Use thereof. 2005-06-30. Academy of Military Medical Sciences. Li S, Ren J, Zhao Y, Lv Q, Guo J .
3. Gryniewicz CM, Reepmeyer JC, Kauffman JF, Buhse LF . Detection of undeclared erectile dysfunction drugs and analogues in dietary supplements by ion mobility spectrometry . . 49 . 3 . 601–606 . April 2009 . 19150190 . 10.1016/j.jpba.2008.12.002 .
4. http://pagingdrgupta.blogs.cnn.com/2010/12/13/fda-warns-consumers-to-avoid-sexual-enhancement-pills/ FDA warns consumers to avoid sexual enhancement pills
5. Reepmeyer JC, d'Avignon DA . Structure elucidation of thioketone analogues of sildenafil detected as adulterants in herbal aphrodisiacs . Journal of Pharmaceutical and Biomedical Analysis . 49 . 1 . 145–150 . January 2009 . 19042103 . 10.1016/j.jpba.2008.10.007 .
6. Balayssac S, Trefi S, Gilard V, Malet-Martino M, Martino R, Delsuc MA . 2D and 3D DOSY 1H 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 . 50 . 4 . 602–612 . November 2009 . 19108978 . 10.1016/j.jpba.2008.10.034 .
7. 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 . 1104 . 1–2 . 113–122 . February 2006 . 16364350 . 10.1016/j.chroma.2005.11.103 .
8. 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 . 20 . 15 . 2317–2327 . 2006 . 16817245 . 10.1002/rcm.2594 . free . 2006RCMS...20.2317G .
9. 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 . 23 . 9 . 870–875 . September 2006 . 16901855 . 10.1080/02652030600803856 . 35240702 .
10. 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 . 69 . 21 . 1951–1958 . November 2006 . 16982533 . 10.1080/15287390600751355 . 2006JTEHA..69.1951S . 40831895 .
11. Venhuis BJ, Blok-Tip L, de Kaste D . Designer drugs in herbal aphrodisiacs . Forensic Science International . 177 . 2–3 . e25–e27 . May 2008 . 18178354 . 10.1016/j.forsciint.2007.11.007 .
12. https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm236538.htm FDA warns consumers to avoid Man Up Now capsules