Aildenafil

Aildenafil (methisosildenafil) is a synthetic chemical compound that is a structural analog of sildenafil (Viagra).[1] It was first reported in 2003,[2] and it is not approved by any health regulation agency. Like sildenafil, aildenafil is a phosphodiesterase type 5 inhibitor.

Aildenafil

Names
IUPAC name 5-(5-(((3R,5S)-3,5-Dimethylpiperazin-1-yl)sulfonyl)-2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(4H)-one
Other names Methisosildenafil
Identifiers
CAS Number	496835-35-9^Y
3D model (JSmol)	Interactive image
ChemSpider	8316620^Y
PubChem CID	16721107
UNII	9T49W8GAX6^Y
CompTox Dashboard (EPA)	DTXSID10197970
InChI InChI=1S/C23H32N6O4S/c1-6-8-18-20-21(28(5)27-18)23(30)26-22(25-20)17-11-16(9-10-19(17)33-7-2)34(31,32)29-12-14(3)24-15(4)13-29/h9-11,14-15,24H,6-8,12-13H2,1-5H3,(H,25,26,30)/t14-,15+^Y Key: NFSWSZIPXJAYLR-GASCZTMLSA-N^Y
SMILES O=S(=O)(c3cc(C\1=N\C(=O)c2c(N/1)c(nn2C)CCC)c(OCC)cc3)N4C[C@H](N[C@@H](C)C4)C
Properties
Chemical formula	C23H32N6O4S
Molar mass	488.61 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is ^YN ?)
Infobox references

Aildenafil 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][7] The United States Food and Drug Administration has warned consumers that any sexual enhancement product that claims to work as well as prescription products is likely to contain such a contaminant.[8]

See also

• Acetildenafil
• Nitrosoprodenafil
• Sulfoaildenafil

References

1. Zhao, Xia; Sun, Peihong; Zhou, Ying; Liu, Yuwang; Zhang, Huilin; Gu, Jingkai; Cui, Yimin (2009). "Pharmacokinetics and safety of aildenafil tablets in healthy Chinese male subjects after multiple dose administration". Zhongguo Linchuang Yaolixue Zazhi. 25 (2): 120–123.
2. Liu, Baoshun. Preparation of pyrazolopyrimidine derivatives for treatment of impotence. WO 2003016313
3. Gryniewicz, CM; Reepmeyer, JC; Kauffman, JF; Buhse, LF (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. Choi, Dong Mi; Park, Sangaeh; Yoon, Tae Hyung; Jeong, Hye Kyoung; Pyo, Jae Sung; Park, Janghyun; Kim, Deukjoon; Kwon, Sung Won (2008). "Determination of analogs of sildenafil and vardenafil in foods by column liquid chromatography with a photodiode array detector, mass spectrometry, and nuclear magnetic resonance spectrometry". Journal of AOAC International. 91 (3): 580–588. PMID 18567304.
5. Reepmeyer, John C.; Woodruff, Jeffrey T. (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". Journal of Pharmaceutical and Biomedical Analysis. 44 (4): 887–893. doi:10.1016/j.jpba.2007.04.011. PMID 17532168.
6. Reepmeyer, John C.; Woodruff, Jeffrey T.; 'Avignon, D. Andre. (2007). "Structure elucidation of a novel analogue of sildenafil detected as an adulterant in an herbal dietary supplement". Journal of Pharmaceutical and Biomedical Analysis. 43 (5): 1615–1621. doi:10.1016/j.jpba.2006.11.037. PMID 17207601.
7. Enforcement Report for June 30, 2010, United States Food and Drug Administration
8. Hidden Risks of Erectile Dysfunction "Treatments" Sold Online, United States Food and Drug Administration, February 21, 2009