Aildenafil

Aildenafil
Clinical data
Other names	Methisosildenafil; Dimethyl sildenafil
Legal status
Legal status	In general, unapproved and unscheduled; Rx in China;
Identifiers
	IUPAC name 5-[5-[(3S,5R)-3,5-dimethylpiperazin-1-yl]sulfonyl-2-ethoxyphenyl]-1-methyl-3-propyl-6H-pyrazolo[4,3-d]pyrimidin-7-one;
CAS Number	496835-35-9;
PubChem CID	135452876;
ChemSpider	8316620;
UNII	9T49W8GAX6;
CompTox Dashboard (EPA)	DTXSID10197970 ;
Chemical and physical data
Formula	C23H32N6O4S
Molar mass	488.61 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCC1=NN(C2=C1N=C(NC2=O)C3=C(C=CC(=C3)S(=O)(=O)N4C[C@H](N[C@H](C4)C)C)OCC)C;
	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+; Key:NFSWSZIPXJAYLR-GASCZTMLSA-N;

Aildenafil (methisosildenafil) is a synthetic drug that is a structural analog of sildenafil (Viagra).^[1] It was first reported in 2003.^[2] Like sildenafil, aildenafil is a phosphodiesterase type 5 inhibitor.

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]

Aildenafil is approved for use in China.^[9]

References

^ Zhao X, Sun P, Zhou Y, Liu Y, Zhang H, Gu J, Cui Y (2009). "Pharmacokinetics and safety of aildenafil tablets in healthy Chinese male subjects after multiple dose administration". Zhongguo Linchuang Yaolixue Zazhi. 25 (2): 120–123.
^ WO 2003016313, Liu B, "New compounds for treating impotence", published 2003-02-27
^ 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): 601–606. doi:10.1016/j.jpba.2008.12.002. PMID 19150190.
^ Choi DM, Park S, Yoon TH, Jeong HK, Pyo JS, Park J, et al. (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. doi:10.1093/jaoac/91.3.580. PMID 18567304.
^ Reepmeyer JC, Woodruff JT (August 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.
^ Reepmeyer JC, Woodruff JT, d'Avignon DA (April 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.
^ Enforcement Report for June 30, 2010, United States Food and Drug Administration
^ Hidden Risks of Erectile Dysfunction "Treatments" Sold Online, United States Food and Drug Administration, February 21, 2009
^ "First China-made drug for erectile dysfunction launched". China Daily. January 19, 2022.

[1] Zhao X, Sun P, Zhou Y, Liu Y, Zhang H, Gu J, Cui Y (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] WO 2003016313, Liu B, "New compounds for treating impotence", published 2003-02-27

[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): 601–606. doi:10.1016/j.jpba.2008.12.002. PMID 19150190.

[4] Choi DM, Park S, Yoon TH, Jeong HK, Pyo JS, Park J, et al. (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. doi:10.1093/jaoac/91.3.580. PMID 18567304.

[5] Reepmeyer JC, Woodruff JT (August 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 JC, Woodruff JT, d'Avignon DA (April 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

[9] "First China-made drug for erectile dysfunction launched". China Daily. January 19, 2022.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

Aildenafil

See also

References