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MedKoo Cat#: 326857 | Name: Aildenafil

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Aildenafil, also known as Methisosildenafil, is a phosphodiesterase type 5 inhibitor and a structural analog of sildenafil (Viagra). It was first reported in 2003, and it is not approved by any health regulation agency. 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. 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.

Chemical Structure

Aildenafil
Aildenafil
CAS#496835-35-9

Theoretical Analysis

MedKoo Cat#: 326857

Name: Aildenafil

CAS#: 496835-35-9

Chemical Formula: C23H32N6O4S

Exact Mass: 488.2206

Molecular Weight: 488.61

Elemental Analysis: C, 56.54; H, 6.60; N, 17.20; O, 13.10; S, 6.56

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Synonym
Methisosildenafil; Aildenafil; Dimethyl sildenafil; Dimethylsildenafil.
IUPAC/Chemical 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
InChi Key
NFSWSZIPXJAYLR-GASCZTMLSA-N
InChi Code
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+
SMILES Code
O=C1C(N(C)N=C2CCC)=C2NC(C3=CC(S(=O)(N4C[C@@H](C)N[C@@H](C)C4)=O)=CC=C3OCC)=N1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 488.61 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Kee CL, Koh HL, Bloodworth BC, Zeng Y, Kiang KH, Low MY, Ge X. Structural elucidation of propoxyphenyl isobutyl aildenafil, adulterant in a health supplement using high-resolution Orbitrap mass spectrometry. J Pharm Biomed Anal. 2014 Sep;98:153-9. doi: 10.1016/j.jpba.2014.05.029. Epub 2014 May 28. PubMed PMID: 24922086. 2: Li Y, Wu L, Gu Y, Si D, Liu C. Metabolism of aildenafil in vivo in rats and in vitro in mouse, rat, dog, and human liver microsomes. Drug Test Anal. 2014 Jun;6(6):552-62. doi: 10.1002/dta.1564. Epub 2013 Dec 6. PubMed PMID: 24311535. 3: Reeuwijk NM, Venhuis BJ, de Kaste D, Hoogenboom LA, Rietjens IM, Martena MJ. Sildenafil and analogous phosphodiesterase type 5 (PDE-5) inhibitors in herbal food supplements sampled on the Dutch market. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2013;30(12):2027-34. doi: 10.1080/19440049.2013.848294. Epub 2013 Nov 21. PubMed PMID: 24261938. 4: Xiao C, Tang M, Li J, Yin CR, Xiang G, Xu L. Determination of sildenafil, vardenafil and aildenafil in human plasma by dispersive liquid-liquid microextraction-back extraction based on ionic liquid and high performance liquid chromatography-ultraviolet detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Jul 15;931:111-6. doi: 10.1016/j.jchromb.2013.05.013. Epub 2013 May 24. PubMed PMID: 23774245. 5: Kee CL, Ge X, Koh HL, Low MY. Isolation and characterization of propoxyphenyl linked sildenafil and thiosildenafil analogues in health supplements. J Pharm Biomed Anal. 2012 Nov;70:265-72. doi: 10.1016/j.jpba.2012.07.008. Epub 2012 Jul 16. PubMed PMID: 22840979. 6: Rezvanfar MA, Rahimi HR, Abdollahi M. ADMET considerations for phosphodiesterase-5 inhibitors. Expert Opin Drug Metab Toxicol. 2012 Oct;8(10):1231-45. doi: 10.1517/17425255.2012.698610. Epub 2012 Jul 7. Review. PubMed PMID: 22769968. 7: Moriyasu T, Minowa K, Sakamoto M, Kishimoto K, Kadoi H, Nakajima J, Mori K, Ogino S, Fukaya H, Shida Y. Differentiation between sulfoaildenafil and its analogs. J AOAC Int. 2011 Nov-Dec;94(6):1770-7. PubMed PMID: 22320083. 8: Demizu Y, Wakana D, Kamakura H, Kurihara M, Okuda H, Goda Y. Identification of mutaprodenafil in a dietary supplement and its subsequent synthesis. Chem Pharm Bull (Tokyo). 2011;59(10):1314-6. PubMed PMID: 21963647. 9: Venhuis BJ, Zomer G, Hamzink M, Meiring HD, Aubin Y, de Kaste D. The identification of a nitrosated prodrug of the PDE-5 inhibitor aildenafil in a dietary supplement: a Viagra with a pop. J Pharm Biomed Anal. 2011 Mar 25;54(4):735-41. doi: 10.1016/j.jpba.2010.11.020. Epub 2010 Nov 21. PubMed PMID: 21145686. 10: Wang J, Jiang Y, Wang Y, Zhao X, Cui Y, Gu J. Liquid chromatography tandem mass spectrometry assay to determine the pharmacokinetics of aildenafil in human plasma. J Pharm Biomed Anal. 2007 May 9;44(1):231-5. Epub 2007 Jan 17. PubMed PMID: 17306493. 11: He ZJ, Zhang K, Jin J, Li NC, Na YQ, Bai WJ, Wang XF, Zhu JC, Jiang H, Yuan RP, Hong BF, Song T, Yang Y, Dai DX. [Aildenafil citrate: a new potent and highly selective phosphodiesterase type 5 inhibitor for the treatment of erectile dysfunction]. Zhonghua Nan Ke Xue. 2006 Dec;12(12):1080-3. Chinese. PubMed PMID: 17201251.