Acetildenafil

drugbox
IUPAC_name = 5- [2-Ethoxy-5- [2-(4-ethyl-piperazin-1-yl)-acetyl] -phenyl] -1-methyl-3-propyl-1,6-dihydro-pyrazolo [4,3-d] pyrimidin-7-one

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CAS_number = 831217-01-7
synonyms = Acetildenafil
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C = 25 | H = 34 | N = 6 | O = 3
molecular_weight = 466.574 g/mol
smiles = CCCc1nn(C)c3c1nc(nc3=O)-c2cc(ccc2OCC)C(=O)CN4CCN(CC)CC4
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Acetildenafil is a designer drug which acts as a phosphodiesterase inhibitor. It is a structural analogue of sildenafil (Viagra) [Blok-Tip L, Zomer B, Bakker F, Hartog KD, Hamzink M, Ten Hove J, Vredenbregt M, De Kaste D. Structure elucidation of sildenafil analogues in herbal products. "Food Additives and Contaminants". 2004 Aug;21(8):737-48. PMID 15370823] which has been detected in numerous different brands of supposedly "herbal" aphrodisiac products sold to boost libido and alleviate erectile dysfunction. [Poon WT, Lam YH, Lai CK, Chan AY, Mak TW. Analogues of erectile dysfunction drugs: an under-recognised threat. "Hong Kong Medical Journal". 2007 Oct;13(5):359-63. PMID 17914141]

A range of designer analogues of legitimate PDE₅ inhibitors such as sildenafil and vardenafil have been detected in recent years as adulturants in over-the-counter herbal aphrodisiac products, [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] [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] [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] 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. [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] 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. [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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