Acetildenafil

• CAT Number: R009641
• CAS Number: 831217-01-7
• Molecular Formula: C25H34N6O3
• Molecular Weight: 466.586
• Purity: ≥95%
• Synonyms: 5-[2-Ethoxy-5-[2-(4-ethyl-1-piperazinyl)acetyl]phenyl]-1,6-dihydro-1-methyl?-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-one; Hongdenafil
• Target: Phosphodiesterase (PDE)
• Storage: -20°C
• IUPAC Name: 5-[2-ethoxy-5-[2-(4-ethylpiperazin-1-yl)acetyl]phenyl]-1-methyl-3-propyl-4H-pyrazolo[4,3-d]pyrimidin-7-one
• InChI: InChI=1S/C25H34N6O3/c1-5-8-19-22-23(29(4)28-19)25(33)27-24(26-22)18-15-17(9-10-21(18)34-7-3)20(32)16-31-13-11-30(6-2)12-14-31/h9-10,15H,5-8,11-14,16H2,1-4H3,(H,26,27,33)
• InChIKey: RRBRQNALHKQCAI-UHFFFAOYSA-N
• SMILES: CCCC1=NN(C2=C1NC(=NC2=O)C3=C(C=CC(=C3)C(=O)CN4CCN(CC4)CC)OCC)C

Acetildenafil (hongdenafil)(CAS: 831217-01-7） is a synthetic drug which acts as a phosphodiesterase inhibitor. It is an analog of sildenafil (Viagra) which has been detected in numerous different brands of supposedly "herbal" aphrodisiac products sold to boost libido and alleviate erectile dysfunction.

A range of designer analogs of licensed PDE5 inhibitors such as sildenafil and vardenafil have been detected in recent years in over-the-counter herbal aphrodisiac products, 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 allows sale of these drugs by competitors only with permission from the patent holders (typically, under a license from the inventors) and to introduce efficacy into otherwise ineffective herbal products. 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 may represent significant health risks to consumers of these products due to their unknown safety profile. Attempts to ban such ingredients have not been successful for the most part, many jurisdictions having laws restricting chemical analogs but only those of narcotics and doping agents. However, at least one court case has resulted in a product being taken off the market.

Reference

[1]. Food Addit Contam. 2006 Sep;23(9):870-5. doi: 10.1080/02652030600803856.
Structural identification of a new acetildenafil analogue from pre-mixed bulk powder intended as a dietary supplement.
Hou P(1), Zou P, Low MY, Chan E, Koh HL.
Author information: (1)Department of Pharmacy, Faculty of Science, National University of Singapore, Science Drive 4, Singapore 117543.
An analogue of acetildenafil was detected in an extract of pre-mixed bulk powder. To our knowledge, the powder was destined to be encapsulated and sold as a dietary supplement. The structure was identified by NMR, HR-ESI-MS, ESI-MSn and FTIR analyses. Owing to the inclusion of a hydroxyl group in acetildenafil, the detected compound was called 'hydroxyacetildenafil'. With increasing use of dietary supplements marketed for penile erectile dysfunction, the detection of analogues of sexual performance enhancers is important and timely.
DOI: 10.1080/02652030600803856 PMID: 16901855 [Indexed for MEDLINE]

[2]. Eur J Mass Spectrom (Chichester). 2007;13(3):233-8. doi: 10.1255/ejms.873.
Liquid chromatography ion trap/time-of-flight mass spectrometric study on the fragmentation of an acetildenafil analogue.
Zou P, Oh SS, Kiang KH, Low MY, Koh HL.
Liquid chromatography ion-trap time-of-flight mass spectrometry was employed to elucidate the fragmentation pathways of an analogue of acetildenafil. Based on the accurate masses of the parent ion, product ions and neutral losses of acetildenafil analogue, its fragmentation pathways were proposed. The information is useful for the on-line structural identification of unknown analogues of acetildenafil found as adulterants in herbal products.
DOI: 10.1255/ejms.873 PMID: 17881792 [Indexed for MEDLINE]