| Revision as of 19:51, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 465936911 of page Acetildenafil for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Latest revision as of 06:59, 5 November 2024 edit Citation bot (talk | contribs)Bots5,418,887 edits Added bibcode. | Use this bot. Report bugs. | Suggested by Dominic3203 | #UCB_webform 32/166 |
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{{Short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| verifiedrevid = 448119769 |
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| Watchedfields = changed |
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| verifiedrevid = 477238943 |
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| IUPAC_name = 5--phenyl]-1-methyl-3-propyl-1,6-dihydro-pyrazolopyrimidin-7-one |
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| IUPAC_name = 5--phenyl]-1-methyl-3-propyl-1,6-dihydro-pyrazolopyrimidin-7-one |
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| image = Acetildenafil.png |
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| image = Acetildenafil.svg |
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| width = 250 |
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| width = 250 |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = |
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| MedlinePlus = a699015 |
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| MedlinePlus = a699015 |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category = |
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| pregnancy_category = |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| legal_CA = <!-- Schedule I --> |
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| legal_CA = <!-- Schedule I --> |
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| legal_UK = <!-- Class A --> |
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| legal_UK = <!-- Class A --> |
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| legal_US = |
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| legal_US = Unapproved and unscheduled |
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| legal_status = |
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| legal_status = |
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| routes_of_administration = |
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| routes_of_administration = ] |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| bioavailability = |
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| protein_bound = |
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| protein_bound = |
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| metabolism = |
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| metabolism = |
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| elimination_half-life = |
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| elimination_half-life = |
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| excretion = |
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| excretion = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = <!-- blanked - oldvalue: 831217-01-7 --> |
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| CAS_number = 831217-01-7 |
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| ATC_prefix = none |
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| ATC_prefix = None |
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| ATC_suffix = |
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| ATC_suffix = |
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| PubChem = |
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| PubChem = 29918992 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| DrugBank = |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = TP0E2BW57H |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 23976138 |
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| ChemSpiderID = 23976138 |
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| ChEBI = 183660 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=25 | H=34 | N=6 | O=3 |
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| C=25 | H=34 | N=6 | O=3 |
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| smiles = CCCc1nn(C)c3c1nc(c3=O)-c2cc(ccc2OCC)C(=O)CN4CCN(CC)CC4 |
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| molecular_weight = 466.574 g/mol |
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| smiles = CCCc1nn(C)c3c1nc(nc3=O)-c2cc(ccc2OCC)C(=O)CN4CCN(CC)CC4 |
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| InChI = 1/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) |
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| InChIKey = RRBRQNALHKQCAI-UHFFFAOYAK |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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) |
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| StdInChI = 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) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = RRBRQNALHKQCAI-UHFFFAOYSA-N |
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| StdInChIKey = RRBRQNALHKQCAI-UHFFFAOYSA-N |
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| synonyms = Acetildenafil |
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| synonyms = |
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}} |
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}} |
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'''Acetildenafil''' ('''hongdenafil''') is a synthetic ] which acts as a ].<ref>{{cite web | title = Acetildenafil | website = Cayman Chemical | url = https://www.caymanchem.com/product/12049 | access-date = 26 Mar 2017}}</ref> It is an ] of ] (Viagra)<ref>{{cite journal | vauthors = Blok-Tip L, Zomer B, Bakker F, Hartog KD, Hamzink M, Ten Hove J, Vredenbregt M, De Kaste D | display-authors = 6 | title = Structure elucidation of sildenafil analogues in herbal products | journal = Food Additives and Contaminants | volume = 21 | issue = 8 | pages = 737–48 | date = August 2004 | pmid = 15370823 | doi = 10.1080/02652030412331272467 | hdl = 10029/11381 | s2cid = 45568769 | hdl-access = free }}</ref> which has been detected in numerous different brands of "herbal ]" products sold in ]s that claim to boost libido and alleviate ].<ref name= Poon >{{cite journal | vauthors = Poon WT, Lam YH, Lai CK, Chan AY, Mak TW | title = Analogues of erectile dysfunction drugs: an under-recognised threat | journal = Hong Kong Medical Journal = Xianggang Yi Xue Za Zhi | volume = 13 | issue = 5 | pages = 359–63 | date = October 2007 | pmid = 17914141 }}</ref> |
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A range of designer analogs of licensed ] inhibitors such as sildenafil and ] have been detected in recent years in over-the-counter herbal aphrodisiac products,<ref>{{cite journal | vauthors = Venhuis BJ, de Kaste D | title = Towards a decade of detecting new analogues of sildenafil, tadalafil and vardenafil in food supplements: a history, analytical aspects and health risks | journal = Journal of Pharmaceutical and Biomedical Analysis | volume = 69 | pages = 196–208 | date = October 2012 | pmid = 22464558 | doi = 10.1016/j.jpba.2012.02.014 }}</ref><ref>{{cite journal | vauthors = Zou P, Oh SS, Hou P, Low MY, Koh HL | title = 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 = Journal of Chromatography A | volume = 1104 | issue = 1–2 | pages = 113–22 | date = February 2006 | pmid = 16364350 | doi = 10.1016/j.chroma.2005.11.103 }}</ref><ref>{{cite journal | vauthors = Gratz SR, Gamble BM, Flurer RA | title = 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 | journal = Rapid Communications in Mass Spectrometry | volume = 20 | issue = 15 | pages = 2317–27 | year = 2006 | pmid = 16817245 | doi = 10.1002/rcm.2594 | bibcode = 2006RCMS...20.2317G | doi-access = free }}</ref><ref>{{cite journal | vauthors = Hou P, Zou P, Low MY, Chan E, Koh HL | title = Structural identification of a new acetildenafil analogue from pre-mixed bulk powder intended as a dietary supplement | journal = Food Additives and Contaminants | volume = 23 | issue = 9 | pages = 870–5 | date = September 2006 | pmid = 16901855 | doi = 10.1080/02652030600803856 | s2cid = 35240702 }}</ref> in an apparent attempt to circumvent both the legal restrictions on sale of erectile dysfunction drugs, which are ] medicines in most Western countries, and the ] 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 ] into otherwise ineffective herbal products. These compounds have been demonstrated to display PDE<sub>5</sub> 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.<ref name= Poon/><ref>{{cite journal | vauthors = Oh SS, Zou P, Low MY, Koh HL | title = Detection of sildenafil analogues in herbal products for erectile dysfunction | journal = Journal of Toxicology and Environmental Health. Part A | volume = 69 | issue = 21 | pages = 1951–8 | date = November 2006 | pmid = 16982533 | doi = 10.1080/15287390600751355 | bibcode = 2006JTEHA..69.1951S | s2cid = 40831895 }}</ref> Attempts to ban such ingredients have not been successful for the most part, many jurisdictions having laws restricting chemical analogs but only those of ] and ] agents. However, at least one court case has resulted in a product being taken off the market.<ref>{{cite journal | vauthors = Venhuis BJ, Blok-Tip L, de Kaste D | title = Designer drugs in herbal aphrodisiacs | journal = Forensic Science International | volume = 177 | issue = 2–3 | pages = e25-7 | date = May 2008 | pmid = 18178354 | doi = 10.1016/j.forsciint.2007.11.007 }}</ref> |
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== See also == |
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== References == |
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{{reflist}} |
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{{Phosphodiesterase inhibitors}} |
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