Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Aceprometazine: Difference between pages
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Saving copy of the {{drugbox}} taken from revid 447576927 of page Aceprometazine for the Chem/Drugbox validation project (updated: ''). |
m Open access bot: hdl updated in citation with #oabot. |
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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 [{{fullurl:Aceprometazine|oldid=447576927}} 447576927] of page [[Aceprometazine]] with values updated to verified values.}} |
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{{Distinguish|Acepromazine}}{{refimprove|date=February 2020}} |
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{{Drugbox |
{{Drugbox |
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| verifiedrevid = |
| verifiedrevid = 477238377 |
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| IUPAC_name = 1-{10-[2-(dimethylamino)propyl]-10''H''-phenothiazin-2-yl}ethanone |
| IUPAC_name = 1-<nowiki/>{10-[2-(dimethylamino)propyl]-10''H''-phenothiazin-2-yl}ethanone |
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| image = Aceprometazine.svg |
| image = Aceprometazine.svg |
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<!--Clinical data--> |
<!--Clinical data--> |
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| tradename = |
| tradename = |
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| legal_status = Rx-only |
| legal_status = Rx-only |
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| routes_of_administration = Oral |
| routes_of_administration = Oral |
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<!--Pharmacokinetic data--> |
<!--Pharmacokinetic data--> |
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| bioavailability = |
| bioavailability = |
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| elimination_half-life = |
| elimination_half-life = |
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| excretion = [[Kidney|Renal]] and fecal |
| excretion = [[Kidney|Renal]] and fecal |
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<!--Identifiers--> |
<!--Identifiers--> |
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| |
| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 13461-01-3 |
| CAS_number = 13461-01-3 |
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| ATC_prefix = none |
| ATC_prefix = none |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 24249 |
| ChemSpiderID = 24249 |
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| ChEMBL = 2104054 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 984N9YTM4Y |
| UNII = 984N9YTM4Y |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 53770 |
| ChEBI = 53770 |
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<!--Chemical data--> |
<!--Chemical data--> |
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| C=19 | H=22 |
| C=19 | H=22 |
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| N=2 | O=1 |
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| S=1 |
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| molecular_weight = 326.456 g/mol |
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| smiles = O=C(c2cc1N(c3c(Sc1cc2)cccc3)CC(N(C)C)C)C |
| smiles = O=C(c2cc1N(c3c(Sc1cc2)cccc3)CC(N(C)C)C)C |
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| InChI = 1/C19H22N2OS/c1-13(20(3)4)12-21-16-7-5-6-8-18(16)23-19-10-9-15(14(2)22)11-17(19)21/h5-11,13H,12H2,1-4H3 |
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| InChIKey = XLOQNFNTQIRSOX-UHFFFAOYAZ |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C19H22N2OS/c1-13(20(3)4)12-21-16-7-5-6-8-18(16)23-19-10-9-15(14(2)22)11-17(19)21/h5-11,13H,12H2,1-4H3 |
| StdInChI = 1S/C19H22N2OS/c1-13(20(3)4)12-21-16-7-5-6-8-18(16)23-19-10-9-15(14(2)22)11-17(19)21/h5-11,13H,12H2,1-4H3 |
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| StdInChIKey = XLOQNFNTQIRSOX-UHFFFAOYSA-N |
| StdInChIKey = XLOQNFNTQIRSOX-UHFFFAOYSA-N |
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}} |
}} |
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'''Aceprometazine''' ([[International Nonproprietary Name|INN]]) is a [[phenothiazine]] derivative [[prescription drug]] with [[neuroleptic]] and [[anti-histamine]] properties It is not widely prescribed, and may be associated with drug-induced Parkinsonism.<ref>{{Cite journal| vauthors = Blanchet PJ, Kivenko V |date=2016-09-23|title=Drug-induced parkinsonism: diagnosis and management|url=https://paperity.org/p/108213136/drug-induced-parkinsonism-diagnosis-and-management|journal= Journal of Parkinsonism and Restless Legs Syndrome|pages=83–91|doi=10.2147/JPRLS.S99197|doi-access=free|hdl=1866/19491|hdl-access=free}}</ref> It may be used in combination with [[meprobamate]] for the treatment of [[sleep disorders]]. This combination is available in [[France]] under the trade name '''Mepronizine'''. |
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It is structurally related to the phenothiazine derivative veterinary drug ''[[acepromazine]]''. |
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==Synthesis== |
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{{font color|red|Note:}} The reason for the rearrangement in the sidechain between the precursor and the product is on account of a [[methadone]]-type [[aziridine]]. |
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[[File:Aceprometazine synthesis.svg|thumb|center|500px|Patent {{Highlight|Ex 6}}:<ref>Martin L Kantor & Tubis Samuel, {{US patent|3100772}} (1963 to Wyeth LLC).</ref>]] |
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2-Acetylphenothiazine [6631-94-3] ('''1''') |
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2-Chloropropyldimethylamine [108-14-5] ('''2''') |
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==References== |
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{{Reflist|2}} |
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{{Dopaminergics}} |
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[[Category:D2 antagonists]] |
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[[Category:Phenothiazines]] |
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[[Category:H1 receptor antagonists]] |
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[[Category:Aromatic ketones]] |
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{{nervous-system-drug-stub}} |
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