Thiopropazate: Difference between revisions

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+{{Short description|Chemical compound}}
 {{Drugbox
+| Watchedfields = changed
-| verifiedrevid = 444226225
+| verifiedrevid = 448240337
 | IUPAC_name = 2-[4-[3-(2-chlorophenothiazin-10-yl)propyl]piperazin-1-yl]ethyl acetate
-| image = Thiopropazate.png
+| image = Thiopropazate.svg
 <!--Clinical data-->
-| tradename =
+| tradename = Artalan, Dartal, Dartalan, Dartan
 | pregnancy_category =
 | legal_status =
 | routes_of_administration =
 <!--Pharmacokinetic data-->
 | bioavailability =
 | protein_bound =
 | metabolism =
 | elimination_half-life =
 | excretion =
 <!--Identifiers-->
+| CAS_number_Ref = {{cascite|correct|??}}
 | CAS_number = 84-06-0
-| ATC_prefix =
+| ATC_prefix = N05
-| ATC_suffix =
+| ATC_suffix = AB05
 | PubChem = 6762
 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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 | ChEBI_Ref = {{ebicite|correct|EBI}}
 | ChEBI = 59119
+| ChEMBL = 1697851
 <!--Chemical data-->
+| C=23 | H=28 | Cl=1 | N=3 | O=2 | S=1
-| chemical_formula = C<sub>23</sub>H<sub>28</sub>ClN<sub>3</sub>O<sub>2</sub>S
-| molecular_weight = 446.01 g/mol
 | smiles = CC(=O)OCCN1CCN(CC1)CCCN2C3=CC=CC=C3SC4=C2C=C(C=C4)Cl
 | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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 }}
-'''Thiopropazate''' ('''Artalan''', '''Dartal''', '''Dartalan''', '''Dartan''') is a [[typical antipsychotic]] of the [[phenothiazine]] class.<ref name="isbn0-412-54090-8">{{cite book | author = | title = Dictionary of organic compounds | publisher = Chapman & Hall | location = London | year = 1996 | page = 5148 | isbn = 0-412-54090-8 | oclc = | doi = | url = http://books.google.com/books?id=r7z8W69GcoMC&lpg=PA5148&dq=thiopropazate%20neuroleptic&as_brr=3&pg=PA5148#v=onepage&q=&f=false}}</ref>
+'''Thiopropazate''' ('''Artalan''', '''Dartal''', '''Dartalan''', '''Dartan''') is a [[typical antipsychotic]] of the [[phenothiazine]] class.<ref name="isbn0-412-54090-8">{{cite book | vauthors = Buckingham J | title = Dictionary of organic compounds | publisher = Chapman & Hall | location = London | year = 1996 | page = 5148 | isbn = 0-412-54090-8 | url = https://books.google.com/books?id=r7z8W69GcoMC&q=thiopropazate%20neuroleptic&pg=PA5148}}</ref> It is a prodrug to [[perphenazine]].
+Thiopropazate is manufactured by Searle (US, UK)  & Boehringer Mannheim (Germany)<ref>Pharmaceutical Manufacturing Encyclopedia p. 3209</ref>
+Thiopropazate is sold by Chembase, AAA Chemistry, ZINC, AKos Consulting & Solutions, Boc Sciences, ChemFrog, and ChemMol<ref>{{cite web | title = Thiopropazate | url = https://pubchem.ncbi.nlm.nih.gov/compound/thiopropazate#section=Top | work = PubChem | publisher = United States Library of Medicine }}</ref>
+==Synthesis==
+[[File:Thiopropazate synthesis.svg|thumb|center|500px|[https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-20-0070 Thieme] Patent:<ref>John W Cusic, {{US patent|2766235}} (1956 to Searle & Co).</ref>]]
+The alkylation of 2-chloro-10-(3-chloropropyl)phenothiazine [2765-59-5] ('''1''') with [[Piperazine]] ('''2''') gives N-Desmethylprochlorperazine [40323-85-1] ('''3'''). Further alkylation with 2-Bromoethyl acetate [927-68-4] ('''4''') gives ''Thiopropazate'' ('''5''').
 == See also ==
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 {{Tricyclics}}
+[[Category:Acetate esters]]
+[[Category:Chloroarenes]]
 [[Category:Phenothiazines]]
 [[Category:Piperazines]]
-[[Category:Organochlorides]]
+[[Category:Typical antipsychotics]]
-[[Category:Acetate esters]]