sulforidazine

{{Short description|Typical antipsychotic medication}}

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| image = Sulforidazine.svg

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| image2 = Sulforidazine3d.png

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| routes_of_administration =

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| metabolism =

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| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 14759-06-9

| ATC_prefix = none

| PubChem = 31765

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| ChemSpiderID = 29458

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = B7599I244X

| ChEBI = 135644

| ChEMBL = 2107268

| IUPAC_name = 10-{2-[(RS)-1-Methylpiperidin-2-yl]ethyl}-2-(methylsulfonyl)-10H-phenothiazine

| C=21 | H=26 | N=2 | O=2 | S=2

| smiles = O=S(=O)(c2cc1N(c3c(Sc1cc2)cccc3)CCC4N(C)CCCC4)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C21H26N2O2S2/c1-22-13-6-5-7-16(22)12-14-23-18-8-3-4-9-20(18)26-21-11-10-17(15-19(21)23)27(2,24)25/h3-4,8-11,15-16H,5-7,12-14H2,1-2H3

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Sulforidazine (Imagotan, Psychoson, Inofal) a typical antipsychotic and a metabolite of thioridazine; it and mesoridazine are more potent than the parent compound, whose pharmacological effects are believed by some to be largely due to its metabolism into sulforidazine and mesoridazine.{{cite journal | vauthors = Niedzwiecki DM, Mailman RB, Cubeddu LX | title = Greater potency of mesoridazine and sulforidazine compared with the parent compound, thioridazine, on striatal dopamine autoreceptors | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 228 | issue = 3 | pages = 636–639 | date = March 1984 | pmid = 6707914 | doi = 10.1016/S0022-3565(25)21884-5 }}

Synthesis

File:Sulforidazine synthesis.svg

Sulforidazine can be synthesized starting 2-bromo-2'-amino-4'-methylsulfonyl-diphenyl sulfide (1).{{cite web | title = Sulforidazine | url = https://pharmaceutical-substances.thieme.com/lexicon/KD-19-0102?searchterm=sulforidazine&context=search | work = Thieme Pharmaceutical Substances }}{{cite journal | doi = 10.1002/hlca.200590089 | title = Facile Syntheses of the Three Major Metabolites of Thioridazine | date = 2005 | vauthors = Morrow RJ, Millership JS, Collier PS | journal = Helvetica Chimica Acta | volume = 88 | issue = 5 | pages = 962–967 }}{{cite patent | country = US | number = 3314948 | inventor = Bruschweiler C, Schwarb G, Winkler H, Renz J | url = https://patents.google.com/patent/US3314948 | gdate = 18 April 1967 | title = Heterocyclic compounds | assign = Sandoz AG | postscript = . }} Acetylation produces 2-bromo-2'-acetamino-4'-methylsulphonyl diphenylsulfide (2), which is then alkylated with 2-(2-chloroethyl)-1-methylpiperidine (3). Deacylation followed by a copper-catalyzed ring-formation reaction produces sulforidazine.

References

{{Reflist}}

{{Antipsychotics}}

{{Adrenergics}}

{{Cholinergics}}

{{Dopaminergics}}

{{Histaminergics}}

{{Tricyclics}}

Category:Abandoned drugs

Category:Typical antipsychotics

Category:Phenothiazines

Category:Piperidines

Category:Tertiary amines