Sulforidazine

Sulforidazine
Clinical data
ATC code
  • none
Identifiers
  • 10-{2-[(RS)-1-Methylpiperidin-2-yl]ethyl}-2-(methylsulfonyl)-10H-phenothiazine
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.035.274
Chemical and physical data
FormulaC21H26N2O2S2
Molar mass402.57 g·mol−1
3D model (JSmol)
  • O=S(=O)(c2cc1N(c3c(Sc1cc2)cccc3)CCC4N(C)CCCC4)C
  • InChI=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 Y
  • Key:FLGCRGJDQJIJAW-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

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.[1]

Synthesis

Sulforidazine can be synthesized starting 2-bromo-2'-amino-4'-methylsulfonyl-diphenyl sulfide (1).[2][3][4] 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

  1. ^ Niedzwiecki DM, Mailman RB, Cubeddu LX (March 1984). "Greater potency of mesoridazine and sulforidazine compared with the parent compound, thioridazine, on striatal dopamine autoreceptors". The Journal of Pharmacology and Experimental Therapeutics. 228 (3): 636–639. doi:10.1016/S0022-3565(25)21884-5. PMID 6707914.
  2. ^ "Sulforidazine". Thieme Pharmaceutical Substances.
  3. ^ Morrow RJ, Millership JS, Collier PS (2005). "Facile Syntheses of the Three Major Metabolites of Thioridazine". Helvetica Chimica Acta. 88 (5): 962–967. doi:10.1002/hlca.200590089.
  4. ^ US 3314948, Bruschweiler C, Schwarb G, Winkler H, Renz J, "Heterocyclic compounds", issued 18 April 1967, assigned to Sandoz AG. 
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