Sulforidazine

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]

Sulforidazine
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • 10-{2-[(RS)-1-Methylpiperidin-2-yl]ethyl}-2-(methylsulfonyl)-10H-phenothiazine
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
ECHA InfoCard100.035.274
Chemical and physical data
FormulaC21H26N2O2S2
Molar mass402.57 g·mol−1
3D model (JSmol)
SMILES
  • O=S(=O)(c2cc1N(c3c(Sc1cc2)cccc3)CCC4N(C)CCCC4)C
InChI
  • 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)

Synthesis
Thieme Synthesis:[2] Patent:[3]

2-bromo-2'-amino-4'-methylsulphonyl-diphenyl Sulphide, CID:43448246 (1) 2-bromo-2'-acetamino-4'-methylsulphonyl diphenylsulphide (2) 2-(2-Chloroethyl)-1-Methylpiperidine [50846-01-0] (3)

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". Journal of Pharmacology and Experimental Therapeutics. 228 (3): 636–9. PMID 6707914.
  2. Morrow, Ryan J.; Millership, Jeff S.; Collier, Paul S. (2005). "Facile Syntheses of the Three Major Metabolites of Thioridazine". Helvetica Chimica Acta. 88 (5): 962–967. doi:10.1002/hlca.200590089.
  3. FR1363683 idem Bruschweiler Conrad, Schwarb Gustav, Winkler Hans, Renz Jany, U.S. Patent 3,314,948 (1967 to Sandoz Ltd).


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