Sulforidazine

Last updated
Sulforidazine
Sulforidazine.svg
Sulforidazine3d.png
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
ECHA InfoCard 100.035.274 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C21H26N2O2S2
Molar mass 402.57 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 Yes check.svgY
  • Key:FLGCRGJDQJIJAW-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (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

Thieme Synthesis: Patent: Sulforidazine synthesis.svg
Thieme Synthesis: Patent:

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)

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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).