Sulforidazine

Sulforidazine

Clinical data
ATC code	none
Identifiers
IUPAC name 10-{2-[(RS)-1-Methylpiperidin-2-yl]ethyl}-2-(methylsulfonyl)-10H-phenothiazine
CAS Number	14759-06-9  N
PubChem CID	31765
ChemSpider	29458  Y
UNII	B7599I244X
ChEBI	CHEBI:135644
ChEMBL	ChEMBL2107268
CompTox Dashboard (EPA)	DTXSID30864531
ECHA InfoCard	100.035.274
Chemical and physical data
Formula	C21H26N2O2S2
Molar mass	402.57 g·mol−1
3D model (JSmol)	Interactive image
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)

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

Synthesis of sulforidazine

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". Journal of Pharmacology and Experimental Therapeutics. 228 (3): 636–9. doi:10.1016/S0022-3565(25)21884-5. PMID   6707914.
2. Thieme
3. 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.
4. FR1363683 idem Bruschweiler Conrad, Schwarb Gustav, Winkler Hans, Renz Jany, U.S. patent 3,314,948 (1967 to Sandoz Ltd)