Fluspirilene

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Fluspirilene
Fluspirilen.svg
Systematic (IUPAC) name
8-[4,4-bis(4-fluorophenyl)butyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
Clinical data
AHFS/Drugs.com International Drug Names
  • (Prescription only)
IM
Identifiers
1841-19-6 YesY
N05AG01
PubChem CID: 3396
IUPHAR ligand 85
DrugBank DB04842 YesY
ChemSpider 3279 YesY
UNII C5QA4GLR9M YesY
KEGG D02629 YesY
ChEMBL CHEMBL46516 YesY
Chemical data
Formula C29H31F2N3O
475.573 g/mol
 YesY (what is this?)  (verify)

Fluspirilene (Redeptin, Imap, R6218) is a diphenylbutylpiperidine typical antipsychotic drug, used for the treatment of schizophrenia.[1] It is administered intramuscularly.[2] It was discovered at Janssen Pharmaceutica in 1963.[3]

Synthesis[edit]

Fluspirilene synthesis: BE 633914 ; P.A.J. Janssen, U.S. Patent 3,238,216 (1963, 1966 both to Janssen).
1-Phenyl-1,3,8-triazaspiro(4,5)decan-4-one synthesis 1,1'-(4-Chlorobutylidene)bis(4-fluorobenzene) synthesis
1-Phenyl-1,3,8-triazaspiro(4,5)decan-4-one synthesis.svg 1,1'-(4-Chlorobutylidene)bis(4-fluorobenzene) synthesis.svg
  1. Reaction of N-benzyl-4-piperidone with KCN and PhNH3+Cl- leads to the α-aminonitrile (c.f. Stecker synthesis).
  2. Hydrolysis of the cyano group by means of sulphuric acid affords the corresponding amide.
  3. Reaction with formamide serves to form the spiroimidazolidone ring.

See also[edit]

References[edit]

  1. ^ van Epen JH (1970). "Experience with fluspirilene (R 6218), a long-acting neuroleptic". Psychiatr Neurol Neurochir 73 (4): 277–284. PMID 5478771. 
  2. ^ Janssen PA, Niemegeers CJ, Schellekens KH, Lenaerts FM, Verbruggen FJ, van Nueten JM, Marsboom RH, Herin VV, Schaper WK (1970). "The pharmacology of fluspirilene (R 6218), a potent, long-acting and injectable neuroleptic drug". Arzneimittelforschung 20 (11): 1689–1698. PMID 4992598. 
  3. ^ C. Janssen, NV Res. Lab., BE 633914  (1963)