| Identification | More | [Name]
Penfluridol | [CAS]
26864-56-2 | [Synonyms]
1-[4,4-BIS(4-FLUOROPHENYL)BUTYL]-4-[4-CHLORO-3(TRIFLUOROMETHYL)PHENYL]-4-PIPERIDINOL
PENFLURIDOL
R16341
1-[4,4-Bis(p-fluorophenyl)butyl]-4-(4-chloro-alpha,alpha,alpha-trifluoro-m-tolyl)-4-piperidinol
1-[4,4-Bis(p-flurophenyl)butyl]-4-(4-chloro-alpha,alpha,alpha-trifluoro-m-tolyl)-4-piperidinol
4-Piperidinol, 1-[4,4-bis(4-fluorophenyl)butyl]-4-[4-chloro-3-(trifluoromethyl)phenyl]-
4-Piperidinol, 4-(4-chloro-alpha,alpha,alpha-trifluoro-m-tolyl)-1-(4,4-bis(p-fluorophenyl)butyl)-
4-piperidinol,1-(4,4-bis(4-fluorophenyl)butyl)-4-(4-chloro-3-(trifluoromethy
4-piperidinol,4-(4-chloro-alpha,alpha,alpha-trifluoro-m-tolyl)-1-(4,4-bis(p-fl
McN-JR-16,341
Penfuridol
Semap
TLP-607
uorophenyl)butyl)-
PROTAMINE SULFATE USP
PENFLURIDOL CP2005
PHENFLURIDOL
1-[4,4-BIS(4-FLUOROPHENYL)BUTYL]-4-[4-CHLORO-3-(TRIFLUOROMETHYL)PHENYL]-4-
1-(4,4-bis(4-fluorophenyl)butyl)-4-(4-chloro-3-(trifluoromethyl)phenyl)piperidin-4-ol
R16341, 1-[4,4-Bis(4-fluorophenyl)butyl]-4-[4-chloro-3(trifluoromethyl)phenyl]-4-piperidinol | [EINECS(EC#)]
248-074-5 | [Molecular Formula]
C28H27ClF5NO | [MDL Number]
MFCD00866714 | [Molecular Weight]
523.97 | [MOL File]
26864-56-2.mol |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
R25:Toxic if swallowed. | [Safety Statements ]
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
TN6957000
| [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29333990 | [Safety Profile]
Poison by ingestion and intravenous routes. Experimental teratogenic and reproductive effects. A neuroleptic agent. When heated to decomposition it emits very toxic fumes of Cl-, F-, and NOx. | [Toxicity]
LD50 orally in mice (day 7): 86.8 mg/kg (Janssen) |
| Hazard Information | Back Directory | [Originator]
Semap,Janssen-Le Brun ,W. Germany ,1975 | [Uses]
antineoplastic | [Uses]
In terms of pharmacological action, penfluridol is similar to pimozide; however, it is significantly longer lasting, which is connected to the slow metabolism of the drug.
Penfluridol is used as a supportive therapy in ambulatory settings for patients suffering
from schizophrenia as well as patients with paranoid, psychotic, and neuroleptic conditions. | [Definition]
ChEBI: 1-[4,4-bis(4-fluorophenyl)butyl]-4-[4-chloro-3-(trifluoromethyl)phenyl]-4-piperidinol is a diarylmethane. | [Manufacturing Process]
A mixture of 24 parts of 4,4-bis(p-fluorophenyl)butyl chloride, 20.9 parts of 4(4-chloro-α,α,α-trifluoro-m-tolyl)-4-piperidinol, 13.8 parts of sodium carbonate, a few crystals of potassium iodide in 600 parts of 4-methyl-2pentanone is stirred and refluxed for 60 hours. The reaction mixture is cooled and 150 parts of water is added. The organic layer is separated, dried, filtered and evaporated. The oily residue is crystallized from diisopropylether, yielding 4-(4chloro-α,α,α-trifluoro-m-tolyl)-1-[4,4-bis(p-fiuorophenyl)butyl]-4piperidinol; melting point 106.5°C. | [Brand name]
Semap (Ortho-McNeil). | [Therapeutic Function]
Antipsychotic | [Biochem/physiol Actions]
Penfluridol is studied in the treatment of schizophrenia, Tourette syndrome and acute psychosis. It also exhibits anticancer activity. | [Synthesis]
Penfluridol, 4-(4-chloro-3-trifluoromethylphenyl)-1-[4,4-bis-(p-fluorophenyl)
butyl]-4-piperidinol (6.6.12), is synthesized implementing a Grignard reaction between
1-carbomethoxypiperidin-4-one and 4-chloro-3-trifluoromethylphenylmagnesium bromide,
giving 1-carbomethoxy-(4-chloro-3-trifluoromethylphenyl)-4-piperidinol (6.6.10). Upon
alkaline hydrolysis of the carbomethoxy group, it turns into (4-chloro-3-trifluoromethylphenyl)-4-piperidinol (6.6.11), the alkylation of which with 1,1-bis(4-fluorophenyl)butyl bromide (6.6.3) gives penfluridol (6.6.12) [67¨C69].
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