Penfluridol

Penfluridol Basic information
Product Name:Penfluridol
Synonyms: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]-;Penfluridol, >=98%;1-[4,4-BIS(4-FLUOROPHENYL)BUTYL]-4-[4-CHLORO-3(TRIFLUOROMETHYL)PHENYL]-4-PIPERIDINOL;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
CAS:26864-56-2
MF:C28H27ClF5NO
MW:523.97
EINECS:248-074-5
Product Categories:API;API intermediates;ONCOVIN
Mol File:26864-56-2.mol
Penfluridol Structure
Penfluridol Chemical Properties
Melting point 105-107°C
Boiling point 587.7±50.0 °C(Predicted)
density 1.2425 (estimate)
storage temp. 2-8°C
solubility H2O: insoluble
form powder
pka13.49±0.20(Predicted)
color white
Merck 14,7087
CAS DataBase Reference26864-56-2(CAS DataBase Reference)
NIST Chemistry ReferencePenfluridol(26864-56-2)
Safety Information
Hazard Codes T
Risk Statements 25
Safety Statements 45
RIDADR UN 2811 6.1/PG 3
WGK Germany 3
RTECS TN6957000
HazardClass 6.1
PackingGroup III
HS Code 29333990
ToxicityLD50 orally in mice (day 7): 86.8 mg/kg (Janssen)
MSDS Information
ProviderLanguage
Penfluridol English
SigmaAldrich English
Penfluridol Usage And Synthesis
OriginatorSemap,Janssen-Le Brun ,W. Germany ,1975
Usesantineoplastic
UsesIn 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.
UsesPenfluridol has been used as an antipsychotic agent:
  • to study its antimetastatic effect on triple-negative breast cancer cells
  • to study its effects on the growth of glioblastoma cell lines,
  • to study its effects on the vascular endothelial growth factor (VEGF)-induced angiogenesis in human umbilical vein endothelial cells (HUVECs)

DefinitionChEBI: 1-[4,4-bis(4-fluorophenyl)butyl]-4-[4-chloro-3-(trifluoromethyl)phenyl]-4-piperidinol is a diarylmethane.
Manufacturing ProcessA 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 nameSemap (Ortho-McNeil).
Therapeutic FunctionAntipsychotic
Biochem/physiol ActionsPenfluridol is studied in the treatment of schizophrenia, Tourette syndrome and acute psychosis. It also exhibits anticancer activity.
Safety ProfilePoison 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.
SynthesisPenfluridol, 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].

Synthesis_26864-56-2

Penfluridol Preparation Products And Raw materials
Raw materialsFluorobenzene
Preparation ProductsN-Carbethoxy-4-piperidone
Triacetonediamine 4-(4-CHLOROPHENYL)PIPERIDINE 4-(3-METHYLPHENYL)PIPERIDINE 4-(3-TRIFLUOROMETHYLPHENYL)PIPERIDINE HYDROCHLORIDE (S)-1-[3-(TRIFLUOROMETHYL)PHENYL]ETHANOL Buprofezin 1-[3-(TRIFLUOROMETHYL)PHENYL]PROPANOL-1 4-M-TOLYL-PIPERIDIN-4-OL Trifluoromethyl (R)-1-(4-CHLOROPHENYL)-1-PROPANOL PHENYL VALERATE 1-[4-CHLORO-3-(TRIFLUOROMETHYL)PHENYL]ETHAN-1-OL Penfluridol 3-(3-TRIFLUOROMETHYL-PHENYL)-PROPYLAMINE Epichlorohydrin DROPERIDOL tert-Butylchlorodiphenylsilane 1-(4-CHLORO-PHENYL)-3-DIMETHYLAMINO-PROPAN-1-OL

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