Penfluridol

Penfluridol

Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	N05AG03 (WHO)
Identifiers
IUPAC name 1-[4,4-bis(4-fluorophenyl)butyl]-4-[4-chloro-3-(trifluoromethyl)phenyl]piperidin-4-ol
CAS Number	26864-56-2 N
PubChem (CID)	33630
ChemSpider	31017 Y
UNII	25TLU22Q8H Y
KEGG	D02630 Y
ChEMBL	CHEMBL47050 Y
ECHA InfoCard	100.043.689
Chemical and physical data
Formula	C28H27ClF5NO
Molar mass	523.965
3D model (Jmol)	Interactive image
SMILES FC(F)(F)c1c(Cl)ccc(c1)C4(O)CCN(CCCC(c2ccc(F)cc2)c3ccc(F)cc3)CC4
InChI InChI=1S/C28H27ClF5NO/c29-26-12-7-21(18-25(26)28(32,33)34)27(36)13-16-35(17-14-27)15-1-2-24(19-3-8-22(30)9-4-19)20-5-10-23(31)11-6-20/h3-12,18,24,36H,1-2,13-17H2 Y Key:MDLAAYDRRZXJIF-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Penfluridol (Semap, Micefal, Longoperidol) is a highly potent, first generation diphenylbutylpiperidine antipsychotic. It was discovered at Janssen Pharmaceutica in 1968. Related to other diphenylbutylpiperidine antipsychotics, pimozide and fluspirilene, penfluridol has an extremely long elimination half-life and its effects last for many days after single oral dose. Its antipsychotic potency, in terms of dose needed to produce comparable effects, is similar to both haloperidol and pimozide. It is only slightly sedative, but often causes extrapyramidal side-effects, such as akathisia, dyskinesiae and pseudo-Parkinsonism. Penfluridol is indicated for antipsychotic treatment of chronic schizophrenia and similar psychotic disorders, it is, however, like most typical antipsychotics, being increasingly replaced by the atypical antipsychotics. Due to its extremely long-lasting effects, it is often prescribed to be taken orally as tablets only once a week (q 7 days). The once-weekly dose is usually 10–60 mg.

See also

• Typical antipsychotic
• Diphenylbutylpiperidine

References

• Janssen PA, Niemegeers CJ, Schellekens KH, Lenaerts FM, Verbruggen FJ, Van Nueten JM, Schaper WK., The pharmacology of penfluridol (R 16341) a new potent and orally long-acting neuroleptic drug, Eur J Pharmacol. 1970 July 15;11(2):139-54.
• van Praag HM, Schut T, Dols L, van Schilfgaarden R., Controlled trial of penfluridol in acute psychosis, Br Med J. 1971 December 18;4(5789):710-3.
• Benkert O, Hippius H.: Psychiatrische Pharmakotherapie, Springer-Verlag, 1976, 2. Auflage. ISBN 3-540-07916-5