Chemistry:Penfluridol

Short description: Chemical compound

Penfluridol

Clinical data
Trade names	Semap
AHFS/Drugs.com	International Drug Names
ATC code	N05AG03 (WHO)
Legal status
Legal status	BR: Class C1 (Other controlled substances)
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
KEGG	D02630 Y
ChEMBL	ChEMBL47050 Y
Chemical and physical data
Formula	C28H27ClF5NO
Molar mass	523.965 g·mol−1
3D model (JSmol)	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. A 2006 systematic review examined the use of penfluridol for people with schizophrenia:

Penfluridol compared to typical antipsychotics (oral) for schizophrenia

Summary
Although there are shortcomings and gaps in the data, there appears to be enough overall consistency for different outcomes. The effectiveness and adverse effects profile of penfluridol are similar to other typical antipsychotics; both oral and depot. Furthermore, penfluridol is shown to be an adequate treatment option for people with schizophrenia, especially those who do not respond to oral medication on a daily basis and do not adapt well to depot drugs. One of the results favouring penfluridol was a lower drop out rate in medium term when compared to depot medications. It is also an option for people with long-term schizophrenia with residual psychotic symptoms who nevertheless need continuous use of antipsychotic medication. An additional benefit of penfluridol is that it is a low-cost intervention.
Outcome Findings in words Findings in numbers Quality of evidence Global state No marked improvement (CGI) Follow-up: 3 to 12 months Penfluridol does not clearly change the chance of experiencing 'no marked improvement' when compared with receiving typical antipsychotic drugs. These findings are based on data of low quality. RR 0.92 (0.68 to 1.24) Low Global state - needing additional antipsychotic Follow-up: less than 3 months There is no clear difference between people given penfluridol and those receiving typical antipsychotics. These findings are based on data of low quality. RR 1.35 (0.90 to 2.01) Low Mental state Average score (BPRS) Follow-up: 3 to 12 months On average, people receiving penfluridol scored higher than people treated with typical antipsychotics (oral) but there was no clear difference between the groups and this finding is based on data of low quality. The meaning of this in day-to-day care is unclear. MD 1.24 higher (4.4 lower to 6.88 higher) Low Adverse events Needing antiparkinsonism medication Follow-up: less than 3 months There is no clear difference between people given penfluridol and those receiving typical antipsychotics (oral). These findings are based on data of low quality. RR 1.09 (0.61 to 1.97) Low Insomnia Follow-up: less than 3 months There is no clear difference between people given penfluridol and those receiving typical antipsychotics (oral). These findings are based on data of low quality. RR 1.07 (0.51 to 2.24) Low No study reported any data on outcomes such as quality of life and information relating to time in services

See also

• Typical antipsychotic
• Diphenylbutylpiperidine
• Fluspirilene
• Pimozide
• Carpipramine (atypical antipsychotic)
• Clocapramine (atypical antipsychotic)

Further reading

• Psychiatrische Pharmakotherapie (2nd ed.). Springer-Verlag. 1976. ISBN 3-540-07916-5.