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Typical antipsychotic
Benperidol
Другие языки:

Benperidol

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Benperidol
Skeletal formula of benperidol
Ball-and-stick model of the benperidol molecule
Clinical data
Trade names Anquil, Frenactil
AHFS/Drugs.com International Drug Names
Routes of
administration		 Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Elimination half-life 8 hours
Identifiers
  • 1-{1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl}-1,3-dihydro-2H-benzimidazol-2-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.016.521
Chemical and physical data
Formula C22H24FN3O2
Molar mass 381.451 g·mol−1
3D model (JSmol)
  • Fc1ccc(cc1)C(=O)CCCN4CCC(N3c2ccccc2NC3=O)CC4
  • InChI=1S/C22H24FN3O2/c23-17-9-7-16(8-10-17)21(27)6-3-13-25-14-11-18(12-15-25)26-20-5-2-1-4-19(20)24-22(26)28/h1-2,4-5,7-10,18H,3,6,11-15H2,(H,24,28) checkY
  • Key:FEBOTPHFXYHVPL-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Benperidol, sold under the trade name Anquil among others, is a typical antipsychotic primarily used to treat hypersexuality syndromes and can be used to treat schizophrenia. It is a highly potent butyrophenone derivative and is the most potent neuroleptic in the European market, with chlorpromazine equivalency as high as 75 to 100 (about 150 to 200% the potency per dose of haloperidol). It is sometimes prescribed to sex offenders as a condition of their parole, as an alternative to anti-androgen drugs such as cyproterone acetate.

Benperidol was discovered by Janssen Pharmaceutica in 1961 and has been marketed since 1966. It is mainly used in Germany, but it is also available in Belgium, Greece, Italy, the Netherlands, and the United Kingdom.

Pharmacology

Pharmacodynamics

Benperidol is a strong dopamine receptor antagonist (D2 (Ki 0.027 nM) and D4 (Ki 0.066 nM)) with weaker serotonin receptor antagonism (5-HT2A (Ki 3.75 nM)). In high doses, it has antihistaminergic and alpha-adrenergic properties. It possesses minimal anticholinergic properties.

Benperidol
Site Ki (nM) Action Ref
5-HT2A 3.75 Antagonist
D1 4,100 Antagonist
D2 0.027 Antagonist
D4 0.06 Antagonist

Pharmacokinetics

Benperidol is absorbed well and undergoes extensive first pass metabolism. One percent of benperidol is excreted in urine. The half-life of benperidol is 8 hours.

Synthesis

Thieme Patent:

4-(2-Keto-1-benzimidazolinyl)piperidine [20662-53-7] (1) is alkylated with 4-Chloro-4'-Fluorobutyrophenone [3874-54-2] (2).

See also


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