Benperidol

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Typical antipsychotic medication

title: "Benperidol" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["anaphrodisiacs", "belgian-inventions", "butyrophenone-antipsychotics", "janssen-pharmaceutica", "4-fluorophenyl-compounds", "piperidinylbenzimidazolines", "typical-antipsychotics"] description: "Typical antipsychotic medication" topic_path: "general/anaphrodisiacs" source: "https://en.wikipedia.org/wiki/Benperidol" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Typical antipsychotic medication ::

::data[format=table title="Infobox drug"]

Field	Value
Verifiedfields	changed
verifiedrevid	459533587
IUPAC_name	1-{1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl}-1,3-dihydro-2H-benzimidazol-2-one
image	Benperidol.svg
image_class	skin-invert-image
alt	Skeletal formula of benperidol
width	250px
image2	Benperidol 3D ball.png
image_class2	bg-transparent
alt2	Ball-and-stick model of the benperidol molecule
width2	250px
tradename	Anquil, Frenactil
Drugs.com
pregnancy_AU
pregnancy_US
legal_AU	S4 (Prescription only)
legal_UK
legal_US	Rx-only
routes_of_administration	Oral
elimination_half-life	8 hours
excretion
CAS_number_Ref
CAS_number	2062-84-2
ATC_prefix	N05
ATC_suffix	AD07
PubChem	16363
DrugBank_Ref
DrugBank	DB12867
ChemSpiderID_Ref
ChemSpiderID	15521
UNII_Ref
UNII	97O6X78C53
ChEMBL_Ref
ChEMBL	297302
KEGG	D02627
ChEBI	93403
C	22
H	24
F	1
N	3
O	2
smiles	Fc1ccc(cc1)C(=O)CCCN4CCC(N3c2ccccc2NC3=O)CC4
StdInChI_Ref
StdInChI	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)
StdInChIKey_Ref
StdInChIKey	FEBOTPHFXYHVPL-UHFFFAOYSA-N
::

| Verifiedfields = changed | verifiedrevid = 459533587 | IUPAC_name = 1-{1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl}-1,3-dihydro-2H-benzimidazol-2-one | image = Benperidol.svg | image_class = skin-invert-image | alt = Skeletal formula of benperidol | width = 250px | image2 = Benperidol 3D ball.png | image_class2 = bg-transparent | alt2 = Ball-and-stick model of the benperidol molecule | width2 = 250px

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, 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. ::data[format=table title="Benperidol{{cite web | vauthors = Roth BL, Driscol J | title = PDSP K_i Database | work = Psychoactive Drug Screening Program (PDSP) | author1-link = Bryan Roth | publisher = University of North Carolina at Chapel Hill and the United States National Institute of Mental Health | access-date = 11 March 2022 | url = https://pdsp.unc.edu/databases/pdsp.php?recDDRadio=recDDRadio&receptorDD=&receptor=&speciesDD=&species=&sourcesDD=&source=&hotLigandDD=&hotLigand=&testLigandDD=&testFreeRadio=testFreeRadio&testLigand=Benperidol&referenceDD=&reference=&KiGreater=&KiLess=&kiAllRadio=all&doQuery=Submit+Query }}"]

Site	Ki (nM)	Action	Ref
5-HT2A	3.75	Antagonist	vauthors = Li P, Snyder GL, Vanover KE
D1	4,100	Antagonist
D2	0.027	Antagonist
D4	0.06	Antagonist
::

Although benperidol was developed relatively early in the history of antipsychotic drugs, it exhibits a uniquely high and selective affinity for the human dopamine D2 receptor when compared with all other human dopamine receptor subtypes. This is evident from its nanomolar binding affinities, which stand out even among both typical and atypical antipsychotics. Benperidol is also considered to possess one of the greatest selectivity ratios for dopamine receptors over 5-HT2A serotonin receptors, although this distinction is surpassed by certain neuroleptics such as amisulpride and sulpiride. Dopamine receptors play central roles not only in cognition, emotion, and motor control—key domains affected in schizophrenia—but also in various unconscious biological processes. The emphasis on D2 receptor blockade in antipsychotic drug design stems from its critical role in these functions and its dense expression in brain regions implicated in schizophrenia, such as the striatum and frontal cortex. Benperidol's preferential binding to the D2 receptor—over other dopamine receptor subtypes such as D3 and D4—is also unusually strong, with approximately a twofold greater selectivity. This distinguishes it from antipsychotics like haloperidol and perphenazine, which show more balanced D2/D3 binding ratios (e.g., 0.7–0.3 or 0.13), as well as from cariprazine, which demonstrates an even higher D3 affinity relative to D2 (D2–D3 ratio of 0.49–0.085).

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

4-(2-Keto-1-benzimidazolinyl)piperidine (1) is alkylated with 4-chloro-4'-Fluorobutyrophenone (2) to produce benperidol (3). ::figure[src="https://upload.wikimedia.org/wikipedia/commons/6/65/Benperidol_synthesis.svg" caption=""] ::

References

(1974-02-01). "Benperidol - a drug for sexual offenders?". BMJ Publishing Group Ltd.
British National Formulary (49th), British Medical Association 2005 p 183
(October 1963). "[Benperidol and promazine: a "double blind" comparative study in mental geriatrics]". Acta Neurologica et Psychiatrica Belgica.
(2001). "Neuroleptika: pharmakologische Grundlagen, klinisches Wissen und therapeutisches Vorgehen; mit 136 Tabellen.". Wiss. Verlag-Ges..
(November 1975). "Endocrine changes in male sexual deviants after treatment with anti-androgens, oestrogens or tranquillizers". The Journal of Endocrinology.
"NCATS Inxight Drugs — BENPERIDOL".
(April 2005). "Benperidol for schizophrenia". The Cochrane Database of Systematic Reviews.
"PDSP K_i Database". University of North Carolina at Chapel Hill and the United States National Institute of Mental Health.
(December 2016). "Dopamine Targeting Drugs for the Treatment of Schizophrenia: Past, Present and Future". Current Topics in Medicinal Chemistry.
(2009). "Amisulpride is a potent 5-HT7 antagonist: Relevance for antidepressant actions in vivo". Psychopharmacology.
(2016). "Dopamine Targeting Drugs for the Treatment of Schizophrenia: Past, Present and Future". Current Topics in Medicinal Chemistry.
(2009). "The story of antipsychotics: Past and present". Indian Journal of Psychiatry.
(2020). "The role of dopamine D(3) receptors in the mechanism of action of cariprazine". CNS Spectrums.
(1998). "Agonist and inverse agonist activity at the dopamine D3 receptor measured by guanosine 5'--gamma-thio-triphosphate--35S- binding". The Journal of Pharmacology and Experimental Therapeutics.
(2016). "Mechanism of action of cariprazine". CNS Spectrums.
"Benperidol". Thieme.
"1-(1-Aroylpropyl-4-piperidyl)-2-benzimidazolinones }} Chemical Abstracts 60, 10690c (1964), corresp. to {{cite patent".

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::