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Benperidol, sold under the trade name Anquil among others, is a typical antipsychotic primarily used to treat
4-(2-Keto-1-benzimidazolinyl)piperidine
hypersexuality
Hypersexuality is extremely frequent or suddenly increased libido. It is controversial whether it should be included as a clinical diagnosis used by mental healthcare professionals. Nymphomania and satyriasis were terms previously used for th ...
syndromes and can be used to treat schizophrenia
Schizophrenia is a mental disorder characterized by continuous or relapsing episodes of psychosis. Major symptoms include hallucinations (typically hearing voices), delusions, and disorganized thinking. Other symptoms include social wi ...
. It is a highly potent butyrophenone derivative and is the most potent neuroleptic on 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 offender
A sex offender (sexual offender, sex abuser, or sexual abuser) is a person who has committed a sex crime. What constitutes a sex crime differs by culture and legal jurisdiction. The majority of convicted sex offenders have convictions for crim ...
s as a condition of their parole
Parole (also known as provisional release or supervised release) is a form of early release of a prison inmate where the prisoner agrees to abide by certain behavioral conditions, including checking-in with their designated parole officers, or ...
, as an alternative to anti-androgen drugs such as cyproterone acetate.
Benperidol was discovered by Janssen Pharmaceutica
Janssen Pharmaceuticals is a pharmaceutical company headquartered in Beerse, Belgium, and wholly-owned by Johnson & Johnson. It was founded in 1953 by Paul Janssen.
In 1961, Janssen Pharmaceuticals was purchased by New Jersey-based America ...
in 1961 and has been marketed since 1966. It is mainly used in Germany
Germany, officially the Federal Republic of Germany (FRG),, is a country in Central Europe. It is the most populous member state of the European Union. Germany lies between the Baltic and North Sea to the north and the Alps to the sou ...
, but it is also available in Belgium
Belgium, ; french: Belgique ; german: Belgien officially the Kingdom of Belgium, is a country in Northwestern Europe. The country is bordered by the Netherlands to the north, Germany to the east, Luxembourg to the southeast, France to ...
, Greece
Greece,, or , romanized: ', officially the Hellenic Republic, is a country in Southeast Europe. It is situated on the southern tip of the Balkans, and is located at the crossroads of Europe, Asia, and Africa. Greece shares land borders wit ...
, Italy
Italy ( it, Italia ), officially the Italian Republic, ) or the Republic of Italy, is a country in Southern Europe. It is located in the middle of the Mediterranean Sea, and its territory largely coincides with the homonymous geographical ...
, the Netherlands
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, and the United Kingdom
The United Kingdom of Great Britain and Northern Ireland, commonly known as the United Kingdom (UK) or Britain, is a country in Europe, off the north-western coast of the European mainland, continental mainland. It comprises England, Scotlan ...
.
Pharmacology
Pharmacodynamics
Benperidol is a strongdopamine
Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic chemical of the catecholamine and phenethylamine families. Dopamine constitutes about 8 ...
receptor antagonist ( D2 (''K''i 0.027 nM) and D4 (''K''i 0.066 nM)) with weaker serotonin receptor antagonism ( 5-HT2A (''K''i 3.75 nM)). In high doses, it has antihistaminergic and alpha-adrenergic properties. It possesses minimal anticholinergic properties.
Pharmacokinetics
Benperidol is absorbed well and undergoes extensivefirst pass metabolism
The first pass effect (also known as first-pass metabolism or presystemic metabolism) is a phenomenon of drug metabolism whereby the concentration of a drug, specifically when administered orally, is greatly reduced before it reaches the systemi ...
. One percent of benperidol is excreted in urine. The half-life of benperidol is 8 hours.
Synthesis
4-(2-Keto-1-benzimidazolinyl)piperidine 0662-53-7 66 may refer to:
* 66 (number)
* One of the years 66 BC, AD 66, 1966, 2066
* "66" (song), a song by Lil Yachty featuring Trippie Redd
*66, a song by The Afghan Whigs, from the album 1965
* Sixty-Six (card game), a German card game
* ''Sixty Six'' ( ...
(1) is alkylated with 4-Chloro-4'-Fluorobutyrophenone 874-54-2(2).
See also
*Timiperone
Timiperone, sold under the brand name Tolopelon, is a typical antipsychotic of the butyrophenone class which is marketed in Japan for the treatment of schizophrenia. It is similar in chemical structure to benperidol, but has a thiourea group ...
has a similar chemical structure
A chemical structure determination includes a chemist's specifying the molecular geometry and, when feasible and necessary, the electronic structure of the target molecule or other solid. Molecular geometry refers to the spatial arrangement of a ...
with a thiourea group instead of a urea group.
* Pimozide & Bezitramide (& Oxiperomide
Oxiperomide is an antipsychotic. Clinical trials demonstrated that it can reduce dyskinesia in patients with Parkinson's disease who are taking dopamine agonists without increasing Parkinsonian symptoms. It does this by selectively antagoniz ...
& Neflumozide
Neflumozide is a novel antipsychotic similar in structure to benperidol.
See also
* Benperidol
Benperidol, sold under the trade name Anquil among others, is a typical antipsychotic primarily used to treat hypersexuality syndromes and can b ...
) are also made from 4-(1-Benzimidazolinone)piperidine precursor
*Droperidol
Droperidol (Inapsine, Droleptan, Dridol, Xomolix, Innovar ombination with fentanyl">fentanyl.html" ;"title="ombination with fentanyl">ombination with fentanyl is an antidopaminergic medication, drug used as an antiemetic (that is, to prevent o ...
is similar, but has a tetrahydropyridine ring.
References
{{Dopaminergics Belgian inventions Benzimidazoles Butyrophenone antipsychotics Janssen Pharmaceutica Fluoroarenes Piperidines Typical antipsychotics