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=== Pharmacodynamics ===
=== Pharmacodynamics ===
Benperidol is a strong [[dopamine]] [[receptor antagonist]] ([[Dopamine receptor D2|D2]] (''K''<sub>i</sub> 0.027 nM) and [[Dopamine receptor D4|D4]] (''K''<sub>i</sub> 0.066 nM))<ref name=":1" /> with weaker [[serotonin]] receptor antagonism ([[5-HT2A receptor|5-HT<sub>2A</sub>]] (''K''<sub>i</sub> 3.75 nM))<ref name=":1" />. In high doses it has antihistaminergic and alpha-adrenergic properties. It's anticholinergic effects are minimal.<ref name=":0">{{Cite journal |last=Schwarz |first=Christian |last2=Hartung |first2=Benno |last3=Leucht |first3=Stefan |date=2005-04-20 |title=Benperidol for schizophrenia |url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7017029/ |journal=The Cochrane Database of Systematic Reviews |volume=2005 |issue=2 |pages=CD003083 |doi=10.1002/14651858.CD003083.pub2 |issn=1469-493X |pmc=7017029 |pmid=15846648}}</ref>
Benperidol is a strong [[dopamine]] [[receptor antagonist]] ([[Dopamine receptor D2|D2]] (''K''<sub>i</sub> 0.027 nM) and [[Dopamine receptor D4|D4]] (''K''<sub>i</sub> 0.066 nM))<ref name=":1" /> with weaker [[serotonin]] receptor antagonism ([[5-HT2A receptor|5-HT<sub>2A</sub>]] (''K''<sub>i</sub> 3.75 nM))<ref name=":1" />. In high doses it has antihistaminergic and alpha-adrenergic properties. It's anticholinergic effects are minimal.<ref name=":0">{{cite journal | vauthors = Leucht S, Hartung B | title = Benperidol for schizophrenia | journal = The Cochrane Database of Systematic Reviews | volume = 2005 | issue = 2 | pages = CD003083 | date = April 2005 | pmid = 15846648 | pmc = 7017029 | doi = 10.1002/14651858.CD003083.pub2 }}</ref>
{| class="wikitable"
{| class="wikitable"
|+Benperidol<ref name="PDSP">{{cite web | title = PDSP K<sub>i</sub> Database | work = Psychoactive Drug Screening Program (PDSP)|author1-link=Bryan Roth | vauthors = Roth BL, Driscol J | 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}}</ref>
|+Benperidol<ref name="PDSP">{{cite web | title = PDSP K<sub>i</sub> Database | work = Psychoactive Drug Screening Program (PDSP)|author1-link=Bryan Roth | vauthors = Roth BL, Driscol J | 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}}</ref>
! Site !! K<sub>i</sub> (nM) !! Action !! Ref
! Site !! K<sub>i</sub> (nM) !! Action !! Ref
|-
|-
| [[5-HT2A receptor|5-HT<sub>2A</sub>]] || 3.75 || Antagonist ||<ref name=":1">{{Cite journal |last=Li |first=Peng |last2=Snyder |first2=Gretchen L. |last3=Vanover |first3=Kimberly E. |date=December 2016 |title=Dopamine Targeting Drugs for the Treatment of Schizophrenia: Past, 
Present and Future |url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5112764/ |journal=Current Topics in Medicinal Chemistry |volume=16 |issue=29 |pages=3385–3403 |doi=10.2174/1568026616666160608084834 |issn=1568-0266 |pmc=5112764 |pmid=27291902}}</ref>
| [[5-HT2A receptor|5-HT<sub>2A</sub>]] || 3.75 || Antagonist ||<ref name=":1">{{cite journal | vauthors = Li P, Snyder GL, Vanover KE | title = Dopamine Targeting Drugs for the Treatment of Schizophrenia: Past, Present and Future | journal = Current Topics in Medicinal Chemistry | volume = 16 | issue = 29 | pages = 3385–3403 | date = December 2016 | pmid = 27291902 | pmc = 5112764 | doi = 10.2174/1568026616666160608084834 }}</ref>
|-
|-
| [[Dopamine D2 receptor|D<sub>2</sub>]] || 0.027 || Antagonist ||<ref name=":1" />
| [[Dopamine D2 receptor|D<sub>2</sub>]] || 0.027 || Antagonist ||<ref name=":1" />

Revision as of 15:49, 10 March 2022

Benperidol
Skeletal formula of benperidol
Ball-and-stick model of the benperidol molecule
Clinical data
Trade namesAnquil, Frenactil
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Elimination half-life8 hours
Identifiers
  • 1-{1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl}-1,3-dihydro-2H-benzimidazol-2-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.016.521 Edit this at Wikidata
Chemical and physical data
FormulaC22H24FN3O2
Molar mass381.451 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[1] among others, is a drug which is a highly potent butyrophenone derivative. It is the most potent neuroleptic on the European market, with chlorpromazine equivalency as high as 75 to 100 (about 150 to 200% potency in terms of dose compared to haloperidol).[2] It is an antipsychotic, which can be used for the treatment of schizophrenia,[3] but it is primarily used to control hypersexuality syndromes[4] and is sometimes prescribed to sex offenders as a condition of their parole, as an alternative to anti-androgen drugs such as cyproterone acetate.[5]

Benperidol was discovered at Janssen Pharmaceutica in 1961.

Pharmacology

Pharmacodynamics

Benperidol is a strong dopamine receptor antagonist (D2 (Ki 0.027 nM) and D4 (Ki 0.066 nM))[6] with weaker serotonin receptor antagonism (5-HT2A (Ki 3.75 nM))[6]. In high doses it has antihistaminergic and alpha-adrenergic properties. It's anticholinergic effects are minimal.[7]

Benperidol[8]
Site Ki (nM) Action Ref
5-HT2A 3.75 Antagonist [6]
D2 0.027 Antagonist [6]
D4 0.06 Antagonist [6]

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.[7]

Synthesis

Benperidol synthesis:[9]

See also

References

  1. ^ Council A, Kuenssberg V (1974-02-01). "Benperidol - a drug for sexual offenders?". Drug and Therapeutics Bulletin. 12 (3). BMJ Publishing Group Ltd: 12. doi:10.1136/dtb.12.3.12. PMID 4457302. S2CID 44581451.
  2. ^ Möller HJ, Müller WE, Bandelow (2001). Neuroleptika: pharmakologische Grundlagen, klinisches Wissen und therapeutisches Vorgehen; mit 136 Tabellen (in German). Wiss. Verlag-Ges. ISBN 3-8047-1773-X.
  3. ^ Bobon J, Collard J, Lecoq R (October 1963). "[Benperidol and promazine: a "double blind" comparative study in mental geriatrics]". Acta Neurologica et Psychiatrica Belgica (in French). 63: 839–43. PMID 14092279.
  4. ^ British National Formulary (49th), British Medical Association 2005 p 183
  5. ^ Murray MA, Bancroft JH, Anderson DC, Tennent TG, Carr PJ (November 1975). "Endocrine changes in male sexual deviants after treatment with anti-androgens, oestrogens or tranquillizers". The Journal of Endocrinology. 67 (2): 179–88. doi:10.1677/joe.0.0670179. PMID 1107462.
  6. ^ a b c d e Li P, Snyder GL, Vanover KE (December 2016). "Dopamine Targeting Drugs for the Treatment of Schizophrenia: Past, Present and Future". Current Topics in Medicinal Chemistry. 16 (29): 3385–3403. doi:10.2174/1568026616666160608084834. PMC 5112764. PMID 27291902.
  7. ^ a b Leucht S, Hartung B (April 2005). "Benperidol for schizophrenia". The Cochrane Database of Systematic Reviews. 2005 (2): CD003083. doi:10.1002/14651858.CD003083.pub2. PMC 7017029. PMID 15846648.
  8. ^ Roth BL, Driscol J. "PDSP Ki Database". Psychoactive Drug Screening Program (PDSP). University of North Carolina at Chapel Hill and the United States National Institute of Mental Health. Retrieved 11 March 2022.
  9. ^ BE 626307  (1963 to Janssen), C.A. 60, 10690c (1964), corresp. to GB 989755, "1-(1-aroylpropyl-4-piperidyl)-2-benzimidazolinones and related compounds", published 1965-04-22, assigned to N.V. Research Laboratorium Dr. C. Janssen .
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