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==Synthesis==
==Synthesis==
[[File:Benperidol synthesis.svg|thumb|center|501px|[https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-02-0036 Thieme] Patent:<ref name=":2">{{Cite patent | country = BE | number = 626307}} (1963 to Janssen), C.A. 60, 10690c (1964), corresp. to {{cite patent | country = GB | number = 989755 | pubdate = 1965-04-22 | title = 1-(1-aroylpropyl-4-piperidyl)-2-benzimidazolinones and related compounds | assign1 = [[Janssen Pharmaceuticals#History|N.V. Research Laboratorium Dr. C. Janssen]]}}.</ref>]]
4-(2-Keto-1-benzimidazolinyl)piperidine ('''1''') is alkylated with 4-chloro-4'-Fluorobutyrophenone ('''2''') to produce benperidol ('''3''').<ref>[https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-02-0036 Thieme]</ref><ref name=":2">{{Cite patent | country = BE | number = 626307}} (1963 to Janssen), C.A. 60, 10690c (1964), corresp. to {{cite patent | country = GB | number = 989755 | pubdate = 1965-04-22 | title = 1-(1-aroylpropyl-4-piperidyl)-2-benzimidazolinones and related compounds | assign1 = [[Janssen Pharmaceuticals#History|N.V. Research Laboratorium Dr. C. Janssen]]}}</ref>
[[File:Benperidol synthesis.svg|thumb|center|501px|]]
4-(2-Keto-1-benzimidazolinyl)piperidine [20662-53-7] ('''1''') is alkylated with 4-Chloro-4'-Fluorobutyrophenone [3874-54-2] ('''2''').


==See also==
==See also==
*[[Timiperone]] has a similar [[chemical structure]] with a [[thiourea]] [[Functional group|group]] instead of a [[urea]] group.
*[[Timiperone]] has a similar [[chemical structure]] with a [[thiourea]] [[Functional group|group]] instead of a [[urea]] group.
*[[Pimozide]] & [[Bezitramide]] (& [[Oxiperomide]] & [[Neflumozide]]) are also made from 4-(1-Benzimidazolinone)piperidine precursor
*[[Pimozide]], [[bezitramide]], [[oxiperomide]], and [[neflumozide]]) are also made from 4-(1-benzimidazolinone)piperidine precursor
*[[Droperidol]] is similar, but has a [[Wikt:tetrahydropyridine|tetrahydropyridine]] ring.
*[[Droperidol]] is similar, but has a [[Wikt:tetrahydropyridine|tetrahydropyridine]] ring.


Revision as of 19:25, 12 June 2024

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
DrugBank
ChemSpider
UNII
KEGG
ChEBI
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 typical antipsychotic primarily used to treat hypersexuality syndromes[2] and can be used to treat schizophrenia.[3] 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).[4] It 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 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.[6]

Pharmacology

Pharmacodynamics

Benperidol is a strong dopamine receptor antagonist (D2 (Ki 0.027 nM) and D4 (Ki 0.066 nM))[7] with weaker serotonin receptor antagonism (5-HT2A (Ki 3.75 nM)).[7] In high doses, it has antihistaminergic and alpha-adrenergic properties. It possesses minimal anticholinergic properties.[8]

Benperidol[9]
Site Ki (nM) Action Ref
5-HT2A 3.75 Antagonist [7]
D1 4,100 Antagonist [7]
D2 0.027 Antagonist [7]
D4 0.06 Antagonist [7]

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.[8]

Synthesis

4-(2-Keto-1-benzimidazolinyl)piperidine (1) is alkylated with 4-chloro-4'-Fluorobutyrophenone (2) to produce benperidol (3).[10][11]

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. ^ British National Formulary (49th), British Medical Association 2005 p 183
  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. ^ 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.
  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. ^ "NCATS Inxight Drugs — BENPERIDOL". Retrieved 13 March 2022.
  7. ^ a b c d e f 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.
  8. ^ 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.
  9. ^ 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.
  10. ^ Thieme
  11. ^ 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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