Benperidol

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

Clinical data
Trade names	Anquil, Frenactil
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	N05AD07 (WHO)
Legal status
Legal status	US: ℞-only
Identifiers
IUPAC name 1-{1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl}-1,3-dihydro-2H-benzimidazol-2-one
CAS Number	2062-84-2
PubChem CID	16363
ChemSpider	15521
UNII	97O6X78C53
ChEMBL	ChEMBL297302
CompTox Dashboard (EPA)	DTXSID7045364
ECHA InfoCard	100.016.521
Chemical and physical data
Formula	C22H24FN3O2
Molar mass	381.451 g·mol^−1
3D model (JSmol)	Interactive image
SMILES Fc1ccc(cc1)C(=O)CCCN4CCC(N3c2ccccc2NC3=O)CC4
InChI 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) Key:FEBOTPHFXYHVPL-UHFFFAOYSA-N
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Benperidol was discovered at Janssen Pharmaceutica in 1961.

Synthesis

Benperidol synthesis:[6]

See also

• Timiperone has the same structure but thiourea instead of normal urea.
• Pimozide & Bezitramide (& Oxiperomide & Neflumozide) are also made from 4-(1-Benzimidazolinone)piperidine precursor
• Droperidol is self-same albeit with a tetrahydropyridine ring.

References

1. Council A, Kuenssberg V (1974-02-01). "Benperidol - a drug for sexual offenders?". Drug and Therapeutics Bulletin. BMJ Publishing Group Ltd. 12: 12.
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. BE 626307 (1963 to Janssen), C.A. 60, 10690c (1964), corresp. to GB 989755.