Benperidol

Benperidol

Clinical data
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	983-42-6
PubChem (CID)	16363
ChemSpider	15521
UNII	97O6X78C53
ChEMBL	CHEMBL297302
Chemical and physical data
Formula	C22H24FN3O2
Molar mass	381.443 g/mol
3D model (Jmol)	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 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).^[1] It is an antipsychotic, which can be used for the treatment of schizophrenia,^[2] but it is primarily used to control antisocial hypersexual behaviour,^[3] and is sometimes prescribed to sex offenders as a condition of their parole, as an alternative to anti-androgen drugs such as cyproterone acetate.^[4]

Benperidol was discovered at Janssen Pharmaceutica in 1961.

Synthesis

Benperidol synthesis:^[5]

See also

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

References

1. Möller; Müller; Bandelow: Neuroleptika, 2001, WVG; ISBN 3-8047-1773-X (in German)
2. Bobon J, Collard J, Lecoq R, Benperidol and promazine: a "double blind" comparative study in mental geriatrics, Acta Neurol Belg. 1963 Oct;63:839-43.
3. British National Formulary (49th), British Medical Association 2005 p 183
4. Murray MA, Bancroft JH, Anderson DC, Tennent TG, Carr PJ., Endocrine changes in male sexual deviants after treatment with anti-androgens, oestrogens or tranquillizers, Journal of Endocrinology. 1975 Nov;67(2):179-88.
5. BE 626307  (1963 to Janssen), C.A. 60, 10690c (1964), corresp. to GB 989755 .