Benperidol

Multi tool use
Benperidol
 |
 |
Clinical data |
Trade names |
Anquil |
AHFS/Drugs.com
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International Drug Names |
Routes of administration |
Oral |
ATC code |
|
Legal status |
Legal status |
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Identifiers |
IUPAC name
- 1-{1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl}-1,3-dihydro-2H-benzimidazol-2-one
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CAS Number |
983-42-6 N
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PubChem CID
|
|
ChemSpider |
15521 Y
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UNII |
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ChEMBL |
ChEMBL297302 Y
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ECHA InfoCard |
100.016.521 
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Chemical and physical data |
Formula |
C22H24FN3O2
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Molar mass |
381.443 g/mol |
3D model (JSmol) |
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SMILES
Fc1ccc(cc1)C(=O)CCCN4CCC(N3c2ccccc2NC3=O)CC4
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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) Y
Key:FEBOTPHFXYHVPL-UHFFFAOYSA-N Y
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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 antisocial hypersexual behaviour,[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.
Synthesis
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
^ "Benperidol - a drug for sexual offenders?". Drug and Therapeutics Bulletin. BMJ Publishing Group Ltd. 12: 12. 1974-02-01..mw-parser-output cite.citation{font-style:inherit}.mw-parser-output q{quotes:"""""""'""'"}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-limited a,.mw-parser-output .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}
^ Möller; Müller; Bandelow: Neuroleptika, 2001, WVG;
ISBN 3-8047-1773-X (in German)
^ 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.
^ British National Formulary (49th), British Medical Association 2005 p 183
^ 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.
^ BE 626307 (1963 to Janssen), C.A. 60, 10690c (1964), corresp. to GB 989755 .
Antipsychotics (N05A)
|
Typical |
Butyrophenones: Benperidol
- Bromperidol
- Droperidol
Haloperidol#
- Moperone
- Pipamperone
- Spiperone
- Timiperone
- Trifluperidol
Diphenylbutylpiperidines: Fluspirilene
- Penfluridol
- Pimozide
Phenothiazines: Acetophenazine
- Butaperazine
Carphenazine (carfenazine)‡
- Chlorpromazine
- Cyamemazine
- Dixyrazine
- Fluphenazine
- Levomepromazine (methotrimeprazine)
- Mesoridazine
- Perazine
- Periciazine
- Perphenazine
- Piperacetazine
- Pipotiazine
- Prochlorperazine
- Promazine
- Sulforidazine
- Thiopropazate
- Thioproperazine
- Thioridazine
- Trifluoperazine
- Triflupromazine
Thioxanthenes: Chlorprothixene
- Clopenthixol
- Flupentixol
- Tiotixene (thiothixene)
- Zuclopenthixol
|
Disputed |
Benzamides: Amisulpride
- Levosulpiride
- Nemonapride
Remoxipride‡
- Sulpiride
- Sultopride
- Tiapride
Veralipride‡
Butyrophenones: Melperone
Tricyclics: Carpipramine
- Clocapramine
- Clorotepine
- Clotiapine
- Loxapine
- Mosapramine
|
Atypical |
Benzisoxazole/benzisothiazoles: Iloperidone
- Lurasidone
- Paliperidone
- Paliperidone palmitate
- Perospirone
Risperidone#
- Ziprasidone
Butyrophenones: Lumateperone†
Phenylpiperazines/quinolinones: Aripiprazole
- Aripiprazole lauroxil
- Brexpiprazole
- Cariprazine
RP-5063†
Tricyclics: Asenapine
Clozapine#
- Olanzapine
- Quetiapine
- Zotepine
Others: Blonanserin
- Pimavanserin
- Sertindole
|
Others |
- Azacyclonol
- Cannabidiol
- Oxypertine
- Reserpine
- Tetrabenazine
|
#WHO-EM
‡Withdrawn from market
Clinical trials:
†Phase III
§Never to phase III
|
Dopamine receptor modulators
|
D1-like |
Agonists |
Benzazepines: 6-Br-APB
- Fenoldopam
- SKF-38,393
- SKF-77,434
- SKF-81,297
- SKF-82,958
- SKF-83,959
- Trepipam
- Zelandopam
Ergolines: Cabergoline
- CY-208,243
- Dihydroergocryptine
- LEK-8829
- Lisuride
- Pergolide
- Terguride
Dihydrexidine derivatives: A-77636
- A-86929
- Adrogolide (ABT-431, DAS-431)
- Dihydrexidine
- Dinapsoline
- Dinoxyline
- Doxanthrine
Phenethylamines: BCO-001
- Deoxyepinephrine (N-methyldopamine, epinine)
- Dopexamine
- Etilevodopa
- Ibopamine
L-DOPA (levodopa)
- Melevodopa
L-Phenylalanine
L-Tyrosine
- XP21279
Others: A-68930
- Apomorphine
- Isocorypalmine
- Nuciferine
- PF-6649751
- PF 6669571
- Propylnorapomorphine
- Rotigotine
- SKF-89,145
- SKF-89,626
- Stepholidine
- Tetrahydropalmatine
|
Antagonists |
Typical antipsychotics: Butaclamol
- Chlorpromazine
- Chlorprothixene
Flupentixol (flupenthixol) (+melitracen)
- Fluphenazine
- Loxapine
Perphenazine (+amitriptyline)
- Pifluthixol
- Thioridazine
- Thiothixene
Trifluoperazine (+tranylcypromine)
- Zuclopenthixol
Atypical antipsychotics: Asenapine
- Clorotepine
- Clotiapine
- Clozapine
- DHA-clozapine
- Fluperlapine
- Iloperidone
- Norclozapine
- Norquetiapine
Olanzapine (++fluoxetine)
- Paliperidone
- Quetiapine
- Risperidone
- Tefludazine
- Zicronapine
- Ziprasidone
- Zotepine
Others: Berupipam
- Ecopipam
- EEDQ
- Metitepine (methiothepin)
- Odapipam
- Perlapine
- SCH-23390
|
|
D2-like |
Agonists |
Adamantanes: Amantadine
- Memantine
- Rimantadine
Aminotetralins: 5-OH-DPAT
- 7-OH-DPAT
- 8-OH-PBZI
- Rotigotine
- UH-232
Ergolines: Bromocriptine
- Cabergoline
- Dihydroergocryptine
- Epicriptine
- Ergocornine
- Lergotrile
- Lisuride
- LSD
- Pergolide
- Terguride
Dihydrexidine derivatives: 2-OH-NPA
- Ciladopa
- Dihydrexidine
- Dinoxyline
- N,N-Propyldihydrexidine
Phenethylamines: Deoxyepinephrine (N-methyldopamine, epinine)
- Dopexamine
- Etilevodopa
- Ibopamine
L-DOPA (levodopa)
L-Phenylalanine
L-Tyrosine
- Melevodopa
- XP21279
Atypical antipsychotics: Alentemol (U-66444B)
Aripiprazole (+sertraline)
- Aripiprazole lauroxil
- Bifeprunox
- Brexpiprazole
- Cariprazine
- F-15063
- Lumateperone
- Norclozapine
- RP-5063
Others: 3-PPP
- A-412997
- ABT-670
- ABT-724
- Adrafinil
- Aplindore
- Apomorphine
- Arketamine
- Armodafinil
- BP-897
- Captodiame
- CP-226,269
- Dizocilpine
- Esketamine
- Flibanserin
- GSK-789,472
- Ketamine
- Mesulergine
- Modafinil
- OSU-6162
- Pardoprunox
- PD-128,907
- PD-168,077
- PF-219,061
- PF-592,379
- Phencyclidine
- Piribedil
- Pramipexole
- Preclamol
- Propylnorapomorphine
- Pukateine
- Quinagolide
- Quinelorane
- Quinpirole
- RDS-127
- Ro10-5824
- Ropinirole
- Roxindole
- Salvinorin A
- SKF-83,959
- Sumanirole
- Talipexole
- Umespirone
- WAY-100,635
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Antagonists |
|
|
- See also: Receptor/signaling modulators
- Adrenergics
- Serotonergics
- Monoamine reuptake inhibitors
- Monoamine releasing agents
- Monoamine metabolism modulators
- Monoamine neurotoxins
|
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