BENPERIDOL

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H24FN3O2
Molecular Weight	381.4433
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

FC1=CC=C(C=C1)C(=O)CCCN2CCC(CC2)N3C(=O)NC4=C3C=CC=C4

InChI

InChIKey=FEBOTPHFXYHVPL-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C22H24FN3O2
Molecular Weight	381.4433
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.netdoctor.co.uk/medicines/depression/a6216/anquil-benperidol/
Curator's Comment: description was created based on several sources, including

Benperidol is a relatively old antipsychotic drug that has been marketed since 1966. It has been used in Germany for 30 years, but is also available in Belgium, Greece, Italy, the Netherlands and the UK. 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). Benperidol was discovered at Janssen Pharmaceutica in 1961. Benperidol is a potent dopamine receptor antagonist, with a high affinity for the D2-sites. The antipsychotic effects of this drug are primarily due to blockade of the D receptors. In terms of D receptor blockade, benperidol is one of the most potent antipsychotic agents, being approximately eight times more potent than haloperidol. Benperidol also acts as a dopamine antagonist in the chemoreceptor trigger zone, giving rise to antiemetic properties. It is also a weak antagonist at muscarinic, histamine H1, and alpha1-adrenoceptors. Adverse effects include extrapyramidal side effects and tardive dykinesia

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine D2 receptor 311 Target ID: CHEMBL217 Sources: http://www.ncbi.nlm.nih.gov/pubmed/15846648	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 305 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11869652	Primary		Approved 8583	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
105.5 ng/mL CLINICAL TRIAL doi:10.1007/bf02247478	6 mg single, intravenous dose: 6 mg route of administration: Intravenous experiment type: SINGLE co-administered:	BENPERIDOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
10.2 ng/mL CLINICAL TRIAL doi:10.1007/bf02247478	6 mg single, oral dose: 6 mg route of administration: Oral experiment type: SINGLE co-administered:	BENPERIDOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
7.3 ng/mL CLINICAL TRIAL doi:10.1007/bf02247478	6 mg single, oral dose: 6 mg route of administration: Oral experiment type: SINGLE co-administered:	BENPERIDOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
157.9 ng × h/mL CLINICAL TRIAL doi:10.1007/bf02247478	6 mg single, intravenous dose: 6 mg route of administration: Intravenous experiment type: SINGLE co-administered:	BENPERIDOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
79.4 ng × h/mL CLINICAL TRIAL doi:10.1007/bf02247478	6 mg single, oral dose: 6 mg route of administration: Oral experiment type: SINGLE co-administered:	BENPERIDOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
64.5 ng × h/mL CLINICAL TRIAL doi:10.1007/bf02247478	6 mg single, oral dose: 6 mg route of administration: Oral experiment type: SINGLE co-administered:	BENPERIDOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
5.8 h CLINICAL TRIAL doi:10.1007/bf02247478	6 mg single, intravenous dose: 6 mg route of administration: Intravenous experiment type: SINGLE co-administered:	BENPERIDOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
5.53 h CLINICAL TRIAL doi:10.1007/bf02247478	6 mg single, oral dose: 6 mg route of administration: Oral experiment type: SINGLE co-administered:	BENPERIDOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
4.65 h CLINICAL TRIAL doi:10.1007/bf02247478	6 mg single, oral dose: 6 mg route of administration: Oral experiment type: SINGLE co-administered:	BENPERIDOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
6 mg single, oral Studied dose Dose: 6 mg Route: oral Route: single Dose: 6 mg Sources: https://pubmed.ncbi.nlm.nih.gov/7701049/	unhealthy Health Status: unhealthy Sex: M+F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/7701049/	Sources: https://pubmed.ncbi.nlm.nih.gov/7701049/
6 mg single, intravenous Studied dose Dose: 6 mg Route: intravenous Route: single Dose: 6 mg Sources: https://pubmed.ncbi.nlm.nih.gov/7701049/	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7701049/	Sources: https://pubmed.ncbi.nlm.nih.gov/7701049/

PubMed

Title	Date	PubMed
Synthesis and characterization of selective dopamine D2 receptor antagonists. 2. Azaindole, benzofuran, and benzothiophene analogs of L-741,626.	2010-07-15	20542439
The effect of antipsychotic medication on sexual function and serum prolactin levels in community-treated schizophrenic patients: results from the Schizophrenia Trial of Aripiprazole (STAR) study (NCT00237913).	2008-12-22	19102734
Validation of the reference tissue model for estimation of dopaminergic D2-like receptor binding with [18F](N-methyl)benperidol in humans.	2008-04	18355689
Radiation dosimetry of N-([11C]methyl)benperidol as determined by whole-body PET imaging of primates.	2008-04	18071701
[Recurrent dysregulation of body temperature during antipsychotic pharmacotherapy].	2008-03	17902059
Comparative evaluation of hERG potassium channel blockade by antipsychotics.	2007-09	17982510
Analysis of pharmacology data and the prediction of adverse drug reactions and off-target effects from chemical structure.	2007-06	17477341
Amisulpride-induced hyperprolactinaemia is not reversed by addition of aripiprazole.	2007-02	16942633
Quantitative determination of forty-eight antidepressants and antipsychotics in human serum by HPLC tandem mass spectrometry: a multi-level, single-sample approach.	2006-10-20	16798119
[Trazodone for the treatment of behavioral and psychological symptoms of dementia (BPSD) in Alzheimer's disease: a retrospective study focused on the aggression and negativism in caregiving situations].	2006-06	16856516
Synthesis and characterization of selective dopamine D2 receptor antagonists.	2006-02-01	16288878
Benperidol for schizophrenia.	2005-04-18	15846648
Olanzapine plasma concentration, average daily dose, and interaction with co-medication in schizophrenic patients.	2004-03	15048613
Complete dopamine D2 receptor occupancy without extrapyramidal side effects under benperidol.	2004-02	14709957
In vivo measurement of D2 receptor density and affinity for 18F-(3-N-methyl)benperidol in the rat striatum with a PET system for small laboratory animals.	2003-04	12679408
Bilateral increase in striatal dopamine D2 receptor density in the 6-hydroxydopamine-lesioned rat: a serial in vivo investigation with small animal PET.	2003-03	12634967
Benperidol for schizophrenia.	2002	11869652
Imaging of striatal dopamine D(2) receptors with a PET system for small laboratory animals in comparison with storage phosphor autoradiography: a validation study with (18)F-(N-methyl)benperidol.	2001-11	11696641
[Drug-induced asterixis amplified by relative hypoglycemia].	1996-04	8684512

Patents

Sample Use Guides

In Vivo Use Guide

adult: 0.003 to 0.01 mg/kg each 12 hours

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:35:41 GMT 2025` Edited by `admin` on `Mon Mar 31 17:35:41 GMT 2025`
Record UNII	97O6X78C53
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ANQUIL

Preferred Name

English

BENPERIDOL

Official Name

English

2H-BENZIMIDAZOL-2-ONE, 1-(1-(4-(4-FLUOROPHENYL)-4-OXOBUTYL)-4-PIPERIDINYL)-1,3-DIHYDRO-

Systematic Name

English

BENPERIDOL [MART.]

Common Name

English

BENPERIDOL [EP MONOGRAPH]

Common Name

English

benperidol [INN]

Common Name

English

1-(1-(3-(P-FLUOROBENZOYL)PROPYL)-4-PIPERIDYL)-2-BENZIMIDAZOLINONE

Common Name

English

Benperidol [WHO-DD]

Common Name

English

MCN-JR-4584

Code

English

BENPERIDOL [MI]

Common Name

English

R-4584

Code

English

BENPERIDOL [USAN]

Common Name

English

NSC-170982

Code

English

Classification Tree Code System Code

WHO-VATC

QN05AD07