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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 of BENPERIDOL

SMILES

FC1=CC=C(C=C1)C(=O)CCCN2CCC(CC2)N3C(=O)NC4=CC=CC=C34

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
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

Originator

Sources: Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales (1961), 155, 2452-5.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[Drug-induced asterixis amplified by relative hypoglycemia].
1996 Apr
Complete dopamine D2 receptor occupancy without extrapyramidal side effects under benperidol.
2004 Feb
Olanzapine plasma concentration, average daily dose, and interaction with co-medication in schizophrenic patients.
2004 Mar
Benperidol for schizophrenia.
2005 Apr 18
Synthesis and characterization of selective dopamine D2 receptor antagonists.
2006 Feb 1
[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 Jun
Validation of the reference tissue model for estimation of dopaminergic D2-like receptor binding with [18F](N-methyl)benperidol in humans.
2008 Apr
Radiation dosimetry of N-([11C]methyl)benperidol as determined by whole-body PET imaging of primates.
2008 Apr
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 Dec 22
Synthesis and characterization of selective dopamine D2 receptor antagonists. 2. Azaindole, benzofuran, and benzothiophene analogs of L-741,626.
2010 Jul 15
Patents

Sample Use Guides

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 Fri Dec 15 15:01:31 GMT 2023
Edited
by admin
on Fri Dec 15 15:01:31 GMT 2023
Record UNII
97O6X78C53
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BENPERIDOL
EP   INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
2H-BENZIMIDAZOL-2-ONE, 1-(1-(4-(4-FLUOROPHENYL)-4-OXOBUTYL)-4-PIPERIDINYL)-1,3-DIHYDRO-
Systematic Name English
ANQUIL
Brand 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
Created by admin on Fri Dec 15 15:01:31 GMT 2023 , Edited by admin on Fri Dec 15 15:01:31 GMT 2023
WHO-ATC N05AD07
Created by admin on Fri Dec 15 15:01:31 GMT 2023 , Edited by admin on Fri Dec 15 15:01:31 GMT 2023
NCI_THESAURUS C66883
Created by admin on Fri Dec 15 15:01:31 GMT 2023 , Edited by admin on Fri Dec 15 15:01:31 GMT 2023
Code System Code Type Description
SMS_ID
100000086355
Created by admin on Fri Dec 15 15:01:31 GMT 2023 , Edited by admin on Fri Dec 15 15:01:31 GMT 2023
PRIMARY
FDA UNII
97O6X78C53
Created by admin on Fri Dec 15 15:01:31 GMT 2023 , Edited by admin on Fri Dec 15 15:01:31 GMT 2023
PRIMARY
MESH
D001544
Created by admin on Fri Dec 15 15:01:31 GMT 2023 , Edited by admin on Fri Dec 15 15:01:31 GMT 2023
PRIMARY
ChEMBL
CHEMBL297302
Created by admin on Fri Dec 15 15:01:31 GMT 2023 , Edited by admin on Fri Dec 15 15:01:31 GMT 2023
PRIMARY
DRUG CENTRAL
312
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PRIMARY
DRUG BANK
DB12867
Created by admin on Fri Dec 15 15:01:31 GMT 2023 , Edited by admin on Fri Dec 15 15:01:31 GMT 2023
PRIMARY
CAS
2062-84-2
Created by admin on Fri Dec 15 15:01:31 GMT 2023 , Edited by admin on Fri Dec 15 15:01:31 GMT 2023
PRIMARY
WIKIPEDIA
BENPERIDOL
Created by admin on Fri Dec 15 15:01:31 GMT 2023 , Edited by admin on Fri Dec 15 15:01:31 GMT 2023
PRIMARY
EPA CompTox
DTXSID7045364
Created by admin on Fri Dec 15 15:01:31 GMT 2023 , Edited by admin on Fri Dec 15 15:01:31 GMT 2023
PRIMARY
NCI_THESAURUS
C81086
Created by admin on Fri Dec 15 15:01:31 GMT 2023 , Edited by admin on Fri Dec 15 15:01:31 GMT 2023
PRIMARY
PUBCHEM
16363
Created by admin on Fri Dec 15 15:01:31 GMT 2023 , Edited by admin on Fri Dec 15 15:01:31 GMT 2023
PRIMARY
NSC
170982
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PRIMARY
MERCK INDEX
m2320
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PRIMARY Merck Index
RXCUI
1373
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PRIMARY RxNorm
EVMPD
SUB05727MIG
Created by admin on Fri Dec 15 15:01:31 GMT 2023 , Edited by admin on Fri Dec 15 15:01:31 GMT 2023
PRIMARY
ECHA (EC/EINECS)
218-172-2
Created by admin on Fri Dec 15 15:01:31 GMT 2023 , Edited by admin on Fri Dec 15 15:01:31 GMT 2023
PRIMARY
INN
1577
Created by admin on Fri Dec 15 15:01:31 GMT 2023 , Edited by admin on Fri Dec 15 15:01:31 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY