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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

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
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 Nov
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 Apr
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
Quantitative determination of forty-eight antidepressants and antipsychotics in human serum by HPLC tandem mass spectrometry: a multi-level, single-sample approach.
2006 Oct 20
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
[Recurrent dysregulation of body temperature during antipsychotic pharmacotherapy].
2008 Mar
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
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
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Code System Code Type Description
SMS_ID
100000086355
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PRIMARY
FDA UNII
97O6X78C53
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MESH
D001544
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ChEMBL
CHEMBL297302
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DRUG CENTRAL
312
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DRUG BANK
DB12867
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CAS
2062-84-2
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WIKIPEDIA
BENPERIDOL
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EPA CompTox
DTXSID7045364
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NCI_THESAURUS
C81086
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PUBCHEM
16363
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NSC
170982
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MERCK INDEX
m2320
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PRIMARY Merck Index
RXCUI
1373
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PRIMARY RxNorm
EVMPD
SUB05727MIG
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ECHA (EC/EINECS)
218-172-2
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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