U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C21H23BrFNO2
Molecular Weight 420.315
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BROMPERIDOL

SMILES

OC1(CCN(CCCC(=O)C2=CC=C(F)C=C2)CC1)C3=CC=C(Br)C=C3

InChI

InChIKey=RKLNONIVDFXQRX-UHFFFAOYSA-N
InChI=1S/C21H23BrFNO2/c22-18-7-5-17(6-8-18)21(26)11-14-24(15-12-21)13-1-2-20(25)16-3-9-19(23)10-4-16/h3-10,26H,1-2,11-15H2

HIDE SMILES / InChI
Bromperidol decanoate is a long-acting antipsychotic medication used in at least Belgium, Germany, Italy, and the Netherlands. In clinical trials, Bromperidol decanoate was effective in the treatment of residual schizophrenia, with significant differences between before and after treatment ratings for symptoms. The preparation seems to be less potent than other depot antipsychotics (such as fluphenazine and haloperidol decanoate) and better than placebo injection. If bromperidol decanoate is available to the clinician it may be a viable choice, especially when there are reasons not to use fluphenazine or haloperidol decanoate.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Clinical experiences in an open and a double-blind trial.
1978 Jan-Feb
Effects and side-effects of bromperidol in comparison with other antipsychotic drugs.
1978 Jan-Feb
Double-blind- evaluation of bromperidol versus haloperidol treatment in chronic psychotic patients.
1978 Jan-Feb
The initial US clinical experience in the management of schizophrenic patients with bromperidol.
1978 Jan-Feb
Open study with bromperidol (C-C 2489), a new neuroleptic, for the determination of the neuroleptic threshold and the neuroleptic-therapeutic range.
1978 Mar
Clinical evaluation of bromperidol versus haloperidol in psychotic patients.
1980
Neuroleptic malignant syndrome after clozapine plus carbamazepine.
1988 Dec 24-31
Positive and negative symptoms, depression and social disability in chronic schizophrenia: a comparative trial of bromperidol and fluphenazine decanoates.
1992 Nov
Possible interaction between cisapride and bromperidol.
1997 Jan
[Involvement of cytochromeP4503A4 in the metabolism of haloperidol and bromperidol].
1998 Feb
Lesioning the thalamus for dyskinesia.
2001
Association between TaqI A dopamine D2 receptor polymorphism and therapeutic response to bromperidol: a preliminary report.
2001
Relationship between Taq1 A dopamine D2 receptor (DRD2) polymorphism and prolactin response to bromperidol.
2001 Apr 8
The -141C Ins/Del polymorphism in the dopamine D2 receptor gene promoter region is associated with anxiolytic and antidepressive effects during treatment with dopamine antagonists in schizophrenic patients.
2001 Aug
No relationship between--141C Ins/Del polymorphism in the promoter region of dopamine D2 receptor and extrapyramidal adverse effects of selective dopamine D2 antagonists in schizophrenic patients: a preliminary study.
2001 Feb 14
[Malignant syndrome caused by a combination of bromperidol and donepezil hydrochloride in a patient with probable dementia with Lewy bodies].
2001 Nov
Comparison of prolactin concentrations between haloperidol and bromperidol treatments in schizophrenic patients.
2002 Apr
The characteristics of side-effects of bromperidol in schizophrenic patients.
2002 Feb
Therapeutic effects of bromperidol on the five dimensions of schizophrenic symptoms.
2002 Jan
Switching to amisulpride due to hepatic complications.
2002 May
Poor reliability of therapeutic drug monitoring data for haloperidol and bromperidol using enzyme immunoassay.
2003 Dec
Screening, library-assisted identification and validated quantification of fifteen neuroleptics and three of their metabolites in plasma by liquid chromatography/mass spectrometry with atmospheric pressure chemical ionization.
2003 Mar
[Frontal dementia or dementia praecox? A case report of a psychotic disorder with a severe decline].
2003 Mar-Apr
Combination of dopamine D2 receptor gene polymorphisms as a possible predictor of treatment-resistance to dopamine antagonists in schizophrenic patients.
2003 Sep
Depot bromperidol decanoate for schizophrenia.
2004
Two cases of deep vein thrombosis associated with antipsychotic drug use.
2004 Aug
[Butyrophenone derivatives].
2004 Dec
Establishment of new cloned enzyme donor immunoassays (CEDIA) for haloperidol and bromperidol.
2004 Jun
Simultaneous determination of haloperidol and bromperidol and their reduced metabolites by liquid-liquid extraction and automated column-switching high-performance liquid chromatography.
2004 Jun 5
Atypical properties of several classes of antipsychotic drugs on the basis of differential induction of Fos-like immunoreactivity in the rat brain.
2004 Nov 26
Effect of quetiapine in the treatment of panic attacks in patients with schizophrenia: 3 case reports.
2004 Winter
Influence of duration of untreated psychosis on auditory P300 in drug-naive and first-episode schizophrenia.
2005 Apr
Treatment with the new antipsychotic sertindole for late-occurring undesirable movement effects.
2005 Nov
Pharmacokinetic parameters of bromperidol in Korean subjects.
2006 Aug
Sensitive determination of 4-(4-bromophenyl)-4-hydroxypiperidine, a metabolite of bromperidol, in rat plasma by HPLC with fluorescence detection after pre-column derivatization using 4-fluoro-7-nitro-2,1,3-benzoxadiazole.
2006 Dec
Association between multidrug resistance 1 (MDR1) gene polymorphisms and therapeutic response to bromperidol in schizophrenic patients: a preliminary study.
2006 Mar
Dopamine D2 receptor gene polymorphisms predict well the response to dopamine antagonists at therapeutic dosages in patients with schizophrenia.
2007 Apr
Pharmacogenetics of antipsychotic adverse effects: Case studies and a literature review for clinicians.
2007 Dec
Donepezil in Alzheimer's disease: From conventional trials to pharmacogenetics.
2007 Jun
Minimizing antipsychotic medication obviated the need for enema against severe constipation leading to paralytic ileus: a case report.
2007 Oct
The effects of atypical and conventional antipsychotics on reduced processing speed and psychomotor slowing in schizophrenia: a cross-sectional exploratory study.
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
Mechanisms of action of antipsychotic drugs of different classes, refractoriness to therapeutic effects of classical neuroleptics, and individual variation in sensitivity to their actions: Part I.
2009 Dec
Automated on-line in-tube solid-phase microextraction coupled with HPLC/MS/MS for the determination of butyrophenone derivatives in human plasma.
2009 Jun
Drugs associated with more suicidal ideations are also associated with more suicide attempts.
2009 Oct 2
Identification and quantification of 30 antipsychotics in blood using LC-MS/MS.
2010 Aug
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Improvement of mutism in a catatonic schizophrenia case by add-on treatment with amantadine.
2010 Jun
Synergistic drug combinations for tuberculosis therapy identified by a novel high-throughput screen.
2011 Aug
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.
2015 Jan 5
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Oral Schizophrenia: Adult: 1-15 mg daily, up to 50 mg daily. Intramuscular Schizophrenia: Adult: Long-term therapy: Up to 300 mg every 4 wk via deep inj. Intramuscular Psychoses: Adult: Long-term therapy: Up to 300 mg every 4 wk via deep inj. Oral Psychoses: Adult: 1-15 mg daily, up to 50 mg daily.
Route of Administration: Other
In Vitro Use Guide
Curator's Comment: In in vivo and in vitro experiements the antidopaminergic action of bromperidol, evaluated by PRL release, can be considered intermediate between pimozide and haloperidol.
Bromperidol is able to antagonize as well as haloperidol the DA-induced LH-RH release.
Name Type Language
BROMPERIDOL
EP   INN   JAN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
R-11333
Code English
1-BUTANONE, 4-(4-(4-BROMOPHENYL)-4-HYDROXY-1-PIPERIDINYL)-1-(4-FLUOROPHENYL)-
Systematic Name English
BROMPERIDOL [EP MONOGRAPH]
Common Name English
NSC-759275
Code English
BROMPERIDOL [MART.]
Common Name English
BROMPERIDOL [MI]
Common Name English
R 11,333
Code English
BROMPERIDOL [JAN]
Common Name English
4-(4-(P-BROMOPHENYL)-4-HYDROXYPIPERIDINO)-4'-FLUOROBUTYROPHENONE
Common Name English
IMPROMEN
Brand Name English
BROMPERIDOL [USAN]
Common Name English
BROMPERIDOL DECANOATE IMPURITY G [EP IMPURITY]
Common Name English
bromperidol [INN]
Common Name English
Bromperidol [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29710
Created by admin on Fri Dec 15 15:00:21 UTC 2023 , Edited by admin on Fri Dec 15 15:00:21 UTC 2023
WHO-VATC QN05AD06
Created by admin on Fri Dec 15 15:00:21 UTC 2023 , Edited by admin on Fri Dec 15 15:00:21 UTC 2023
WHO-ATC N05AD06
Created by admin on Fri Dec 15 15:00:21 UTC 2023 , Edited by admin on Fri Dec 15 15:00:21 UTC 2023
Code System Code Type Description
EVMPD
SUB05923MIG
Created by admin on Fri Dec 15 15:00:21 UTC 2023 , Edited by admin on Fri Dec 15 15:00:21 UTC 2023
PRIMARY
INN
3737
Created by admin on Fri Dec 15 15:00:21 UTC 2023 , Edited by admin on Fri Dec 15 15:00:21 UTC 2023
PRIMARY
DRUG CENTRAL
407
Created by admin on Fri Dec 15 15:00:21 UTC 2023 , Edited by admin on Fri Dec 15 15:00:21 UTC 2023
PRIMARY
SMS_ID
100000091973
Created by admin on Fri Dec 15 15:00:21 UTC 2023 , Edited by admin on Fri Dec 15 15:00:21 UTC 2023
PRIMARY
EPA CompTox
DTXSID0022690
Created by admin on Fri Dec 15 15:00:21 UTC 2023 , Edited by admin on Fri Dec 15 15:00:21 UTC 2023
PRIMARY
NCI_THESAURUS
C76439
Created by admin on Fri Dec 15 15:00:21 UTC 2023 , Edited by admin on Fri Dec 15 15:00:21 UTC 2023
PRIMARY
DRUG BANK
DB12401
Created by admin on Fri Dec 15 15:00:21 UTC 2023 , Edited by admin on Fri Dec 15 15:00:21 UTC 2023
PRIMARY
FDA UNII
LYH6F7I22E
Created by admin on Fri Dec 15 15:00:21 UTC 2023 , Edited by admin on Fri Dec 15 15:00:21 UTC 2023
PRIMARY
MERCK INDEX
m2722
Created by admin on Fri Dec 15 15:00:21 UTC 2023 , Edited by admin on Fri Dec 15 15:00:21 UTC 2023
PRIMARY Merck Index
MESH
C006820
Created by admin on Fri Dec 15 15:00:21 UTC 2023 , Edited by admin on Fri Dec 15 15:00:21 UTC 2023
PRIMARY
WIKIPEDIA
BROMPERIDOL
Created by admin on Fri Dec 15 15:00:21 UTC 2023 , Edited by admin on Fri Dec 15 15:00:21 UTC 2023
PRIMARY
NSC
759275
Created by admin on Fri Dec 15 15:00:21 UTC 2023 , Edited by admin on Fri Dec 15 15:00:21 UTC 2023
PRIMARY
ECHA (EC/EINECS)
233-943-3
Created by admin on Fri Dec 15 15:00:21 UTC 2023 , Edited by admin on Fri Dec 15 15:00:21 UTC 2023
PRIMARY
RXCUI
19777
Created by admin on Fri Dec 15 15:00:21 UTC 2023 , Edited by admin on Fri Dec 15 15:00:21 UTC 2023
PRIMARY RxNorm
CAS
10457-90-6
Created by admin on Fri Dec 15 15:00:21 UTC 2023 , Edited by admin on Fri Dec 15 15:00:21 UTC 2023
PRIMARY
ChEMBL
CHEMBL28218
Created by admin on Fri Dec 15 15:00:21 UTC 2023 , Edited by admin on Fri Dec 15 15:00:21 UTC 2023
PRIMARY
PUBCHEM
2448
Created by admin on Fri Dec 15 15:00:21 UTC 2023 , Edited by admin on Fri Dec 15 15:00:21 UTC 2023
PRIMARY