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Details

Stereochemistry ACHIRAL
Molecular Formula C31H41BrFNO3
Molecular Weight 574.565
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BROMPERIDOL DECANOATE

SMILES

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

InChI

InChIKey=ZINCPWWBSRSXBH-UHFFFAOYSA-N
InChI=1S/C31H41BrFNO3/c1-2-3-4-5-6-7-8-11-30(36)37-31(26-14-16-27(32)17-15-26)20-23-34(24-21-31)22-9-10-29(35)25-12-18-28(33)19-13-25/h12-19H,2-11,20-24H2,1H3

HIDE SMILES / InChI
Molecular Formula C31H41BrFNO3
Molecular Weight 574.565
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
Antagonist
2778
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
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
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

EP0454773
2

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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:48:16 GMT 2023
Edited
by admin
on Fri Dec 15 17:48:16 GMT 2023
Record UNII
73LG72M4LV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BROMPERIDOL DECANOATE
EP   MART.   USAN   USP-RS   WHO-DD  
USAN  
Official Name English
BROMPERIDOL DECANOATE [USP-RS]
Common Name English
BROMPERIDOL DECANOATE [MART.]
Common Name English
4-(4-(P-BROMOPHENYL)-4-HYDROXYPIPERIDINOL)-4'-FLUOROBUTYROPHENONE DECANOATE
Common Name English
DECANOIC ACID, 4-(4-BROMOPHENYL)-1-(4-(4-FLUOROPHENYL)-4-OXOBUTYL)-4-PIPERIDINYL ESTER
Common Name English
R-46541
Code English
BROMPERIDOL DECANOATE [EP MONOGRAPH]
Common Name English
Bromperidol decanoate [WHO-DD]
Common Name English
BROMPERIDOL DECANOATE (ESTER)
Common Name English
BROMPERIDOL DECANOATE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29710
Created by admin on Fri Dec 15 17:48:16 GMT 2023 , Edited by admin on Fri Dec 15 17:48:16 GMT 2023
Code System Code Type Description
EVMPD
SUB00880MIG
Created by admin on Fri Dec 15 17:48:16 GMT 2023 , Edited by admin on Fri Dec 15 17:48:16 GMT 2023
PRIMARY
RXCUI
186024
Created by admin on Fri Dec 15 17:48:16 GMT 2023 , Edited by admin on Fri Dec 15 17:48:16 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL2106135
Created by admin on Fri Dec 15 17:48:16 GMT 2023 , Edited by admin on Fri Dec 15 17:48:16 GMT 2023
PRIMARY
SMS_ID
100000085143
Created by admin on Fri Dec 15 17:48:16 GMT 2023 , Edited by admin on Fri Dec 15 17:48:16 GMT 2023
PRIMARY
CAS
75067-66-2
Created by admin on Fri Dec 15 17:48:16 GMT 2023 , Edited by admin on Fri Dec 15 17:48:16 GMT 2023
PRIMARY
RS_ITEM_NUM
1077887
Created by admin on Fri Dec 15 17:48:16 GMT 2023 , Edited by admin on Fri Dec 15 17:48:16 GMT 2023
PRIMARY
ECHA (EC/EINECS)
278-065-1
Created by admin on Fri Dec 15 17:48:16 GMT 2023 , Edited by admin on Fri Dec 15 17:48:16 GMT 2023
PRIMARY
FDA UNII
73LG72M4LV
Created by admin on Fri Dec 15 17:48:16 GMT 2023 , Edited by admin on Fri Dec 15 17:48:16 GMT 2023
PRIMARY
MESH
C077144
Created by admin on Fri Dec 15 17:48:16 GMT 2023 , Edited by admin on Fri Dec 15 17:48:16 GMT 2023
PRIMARY
NCI_THESAURUS
C142969
Created by admin on Fri Dec 15 17:48:16 GMT 2023 , Edited by admin on Fri Dec 15 17:48:16 GMT 2023
PRIMARY
WIKIPEDIA
Bromperidol decanoate
Created by admin on Fri Dec 15 17:48:16 GMT 2023 , Edited by admin on Fri Dec 15 17:48:16 GMT 2023
PRIMARY
PUBCHEM
156321
Created by admin on Fri Dec 15 17:48:16 GMT 2023 , Edited by admin on Fri Dec 15 17:48:16 GMT 2023
PRIMARY
EPA CompTox
DTXSID30226039
Created by admin on Fri Dec 15 17:48:16 GMT 2023 , Edited by admin on Fri Dec 15 17:48:16 GMT 2023
PRIMARY
Related Record Type Details
Structure of BROMPERIDOL DECANOATE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
Related Record Type Details
Structure of BROMPERIDOL
METABOLITE ACTIVE -> PRODRUG
Related Record Type Details
Structure of 4-(4-BROMOPHENYL)-1-(4-(2-FLUOROPHENYL)-4-OXOBUTYL)-PIPERIDIN-4-YL DECANOATE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of BROMPERIDOL OCTANOATE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of BROMPERIDOL UNDECANOATE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 4-(4-BROMOPHENYL)-1-(4-(4-(4-(4-BROMOPHENYL)-4-HYDROXYPIPERIDIN-1-YL)PHENYL)-4-OXOBUTYL)PIPERIDIN-4-YL DECANOATE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 4-(BIPHENYL-4-YL)-1-(4-(4-FLUOROPHENYL)-4-OXOBUTYL)PIPERIDIN-4-YL DECANOATE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of BROMPERIDOL DODECANOATE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 4-(4-BROMOPHENYL)-1-(4-(3-ETHYL-4-FLUOROPHENYL)-4-OXOBUTYL)-PIPERIDIN-4-YL DECANOATE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 4-(4'-BROMOBIPHENYL-4-YL)-1-(4-(4-FLUOROPHENYL)-4-OXOBUTYL)PIPERIDIN-4-YL DECANOATE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of BROMPERIDOL
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of DECHLORO HALOPERIDOL DECANOATE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of BROMPERIDOL NONANOATE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of BROMPERIDOL
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