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

Molecular Formula C21H23BrFNO2
Molecular Weight 420.315
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Bromperidol (marketed as Bromidol, Bromodol) is a butyrophenone derivative. It is a potent and long-acting neuroleptic, used as an antipsychotic in the treatment of schizophrenia. It was discovered at Janssen Pharmaceutica in 1966. Bromperidol is a bromine analog of Haloperidol hydrochloride (sc-203593) which functions as a D2DR (dopamine D2 receptor) antagonist. Studies suggest that cytochrome CYP3A4 catalyzes the dehydration of Bromperidol and N-dealkylation of Bromperidol. In addition, CYP3A4 can oxidize N-dealkylated Bromperidol back into Bromperidol. Alternately, Bromperidol antagonizes the Neuroendocrine DA receptors which regulate hypothalamic LH-RH release.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
8.5 ng/mL
0.18 mg/kg bw single, oral
dose: 0.18 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMPERIDOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
0.53 ng/mL
3 mg single, oral
dose: 3 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMPERIDOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2.38 ng/mL
6 mg single, oral
dose: 6 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMPERIDOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
150 ng × h/mL
0.18 mg/kg bw single, oral
dose: 0.18 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMPERIDOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
11.78 ng × h/mL
3 mg single, oral
dose: 3 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMPERIDOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
54.69 ng × h/mL
6 mg single, oral
dose: 6 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMPERIDOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
20.4 h
0.18 mg/kg bw single, oral
dose: 0.18 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMPERIDOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
24.1 h
3 mg single, oral
dose: 3 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMPERIDOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
38.7 h
6 mg single, oral
dose: 6 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMPERIDOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
60 mg 1 times / day multiple, oral
Highest studied dose
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Disc. AE: Depression, Akathisia...
Other AEs: Galactorrhea, Drowsiness...
AEs leading to
discontinuation/dose reduction:
Depression
Akathisia (4.3%)
Tremor (4.3%)
Other AEs:
Galactorrhea (13%)
Drowsiness
Excitement
Dry mouth
Blurred vision (13%)
asal congestion
Increased salivation
Constipation
Sources:
AEs

AEs

AESignificanceDosePopulation
Constipation
60 mg 1 times / day multiple, oral
Highest studied dose
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Drowsiness
60 mg 1 times / day multiple, oral
Highest studied dose
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Dry mouth
60 mg 1 times / day multiple, oral
Highest studied dose
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Excitement
60 mg 1 times / day multiple, oral
Highest studied dose
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Increased salivation
60 mg 1 times / day multiple, oral
Highest studied dose
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
asal congestion
60 mg 1 times / day multiple, oral
Highest studied dose
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Blurred vision 13%
60 mg 1 times / day multiple, oral
Highest studied dose
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Galactorrhea 13%
60 mg 1 times / day multiple, oral
Highest studied dose
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Akathisia 4.3%
Disc. AE
60 mg 1 times / day multiple, oral
Highest studied dose
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Tremor 4.3%
Disc. AE
60 mg 1 times / day multiple, oral
Highest studied dose
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Depression Disc. AE
60 mg 1 times / day multiple, oral
Highest studied dose
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.
2015-01-05
Synergistic drug combinations for tuberculosis therapy identified by a novel high-throughput screen.
2011-08
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010-12
Identification and quantification of 30 antipsychotics in blood using LC-MS/MS.
2010-08
Improvement of mutism in a catatonic schizophrenia case by add-on treatment with amantadine.
2010-06
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.
2009-12
Drugs associated with more suicidal ideations are also associated with more suicide attempts.
2009-10-02
Automated on-line in-tube solid-phase microextraction coupled with HPLC/MS/MS for the determination of butyrophenone derivatives in human plasma.
2009-06
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
The effects of atypical and conventional antipsychotics on reduced processing speed and psychomotor slowing in schizophrenia: a cross-sectional exploratory study.
2008-04
Pharmacogenetics of antipsychotic adverse effects: Case studies and a literature review for clinicians.
2007-12
Minimizing antipsychotic medication obviated the need for enema against severe constipation leading to paralytic ileus: a case report.
2007-10
Donepezil in Alzheimer's disease: From conventional trials to pharmacogenetics.
2007-06
Dopamine D2 receptor gene polymorphisms predict well the response to dopamine antagonists at therapeutic dosages in patients with schizophrenia.
2007-04
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.
2006-12
Pharmacokinetic parameters of bromperidol in Korean subjects.
2006-08
Association between multidrug resistance 1 (MDR1) gene polymorphisms and therapeutic response to bromperidol in schizophrenic patients: a preliminary study.
2006-03
Treatment with the new antipsychotic sertindole for late-occurring undesirable movement effects.
2005-11
Influence of duration of untreated psychosis on auditory P300 in drug-naive and first-episode schizophrenia.
2005-04
[Butyrophenone derivatives].
2004-12
Atypical properties of several classes of antipsychotic drugs on the basis of differential induction of Fos-like immunoreactivity in the rat brain.
2004-11-26
Two cases of deep vein thrombosis associated with antipsychotic drug use.
2004-08
Simultaneous determination of haloperidol and bromperidol and their reduced metabolites by liquid-liquid extraction and automated column-switching high-performance liquid chromatography.
2004-06-05
Establishment of new cloned enzyme donor immunoassays (CEDIA) for haloperidol and bromperidol.
2004-06
Depot bromperidol decanoate for schizophrenia.
2004
Effect of quetiapine in the treatment of panic attacks in patients with schizophrenia: 3 case reports.
2004
Poor reliability of therapeutic drug monitoring data for haloperidol and bromperidol using enzyme immunoassay.
2003-12
[Frontal dementia or dementia praecox? A case report of a psychotic disorder with a severe decline].
2003-10-22
Combination of dopamine D2 receptor gene polymorphisms as a possible predictor of treatment-resistance to dopamine antagonists in schizophrenic patients.
2003-09
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.
2003-03
Switching to amisulpride due to hepatic complications.
2002-05
Comparison of prolactin concentrations between haloperidol and bromperidol treatments in schizophrenic patients.
2002-04
The characteristics of side-effects of bromperidol in schizophrenic patients.
2002-02
Therapeutic effects of bromperidol on the five dimensions of schizophrenic symptoms.
2002-01
[Malignant syndrome caused by a combination of bromperidol and donepezil hydrochloride in a patient with probable dementia with Lewy bodies].
2001-11
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.
2001-08
Relationship between Taq1 A dopamine D2 receptor (DRD2) polymorphism and prolactin response to bromperidol.
2001-04-08
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.
2001-02-14
Lesioning the thalamus for dyskinesia.
2001
Association between TaqI A dopamine D2 receptor polymorphism and therapeutic response to bromperidol: a preliminary report.
2001
[Involvement of cytochromeP4503A4 in the metabolism of haloperidol and bromperidol].
1998-02
Possible interaction between cisapride and bromperidol.
1997-01
Positive and negative symptoms, depression and social disability in chronic schizophrenia: a comparative trial of bromperidol and fluphenazine decanoates.
1992-11
Neuroleptic malignant syndrome after clozapine plus carbamazepine.
1988-12-24
Clinical evaluation of bromperidol versus haloperidol in psychotic patients.
1980
Open study with bromperidol (C-C 2489), a new neuroleptic, for the determination of the neuroleptic threshold and the neuroleptic-therapeutic range.
1978-03
Clinical experiences in an open and a double-blind trial.
1978-01-01
Effects and side-effects of bromperidol in comparison with other antipsychotic drugs.
1978-01-01
Double-blind- evaluation of bromperidol versus haloperidol treatment in chronic psychotic patients.
1978-01-01
The initial US clinical experience in the management of schizophrenic patients with bromperidol.
1978-01-01
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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:34:51 GMT 2025
Edited
by admin
on Mon Mar 31 17:34:51 GMT 2025
Record UNII
LYH6F7I22E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BROMPERIDOL
EP   INN   JAN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
IMPROMEN
Preferred 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
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 Mon Mar 31 17:34:51 GMT 2025 , Edited by admin on Mon Mar 31 17:34:51 GMT 2025
WHO-VATC QN05AD06
Created by admin on Mon Mar 31 17:34:51 GMT 2025 , Edited by admin on Mon Mar 31 17:34:51 GMT 2025
WHO-ATC N05AD06
Created by admin on Mon Mar 31 17:34:51 GMT 2025 , Edited by admin on Mon Mar 31 17:34:51 GMT 2025
Code System Code Type Description
EVMPD
SUB05923MIG
Created by admin on Mon Mar 31 17:34:51 GMT 2025 , Edited by admin on Mon Mar 31 17:34:51 GMT 2025
PRIMARY
INN
3737
Created by admin on Mon Mar 31 17:34:51 GMT 2025 , Edited by admin on Mon Mar 31 17:34:51 GMT 2025
PRIMARY
DRUG CENTRAL
407
Created by admin on Mon Mar 31 17:34:51 GMT 2025 , Edited by admin on Mon Mar 31 17:34:51 GMT 2025
PRIMARY
SMS_ID
100000091973
Created by admin on Mon Mar 31 17:34:51 GMT 2025 , Edited by admin on Mon Mar 31 17:34:51 GMT 2025
PRIMARY
EPA CompTox
DTXSID0022690
Created by admin on Mon Mar 31 17:34:51 GMT 2025 , Edited by admin on Mon Mar 31 17:34:51 GMT 2025
PRIMARY
NCI_THESAURUS
C76439
Created by admin on Mon Mar 31 17:34:51 GMT 2025 , Edited by admin on Mon Mar 31 17:34:51 GMT 2025
PRIMARY
DRUG BANK
DB12401
Created by admin on Mon Mar 31 17:34:51 GMT 2025 , Edited by admin on Mon Mar 31 17:34:51 GMT 2025
PRIMARY
FDA UNII
LYH6F7I22E
Created by admin on Mon Mar 31 17:34:51 GMT 2025 , Edited by admin on Mon Mar 31 17:34:51 GMT 2025
PRIMARY
MERCK INDEX
m2722
Created by admin on Mon Mar 31 17:34:51 GMT 2025 , Edited by admin on Mon Mar 31 17:34:51 GMT 2025
PRIMARY Merck Index
MESH
C006820
Created by admin on Mon Mar 31 17:34:51 GMT 2025 , Edited by admin on Mon Mar 31 17:34:51 GMT 2025
PRIMARY
WIKIPEDIA
BROMPERIDOL
Created by admin on Mon Mar 31 17:34:51 GMT 2025 , Edited by admin on Mon Mar 31 17:34:51 GMT 2025
PRIMARY
NSC
759275
Created by admin on Mon Mar 31 17:34:51 GMT 2025 , Edited by admin on Mon Mar 31 17:34:51 GMT 2025
PRIMARY
ECHA (EC/EINECS)
233-943-3
Created by admin on Mon Mar 31 17:34:51 GMT 2025 , Edited by admin on Mon Mar 31 17:34:51 GMT 2025
PRIMARY
RXCUI
19777
Created by admin on Mon Mar 31 17:34:51 GMT 2025 , Edited by admin on Mon Mar 31 17:34:51 GMT 2025
PRIMARY RxNorm
CAS
10457-90-6
Created by admin on Mon Mar 31 17:34:51 GMT 2025 , Edited by admin on Mon Mar 31 17:34:51 GMT 2025
PRIMARY
ChEMBL
CHEMBL28218
Created by admin on Mon Mar 31 17:34:51 GMT 2025 , Edited by admin on Mon Mar 31 17:34:51 GMT 2025
PRIMARY
PUBCHEM
2448
Created by admin on Mon Mar 31 17:34:51 GMT 2025 , Edited by admin on Mon Mar 31 17:34:51 GMT 2025
PRIMARY
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