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
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
| 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
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL339 |
|||
Target ID: CHEMBL217 Sources: https://www.genome.jp/dbget-bin/www_bget?D02626 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
8.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16915578/ |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
150 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16915578/ |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
20.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16915578/ |
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
| Dose | Population | Adverse 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 Other AEs:Akathisia (4.3%) Tremor (4.3%) Galactorrhea (13%) Sources: Drowsiness Excitement Dry mouth Blurred vision (13%) asal congestion Increased salivation Constipation |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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
| Title | Date | PubMed |
|---|---|---|
| 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
Sample Use Guides
In Vivo Use Guide
Sources: http://www.ndrugs.com/?s=bromperidol
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/417559
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
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admin
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Mon Mar 31 17:34:51 GMT 2025
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| Record UNII |
LYH6F7I22E
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Validated (UNII)
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C29710
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QN05AD06
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N05AD06
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SUB05923MIG
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C76439
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DB12401
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m2722
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C006820
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BROMPERIDOL
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759275
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233-943-3
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19777
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10457-90-6
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CHEMBL28218
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2448
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