BROMPERIDOL DECANOATE

Possibly Marketed Outside US

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

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine D2 receptor 311	Antagonist 2,849
Dopamine D2 receptor 311	Antagonist 2,849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 305	Primary		Approved 8,583	Unknown

C_max

Value	Dose	Analyte	Population
8.5 ng/mL	0.18 mg/kg bw single, oral	BROMPERIDOL plasma	Homo sapiens
0.53 ng/mL	3 mg single, oral	BROMPERIDOL plasma	Homo sapiens
2.38 ng/mL	6 mg single, oral	BROMPERIDOL plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
150 ng × h/mL	0.18 mg/kg bw single, oral	BROMPERIDOL plasma	Homo sapiens
11.78 ng × h/mL	3 mg single, oral	BROMPERIDOL plasma	Homo sapiens
54.69 ng × h/mL	6 mg single, oral	BROMPERIDOL plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
20.4 h	0.18 mg/kg bw single, oral	BROMPERIDOL plasma	Homo sapiens
24.1 h	3 mg single, oral	BROMPERIDOL plasma	Homo sapiens
38.7 h	6 mg single, oral	BROMPERIDOL plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
60 mg 1 times / day multiple, oral Highest studied dose	unhealthy, ADULT	Disc. AE: Depression, Akathisia... Other AEs: Galactorrhea, Drowsiness...

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AEs

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AE	Dose	Population
Constipation	60 mg 1 times / day multiple, oral Highest studied dose	unhealthy, ADULT
Drowsiness	60 mg 1 times / day multiple, oral Highest studied dose	unhealthy, ADULT
Dry mouth	60 mg 1 times / day multiple, oral Highest studied dose	unhealthy, ADULT
Excitement	60 mg 1 times / day multiple, oral Highest studied dose	unhealthy, ADULT
Increased salivation	60 mg 1 times / day multiple, oral Highest studied dose	unhealthy, ADULT

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PubMed

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Title	Date	PubMed
Clinical experiences in an open and a double-blind trial.	1978 Jan-Feb	347884
Positive and negative symptoms, depression and social disability in chronic schizophrenia: a comparative trial of bromperidol and fluphenazine decanoates.	1992 Nov	1487623
[Involvement of cytochromeP4503A4 in the metabolism of haloperidol and bromperidol].	1998 Feb	9592806
Relationship between Taq1 A dopamine D2 receptor (DRD2) polymorphism and prolactin response to bromperidol.	2001 Apr 8	11353448
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	11223117

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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

Bromperidol is able to antagonize as well as haloperidol the DA-induced LH-RH release.

Substance Class	Chemical
Record UNII	73LG72M4LV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BROMPERIDOL DECANOATE

Official Name

English

R-46541

Preferred 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

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Classification Tree

Code System

Code

Agent Affecting Nervous System

NCI_THESAURUS

C29710

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Code System

Code

Type

Description

EVMPD

SUB00880MIG

PRIMARY

RXCUI

186024

PRIMARY

RxNorm

ChEMBL

CHEMBL2106135

PRIMARY

SMS_ID

100000085143

PRIMARY

CAS

75067-66-2

PRIMARY

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BROMPERIDOL DECANOATE

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Interaction Type:

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IMPURITY -> PARENT

Interaction Type:

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Qualification:

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Amount:

RELATIONSHIP_AMOUNT [<0.5] PERCENT PEAK AREA (limits)


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IMPURITY -> PARENT

Interaction Type:

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Amount:

RELATIONSHIP_AMOUNT [<0.5] PERCENT PEAK AREA (limits)


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BROMPERIDOL UNDECANOATE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

RELATIONSHIP_AMOUNT [<0.5] PERCENT PEAK AREA (limits)


					50M4ORZ9YG

4-(4-BROMOPHENYL)-1-(4-(4-(4-(4-BROMOPHENYL)-4-HYDROXYPIPERIDIN-1-YL)PHENYL)-4-OXOBUTYL)PIPERIDIN-4-YL DECANOATE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

RELATIONSHIP_AMOUNT [<0.5] PERCENT PEAK AREA (limits)


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4-(BIPHENYL-4-YL)-1-(4-(4-FLUOROPHENYL)-4-OXOBUTYL)PIPERIDIN-4-YL DECANOATE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

RELATIONSHIP_AMOUNT [<0.5] PERCENT PEAK AREA (limits)

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SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

PubMed

Patents

Sample Use Guides

C_max

T_1/2