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Details

Stereochemistry ACHIRAL
Molecular Formula C21H25NO.BrH
Molecular Weight 388.341
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Benztropine hydrobromide

SMILES

Br.CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(C3=CC=CC=C3)C4=CC=CC=C4

InChI

InChIKey=DFENFKJORSPHQZ-BWSPSPBFSA-N
InChI=1S/C21H25NO.BrH/c1-22-18-12-13-19(22)15-20(14-18)23-21(16-8-4-2-5-9-16)17-10-6-3-7-11-17;/h2-11,18-21H,12-15H2,1H3;1H/t18-,19+,20+;

HIDE SMILES / InChI

Molecular Formula BrH
Molecular Weight 80.912
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C21H25NO
Molecular Weight 307.4293
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including http://www.drugbank.ca/drugs/DB00245

Benztropine is an anticholinergic used in the symptomatic treatment of all etiologic groups of parkinsonism and drug-induced extrapyramidal reactions (except tardive dyskinesia). Benztropine possesses both anticholinergic and antihistaminic effects, although only the former has been established as therapeutically significant in the management of parkinsonism. Benztropine's anticholinergic activity is about equal to that of atropine. Benztropine also inhibits dopamine reuptake via the dopamine transporter at nerve terminals. Benztropine is a selective M1 muscarinic acetylcholine receptor antagonist. It is able to discriminate between the M1 (cortical or neuronal) and the peripheral muscarinic subtypes (cardiac and glandular). Benztropine partially blocks cholinergic activity in the CNS, which is responsible for the symptoms of Parkinson's disease. It is also thought to increase the availability of dopamine, a brain chemical that is critical in the initiation and smooth control of voluntary muscle movement. Used as an adjunct in the therapy of all forms of parkinsonism and also for use in the control of extrapyramidal disorders due to neuroleptic drugs.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
312.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
COGENTIN

Approved Use

For use as an adjunct in the therapy of all forms of parkinsonism Useful also in the control of extrapyramidal disorders (except tardive dyskinesia) due to neuroleptic drugs (e.g., phenothiazines).

Launch Date

1959
Secondary
COGENTIN

Approved Use

For use as an adjunct in the therapy of all forms of parkinsonism Useful also in the control of extrapyramidal disorders (except tardive dyskinesia) due to neuroleptic drugs (e.g., phenothiazines).

Launch Date

1959
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.5 ng/mL
1.5 mg single, oral
dose: 1.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BENZTROPINE unknown
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7 h
1.5 mg single, oral
dose: 1.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BENZTROPINE unknown
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
5%
1.5 mg single, oral
dose: 1.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BENZTROPINE unknown
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
2 mg 3 times / day multiple, oral
Recommended
Dose: 2 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2 mg, 3 times / day
Sources:
unhealthy, 20-66
n = 19
Health Status: unhealthy
Condition: neuroleptic-induced extrapyramidal symptoms
Age Group: 20-66
Sex: M+F
Population Size: 19
Sources:
Other AEs: Dry mouth, Visual disturbance...
Other AEs:
Dry mouth (grade 1-2, 26%)
Visual disturbance (grade 1-2, 32%)
Constipation (grade 1-2, 10.5%)
Sources:
2.25 mg 2 times / day multiple, oral (max)
Studied dose
Dose: 2.25 mg, 2 times / day
Route: oral
Route: multiple
Dose: 2.25 mg, 2 times / day
Sources:
unhealthy, 21 - 80
n = 19
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 21 - 80
Sex: M+F
Population Size: 19
Sources:
Other AEs: Confusion, Memory disturbance...
Other AEs:
Confusion (32%)
Memory disturbance (26%)
Lightheadedness (16%)
Blurred vision (10.5%)
Sources:
2.25 mg 2 times / day multiple, oral (max)
Studied dose
Dose: 2.25 mg, 2 times / day
Route: oral
Route: multiple
Dose: 2.25 mg, 2 times / day
Sources:
unhealthy, 21 - 80
n = 19
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 21 - 80
Sex: M+F
Population Size: 19
Sources:
Other AEs: Dry mouth...
Other AEs:
Dry mouth (63%)
Sources:
2 mg 1 times / day multiple, parenteral (max)
Recommended
Dose: 2 mg, 1 times / day
Route: parenteral
Route: multiple
Dose: 2 mg, 1 times / day
Co-administed with::
phenothiazines
Sources:
unhealthy
Health Status: unhealthy
Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs
Sources:
Disc. AE: Paralytic ileus...
AEs leading to
discontinuation/dose reduction:
Paralytic ileus (grade 3-5)
Sources:
2 mg 1 times / day multiple, parenteral (max)
Recommended
Dose: 2 mg, 1 times / day
Route: parenteral
Route: multiple
Dose: 2 mg, 1 times / day
Co-administed with::
tricyclic antidepressants
Sources:
unhealthy
Health Status: unhealthy
Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs
Sources:
Disc. AE: Paralytic ileus...
AEs leading to
discontinuation/dose reduction:
Paralytic ileus (grade 3-5)
Sources:
2 mg 1 times / day multiple, parenteral (max)
Recommended
Dose: 2 mg, 1 times / day
Route: parenteral
Route: multiple
Dose: 2 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs
Sources:
Other AEs: Mental impairment...
2 mg 2 times / day steady, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: steady
Dose: 2 mg, 2 times / day
Sources:
unhealthy
n = 21
Health Status: unhealthy
Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders
Sex: M+F
Population Size: 21
Sources:
Other AEs: Appetite lost, Dry mouth...
Other AEs:
Appetite lost (33%)
Dry mouth (24%)
Constipation (29%)
Listlessness (24%)
Urinary retention (19%)
Blurred vision (19%)
Muscle weakness (19%)
Excitement (10.5%)
Sweating decreased (14%)
Mental confusion (10.5%)
Skin rash (10.5%)
Nausea (10.5%)
Vomiting (10.5%)
Nervousness (10.5%)
Sources:
6 mg 1 times / day multiple, parenteral (max)
Recommended
Dose: 6 mg, 1 times / day
Route: parenteral
Route: multiple
Dose: 6 mg, 1 times / day
Co-administed with::
phenothiazines
Sources:
unhealthy
Health Status: unhealthy
Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs
Sources:
Other AEs: Hyperthermia, Heat stroke...
Other AEs:
Hyperthermia (grade 3-5)
Heat stroke (grade 3-5)
Sources:
6 mg 1 times / day multiple, parenteral (max)
Recommended
Dose: 6 mg, 1 times / day
Route: parenteral
Route: multiple
Dose: 6 mg, 1 times / day
Co-administed with::
tricyclic antidepressants
Sources:
unhealthy
Health Status: unhealthy
Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs
Sources:
Other AEs: Hyperthermia, Heat stroke...
Other AEs:
Hyperthermia (grade 3-5)
Heat stroke (grade 3-5)
Sources:
6 mg 1 times / day multiple, parenteral (max)
Recommended
Dose: 6 mg, 1 times / day
Route: parenteral
Route: multiple
Dose: 6 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs
Sources:
Other AEs: Physical impairment, Anhidrosis...
Other AEs:
Physical impairment
Anhidrosis (grade 3-5)
Sources:
AEs

AEs

AESignificanceDosePopulation
Constipation grade 1-2, 10.5%
2 mg 3 times / day multiple, oral
Recommended
Dose: 2 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2 mg, 3 times / day
Sources:
unhealthy, 20-66
n = 19
Health Status: unhealthy
Condition: neuroleptic-induced extrapyramidal symptoms
Age Group: 20-66
Sex: M+F
Population Size: 19
Sources:
Dry mouth grade 1-2, 26%
2 mg 3 times / day multiple, oral
Recommended
Dose: 2 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2 mg, 3 times / day
Sources:
unhealthy, 20-66
n = 19
Health Status: unhealthy
Condition: neuroleptic-induced extrapyramidal symptoms
Age Group: 20-66
Sex: M+F
Population Size: 19
Sources:
Visual disturbance grade 1-2, 32%
2 mg 3 times / day multiple, oral
Recommended
Dose: 2 mg, 3 times / day
Route: oral
Route: multiple
Dose: 2 mg, 3 times / day
Sources:
unhealthy, 20-66
n = 19
Health Status: unhealthy
Condition: neuroleptic-induced extrapyramidal symptoms
Age Group: 20-66
Sex: M+F
Population Size: 19
Sources:
Blurred vision 10.5%
2.25 mg 2 times / day multiple, oral (max)
Studied dose
Dose: 2.25 mg, 2 times / day
Route: oral
Route: multiple
Dose: 2.25 mg, 2 times / day
Sources:
unhealthy, 21 - 80
n = 19
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 21 - 80
Sex: M+F
Population Size: 19
Sources:
Lightheadedness 16%
2.25 mg 2 times / day multiple, oral (max)
Studied dose
Dose: 2.25 mg, 2 times / day
Route: oral
Route: multiple
Dose: 2.25 mg, 2 times / day
Sources:
unhealthy, 21 - 80
n = 19
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 21 - 80
Sex: M+F
Population Size: 19
Sources:
Memory disturbance 26%
2.25 mg 2 times / day multiple, oral (max)
Studied dose
Dose: 2.25 mg, 2 times / day
Route: oral
Route: multiple
Dose: 2.25 mg, 2 times / day
Sources:
unhealthy, 21 - 80
n = 19
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 21 - 80
Sex: M+F
Population Size: 19
Sources:
Confusion 32%
2.25 mg 2 times / day multiple, oral (max)
Studied dose
Dose: 2.25 mg, 2 times / day
Route: oral
Route: multiple
Dose: 2.25 mg, 2 times / day
Sources:
unhealthy, 21 - 80
n = 19
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 21 - 80
Sex: M+F
Population Size: 19
Sources:
Dry mouth 63%
2.25 mg 2 times / day multiple, oral (max)
Studied dose
Dose: 2.25 mg, 2 times / day
Route: oral
Route: multiple
Dose: 2.25 mg, 2 times / day
Sources:
unhealthy, 21 - 80
n = 19
Health Status: unhealthy
Condition: Parkinson's disease
Age Group: 21 - 80
Sex: M+F
Population Size: 19
Sources:
Paralytic ileus grade 3-5
Disc. AE
2 mg 1 times / day multiple, parenteral (max)
Recommended
Dose: 2 mg, 1 times / day
Route: parenteral
Route: multiple
Dose: 2 mg, 1 times / day
Co-administed with::
phenothiazines
Sources:
unhealthy
Health Status: unhealthy
Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs
Sources:
Paralytic ileus grade 3-5
Disc. AE
2 mg 1 times / day multiple, parenteral (max)
Recommended
Dose: 2 mg, 1 times / day
Route: parenteral
Route: multiple
Dose: 2 mg, 1 times / day
Co-administed with::
tricyclic antidepressants
Sources:
unhealthy
Health Status: unhealthy
Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs
Sources:
Mental impairment
2 mg 1 times / day multiple, parenteral (max)
Recommended
Dose: 2 mg, 1 times / day
Route: parenteral
Route: multiple
Dose: 2 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs
Sources:
Excitement 10.5%
2 mg 2 times / day steady, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: steady
Dose: 2 mg, 2 times / day
Sources:
unhealthy
n = 21
Health Status: unhealthy
Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders
Sex: M+F
Population Size: 21
Sources:
Mental confusion 10.5%
2 mg 2 times / day steady, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: steady
Dose: 2 mg, 2 times / day
Sources:
unhealthy
n = 21
Health Status: unhealthy
Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders
Sex: M+F
Population Size: 21
Sources:
Nausea 10.5%
2 mg 2 times / day steady, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: steady
Dose: 2 mg, 2 times / day
Sources:
unhealthy
n = 21
Health Status: unhealthy
Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders
Sex: M+F
Population Size: 21
Sources:
Nervousness 10.5%
2 mg 2 times / day steady, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: steady
Dose: 2 mg, 2 times / day
Sources:
unhealthy
n = 21
Health Status: unhealthy
Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders
Sex: M+F
Population Size: 21
Sources:
Skin rash 10.5%
2 mg 2 times / day steady, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: steady
Dose: 2 mg, 2 times / day
Sources:
unhealthy
n = 21
Health Status: unhealthy
Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders
Sex: M+F
Population Size: 21
Sources:
Vomiting 10.5%
2 mg 2 times / day steady, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: steady
Dose: 2 mg, 2 times / day
Sources:
unhealthy
n = 21
Health Status: unhealthy
Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders
Sex: M+F
Population Size: 21
Sources:
Sweating decreased 14%
2 mg 2 times / day steady, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: steady
Dose: 2 mg, 2 times / day
Sources:
unhealthy
n = 21
Health Status: unhealthy
Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders
Sex: M+F
Population Size: 21
Sources:
Blurred vision 19%
2 mg 2 times / day steady, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: steady
Dose: 2 mg, 2 times / day
Sources:
unhealthy
n = 21
Health Status: unhealthy
Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders
Sex: M+F
Population Size: 21
Sources:
Muscle weakness 19%
2 mg 2 times / day steady, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: steady
Dose: 2 mg, 2 times / day
Sources:
unhealthy
n = 21
Health Status: unhealthy
Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders
Sex: M+F
Population Size: 21
Sources:
Urinary retention 19%
2 mg 2 times / day steady, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: steady
Dose: 2 mg, 2 times / day
Sources:
unhealthy
n = 21
Health Status: unhealthy
Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders
Sex: M+F
Population Size: 21
Sources:
Dry mouth 24%
2 mg 2 times / day steady, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: steady
Dose: 2 mg, 2 times / day
Sources:
unhealthy
n = 21
Health Status: unhealthy
Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders
Sex: M+F
Population Size: 21
Sources:
Listlessness 24%
2 mg 2 times / day steady, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: steady
Dose: 2 mg, 2 times / day
Sources:
unhealthy
n = 21
Health Status: unhealthy
Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders
Sex: M+F
Population Size: 21
Sources:
Constipation 29%
2 mg 2 times / day steady, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: steady
Dose: 2 mg, 2 times / day
Sources:
unhealthy
n = 21
Health Status: unhealthy
Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders
Sex: M+F
Population Size: 21
Sources:
Appetite lost 33%
2 mg 2 times / day steady, oral
Recommended
Dose: 2 mg, 2 times / day
Route: oral
Route: steady
Dose: 2 mg, 2 times / day
Sources:
unhealthy
n = 21
Health Status: unhealthy
Condition: Schizophrenia|Drug-Induced Extrapyramidal Disorders
Sex: M+F
Population Size: 21
Sources:
Heat stroke grade 3-5
6 mg 1 times / day multiple, parenteral (max)
Recommended
Dose: 6 mg, 1 times / day
Route: parenteral
Route: multiple
Dose: 6 mg, 1 times / day
Co-administed with::
phenothiazines
Sources:
unhealthy
Health Status: unhealthy
Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs
Sources:
Hyperthermia grade 3-5
6 mg 1 times / day multiple, parenteral (max)
Recommended
Dose: 6 mg, 1 times / day
Route: parenteral
Route: multiple
Dose: 6 mg, 1 times / day
Co-administed with::
phenothiazines
Sources:
unhealthy
Health Status: unhealthy
Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs
Sources:
Heat stroke grade 3-5
6 mg 1 times / day multiple, parenteral (max)
Recommended
Dose: 6 mg, 1 times / day
Route: parenteral
Route: multiple
Dose: 6 mg, 1 times / day
Co-administed with::
tricyclic antidepressants
Sources:
unhealthy
Health Status: unhealthy
Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs
Sources:
Hyperthermia grade 3-5
6 mg 1 times / day multiple, parenteral (max)
Recommended
Dose: 6 mg, 1 times / day
Route: parenteral
Route: multiple
Dose: 6 mg, 1 times / day
Co-administed with::
tricyclic antidepressants
Sources:
unhealthy
Health Status: unhealthy
Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs
Sources:
Physical impairment
6 mg 1 times / day multiple, parenteral (max)
Recommended
Dose: 6 mg, 1 times / day
Route: parenteral
Route: multiple
Dose: 6 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs
Sources:
Anhidrosis grade 3-5
6 mg 1 times / day multiple, parenteral (max)
Recommended
Dose: 6 mg, 1 times / day
Route: parenteral
Route: multiple
Dose: 6 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Parkinsonism|Extrapyramidal disorders due to neuroleptic drugs
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Intermittent neuroleptic treatment and risk for tardive dyskinesia: Curaçao Extrapyramidal Syndromes Study III.
1998 Apr
Risk factors for tardive dyskinesia in a large population of youths and adults.
2001 Aug
Patents

Sample Use Guides

The usual daily dose is 1 to 2 mg, with a range of 0.5 to 6 mg parenterally.
Route of Administration: Parenteral
In Vitro Use Guide
Benztropine inhibited veratridine-induced efflux of K+, membrane depolarization and release of amino acid neurotransmitters with Kd of 2 uM.
Substance Class Chemical
Created
by admin
on Sat Dec 16 19:15:42 GMT 2023
Edited
by admin
on Sat Dec 16 19:15:42 GMT 2023
Record UNII
464GRB9DVD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Benztropine hydrobromide
Common Name English
8-Azabicyclo[3.2.1]octane, 3-(diphenylmethoxy)-8-methyl-, hydrobromide, (3-endo)-
Systematic Name English
Benzatropine hydrobromide
Common Name English
Benzatropine hydrobromide [WHO-DD]
Common Name English
Code System Code Type Description
FDA UNII
464GRB9DVD
Created by admin on Sat Dec 16 19:15:42 GMT 2023 , Edited by admin on Sat Dec 16 19:15:42 GMT 2023
PRIMARY
EPA CompTox
DTXSID90360822
Created by admin on Sat Dec 16 19:15:42 GMT 2023 , Edited by admin on Sat Dec 16 19:15:42 GMT 2023
PRIMARY
CAS
6148-20-5
Created by admin on Sat Dec 16 19:15:42 GMT 2023 , Edited by admin on Sat Dec 16 19:15:42 GMT 2023
PRIMARY
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