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Details

Stereochemistry ACHIRAL
Molecular Formula C21H25NO
Molecular Weight 307.4293
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BENZTROPINE

SMILES

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

InChI

InChIKey=GIJXKZJWITVLHI-PMOLBWCYSA-N
InChI=1S/C21H25NO/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/t18-,19+,20+

HIDE SMILES / InChI

Molecular Formula C21H25NO
Molecular Weight 307.4293
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
312.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
COGENTIN
Secondary
COGENTIN

Cmax

ValueDoseCo-administeredAnalytePopulation
2.5 ng/mL
1.5 mg single, oral
BENZTROPINE unknown
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
7 h
1.5 mg single, oral
BENZTROPINE unknown
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
5%
1.5 mg single, oral
BENZTROPINE unknown
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
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
Record UNII
1NHL2J4X8K
Record Status Validated (UNII)
Record Version