General
Preferred name
benzatropine
Synonyms
BENZTROPINE ()
Benzotropine mesylate ()
Benztropine methanesulfonate ()
Benzatropine mesylate ()
BENZTROPINE MESYLATE ()
3-Diphenylmethoxytropane mesylate ()
Cogentin mesylate, Benztropine methanesulfonate ()
Cogentin ()
Benztropine Mesilate ()
NSC-169913 ()
Benzatropine mesilate ()
Benzatropina ()
Cobrentin ()
Benzatropine ()
NK-02 ()
Benztropine ()
Benztropine (mesylate) ()
P&D ID
PD010149
CAS
132-17-2
86-13-5
Tags
available
drug
Approved by
FDA
First approval
1954
Drug Status
approved
Max Phase
4.0
Drug indication
Antiparkinsonian
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
METABOLISM
Benztropine has been shown to undergo metabolism mainly marked by N-oxidation, N-dealkylation and ring hydroxylation.[A175087] The extensive metabolism of benztropine produces eight phase-I metabolites plus four glucuronide conjugates.[A1628]
ROE
Benztropine is mainly excreted in the urine but it is also found in the feces unchanged.[A1628]
PHARMACODYNAMICS
The inhibition of dopamine reuptake by benztropine produces a dose-dependent increase of dopamine in the nerve terminal of the dopaminergic system.[A1628] Clinically the activity of benztropine is observed after 1-2 hours of oral administration and after a few minutes of intramuscular administration with a last-longing effect of about 24 hours. Reports have indicated that benztropine has a very large sedative effect.[A1628] The antihistaminic effect of benztropine is very similar to the effect found in [pyrilamine] and the anticholinergic activity was found to be equal to [atropine] _ex vivo_ and of about 50% activity _in vivo_.[F3679]
TOXICITY
The oral LD50 of benztropine is reported to be of 940 mg/kg in rats.[MSDS] In the presence of overdose with benztropine, it has been observed symptoms of circulatory collapse, cardiac arrest, respiratory depression, respiratory arrest, psychosis, shock, coma, seizure, ataxia, combativeness, anhidrosis, hyperthermia, fever, dysphagia, decreased bowel sounds and sluggish pupils.[F3682]
HALF-LIFE
The elimination half-life of benztropine is very variable and it is reported to be of around 36 hours.[F3682]
MOA
Benztropine is an agent with anti-muscarinic and antihistaminic effects. Its main mechanism of action is presented by the selective inhibition of dopamine transporters but it also presents affinity for histamine and muscarine receptors.[A175084] It is widely known that benztropine is a potent inhibitor of presynaptic carrier-mediated dopamine transport. As well, it is known to be an analog of atropine and hence, it has a large affinity for muscarinic receptors M1 in the human brain. Once bound, benztropine blocks the activity of the muscarinic receptors mainly in the striatum.[A1628] The increased advantage of benztropine lays on the antagonism of acetylcholine activity which corrects the imbalance between dopamine and acetylcholine in Parkinson patients.[F3679]
INDICATION
Benztropine is indicated to be used as an adjunct in the therapy of all forms of parkinsonism. It can also be used for the control of extrapyramidal disorders due to neuroleptic drugs.[T203] The extrapyramidal symptoms are defined as drug-induced disorders that include symptoms of dystonia, akathisia, parkinsonism, bradykinesia, tremors, and dyskinesia.[A175120] Parkinsonism is a general term that refers to the group of neurological disorders that produce symptoms similar to Parkinson's disease such as tremors, slow movement, and stiffness. The parkinsonism includes a large number of disorders and some of them have not been clearly defined.[L5509]
ABSORPTION
Oral administration of 1.5 mg of benztropine is slowly absorbed in the gastrointestinal tract and it reaches a peak concentration of 2.5 ng/ml in about 7 hours.[A175087] It has an approximate oral bioavailability of 29%.[T445]
PHARMACODYNAMICS
The inhibition of dopamine reuptake by benztropine produces a dose-dependent increase of dopamine in the nerve terminal of the dopaminergic system.[A1628] ; ; Clinically the activity of benztropine is observed after 1-2 hours of oral administration and after a few minutes of intramuscular administration with a last-longing effect of about 24 hours. Reports have indicated that benztropine has a very large sedative effect.[A1628]; ; The antihistaminic effect of benztropine is very similar to the effect found in [pyrilamine] and the anticholinergic activity was found to be equal to [atropine] _ex vivo_ and of about 50% activity _in vivo_.[F3679]
MOA
Benztropine is an agent with anti-muscarinic and antihistaminic effects. Its main mechanism of action is presented by the selective inhibition of dopamine transporters but it also presents affinity for histamine and muscarine receptors.[A175084]; ; It is widely known that benztropine is a potent inhibitor of presynaptic carrier-mediated dopamine transport. As well, it is known to be an analog of atropine and hence, it has a large affinity for muscarinic receptors M1 in the human brain. Once bound, benztropine blocks the activity of the muscarinic receptors mainly in the striatum.[A1628]; ; The increased advantage of benztropine lays on the antagonism of acetylcholine activity which corrects the imbalance between dopamine and acetylcholine in Parkinson patients.[F3679]
INDICATION
Benztropine is indicated to be used as an adjunct in the therapy of all forms of parkinsonism. It can also be used for the control of extrapyramidal disorders due to neuroleptic drugs.[T203]; ; The extrapyramidal symptoms are defined as drug-induced disorders that include symptoms of dystonia, akathisia, parkinsonism, bradykinesia, tremors, and dyskinesia.[A175120] ; ; Parkinsonism is a general term that refers to the group of neurological disorders that produce symptoms similar to Parkinson's disease such as tremors, slow movement, and stiffness. The parkinsonism includes a large number of disorders and some of them have not been clearly defined.[L5509]
TOXICITY
The oral LD50 of benztropine is reported to be of 940 mg/kg in rats.[MSDS] In the presence of overdose with benztropine, it has been observed symptoms of circulatory collapse, cardiac arrest, respiratory depression, respiratory arrest, psychosis, shock, coma, seizure, ataxia, combativeness, anhidrosis, hyperthermia, fever, dysphagia, decreased bowel sounds and sluggish pupils.[F3682]; ; ; ;
DESCRIPTION
Benzatropine (benztropine) is an anticholinergic drug. PubChem CID 1201549 represents an alternative isomer of this compound.
Benzatropine is reported as an inhibitor of the neutral amino acid transporter B0AT1 (SLC6A19) , a recently identified molecular target for treatment of type 2 diabetes and related disorders . Note that the mesylate salt was used in the experiments reported in . B0AT1 has been identified as a potential ancillary protein for SARS-CoV-2 entry into host cells. Benzatropine was reported to inhibit SARS-CoV-2 infection in vitro . (GtoPdb)
Benzatropine is reported as an inhibitor of the neutral amino acid transporter B0AT1 (SLC6A19) , a recently identified molecular target for treatment of type 2 diabetes and related disorders . Note that the mesylate salt was used in the experiments reported in . B0AT1 has been identified as a potential ancillary protein for SARS-CoV-2 entry into host cells. Benzatropine was reported to inhibit SARS-CoV-2 infection in vitro . (GtoPdb)
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Cell lines
0
Organisms
7
Compound Sets
20
Cayman Chemical Bioactives
ChEMBL Approved Drugs
ChEMBL Drugs
Concise Guide to Pharmacology 2017/18
Concise Guide to Pharmacology 2019/20
Concise Guide to Pharmacology 2021/22
Concise Guide to Pharmacology 2023/24
Drug Repurposing Hub
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
Enamine BioReference Compounds
Guide to Pharmacology
LSP-MoA library (Laboratory of Systems Pharmacology)
NCATS Inxight Approved Drugs
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
TargetMol Bioactive Compound Library
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
51
Molecular Weight
307.19
Hydrogen Bond Acceptors
2
Hydrogen Bond Donors
0
Rotatable Bonds
4
Ring Count
4
Aromatic Ring Count
2
cLogP
4.42
TPSA
12.47
Fraction CSP3
0.43
Chiral centers
3.0
Largest ring
6.0
QED
0.83
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Pathway
GPCR/G protein
Neuroscience
Target
DAT
CHRM1, HRH1, SLC6A3
Dopamine Receptor
MOA
Dopamine Receptor antagonist
acetylcholine receptor antagonist
Indication
extrapyramidal symptoms (EPS), Parkinson's Disease
Source data
