benzatropine   Click here for help

GtoPdb Ligand ID: 7601

Synonyms: benztropine | benztropine mesylate | Cogentin®
Approved drug PDB Ligand
benzatropine is an approved drug (FDA (1954))
Compound class: Synthetic organic
Comment: 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) [1], a recently identified molecular target for treatment of type 2 diabetes and related disorders [2]. Note that the mesylate salt was used in the experiments reported in [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 12.47
Molecular weight 307.19
XLogP 4.28
No. Lipinski's rules broken 0
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Canonical SMILES CN1C2CCC1CC(C2)OC(c1ccccc1)c1ccccc1
Isomeric SMILES CN1[C@@H]2CC[C@H]1C[C@H](C2)OC(c1ccccc1)c1ccccc1
InChI 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+
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Summary of Clinical Use Click here for help
Used in the symptomatic treatment of Parkinson's disease. May also be used to treat extrapyramidal symptoms, such as dystonia and Parkinsonism, which can be side effects of some antipsychotic drugs such as chlorpromazine, fluphenazine and perphenazine.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Benzatropine is a centrally acting antagonist of muscarinic acetylcholine receptors. In addition, benzatropine inhibits the reuptake of dopamine at nerve terminals via the dopamine transporter (SLC6A3). Dopamine-acetylcholine imbalance caused by a decrease in dopaminergic activity, is believed to be responsible for the symptoms of Parkinson's disease and extrapyramidal reactions. The dual effect of benzatropine is believed to restore the balance between these neurotransmitters.
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