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
SMILES / InChI / InChIKey
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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+
InChI Key GIJXKZJWITVLHI-PMOLBWCYSA-N
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
M1 receptor Rn Antagonist Antagonist 9.0 pKi - 3
pKi 9.0 (Ki 9.5x10-10 M) [3]
Description: Displacement binding experiment using homogenised rat caudate putamen.
M2 receptor Rn Antagonist Antagonist 8.6 pKi - 3
pKi 8.6 (Ki 2.6x10-9 M) [3]
Description: Displacement binding assay using homogenised rat caudate putamen.
Selectivity at transporters
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
DAT Rn Inhibitor Inhibition 6.9 pKi - 3
pKi 6.9 (Ki 1.18x10-7 M) [3]
Description: Displacement of [3H]WIN35,428 binding to homogenised rat caudate putamen.
B0AT1 Hs Inhibitor Inhibition 4.4 pIC50 - 1
pIC50 4.4 (IC50 4.4x10-5 M) [1]