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
References
1. Cheng Q, Shah N, Bröer A, Fairweather S, Jiang Y, Schmoll D, Corry B, Bröer S. (2017)
Identification of novel inhibitors of the amino acid transporter B0 AT1 (SLC6A19), a potential target to induce protein restriction and to treat type 2 diabetes.
Br J Pharmacol, 174 (6): 468-482. [PMID:28176326]
2. Jiang Y, Rose AJ, Sijmonsma TP, Bröer A, Pfenninger A, Herzig S, Schmoll D, Bröer S. (2015)
Mice lacking neutral amino acid transporter B(0)AT1 (Slc6a19) have elevated levels of FGF21 and GLP-1 and improved glycaemic control.
Mol Metab, 4 (5): 406-17. [PMID:25973388]
3. Newman AH, Kline RH, Allen AC, Izenwasser S, George C, Katz JL. (1995)
Novel 4'-substituted and 4',4"-disubstituted 3 alpha-(diphenylmethoxy)tropane analogs as potent and selective dopamine uptake inhibitors.
J Med Chem, 38 (20): 3933-40. [PMID:7562926]