tetrabenazine   

GtoPdb Ligand ID: 4834

Abbreviated name: TBZ
Synonyms: Nitoman® | Revocon® | Ro-19569
tetrabenazine is an approved drug (FDA (2008))
Compound class: Synthetic organic
Comment: Tetrabenazine is an inhibitor of the vesicular monoamine transporter type 2 (VMAT2; SLC18A2). Tetrabenazine was the first dopamine-depleting drug approved in the US for the treatment of Huntington's disease. The potential for using dopamine-depleters to manage hyperkinetic movement disorders is reviewed in [2]. Since the approval of tetrabenazine, the deuterated analogue deutetrabenazine has been a granted marketing authorisation by the FDA (April 2107), and valbenazine is in clinical trial for tardive dyskinesia and Tourette syndrome
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 38.77
Molecular weight 317.2
XLogP 2.65
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES COc1cc2c(cc1OC)CCN1C2CC(=O)C(C1)CC(C)C
Isomeric SMILES COc1cc2c(cc1OC)CCN1C2CC(=O)C(C1)CC(C)C
InChI InChI=1S/C19H27NO3/c1-12(2)7-14-11-20-6-5-13-8-18(22-3)19(23-4)9-15(13)16(20)10-17(14)21/h8-9,12,14,16H,5-7,10-11H2,1-4H3
InChI Key MKJIEFSOBYUXJB-UHFFFAOYSA-N
References
1. Erickson JD, Schafer MK, Bonner TI, Eiden LE, Weihe E. (1996)
Distinct pharmacological properties and distribution in neurons and endocrine cells of two isoforms of the human vesicular monoamine transporter.
Proc. Natl. Acad. Sci. U.S.A., 93 (10): 5166-71. [PMID:8643547]
2. Jankovic J. (2016)
Dopamine depleters in the treatment of hyperkinetic movement disorders.
Expert Opin Pharmacother, 17 (18): 2461-2470. [PMID:27819145]