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
No information available.
Summary of Clinical Use
Tetrabenazine has been used in the past as an antipsychotic, but is now used primarily in the symptomatic treatment of hyperkinetic disorders including chorea in Huntington's disease, Tourette syndrome and tardive dyskinesia.
Mechanism Of Action and Pharmacodynamic Effects
Reversibly inhibits the vesicular monoamine transporter 2 (SLC18A2). This decreases the amount of the monoamine neurotransmitters serotonin, norepinephrine, and dopamine stored in presynaptic vesicles, and results in increased metabolism of the extra-vesicular neurotransmitters by monoamine oxidase. This leads to an net reduction in catecholamine-driven neuro-activity. The principal action is believed to be depletion of presynaptic dopamine levels.
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