tetrabenazine   Click here for help

GtoPdb Ligand ID: 4834

Abbreviated name: TBZ
Synonyms: Nitoman® | Revocon® | Ro-19569
Approved drug
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
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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 Click here for help
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 Click here for help
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.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com