deutetrabenazine   

GtoPdb Ligand ID: 8707

Synonyms: Austedo® | SD-809 | SD809 | tetrabenazine D6
deutetrabenazine is an approved drug (FDA (2017))
Compound class: Synthetic organic
Comment: This is an orally available, deuterated analogue of tetrabenazine which can be administered in lower doses and in a simplified dosing regimen. Deutetrabenazine is the first ever deuterated drug to be approved.

In drug discovery, replacing hydrogen atoms in drug compounds with deuterium (deuteration) is a technique employed to inhibit degradation of the drug and its active metabolites. The presence of the deuterium atoms attenuates CYP2D6-driven metabolic breakdown of the compound. This effects an increase in circulating half-lives and improves the duration of therapeutic effect and decreases the dose required to achieve therapeutic concentration [4].
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 CC(C[C@@H]1CN2CCc3c([C@H]2CC1=O)cc(c(c3)OC([2H])([2H])[2H])OC([2H])([2H])[2H])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/t14-,16-/m1/s1/i3D3,4D3
InChI Key MKJIEFSOBYUXJB-VFJJUKLQSA-N
Bioactivity Comments
The inhibitory ability of deutetrabenazine is likely to be similar to that of its parent compound, tetrabenazine. We have mapped deutetrabenazine to SLC18A2, based on its relationship to the parent molecule, but have been unable to find confirmatory activity data.
Selectivity at transporters
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Vesicular monoamine transporter 2 Hs Inhibitor Inhibition - - -