Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00184)
Name
Deutetrabenazine
Synonyms    Click to Show/Hide the Synonyms of This API
Deutetrabenazine; Tetrabenazine D6; 1392826-25-3; Tetrabenazine-d6; Austedo; (3R,11bR)-3-(2-methylpropyl)-9,10-bis(trideuteriomethoxy)-1,3,4,6,7,11b-hexahydrobenzo[a]quinolizin-2-one; SD-809; rel-(3R,11bR)-3-isobutyl-9,10-bis(methoxy-d3)-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one; Austedo (TN); Deutetrabenazine (USAN/INN); GTPL8707; SCHEMBL16227993; HY-B0590S; EX-A4770; Ro 1-9569 D6; D10701; Q27077026; UNII-P341G6W9NB component MKJIEFSOBYUXJB-VFJJUKLQSA-N; [2H6]-(+)-Tetrabenazine; [2H6]-(+)- 9,10-Dimethoxy-1,3R,4,6,7,11bR-hexahydro-3-isobutyl-2H-benzo[a]quinolizin-2-one
Clinical Status
Approved
Disease Indication Huntington disease ICD-11: 8A01 [1]
PubChem CID
73437646
Formula
C19H27NO3
Canonical SMILES
[2H]C([2H])([2H])OC1=C(C=C2[C@H]3CC(=O)[C@@H](CN3CCC2=C1)CC(C)C)OC([2H])([2H])[2H]
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
InChIKey
MKJIEFSOBYUXJB-VFJJUKLQSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=73437646"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 323.5 Topological Polar Surface Area 38.8
XlogP 2.9 Complexity 425
Heavy Atom Count 23 Rotatable Bond Count 4
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Full List of Drug Formulations (DFMs) Containing This API
          Deutetrabenazine 12 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Butylated hydroxytoluene; Butyl alcohol; Fd&c blue no. 2; Fd&c yellow no. 6; Magnesium stearate; Mannitol; Ammonia; Butylated hydroxyanisole; Ferrosoferric oxide; Propylene glycol; Talc; Titanium dioxide; Polysorbate 80; Microcrystalline cellulose; Polyethylene glycol, unspecified; Polyvinyl alcohol, unspecified; Povidone, unspecified; Shellac
                   Dosage Form Oral Tablet
                   Company Teva Neuroscience
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Butylated hydroxytoluene DIG Info Carbonic anhydrase II (Ki = 630 nM) [2]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [3]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [4]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [5]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [6]
Butylhydroxyanisole DIG Info Prostaglandin G/H synthase 2 (IC50 = 2.6 uM) [4]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [7]
          Deutetrabenazine 6 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Butylated hydroxytoluene; Fd&c red no. 40; Butyl alcohol; Fd&c blue no. 2; Magnesium stearate; Mannitol; Ammonia; Butylated hydroxyanisole; Ferrosoferric oxide; Propylene glycol; Talc; Titanium dioxide; Polysorbate 80; Microcrystalline cellulose; Polyethylene glycol, unspecified; Polyvinyl alcohol, unspecified; Povidone, unspecified; Shellac
                   Dosage Form Oral Tablet
                   Company Teva Neuroscience
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 4.7 uM) [4]
Butylated hydroxytoluene DIG Info Carbonic anhydrase II (Ki = 630 nM) [2]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [4]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [5]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [6]
Butylhydroxyanisole DIG Info Prostaglandin G/H synthase 2 (IC50 = 2.6 uM) [4]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [7]
          Deutetrabenazine 9 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Butylated hydroxytoluene; Butyl alcohol; Fd&c blue no. 2; Magnesium stearate; Mannitol; Ammonia; Butylated hydroxyanisole; Ferrosoferric oxide; Propylene glycol; Talc; Titanium dioxide; Polysorbate 80; Microcrystalline cellulose; Polyethylene glycol, unspecified; Polyvinyl alcohol, unspecified; Povidone, unspecified; Shellac
                   Dosage Form Oral Tablet
                   Company Teva Neuroscience
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Butylated hydroxytoluene DIG Info Carbonic anhydrase II (Ki = 630 nM) [2]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [4]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [5]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [6]
Butylhydroxyanisole DIG Info Prostaglandin G/H synthase 2 (IC50 = 2.6 uM) [4]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [7]
References
1 FDA label for approved deutetrabenazine from the official website of the U.S. Food and Drug Administration.
2 Carbonic anhydrase inhibitors. Inhibition of human erythrocyte isozymes I and II with a series of antioxidant phenols. Bioorg Med Chem. 2009 Apr 15; 17(8):3207-11.
3 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
4 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
5 Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. Bioorg Med Chem Lett. 2017 Jun 1; 27(11):2239-2258.
6 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.
7 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.

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