Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0445)
Drug Name
Deutetrabenazine
Synonyms
Deutetrabenazine; Deutetrabenazine [USAN:INN]; Dutetrabenazine; SD 809; SD-809; Tetrabenazine-d6; (3RS,11Brs)-9,10-di((2H3)methoxy)-3-(2-methylpropyl)-1,3,4,6,7,11b-hexahydro-2H-benzo(a)quinolizin-2-one; 1392826-25-3; Austedo; 2H-Benzo(a)quinolizin-2-one, 1,3,4,6,7,11b-hexahydro-9,10-di(methoxy-d3)-3-(2-methylpropyl)-, (3R,11bR)-rel-; DB12161; SCHEMBL16228022; SD809
Indication Huntington disease [ICD11: 8A01] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 323.5 Topological Polar Surface Area 38.8
Heavy Atom Count 23 Rotatable Bond Count 4
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
73442840
PubChem SID
311000000
CAS Number
1392826-25-3
TTD Drug ID
D0E7ZU
Formula
C19H27NO3
Canonical SMILES
CC(C)CC1CN2CCC3=CC(=C(C=C3C2CC1=O)OC)OC
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-/m0/s1/i3D3,4D3
InChIKey
MKJIEFSOBYUXJB-WEZHFFAMSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Cis (2,3)-Dihydro Tetrabenazine-d6 DM000795
146014916
Unclear 1 [3]
D6alpha-dihydrotetrabenazine DM000791
76973986
Unclear 1 [3]
Deutetrabenazine metabolite M4 DM000800
131635369
Oxidation - Hydroxylation 1 [3]
D3-10-O-Desmethyl-Alpha-Htbz DM000794
146019563
Oxidation - Demethylation 2 [3]
D3-10-O-Desmethyl-beta-Htbz DM000798
1176932
Oxidation - Demethylation 2 [3]
D3-9-O-Desmethyl-Alpha-Htbz DM000792
146014889
Oxidation - Demethylation 2 [3]
D3-9-O-Desmethyl-beta-Htbz DM000796
146014896
Oxidation - Demethylation 2 [3]
Deutetrabenazine metabolite M1 DM000799
146014925
Unclear 2 [3]
Sulfate of O\desmethyl alpha\HTBZ DM000793 N. A. Conjugation - Sulfation 3 [3]
Sulfate of O\desmethyl beta\HTBZ DM000797 N. A. Conjugation - Sulfation 3 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000786 Deutetrabenazine D6alpha-dihydrotetrabenazine Unclear CBR3 [3]
MR000787 Deutetrabenazine Cis (2,3)-Dihydro Tetrabenazine-d6 Unclear CBR3 [3]
MR000788 Deutetrabenazine Deutetrabenazine metabolite M4 Oxidation - Hydroxylation Unclear [3]
MR000781 Cis (2,3)-Dihydro Tetrabenazine-d6 D3-9-O-Desmethyl-beta-Htbz Oxidation - Demethylation CYP2D6 [3]
MR000782 Cis (2,3)-Dihydro Tetrabenazine-d6 D3-10-O-Desmethyl-beta-Htbz Oxidation - Demethylation CYP2D6 [3]
MR000783 Cis (2,3)-Dihydro Tetrabenazine-d6 Deutetrabenazine metabolite M1 Unclear CYP2D6 [3]
MR000777 D6alpha-dihydrotetrabenazine D3-9-O-Desmethyl-Alpha-Htbz Oxidation - Demethylation CYP2D6 [3]
MR000778 D6alpha-dihydrotetrabenazine D3-10-O-Desmethyl-Alpha-Htbz Oxidation - Demethylation CYP2D6 [3]
MR000780 D3-10-O-Desmethyl-Alpha-Htbz Sulfate of O\desmethyl alpha\HTBZ Conjugation - Sulfation Unclear [3]
MR000785 D3-10-O-Desmethyl-beta-Htbz Sulfate of O\desmethyl beta\HTBZ Conjugation - Sulfation Unclear [3]
MR000779 D3-9-O-Desmethyl-Alpha-Htbz Sulfate of O\desmethyl alpha\HTBZ Conjugation - Sulfation Unclear [3]
MR000784 D3-9-O-Desmethyl-beta-Htbz Sulfate of O\desmethyl beta\HTBZ Conjugation - Sulfation Unclear [3]
⏷ Show the Full List of 12 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
NADPH-dependent carbonyl reductase 3 (CBR3) DME0068 Homo sapiens
CBR3_HUMAN
1.1.1.184
[3]
References
1 Deutetrabenazine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 FDA Label of Deutetrabenazine. The 2020 official website of the U.S. Food and Drug Administration.
3 Pharmacokinetic and Metabolic Profile of Deutetrabenazine (TEV-50717) Compared With Tetrabenazine in Healthy Volunteers Clin Transl Sci. 2020 Jul;13(4):707-717. doi: 10.1111/cts.12754.

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