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

General Information of Drug (ID: DR1665)
Drug Name
Valbenazine
Prodrug Info Valbenazine is the prodrug of Alpha-dihydrotetrabenazine
Synonyms
Valbenazine; Valbenazine [USAN:INN]; Ingrezza; NBI 98854; 1025504-45-3; 54K37P50KH; L-Valine, (2R,3R,11bR)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-yl ester; L-Valine, (2R,3R,11bR)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-yl ester;L-Valine, (2R,3R,11bR)-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo[a]quinolizin-2-yl ester; UNII-54K37P50KH
Indication Dyskinesia [ICD11: 8A02] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 418.6 Topological Polar Surface Area 74
Heavy Atom Count 30 Rotatable Bond Count 8
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
24795069
PubChem SID
49738821 ; 57114321 ; 163370736 ; 164133227 ; 198945028 ; 224577868 ; 240859006 ; 246330347 ; 252166894
CAS Number
1025504-45-3
TTD Drug ID
D0IX1I
Formula
C24H38N2O4
Canonical SMILES
CC(C)CC1CN2CCC3=CC(=C(C=C3C2CC1OC(=O)C(C(C)C)N)OC)OC
InChI
1S/C24H38N2O4/c1-14(2)9-17-13-26-8-7-16-10-21(28-5)22(29-6)11-18(16)19(26)12-20(17)30-24(27)23(25)15(3)4/h10-11,14-15,17,19-20,23H,7-9,12-13,25H2,1-6H3/t17-,19-,20-,23+/m1/s1
InChIKey
GEJDGVNQKABXKG-CFKGEZKQSA-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
Alpha-dihydrotetrabenazine DM002422
14580381
Hydrolysis - Hydrolysis 1 [3] , [4]
NBI-136110 DM002421
133082445
Oxidation - Oxidation 1 [3]
[+]alpha-HTBZ DM002422 N. A. Hydrolysis - Hydrolysis 1 [3] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002484 Valbenazine NBI-136110 Oxidation - Oxidation Unclear [3]
MR002485 Valbenazine [+]alpha-HTBZ Hydrolysis - Hydrolysis ES [3], [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
References
1 Valbenazine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Tardive dyskinesia: placing vesicular monoamine transporter type 2 (VMAT2) inhibitors into clinical perspective. Expert Rev Neurother. 2018 Apr;18(4):323-332.
3 Pharmacologic Characterization of Valbenazine (NBI-98854) and Its Metabolites J Pharmacol Exp Ther. 2017 Jun;361(3):454-461. doi: 10.1124/jpet.116.239160.
4 Pharmacokinetic and Pharmacologic Characterization of the Dihydrotetrabenazine Isomers of Deutetrabenazine and Valbenazine. Clin Pharmacol Drug Dev. 2023 Apr;12(4):447-456. doi: 10.1002/cpdd.1205.

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