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

General Information of Drug (ID: DR3552)
Drug Name
Ingrezza
Prodrug Info Ingrezza is the prodrug of Alpha-dihydrotetrabenazine
Synonyms
Valbenazine; 1025504-45-3; UNII-54K37P50KH; Valbenazine free base; NBI 98854; 54K37P50KH; 1025504-45-3 (free base); (2R,3R,11bR)-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-yl L-valinate; 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; Valbenazine [USAN:INN]; 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; ValbenazineNBI-98854; Valbenazine (USAN/INN); GTPL8694; CHEMBL2364639; SCHEMBL15932979; EX-A2002; MFCD28963976; ZINC43195697; CS-5908; DB11915; SB17456; NCGC00522306-02; [(2R,3R,11bR)-9,10-dimethoxy-3-(2-methylpropyl)-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-2-yl] (2S)-2-amino-3-methylbutanoate; AC-30929; AS-35294; HY-16771; D10675; NBI-98854;NBI98854;NBI 98854; Q27089118; (2R,3R,11bR)-9,10-Dimethoxy-3-(2-methylpropyl)-1,3,4,6,7,11b-hexahydro-2H- benzo(a)quinolizin-2-yl L-valinate; (S)-2-amino-3-methyl-butyric acid (2R,3R,11bR)-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-yl ester; [(2R,3R,11bR)-9,10-dimethoxy-3-(2-methylpropyl)-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-2-yl] (2S)-2-amino-3-methylbutanoate; Valine 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-2H-benzo(a)quinolizin-2-yl ester
Indication Dyskinesia [ICD11: 8A02] Phase 4 [1]
Tourette syndrome [ICD11: ICD11: 8A05] Phase 2 [2]
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
CAS Number
1025504-45-3
TTD Drug ID
D63WMQ
Formula
C24H38N2O4
Canonical SMILES
CC(C)C[C@@H]1CN2CCC3=CC(=C(C=C3[C@H]2C[C@H]1OC(=O)[C@H](C(C)C)N)OC)OC
InChI
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 [4]
NBI-136110 DM002421
133082445
Oxidation - Oxidation 1 [4] , [3]
[+]alpha-HTBZ DM002422 N. A. Hydrolysis - Hydrolysis 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009235 Ingrezza NBI-136110 Oxidation - Oxidation CYP3A4 ... [4], [3]
MR009236 Ingrezza (+)-alpha-HTBZ Hydrolysis - Hydrolysis ES [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
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[4]
References
1 ClinicalTrials.gov (NCT03698331) The Potential for Clinical Dependence and Withdrawal Symptoms Associated With Valbenazine. U.S. National Institutes of Health.
2 ClinicalTrials.gov (NCT03732534) Rollover Study for Continuing NBI-98854 Administration in Pediatric Subjects With Tourette Syndrome. U.S. National Institutes of Health.
3 VMAT2 Inhibitors in Neuropsychiatric Disorders
4 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.

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