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

General Information of Drug (ID: DR0136)
Drug Name
Aripiprazole lauroxil
Prodrug Info Aripiprazole lauroxil is the prodrug of N-hydroxymethyl-aripiprazole
Synonyms
Aripiprazole lauroxil; Aripiprazole lauroxil (USAN); Aripiprazole lauroxil [USAN]; Aristada; Aristada (TN); B786J7A343; Dodecanoic acid, (7-(4-(4-(2,3-dichlorophenyl)-1-piperazinyl)butoxy)-3,4-dihydro-2-oxo-1(2H)-quinolinyl)methyl ester; RDC 3317; RDC-3317; UNII-B786J7A343; [7-{4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butoxy}-2-oxo-3,4-dihydroquinolin-1(2H)-yl]methyl dodecanoate; (7-(4-(4-(2,3-Dichlorophenyl)piperazin-1-yl)butoxy)-2-oxo-3,4-dihydroquinolin-1(2H)-yl)methyl dodecanoate; 1259305-29-7; ALKS 9070; ALKS 9072
Indication Schizophrenia [ICD11: 6A20] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 660.7 Topological Polar Surface Area 62.3
Heavy Atom Count 45 Rotatable Bond Count 20
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
49831411
ChEBI ID
CHEBI:90930
CAS Number
1259305-29-7
TTD Drug ID
D0H3HM
Formula
C36H51Cl2N3O4
Canonical SMILES
CCCCCCCCCCCC(=O)OCN1C(=O)CCC2=C1C=C(C=C2)OCCCCN3CCN(CC3)C4=C(C(=CC=C4)Cl)Cl
InChI
1S/C36H51Cl2N3O4/c1-2-3-4-5-6-7-8-9-10-16-35(43)45-28-41-33-27-30(19-17-29(33)18-20-34(41)42)44-26-12-11-21-39-22-24-40(25-23-39)32-15-13-14-31(37)36(32)38/h13-15,17,19,27H,2-12,16,18,20-26,28H2,1H3
InChIKey
DDINXHAORAAYAD-UHFFFAOYSA-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
Lauric acid DM003107
3893
Hydrolysis - Esterase Hydrolysis 1 [4] , [5]
N-hydroxymethyl-aripiprazole DM001745
58096483
Hydrolysis - Esterase Hydrolysis 1 [4] , [5]
Aripiprazole DM001746
60795
Hydrolysis - Hydrolysis 2 [4] , [5]
Formaldehyde DM001748
712
Hydrolysis - Hydrolysis 2 [4] , [5]
Dehydro-aripiprazole DM001747
10114519
Oxidation - Dehydrogenation 3 [4] , [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000291 Aripiprazole lauroxil N-hydroxymethyl-aripiprazole Hydrolysis - Esterase Hydrolysis Unclear [4], [5]
MR000292 Aripiprazole lauroxil Lauric acid Hydrolysis - Esterase Hydrolysis Unclear [4], [5]
MR000288 N-hydroxymethyl-aripiprazole Aripiprazole Hydrolysis - Hydrolysis Unclear [4], [5]
MR000289 N-hydroxymethyl-aripiprazole Formaldehyde Hydrolysis - Hydrolysis Unclear [4], [5]
MR000290 Aripiprazole Dehydro-aripiprazole Oxidation - Dehydrogenation CYP3A4 ... [4], [5]
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]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[3]
References
1 Aripiprazole Lauroxil was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Aripiprazole: a review of its use in schizophrenia and schizoaffective disorder. Drugs. 2004;64(15):1715-36.
3 Drug Interactions Flockhart Table
4 Aripiprazole Lauroxil: Pharmacokinetic Profile of This Long-Acting Injectable Antipsychotic in Persons With Schizophrenia J Clin Psychopharmacol. 2017 Jun;37(3):289-295. doi: 10.1097/JCP.0000000000000691.
5 Biological conversion of?aripiprazole lauroxil - An N-acyloxymethyl aripiprazole prodrug Results Pharma Sci. 2014 May 2;4:19-25. doi: 10.1016/j.rinphs.2014.04.002.

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