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

General Information of Drug (ID: DR0989)
Drug Name
Loxapine succinate
Synonyms
Loxapine (succinate); Loxapine succinate; Loxapine succinate salt; Loxapine, Succinate; Loxapine,succinate; X59SG0MRYU; 2-Chloro-11-(4-methyl-1-piperazinyl)dibenz(b,f)(1,4)oxazepine succinate (1:1); 2-chloro-11-(4-methyl-1-piperazinyl)dibenzo[b,f][1,4]oxazepine succinate; 27833-64-3; CAS-27833-64-3; CCRIS 1917; CL 71563; CPD000058470; DSSTox_CID_25227; DSSTox_GSID_45227; DSSTox_RID_80764; EINECS 248-682-0; MFCD00069298; MLS000069383; NCGC00016160-02; SMR000058470; UNII-X59SG0MRYU; Cloxazepin; Daxolin; Lederle
Indication Schizophrenia [ICD11: 6A20] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 445.9 Topological Polar Surface Area 103
Heavy Atom Count 31 Rotatable Bond Count 4
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
71399
ChEBI ID
CHEBI:6549
CAS Number
27833-64-3
TTD Drug ID
D0U5OE
Formula
C22H24ClN3O5
Canonical SMILES
CN1CCN(CC1)C2=NC3=CC=CC=C3OC4=C2C=C(C=C4)Cl.C(CC(=O)O)C(=O)O
InChI
1S/C18H18ClN3O.C4H6O4/c1-21-8-10-22(11-9-21)18-14-12-13(19)6-7-16(14)23-17-5-3-2-4-15(17)20-18;5-3(6)1-2-4(7)8/h2-7,12H,8-11H2,1H3;1-2H2,(H,5,6)(H,7,8)
InChIKey
YQZBAXDVDZTKEQ-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
7-Hydroxyloxapine DM006445
193253
Oxidation - Oxidationn 1 [2]
8-Hydroxyloxapine DM006447
43655
Oxidation - Oxidationn 1 [2]
Amoxapine DM006446
2170
Oxidation - Oxidationn 1 [2]
Loxapine N-oxide DM006444
91810511
Oxidation - Oxidationn 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006925 Loxapine succinate Loxapine N-oxide Oxidation - Oxidationn CYP3A4 ... [2]
MR006926 Loxapine succinate 7-Hydroxyloxapine Oxidation - Oxidationn CYP2D6 ... [2]
MR006927 Loxapine succinate Amoxapine Oxidation - Oxidationn CYP3A4 ... [2]
MR006928 Loxapine succinate 8-Hydroxyloxapine Oxidation - Oxidationn CYP1A2 [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 1B1 (CYP1B1) DME0023 Homo sapiens
CP1B1_HUMAN
1.14.14.1
[2]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[2]
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
[2]
Flavin-containing monooxygenase (FMO) DMEN075 . Not Available Not Available [2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
Unclear metabolic mechanism (DME-unclear) DME1406 Collinsella aerofaciens Not Available Not Available [3]
⏷ Show the Full List of 10  DME(s)
References
1 Loxapine Succinate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 In vitro identification of the human cytochrome p450 enzymes involved in the oxidative metabolism of loxapine. Biopharm Drug Dispos. 2011 Oct;32(7):398-407.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.

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