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

General Information of Drug (ID: DR0103)
Drug Name
Amoxapine
Synonyms
Amoxan; Amoxapina; Amoxapina [INN-Spanish]; Amoxapinum; Amoxapinum [INN-Latin]; Amoxepine; Ascendin; Asendin; Asendis; Demolox; Desmethylloxapin; Moxadil; amoxapine; 14028-44-5; 2-Chlor-11-(1-piperazinyl)dibenz(b,f)(1,4)oxazepin; 2-Chloro-11-(1-piperazinyl)dibenz(b,f)(1,4)oxazepine; 2-Chloro-11-(1-piperazinyl)dibenz[b,f][1,4]oxazepine; BRN 0832057; C17H16ClN3O; CHEMBL1113; CL 67772; CL-67772; Dibenz[b,f][1,4]oxazepine, 2-chloro-11-(1-piperazinyl)-; EINECS 237-867-1; MFCD00069210; MLS000069371; UNII-R63VQ857OT
Indication Depression [ICD11: 6A71] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 313.8 Topological Polar Surface Area 36.9
Heavy Atom Count 22 Rotatable Bond Count 1
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
2170
PubChem SID
855963 ; 4621375 ; 7847295 ; 7978696 ; 8150155 ; 8151476 ; 10321488 ; 10507662 ; 11110675 ; 11110676 ; 11335411 ; 11360650 ; 11363340 ; 11365902 ; 11368464 ; 11371973 ; 11374794 ; 11376626 ; 11461622 ; 11466130 ; 11467250 ; 11484886 ; 11485759 ; 11489061 ; 11490882 ; 11493032 ; 11494260 ; 12013426 ; 14950373 ; 17404679 ; 24278075 ; 26613170 ; 26680165 ; 26747067 ; 26751577 ; 29221349 ; 46509117 ; 47291025 ; 47662153 ; 47662154 ; 47662155 ; 47736356 ; 48110341 ; 48110342 ; 48110343 ; 48259108 ; 48334368 ; 48415558 ; 49698344 ; 49846684
ChEBI ID
CHEBI:2675
CAS Number
14028-44-5
TTD Drug ID
D09IOI
Formula
C17H16ClN3O
Canonical SMILES
C1CN(CCN1)C2=NC3=CC=CC=C3OC4=C2C=C(C=C4)Cl
InChI
1S/C17H16ClN3O/c18-12-5-6-15-13(11-12)17(21-9-7-19-8-10-21)20-14-3-1-2-4-16(14)22-15/h1-6,11,19H,7-10H2
InChIKey
QWGDMFLQWFTERH-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-hydroxyamoxapine DM001347
162242
Oxidation - Hydroxylation 1 [3] , [4]
8-hydroxyamoxapine DM001348
43656
Oxidation - Hydroxylation 1 [3] , [4]
N-Formyl-7-hydroxyamoxapine DM001349 N. A. Unclear 1 [5]
N-Formylamoxapine DM001350
606205
Unclear 1 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000205 Amoxapine 7-hydroxyamoxapine Oxidation - Hydroxylation CYP2D6 [3], [4]
MR000206 Amoxapine 8-hydroxyamoxapine Oxidation - Hydroxylation CYP1A2 [3], [4]
MR000207 Amoxapine N-Formyl-7-hydroxyamoxapine Unclear Unclear [5]
MR000208 Amoxapine N-Formylamoxapine Unclear Unclear [5]
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]
References
1 Loxapine Succinate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Addition of amoxapine improves positive and negative symptoms in a patient with schizophrenia Ther Adv Psychopharmacol. 2013 Dec;3(6):340-2. doi: 10.1177/2045125313499363.
3 Addition of amoxapine improves positive and negative symptoms in a patient with schizophrenia. Ther Adv Psychopharmacol. 2013 Dec;3(6):340-2.
4 DrugBank(Pharmacology-Metabolism)Amoxapine
5 Transformation of amoxapine by Cunninghamella elegans Appl Environ Microbiol. 2000 Aug;66(8):3646-9. doi: 10.1128/AEM.66.8.3646-3649.2000.

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