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

General Information of Drug (ID: DR0146)
Drug Name
Asenapine maleate
Synonyms
Asenapine (maleate); Asenapine maleate (JAN/USAN); Asenapine maleate [USAN]; Asenapine maleate, >=98% (HPLC); Asenapine/; C17H16ClNO.C4H4O4; CHEBI:71248; CS-0859; Asenapine; Asenapine [INN:BAN]; BCPP000385; CHEBI:71257; CHEMBL504548; EINECS 265-829-4; GTPL22; HSDB 8061; PDSP2_001584; SCHEMBL678411; VSWBSWWIRNCQIJ-HUUCEWRRSA-N; ZINC2299; trans-5-Chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz(2,3:6,7)oxepino(4,5-c)pyrrole; trans-5-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz[2,3:6,7]oxepino[4,5-c]pyrrole; (3aS,12bS)-5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole; (S,S)-asenapine; 65576-45-6; AC1L4SHR; EINECS 288-064-8; GMDCDXMAFMEDAG-CHHFXETESA-N; HY-11100; MFCD00900588; MK-8274; Org 5222; Org 5222 maleate; SC-82643; SCH-900274; SCHEMBL175228; Saphris; Saphris (TN); s1283; trans-5-Chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz(2,3:6,7)oxepino(4,5-c)pyrrole maleate; (S,S)-Asenapine Maleate; ABP000604; AKOS015951084
Indication Schizophrenia [ICD11: 6A20] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 401.8 Topological Polar Surface Area 87.1
Heavy Atom Count 28 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
6917875
ChEBI ID
CHEBI:71248
CAS Number
85650-56-2
TTD Drug ID
D00JRA
Formula
C21H20ClNO5
Canonical SMILES
CN1CC2C(C1)C3=C(C=CC(=C3)Cl)OC4=CC=CC=C24.C(=CC(=O)O)C(=O)O
InChI
1S/C17H16ClNO.C4H4O4/c1-19-9-14-12-4-2-3-5-16(12)20-17-7-6-11(18)8-13(17)15(14)10-19;5-3(6)1-2-4(7)8/h2-8,14-15H,9-10H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t14-,15-;/m1./s1
InChIKey
GMDCDXMAFMEDAG-CHHFXETESA-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
10,11-dihydroxyasenapine DM001768
70795523
Unclear 1 [2]
Asenapine-N-glucuronide DM001769
129011585
Conjugation - N-Glucuronidation 1 [2]
Asenapine-N-oxide DM001770
14577087
Unclear 1 [2]
N-desmethylasenapine DM001762 N. A. Unclear 1 [2]
10,11-dihydroxy-N-desmethyl asenapine DM001763
139593534
Unclear 2 [2]
11-hydroxy-N-formyl-N-desmethylasenapine DM001765
156596474
Unclear 2 [2]
Asenapine maleate glucuronide metabolite DM001764 N. A. Conjugation - Glucuronidation 2 [2]
Hydroxy-N-formyl-N-desmethylasenapine DM001767 N. A. Unclear 2 [2]
N-desmethylasenapine-N-carbamoylglucuronide DM001766 N. A. Unclear 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000326 Asenapine maleate N-desmethylasenapine Unclear Unclear [2]
MR000327 Asenapine maleate 10,11-dihydroxyasenapine Unclear Unclear [2]
MR000328 Asenapine maleate Asenapine-N-glucuronide Conjugation - N-Glucuronidation UGT1A4 [2]
MR000329 Asenapine maleate Asenapine-N-oxide Unclear Unclear [2]
MR000321 N-desmethylasenapine 10,11-dihydroxy-N-desmethyl asenapine Unclear Unclear [2]
MR000322 N-desmethylasenapine Asenapine maleate glucuronide metabolite Conjugation - Glucuronidation Unclear [2]
MR000323 N-desmethylasenapine 11-hydroxy-N-formyl-N-desmethylasenapine Unclear Unclear [2]
MR000324 N-desmethylasenapine N-desmethylasenapine-N-carbamoylglucuronide Unclear Unclear [2]
MR000325 N-desmethylasenapine Hydroxy-N-formyl-N-desmethylasenapine Unclear Unclear [2]
⏷ Show the Full List of 9 MR(s)
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]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
UDP-glucuronosyltransferase 1A4 (UGT1A4) DME0048 Homo sapiens
UD14_HUMAN
2.4.1.17
[3]
References
1 Asenapine Maleate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Asenapine review, part I: chemistry, receptor affinity profile, pharmacokinetics and metabolism. Expert Opin Drug Metab Toxicol. 2014 Jun;10(6):893-903.
3 Asenapine for the treatment of manic and mixed episodes associated with bipolar I disorder: from clinical research to clinical practice. Expert Opin Pharmacother. 2013 Mar;14(4):489-504.

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