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

General Information of Drug (ID: DR0165)
Drug Name
Azelastine
Synonyms
Azelastina; Azelastina [INN-Spanish]; Azelastine [INN:BAN]; Azelastinum; Azelastinum [INN-Latin]; MBUVEWMHONZEQD-UHFFFAOYSA-N; Optilast; azelastine; 4-((4-Chlorophenyl)methyl)-2-(hexahydro-1-methyl-1H-azepin-4-yl)-1(2H)-phthalazinone hydrochloride; 4-(4-chlorobenzyl)-2-(1-methylazepan-4-yl)phthalazin-1(2H)-one; 4-(p-Chlorobenzyl)-2-(hexahydro-1-methyl-1H-azepin-4-yl)-1-(2H)-phthalazinone; 4-[(4-chlorophenyl)methyl]-2-(1-methylazepan-4-yl)phthalazin-1-one; 58581-89-8; A-5610; BRN 0900747; C22H24ClN3O; CHEBI:2950; CHEMBL639
Indication Allergic rhinitis [ICD11: CA08] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 381.9 Topological Polar Surface Area 35.9
Heavy Atom Count 27 Rotatable Bond Count 3
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
2267
PubChem SID
9970 ; 4503340 ; 7978748 ; 8151525 ; 11373087 ; 11484393 ; 11488465 ; 11491799 ; 14829436 ; 29221440 ; 46507582 ; 47953967 ; 48415598 ; 50010207 ; 50122563 ; 50854757 ; 51091808 ; 57321230 ; 81040982 ; 85209838 ; 85788529 ; 87245030 ; 87350406 ; 103188977 ; 104300096 ; 124893571 ; 125353726 ; 126686074 ; 128573214 ; 131344384 ; 134337644 ; 135027355 ; 137175390 ; 139157643 ; 152034299 ; 160964310 ; 162173200 ; 162876873 ; 163414086 ; 164788079 ; 164833138 ; 172912872 ; 174007265 ; 176485063 ; 178103698 ; 179116569 ; 179499903 ; 184643901 ; 210279616 ; 210281939
ChEBI ID
CHEBI:2950
CAS Number
58581-89-8
TTD Drug ID
D00JVR
Formula
C22H24ClN3O
Canonical SMILES
CN1CCCC(CC1)N2C(=O)C3=CC=CC=C3C(=N2)CC4=CC=C(C=C4)Cl
InChI
1S/C22H24ClN3O/c1-25-13-4-5-18(12-14-25)26-22(27)20-7-3-2-6-19(20)21(24-26)15-16-8-10-17(23)11-9-16/h2-3,6-11,18H,4-5,12-15H2,1H3
InChIKey
MBUVEWMHONZEQD-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
6-hydroxyazelastine DM018066 N. A. Unclear - Unclear 1 [5]
7-hydroxyazelastine DM018067 N. A. Unclear - Unclear 1 [5]
AZ-N-oxides DM018068 N. A. Unclear - Unclear 1 [5]
Demethylazelastine DM018065 N. A. Unclear - Unclear 1 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009905 Azelastine Demethylazelastine Unclear - Unclear Unclear [6]
MR009906 Azelastine 6-hydroxyazelastine Unclear - Unclear Unclear [5]
MR009907 Azelastine 7-hydroxyazelastine Unclear - Unclear Unclear [5]
MR009908 Azelastine AZ-N-oxides Unclear - 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 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[4]
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]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
⏷ Show the Full List of 8  DME(s)
References
1 Azelastine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 In vitro identification of the human cytochrome P-450 enzymes involved in the N-demethylation of azelastine. Drug Metab Dispos. 1999 Aug;27(8):942-6.
3 Azelastine N-demethylation by cytochrome P-450 (CYP)3A4, CYP2D6, and CYP1A2 in human liver microsomes: evaluation of approach to predict the contribution of multiple CYPs. Drug Metab Dispos. 1999 Dec;27(12):1381-91.
4 Inhibitory effects of azelastine and its metabolites on drug oxidation catalyzed by human cytochrome P-450 enzymes. Drug Metab Dispos. 1999 Jul;27(7):792-7.
5 Simultaneous enantioselective separation of azelastine and three of its metabolites for the investigation of the enantiomeric metabolism in rats. I. Liquid chromatography-ionspray tandem mass spectrometry and electrokinetic capillary chromatography
6 Simultaneous determination of azelastine and its major metabolite desmethylazelastine in human plasma using high performance liquid chromatography-tandem mass spectrometry

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