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

General Information of Drug (ID: DR0937)
Drug Name
Levocetirizine
Synonyms
Levocetirizine; Xarlin; Cetirizine-d4; Levocetrizine; (-)-Cetirizine; (-)-Cetirizine Dihydrochloride; (2-(4-((R-p-Chloro-alpha-phenylbenzyl)-1-piperazinyl)ethoxy)acetic acid; (2-{4-[(R)-(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl}ethoxy)acetic acid; (R)-2-(2-(4-((4-Chlorophenyl)(phenyl)methyl)piperazin-1-yl)ethoxy)acetic acid; (R)-cetirizine; 130018-77-8; 6U5EA9RT2O; Acetic acid, (2-(4-((R)-(4-chlorophenyl)phenylmethyl)-1-piperazinyl)ethoxy)-; UNII-6U5EA9RT2O
Indication Allergic rhinitis [ICD11: CA08] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 388.9 Topological Polar Surface Area 53
Heavy Atom Count 27 Rotatable Bond Count 8
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
1549000
PubChem SID
11545046 ; 14927596 ; 26719822 ; 32248928 ; 46386593 ; 47583669 ; 47805464 ; 48179644 ; 48253864 ; 49681558 ; 49861381 ; 50276924 ; 51091738 ; 57409063 ; 92308500 ; 92714143 ; 93166949 ; 93302554 ; 103771174 ; 110525158 ; 124659008 ; 124799922 ; 126629651 ; 126655634 ; 126670860 ; 131297234 ; 134338605 ; 135107372 ; 135650416 ; 136211813 ; 136351130 ; 137001886 ; 139283254 ; 143494987 ; 152235888 ; 162258150 ; 163423572 ; 164837925 ; 172080394 ; 172859038 ; 175267409 ; 175270481 ; 179149784 ; 184548289 ; 184654357 ; 196111560 ; 211534825 ; 223258882 ; 223582092 ; 223657396
ChEBI ID
CHEBI:94559
CAS Number
130018-77-8
TTD Drug ID
D0M8PW
Formula
C21H25ClN2O3
Canonical SMILES
C1CN(CCN1CCOCC(=O)O)C(C2=CC=CC=C2)C3=CC=C(C=C3)Cl
InChI
1S/C21H25ClN2O3/c22-19-8-6-18(7-9-19)21(17-4-2-1-3-5-17)24-12-10-23(11-13-24)14-15-27-16-20(25)26/h1-9,21H,10-16H2,(H,25,26)/t21-/m1/s1
InChIKey
ZKLPARSLTMPFCP-OAQYLSRUSA-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
Levocetirizine Dihydrodiol metabolite (M2) DM000267 N. A. Unclear 1 [3]
Levocetirizine Hydroxy metabolite (M5) DM000268 N. A. Unclear 1 [3]
Levocetirizine N-dealkylated and Aromatic Hydroxylated metabolite (M9) DM000271 N. A. Unclear 1 [3]
Levocetirizine N-oxide metabolite (M3) DM000273 N. A. Oxidation - N-Oxidation 1 [3]
Levocetirizine O-dealkylated metabolite (M6) DM000274 N. A. Oxidation - O-Dealkylation 1 [3]
Levocetirizine Taurine conjugated metabolite (M8) DM000275 N. A. Conjugation - Taurine Conjugation 1 [3]
Levocetirizine 4-chloro-4'-hydroxybenzhydryl Mercapturate metabolites (M10a and M10b) DM000272 N. A. Unclear 2 [3]
Levocetirizine Hydroxy metabolite (M5) DM000268 N. A. Unclear 2 [3]
Levocetirizine Hydroxymethoxy metabolite (M4) DM000269 N. A. Unclear 2 [3]
Levocetirizine O-glucuronidated metabolite (M1) DM000270 N. A. Unclear 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001479 Levocetirizine Levocetirizine Dihydrodiol metabolite (M2) Unclear Unclear [3]
MR001480 Levocetirizine Levocetirizine Hydroxy metabolite (M5) Unclear Unclear [3]
MR001481 Levocetirizine Levocetirizine N-dealkylated and Aromatic Hydroxylated metabolite (M9) Unclear Unclear [3]
MR001482 Levocetirizine Levocetirizine N-oxide metabolite (M3) Oxidation - N-Oxidation Unclear [3]
MR001483 Levocetirizine Levocetirizine O-dealkylated metabolite (M6) Oxidation - O-Dealkylation Unclear [3]
MR001484 Levocetirizine Levocetirizine Taurine conjugated metabolite (M8) Conjugation - Taurine Conjugation Unclear [3]
MR001475 Levocetirizine Dihydrodiol metabolite (M2) Levocetirizine Hydroxy metabolite (M5) Unclear Unclear [3]
MR001476 Levocetirizine Dihydrodiol metabolite (M2) Levocetirizine Hydroxymethoxy metabolite (M4) Unclear Unclear [3]
MR001477 Levocetirizine Hydroxy metabolite (M5) Levocetirizine O-glucuronidated metabolite (M1) Unclear Unclear [3]
MR001478 Levocetirizine N-dealkylated and Aromatic Hydroxylated metabolite (M9) Levocetirizine 4-chloro-4'-hydroxybenzhydryl Mercapturate metabolites (M10a and M10b) Unclear Unclear [3]
⏷ Show the Full List of 10 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 Levocetirizine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 FDA label of Levocetirizine dihydrochloride. The 2020 official website of the U.S. Food and Drug Administration.
3 Absorption, distribution, metabolism and excretion of [14C]levocetirizine, the R enantiomer of cetirizine, in healthy volunteers Eur J Clin Pharmacol. 2001 Oct;57(8):571-82. doi: 10.1007/s002280100364.

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