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

General Information of Drug (ID: DR1224)
Drug Name
Oxymetazoline
Synonyms
Oximetazolina [INN-Spanish]; Oximetazolinum; Oxylazine; Oxymetazoline [INN:BAN]; Oxymetazolinum; Oxymetazolinum [INN-Latin]; Oxymethazoline; Oxymetozoline; Rhinofrenol; Rhinolitan; Sinerol; Visine L.R; oxymetazoline; 1491-59-4; Iliadin; Nafrine; Navasin; Navisin; Nezeril; 2-(4-tert-Butyl-2,6-dimethyl-3-hydroxybenzyl)-2-imidazoline; 6-t-Butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenol; 6-tert-Butyl-3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethylphenol; Afrin; EINECS 216-079-1; H 990; HSDB 3143; Hazol; UNII-8VLN5B44ZY
Indication Erythema multiforme [ICD11: EB12] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 260.37 Topological Polar Surface Area 44.6
Heavy Atom Count 19 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
4636
PubChem SID
9567 ; 840961 ; 841971 ; 5214260 ; 7980233 ; 8152848 ; 10508603 ; 11111570 ; 11111571 ; 11113337 ; 11335742 ; 11360981 ; 11363945 ; 11366507 ; 11369069 ; 11371745 ; 11374047 ; 11377231 ; 11461953 ; 11466252 ; 11467372 ; 11484831 ; 11485924 ; 11488814 ; 11490349 ; 11492279 ; 11494865 ; 15221519 ; 26751491 ; 26751492 ; 29223725 ; 46505622 ; 47216754 ; 47365161 ; 47365162 ; 47440226 ; 47588971 ; 47810731 ; 47810732 ; 47959714 ; 47959715 ; 48110433 ; 49698392 ; 50005142 ; 50100299 ; 50104031 ; 50611492 ; 56313774 ; 57322367 ; 85209219
ChEBI ID
CHEBI:7862
CAS Number
1491-59-4
TTD Drug ID
D09EBS
Formula
C16H24N2O
Canonical SMILES
CC1=CC(=C(C(=C1CC2=NCCN2)C)O)C(C)(C)C
InChI
1S/C16H24N2O/c1-10-8-13(16(3,4)5)15(19)11(2)12(10)9-14-17-6-7-18-14/h8,19H,6-7,9H2,1-5H3,(H,17,18)
InChIKey
WYWIFABBXFUGLM-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
Oxymetazoline metabolite M2 DM001127
71315346
Oxidation - Oxidative Dehydrogenation 1 [4]
Oxymetazoline metabolite M8 DM001131 N. A. Conjugation - Conjugation 1 [4]
Oxymetazoline O-glucuronidation DM001133 N. A. Conjugation - O-Glucuronidation 1 [4] , [3]
Oxymetazoline metabolite M1 DM001132
118753142
Oxidation - Hydroxylation 2 [4]
Oxymetazoline metabolite M3 DM001128
118753143
Oxidation - Monohydroxylation 2 [4]
Oxymetazoline metabolite M6 DM001130 N. A. Conjugation - Conjugation 2 [4]
Oxymetazoline metabolite M7 DM001129 N. A. Conjugation - Conjugation 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003156 Oxymetazoline Oxymetazoline metabolite M2 Oxidation - Oxidative Dehydrogenation CYP2C19 [4]
MR003157 Oxymetazoline Oxymetazoline metabolite M8 Conjugation - Conjugation Unclear [4]
MR003158 Oxymetazoline Oxymetazoline O-glucuronidation Conjugation - O-Glucuronidation UGT1A9 ... [4], [3]
MR003152 Oxymetazoline metabolite M2 Oxymetazoline metabolite M3 Oxidation - Monohydroxylation CYP2C19 [4]
MR003153 Oxymetazoline metabolite M2 Oxymetazoline metabolite M7 Conjugation - Conjugation Unclear [4]
MR003154 Oxymetazoline metabolite M2 Oxymetazoline metabolite M6 Conjugation - Conjugation Unclear [4]
MR003155 Oxymetazoline metabolite M8 Oxymetazoline metabolite M1 Oxidation - Hydroxylation CYP2C19 [4]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 2A1 (UGT2A1) DME0622 Homo sapiens
UD2A1_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 2A2(UGT2A2) DMEN887 .
UD2A2_HUMAN
2.4.1.17
[3]
References
1 Oxymetazoline was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 In vitro metabolism of oxymetazoline: evidence for bioactivation to a reactive metabolite Drug Metab Dispos. 2011 Apr;39(4):693-702. doi: 10.1124/dmd.110.036004.
3 Identification and characterization of oxymetazoline glucuronidation in human liver microsomes: evidence for the involvement of UGT1A9. J Pharm Sci. 2011 Feb;100(2):784-93.
4 In vitro metabolism of oxymetazoline: evidence for bioactivation to a reactive metabolite. Drug Metab Dispos. 2011 Apr;39(4):693-702.

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