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

General Information of Drug (ID: DR5306)
Drug Name
Antazoline
Synonyms
Analergine; Antastan; Antasten; Antazolin; Antazolina; Antazolinum; Antihistal; Antistin; Antistine; Azalone; Histostab;Imidamin; Imidamine; Phenazolin; Phenazoline; Antazolina [Spanish]; Antazolinum [Latin]; Antazolina [INN-Spanish]; Antazoline (INN); Antazoline [INN:BAN]; Antazolinum [INN-Latin]; Ben-A-hist; N-Benzyl-N-(4,5-dihydro-1H-imidazol-2-ylmethyl)aniline; N-(4,5-dihydro-1H-imidazol-2-ylmethyl)-N-(phenylmethyl)aniline; 2-(N-Benzylanilinomethyl)-2-imidazoline; 2-(N-Phenyl-N-benzylaminomethyl)imidazoline; 2-Phenyl-benzyl-amino-methylimidazolin; 2-Phenyl-benzyl-amino-methylimidazolin [German]; 4,5-Dihydro-N-phenyl-N-phenylmethyl-1H-imidazole-2-methanamine; 5512-M
Indication Nasal congestion [ICD11: MD11] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 265.35 Topological Polar Surface Area 27.6
Heavy Atom Count 20 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
2200
ChEBI ID
CHEBI:84115
CAS Number
91-75-8
TTD Drug ID
D06FZX
Formula
C17H19N3
Canonical SMILES
C1CN=C(N1)CN(CC2=CC=CC=C2)C3=CC=CC=C3
InChI
InChI=1S/C17H19N3/c1-3-7-15(8-4-1)13-20(14-17-18-11-12-19-17)16-9-5-2-6-10-16/h1-10H,11-14H2,(H,18,19)
InChIKey
REYFJDPCWQRWAA-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
Antazoline B DM018804 N. A. Oxidation - Hydroxylation 1 [2]
Antazoline M1 DM016578
129897198
Unclear - Unclear 1 [3]
Antazoline M2 DM018808 N. A. Oxidation - Hydroxylation 1 [3]
Antazoline M4 DM018819 N. A. Conjugation - Glucuronidation 1 [2]
Antazoline A DM018809 N. A. Oxidation - Hydroxylation 2 [2]
Antazoline C DM016422
91901960
Unclear - Unclear 2 [2]
Antazoline D DM014909
7637
Unclear - Unclear 2 [2]
Antazoline M3 DM018816 N. A. Conjugation - Glucuronidation 2 [2]
Antazoline M5 DM018817 N. A. Conjugation - Glucuronidation 2 [2]
Antazoline MW299 DM018813 N. A. Unclear - Unclear 2 [2]
Antazoline MW351 DM018818 N. A. Conjugation - Glucuronidation 2 [2]
Antazoline MW361 DM018815 N. A. Oxidation - Sulfoxidation 2 [2]
Antazoline M6 DM018810 N. A. Conjugation - Glucuronidation 3 [2]
Antazoline M7 DM018812 N. A. Conjugation - Glucuronidation 3 [2]
Antazoline M8 DM018807 N. A. Conjugation - Glucuronidation 3 [2]
Antazoline MW295 DM018805 N. A. Oxidation - Hydroxylation 3 [2]
Antazoline MW475 DM018814 N. A. Conjugation - Glucuronidation 3 [2]
Antazoline MW487b DM018811 N. A. Conjugation - Glucuronidation 3 [2]
Antazoline MW485 DM018806 N. A. Conjugation - Glucuronidation 4 [2]
⏷ Show the Full List of 19  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR011152 Antazoline Antazoline B Oxidation - Hydroxylation Unclear [2]
MR011157 Antazoline Antazoline M2 Oxidation - Hydroxylation Unclear [3]
MR011168 Antazoline Antazoline M1 Unclear - Unclear Unclear [3]
MR011170 Antazoline Antazoline M4 Conjugation - Glucuronidation Unclear [2]
MR011153 Antazoline B Antazoline C Unclear - Unclear Unclear [2]
MR011169 Antazoline M1 Antazoline MW351 Conjugation - Glucuronidation Unclear [2]
MR011158 Antazoline M2 Antazoline A Oxidation - Hydroxylation Unclear [2]
MR011161 Antazoline M2 Antazoline D Unclear - Unclear Unclear [2]
MR011163 Antazoline M2 Antazoline MW299 Unclear - Unclear Unclear [2]
MR011165 Antazoline M2 Antazoline MW361 Oxidation - Sulfoxidation Unclear [2]
MR011166 Antazoline M2 Antazoline M3 Conjugation - Glucuronidation Unclear [2]
MR011167 Antazoline M2 Antazoline M5 Conjugation - Glucuronidation Unclear [2]
MR011159 Antazoline A Antazoline M6 Conjugation - Glucuronidation Unclear [2]
MR011160 Antazoline A Antazoline MW487b Conjugation - Glucuronidation Unclear [2]
MR011154 Antazoline C Antazoline MW295 Oxidation - Hydroxylation Unclear [2]
MR011156 Antazoline C Antazoline M8 Conjugation - Glucuronidation Unclear [2]
MR011162 Antazoline D Antazoline M7 Conjugation - Glucuronidation Unclear [2]
MR011164 Antazoline MW299 Antazoline MW475 Conjugation - Glucuronidation Unclear [2]
MR011155 Antazoline MW295 Antazoline MW485 Conjugation - Glucuronidation Unclear [2]
⏷ Show the Full List of 19 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
References
1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7116).
2 Characterization of In Vitro and In Vivo Metabolism of Antazoline Using Liquid Chromatography-Tandem Mass Spectrometry
3 Development and Performance Verification of the PBPK Model for Antazoline and Its Metabolite and Its Utilization for Pharmacological Hypotheses Formulating

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