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

General Information of Drug (ID: DR5078)
Drug Name
Doxylamine
Synonyms
Dossilamina; Doxilamina; Doxilminio; Doxylaminum; Dossilamina [DCIT]; Diclectin (TN); Dolased (TN); Donormyl (TN); Dormidina (TN); Doxilminio [INN-Spanish]; Doxylamine (INN); Doxylamine [INN:BAN]; Doxylaminum [INN-Latin]; Dozile (TN); Evanorm (TN); Mersyndol (TN); Restavit (TN); Somnil (TN); Syndol (TN); Unisom-2 (TN); Phenyl-2-pyridylmethyl-beta-N,N-dimethylaminoethyl ether; N,N-Dimethyl-2-(1-phenyl-1-(2-pyridinyl)ethoxy)ethanamine; N,N-dimethyl-2-(1-phenyl-1-pyridin-2-ylethoxy)ethanamine; N,N-dimethyl-2-[(1-phenyl-1-pyridin-2-ylethyl)oxy]ethanamine; N,N-dimethyl-2-[1-phenyl-1-(pyridin-2-yl)ethoxy]ethanamine; 2-(alpha-(2-(Dimethylamino)ethoxy)-alpha-methylbenzyl)pyridine; 2-Dimethylaminoethoxyphenylmethyl-2-picoline
Indication Morning sickness [ICD11: SC00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 270.37 Topological Polar Surface Area 25.4
Heavy Atom Count 20 Rotatable Bond Count 6
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
3162
ChEBI ID
CHEBI:51380
CAS Number
469-21-6
TTD Drug ID
D0Y2LR
Formula
C17H22N2O
Canonical SMILES
CC(C1=CC=CC=C1)(C2=CC=CC=N2)OCCN(C)C
InChI
InChI=1S/C17H22N2O/c1-17(20-14-13-19(2)3,15-9-5-4-6-10-15)16-11-7-8-12-18-16/h4-12H,13-14H2,1-3H3
InChIKey
HCFDWZZGGLSKEP-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
Acid DM016170
54409544
Unclear - Unclear 1 [2]
Alcohol DM001094 N. A. Unclear - Unclear 1 [2]
Doxylamine metabolite IV DM016377
86142025
Oxidation - Doxylamine pyridine N-oxidation 1 [3]
Doxylamine metabolite IX DM015084
86883
Unclear - Unclear 1 [3]
Doxylamine metabolite V DM015185
135338
Unclear - Unclear 1 [3]
Doxylamine metabolite VII DM017034 N. A. Unclear - Unclear 1 [3]
Doxylamine metabolite VIII DM015789
11789877
Unclear - Unclear 1 [3]
Doxylamine metabolite XV DM017032 N. A. Unclear - Unclear 1 [3]
Doxylamine metabolite VI DM016312
71401588
Unclear - Unclear 2 [3]
Doxylamine metabolite X DM017036 N. A. Unclear - Unclear 2 [3]
Doxylamine metabolite XI DM017035 N. A. Unclear - Unclear 2 [3]
Doxylamine metabolite XII DM017033 N. A. Unclear - Phenolic N-desmethyldoxylamine 2 [3]
Doxylamine metabolite XIV DM016381
86254255
Unclear - Unclear 2 [3]
Doxylamine metabolite XVII DM015326
602844
Conjugation - N-acetyl conjugation 2 [3]
Doxylamine metabolite II DM016363
85603461
Oxidation - Doxylamine aliphatic N-oxidation 3 [3]
Doxylamine metabolite XIII DM015822
13192882
Unclear - Unclear 3 [3]
Doxylamine metabolite XVI DM015325
602704
Conjugation - N-acetyl conjugation 3 [3]
⏷ Show the Full List of 17  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007969 Doxylamine Doxylamine metabolite V Unclear - Unclear Unclear [3]
MR007972 Doxylamine Doxylamine metabolite IX Unclear - Unclear Unclear [3]
MR007975 Doxylamine Doxylamine metabolite XV Unclear - Unclear Unclear [3]
MR007979 Doxylamine Doxylamine metabolite VII Unclear - Unclear Unclear [3]
MR007982 Doxylamine Doxylamine metabolite VIII Unclear - Unclear Unclear [3]
MR007985 Doxylamine Doxylamine metabolite IV Oxidation - Doxylamine pyridine N-oxidation Unclear [3]
MR007986 Doxylamine Acid Unclear - Unclear Unclear [2]
MR007987 Doxylamine Alcohol Unclear - Unclear Unclear [2]
MR007973 Doxylamine metabolite IX Doxylamine metabolite XIV Unclear - Unclear Unclear [3]
MR007981 Doxylamine metabolite IX Doxylamine metabolite XI Unclear - Unclear Unclear [3]
MR007970 Doxylamine metabolite V Doxylamine metabolite VI Unclear - Unclear Unclear [3]
MR007977 Doxylamine metabolite V Doxylamine metabolite XVII Conjugation - N-acetyl conjugation Unclear [3]
MR007978 Doxylamine metabolite V Doxylamine metabolite XII Unclear - Phenolic N-desmethyldoxylamine Unclear [3]
MR007980 Doxylamine metabolite VII Doxylamine metabolite XII Unclear - Phenolic N-desmethyldoxylamine Unclear [3]
MR007983 Doxylamine metabolite VIII Doxylamine metabolite X Unclear - Unclear Unclear [3]
MR007976 Doxylamine metabolite XV Doxylamine metabolite XIV Unclear - Unclear Unclear [3]
MR007971 Doxylamine metabolite VI Doxylamine metabolite XVI Conjugation - N-acetyl conjugation Unclear [3]
MR007984 Doxylamine metabolite X Doxylamine metabolite II Oxidation - Doxylamine aliphatic N-oxidation Unclear [3]
MR007974 Doxylamine metabolite XIV Doxylamine metabolite XIII Unclear - Unclear Unclear [3]
⏷ Show the Full List of 19 MR(s)
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: 7171).
2 Metabolism of 14C-labeled doxylamine succinate (Bendectin) in the rhesus monkey (Macaca mulatta)
3 Doxylamine metabolism in rat and monkey

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