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

General Information of Drug (ID: DR0544)
Drug Name
Doxepin hydrochloride
Synonyms
Doxepin (Hydrochloride); Doxepin HCl; Doxepin Hydrochloride; Doxepine hydrochloride; Doxepin; Doxepin [USAN]; Doxepina [INN-Spanish]; Doxepine; Doxepinum [INN-Latin]; HSDB 3069; MF 10; N,N-Dimethyldibenz(b,e)oxepin-delta(11(6H),gamma)-propylamine; UNII-851NLB57HQ; Trans-doxepin; (e)-doxepin; 11-(3-(Dimethylamino)propylidene)-6H-dibenz(b,e)oxepine; 11-(3-Dimethylamino-propyliden)-6,11-dihydro-dibenz(b,e)oxipin; 11-(3-Dimethylaminopropylidene)-6,11-dihydrodibenz(b,e)oxipin; 1668-19-5; 851NLB57HQ; CCRIS 9176; Cidoxepin [INN]; Cidoxepina; Cidoxepinum; EINECS 214-966-8; MF 10 HCl; MLS000069794; N,N-Dimethyldibenz(b,e)oxepin-delta(sup 11(6H),gamma)-propylamine hydrochloride; NSC-108160; Novoxapin; Novoxapin hydrochloride; SMR000058230; Silenor; Toruan; UNII-CU61C5RH24; 11-(3-(Dimethylamino)propylidene)-6,11-dihydrodibenz(b,e)oxepin hydrochloride; 1229-29-4; Aponal; C19H21NO.HCl; CU61C5RH24
Indication Depression [ICD11: 6A71] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 315.8 Topological Polar Surface Area 12.5
Heavy Atom Count 22 Rotatable Bond Count 3
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
6419921
ChEBI ID
CHEBI:4711
CAS Number
1229-29-4
TTD Drug ID
D06FES
Formula
C19H22ClNO
Canonical SMILES
CN(C)CCC=C1C2=CC=CC=C2COC3=CC=CC=C31.Cl
InChI
1S/C19H21NO.ClH/c1-20(2)13-7-11-17-16-9-4-3-8-15(16)14-21-19-12-6-5-10-18(17)19;/h3-6,8-12H,7,13-14H2,1-2H3;1H/b17-11+;
InChIKey
MHNSPTUQQIYJOT-SJDTYFKWSA-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
(E)-2-hydroxydoxepin DM006219
67319009
Oxidation - Hydrolyzationn 1 [5]
Doxepin N-oxide DM006217
100995277
Oxidation - Oxidationn 1 [6]
Formaldehyde DM001748
712
Oxidation - N-demethylation 1 [6]
N-desmethyldoxepin DM006213
6433351
Oxidation - N-demethylation 1 [6]
(E)-2-hydroxy-N-desmethyldoxepin DM006220
59023618
Oxidation - Demethylation 2 [6]
Doxepin N-oxide glucuronide DM006218
131770046
Conjugation - Glucuronidation 2 [6]
Hydroxydesmethyl doxepin DM006214
67320762
Oxidation - Hydrolyzationn 2 [6]
Hydroxydoxepin glucuronide DM006221 N. A. Conjugation - Glucuronidation 2 [6]
Didesmethyl doxepin DM006216
6434755
Oxidation - N-demethylation 3 [6]
Hydroxydesmethyl doxepin glucuronide DM006215
131769921
Conjugation - Glucuronidation 3 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006661 Doxepin hydrochloride N-desmethyldoxepin Oxidation - N-demethylation CYP2D6 ... [6]
MR006665 Doxepin hydrochloride Formaldehyde Oxidation - N-demethylation Unclear [6]
MR006666 Doxepin hydrochloride Doxepin N-oxide Oxidation - Oxidationn Unclear [6]
MR006668 Doxepin hydrochloride (E)-2-hydroxydoxepin Oxidation - Hydrolyzationn CYP2D6 [5]
MR006669 (E)-2-hydroxydoxepin (E)-2-hydroxy-N-desmethyldoxepin Oxidation - Demethylation Unclear [6]
MR006670 (E)-2-hydroxydoxepin Hydroxydoxepin glucuronide Conjugation - Glucuronidation Unclear [6]
MR006667 Doxepin N-oxide Doxepin N-oxide glucuronide Conjugation - Glucuronidation Unclear [6]
MR006662 N-desmethyldoxepin Hydroxydesmethyl doxepin Oxidation - Hydrolyzationn CYP2D6 [6]
MR006663 Hydroxydesmethyl doxepin Hydroxydesmethyl doxepin glucuronide Conjugation - Glucuronidation Unclear [6]
MR006664 Hydroxydesmethyl doxepin Didesmethyl doxepin Oxidation - N-demethylation Unclear [6]
⏷ 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 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
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]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
References
1 Doxepin Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 The N-demethylation of the doxepin isomers is mainly catalyzed by the polymorphic CYP2C19. Pharm Res. 2002 Jul;19(7):1034-7.
3 Contributions of CYP2D6, CYP2C9 and CYP2C19 to the biotransformation of E- and Z-doxepin in healthy volunteers. Pharmacogenetics. 2002 Oct;12(7):571-80.
4 Doxepin inhibits CYP2D6 activity in vivo. Pol J Pharmacol. 2004 Jul-Aug;56(4):491-4.
5 DrugBank(Pharmacology-Metabolism):Doxepin hydrochloride
6 Pharmacogenomics knowledge for personalized medicine Clin Pharmacol Ther. 2012 Oct;92(4):414-7. doi: 10.1038/clpt.2012.96.

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