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Details

Stereochemistry ACHIRAL
Molecular Formula C18H19NO
Molecular Weight 265.3496
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of DESMETHYLDOXEPIN, (Z)-

SMILES

CNCC\C=C1\C2=CC=CC=C2COC3=CC=CC=C13

InChI

InChIKey=HVKCEFHNSNZIHO-YBEGLDIGSA-N
InChI=1S/C18H19NO/c1-19-12-6-10-16-15-8-3-2-7-14(15)13-20-18-11-5-4-9-17(16)18/h2-5,7-11,19H,6,12-13H2,1H3/b16-10-

HIDE SMILES / InChI
Molecular Formula C18H19NO
Molecular Weight 265.3496
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Z-N-desmethyldoxepin is an active metabolite of doxepin, a tricyclic antidepressant. Z-N-desmethyldoxepin appeared to be a terminal oxidative metabolite, in comparison with isomeric form E-N-desmethyl-doxepin, which is undergone further oxidation under the action of CYP2D6 activity.

Originator

Ghabrial, H.|Prakash, C.|Tacke, U.G.|Blair, I.A.|Wilkinson, G.R.
4
Curator's Comment: College of Pharmacy, University of Saskatchewan

Approval Year

Unknown
139594
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Contributions of CYP2D6, CYP2C9 and CYP2C19 to the biotransformation of E- and Z-doxepin in healthy volunteers.
2002 Oct
[Trazodone for the treatment of behavioral and psychological symptoms of dementia (BPSD) in Alzheimer's disease: a retrospective study focused on the aggression and negativism in caregiving situations].
2006 Jun
Patents

Patents

20070281990
4
JP2007525670A
148
JP2009519467A
53

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
In 'metabolic consumption' experiments with liver microsomes (having measurable CYP2D6 activity) and initial substrate concentration of 1 microM, the consumption of E-doxepin was greater than that of Z-doxepin. With N-desmethyldoxepin, quinidine inhibited the consumption of E-N-desmethyl-doxepin whereas Z-N-desmethyldoxepin appeared to be a terminal oxidative metabolite. CYP2D6 is a major oxidative enzyme in doxepin metabolism; predominantly catalysing hydroxylation with an exclusive preference for the E-isomers. The relatively more rapid metabolism of E-isomeric forms, and the limited metabolic pathways for the Z-isomers explained the apparent enrichment of Z-N-desmethyldoxepin.
Substance Class Chemical
Created
by admin
on Sat Dec 16 05:27:23 UTC 2023
Edited
by admin
on Sat Dec 16 05:27:23 UTC 2023
Record UNII
SB853T8Y6O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DESMETHYLDOXEPIN, (Z)-
Common Name English
CIS-DESMETHYLDOXEPIN
Common Name English
(Z)-DESMETHYLDOXEPIN
Common Name English
1-PROPANAMINE, 3-DIBENZ(B,E)OXEPIN-11(6H)-YLIDENE-N-METHYL-, (3Z)-
Systematic Name English
1-PROPANAMINE, 3-DIBENZ(B,E)OXEPIN-11(6H)-YLIDENE-N-METHYL-, (Z)-
Systematic Name English
Code System Code Type Description
PUBCHEM
5353833
Created by admin on Sat Dec 16 05:27:23 UTC 2023 , Edited by admin on Sat Dec 16 05:27:23 UTC 2023
PRIMARY
CAS
58534-46-6
Created by admin on Sat Dec 16 05:27:23 UTC 2023 , Edited by admin on Sat Dec 16 05:27:23 UTC 2023
PRIMARY
CHEBI
142339
Created by admin on Sat Dec 16 05:27:23 UTC 2023 , Edited by admin on Sat Dec 16 05:27:23 UTC 2023
PRIMARY
FDA UNII
SB853T8Y6O
Created by admin on Sat Dec 16 05:27:23 UTC 2023 , Edited by admin on Sat Dec 16 05:27:23 UTC 2023
PRIMARY
NIH
NCATS
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