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desmethyldoxepin

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

desmethyldoxepin: active metabolite if doxepin; RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

desmethyldoxepin : A dibenzooxepine resulting from the demethylation of the antidepressant doxepin. It is the active metabolite of doxepin. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

(Z)-desmethyldoxepin : The (Z)-isomer of desmethyldoxepin. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID5353833
CHEBI ID142339
CHEBI ID141547
SCHEMBL ID342603
MeSH IDM0092106

Synonyms (30)

Synonym
desmethyldoxepin
nordoxepin
desmethyldoxepine
3-(dibenzo[b,e]oxepin-11(6h)-ylidene)-n-methylpropan-1-amine
cis-n-desmethyldoxepin
3-(dibenzo[b,e]oxepin-11(6h)-ylidene)-n-methyl-1-propanamine
CHEBI:142339
(z)-desmethyldoxepin
58534-46-6
3-(6h-dibenz[b,e]oxepin-11-ylidene)-n-methylpropylamine
(z)-n-desmethyldoxepin
CHEBI:141547
11-(3-methylamino-propyliden)-dibenzo[b,e]oxepin
cis-desmethyldoxepin
(3z)-3-(dibenzo[b,e]oxepin-11(6h)-ylidene)-n-methylpropan-1-amine
z-desmethyldoxepin
desmethyldoxepin, (z)-
unii-sb853t8y6o
sb853t8y6o ,
1-propanamine, 3-dibenz(b,e)oxepin-11(6h)-ylidene-n-methyl-, (3z)-
1-propanamine, 3-dibenz(b,e)oxepin-11(6h)-ylidene-n-methyl-, (z)-
SCHEMBL342603
(3z)-3-dibenzo[b,e]oxepin-11(6h)-ylidene-n-methyl-1-propanamine #
HVKCEFHNSNZIHO-YBEGLDIGSA-N
desmethyldoxepin (hydrochloride)
Q27289123
methyl(3-{9-oxatricyclo[9.4.0.0,3,8]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene}propyl)amine
EN300-1719055
DTXSID701177750
(3z)-3-dibenz[b,e]oxepin-11(6h)-ylidene-n-methyl-1-propanamine

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"To report adverse effects in a newborn infant whose mother had been treated with doxepin during pregnancy and while breast-feeding."( Adverse effects in a newborn infant breast-fed by a mother treated with doxepin.
Frey, OR; Scheidt, P; von Brenndorff, AI, 1999
)
0.3
" All adverse effects subsided within 48 hours after breast-feeding was stopped."( Adverse effects in a newborn infant breast-fed by a mother treated with doxepin.
Frey, OR; Scheidt, P; von Brenndorff, AI, 1999
)
0.3
"Despite the small doses of doxepin and its active metabolite ingested by breast-fed babies, there is a risk of accumulation and resultant adverse effects."( Adverse effects in a newborn infant breast-fed by a mother treated with doxepin.
Frey, OR; Scheidt, P; von Brenndorff, AI, 1999
)
0.3

Pharmacokinetics

We evaluated the pharmacokinetic profile of doxepin and desmethyldoxepin after topical application of doXepin hydrochloride 5% cream alone or in combination with 0.5%.

ExcerptReferenceRelevance
" Results for total doxepin showed wide intersubject variation in all pharmacokinetic parameters except tmax and Cmax."( Stereoselective pharmacokinetics of doxepin isomers.
Cooper, JK; Gurnsey, T; Hawes, EM; Hubbard, JW; Korchinski, ED; McKay, G; Midha, KK; Schwede, R, 1992
)
0.28
"In eight healthy young volunteers, 15 g of activated charcoal administered orally 30 min after 50 mg of doxepin, reduced the achieved peak concentration of the drug in serum by 70% and total availability by 49%."( Effect of single and repeated doses of activated charcoal on the pharmacokinetics of doxepin.
Iisalo, E; Scheinin, M; Virtanen, R, 1985
)
0.27
" Serum samples were obtained and pharmacokinetic parameters estimated from the dose-normalized serum concentrations of doxepin and desmethyldoxepin."( Pharmacokinetics of doxepin in subjects with pruritic atopic dermatitis.
Cohen, L; Drake, LA; Flood, JG; Gillies, R; Phillips, SB; Riordan, AT; Stiller, MJ, 1999
)
0.3
"We retrospectively analysed pharmacokinetic therapeutic drug-monitoring data in 114 psychiatric patients (79 females, 35 males) treated with doxepine for a period of 22-306 days, mostly due to major depression."( Pharmacokinetics of doxepin and desmethyldoxepin: an evaluation with the population approach.
Gleiter, CH; Meineke, I; Meyer-Barner, M; Schreeb, KH, 2002
)
0.31

Bioavailability

ExcerptReferenceRelevance
" Relative bioavailability during concurrent cimetidine treatment was 123% of that during the control trial."( Doxepin-cimetidine interaction: increased doxepin bioavailability during cimetidine treatment.
Abernethy, DR; Todd, EL, 1986
)
0.27
" The method is sensitive enough to be used in drug bioavailability studies with doxepin."( Determination of doxepin and desmethyldoxepin in human plasma using liquid chromatography-tandem mass spectrometry.
Badenhorst, D; de Jager, AD; Hundt, AF; Hundt, HK; Scanes, T; Sutherland, FC; Swart, KJ, 2000
)
0.31
" Diltiazem HCl ER tablets administered in the evening exhibited 17% and 22% greater bioavailability compared to morning administration under single-dose and steady-state conditions, respectively."( Pharmacokinetics of a novel diltiazem HCl extended-release tablet formulation for evening administration.
Albert, KS; Eradiri, O; Lai, JC; Sista, S, 2003
)
0.32

Dosage Studied

ExcerptRelevanceReference
" Mean DMD t1/2 was not significantly affected by multiple dosing (34."( Multiple-dose doxepin kinetics in depressed patients.
Fann, WE; Faulkner, RD; Lee, CS; Lewis, WA; Pitts, WM, 1983
)
0.27
" The dialysis experiments show that modification of the usual dosage regimen is not necessary during hemodialysis or on dialysis days."( Hemodialysis of doxepin and desmethyldoxepin in uremic patients.
Faulkner, RD; Lee, CS; Senekjian, HO, 1984
)
0.27
"A study of 23 patients (16 females, 7 males), diagnosed as suffering from anxiety, was carried out using a flexible dosage regimen of doxepin."( Doxepin plasma levels and anxiolytic response.
Bianchi, GN; Burrows, GD; Maguire, KP; Norman, TR; Wurm, JM, 1980
)
0.26
" The method has been applied to analyses of plasma and urine samples from human volunteers and animals dosed with doxepin."( Stereoselective and simultaneous measurement of cis- and trans-isomers of doxepin and N-desmethyldoxepin in plasma or urine by high-performance liquid chromatography.
Hubbard, JW; McKay, G; Midha, KK; Yan, J, 1997
)
0.3
" It is therefore probable that the defective genotype has contributed to the death, possibly involving repeated high dosage of doxepin."( A fatal doxepin poisoning associated with a defective CYP2D6 genotype.
Koski, A; Ojanperä, I; Sajantila, A; Sistonen, J; Vuori, E, 2007
)
0.34
" Dox concentration measured from two cases was well within a concentration range considered therapeutic, whereas subtherapeutic dosing may have occurred in another two cases."( Doxepin and nordoxepin concentrations in body fluids and tissues in doxepin associated deaths.
Dettling, A; Gronewold, A; Haffner, HT; Skopp, G, 2009
)
0.35
" The plasma concentration of both doxepin and nordoxepin correlated significantly with the oral dosage of doxepin (doxepin: r = +0."( Doxepin concentrations in plasma and cerebrospinal fluid.
Fassbender, K; Maurer, HH; Remane, D; Schomburg, R; Spiegel, J, 2011
)
0.37
" Hence, a different dosing strategy is required among smoking and nonsmoking patients."( Analysis of smoking behavior on the pharmacokinetics of antidepressants and antipsychotics: evidence for the role of alternative pathways apart from CYP1A2.
Deckert, J; Hommers, LG; Menke, A; Samanski, L; Scherf-Clavel, M; Unterecker, S, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
desmethyldoxepinA dibenzooxepine resulting from the demethylation of the antidepressant doxepin. It is the active metabolite of doxepin.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (1)

PathwayProteinsCompounds
Doxepin Metabolism Pathway516

Research

Studies (46)

TimeframeStudies, This Drug (%)All Drugs %
pre-199022 (47.83)18.7374
1990's10 (21.74)18.2507
2000's10 (21.74)29.6817
2010's2 (4.35)24.3611
2020's2 (4.35)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials6 (12.24%)5.53%
Reviews2 (4.08%)6.00%
Case Studies5 (10.20%)4.05%
Observational0 (0.00%)0.25%
Other36 (73.47%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]