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Drug

D1389 | Doxepin

Molecular Formula C19H21NO
Molecular Weight 279.4
Structure
State solid
Clearance The mean total apparent plasma clearance of a single oral dose of 50 mg doxepin in healthy individuals is 0.93 l/hr/kg.[A1945]
Volume of distribution The mean apparent volume of distribution of doxepin is reported to be of 20 L/kg.[T388]
Route of elimination The elimination profile of doxepin is presented as biphasic.[A1945] It is excreted in the urine mainly in the form of glucuronide conjugates. Less than 3% of a doxepin dose is excreted in the urine as parent compound or nordoxepin.[L1347]
Protein binding Equilibrium dialysis indicates a mean protein binding of 75.5% for doxepin and 76% for desmethyldoxepin.[A1945]
Half life The mean elimination half-life is reported to be of 15 hours.[T388]
Absorption Doxepin is moderately absorbed following oral ingestion with a bioavailability of 30%.[T388] The median peak concentration of doxepin ranges from 8.8-45.8 ng/ml and it is achieved 3.5 hours after initial administration. Its absorption is increased with concomitant administration of a high-fat meal.[L5995]
Description a psychotropic agent with antidepressant and anxiolytic properties

D

N

N06AA12 Doxepin


[N06AA] Non-selective monoamine reuptake inhibitors


[N06A] ANTIDEPRESSANTS


[N06] PSYCHOANALEPTICS


[N] Nervous system

D04AX01 Doxepin


[D04AX] Other antipruritics


[D04A] ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.


[D04] ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.


[D] Dermatological drugs

Toxicity Dose Time Species Model Method Action Positive criterion Reference
ELONGATION mouse neuron Mitochondrial morphology and neurite area measurements induce 269

Organism Test type Route Dose (normalized dose) Effect Source
mouse LD50 oral 135mg/kg (135mg/kg) Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 863, 1965.
mouse LD50 intravenous 26mg/kg (26mg/kg) Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 863, 1965.
rat LD50 intravenous 16mg/kg (16mg/kg) Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 863, 1965.
human LDLo oral 60mg/kg (60mg/kg) lungs, thorax, or respiration: bronchiectasis Clinical Toxicology. Vol. 10, Pg. 327, 1977.
mouse LD50 intraperitoneal 79mg/kg (79mg/kg) Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 863, 1965.
rat LD50 oral 147mg/kg (147mg/kg) Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 863, 1965.
rat LD50 intraperitoneal 182mg/kg (182mg/kg) Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 863, 1965.
rabbit LD50 intravenous 11mg/kg (11mg/kg) Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 863, 1965.


  • (3E)-3-(6H-benzo[c][1]benzoxepin-11-ylidene)-N,N-dimethylpropan-1-amine (3e)-3-(Dibenzo[b,E]oxepin-11(6h)-Ylidene)-N,N-Dimethylpropan-1-Amine (E)-3-(Dibenzo[b,e]oxepin-11(6H)-ylidene)-N,N-dimethylpropan-1-amine
    (e)-doxepin 1-Propanamine, 3-dibenz(b,e)oxepin-11(6H)-ylidene-N,N-dimethyl- 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
    3-(Dibenzo[b,e]oxepin-11(6H)-ylidene)-N,N-dimethyl-1-propanamine 3-(Dibenzo[b,e]oxepin-11(6H)-ylidene)-N,N-dimethylpropan-1-amine 3607-34-9
    5EH 851NLB57HQ AX8126881
    BDBM112780 BPBio1_000118 BRD-K36616567-003-01-5
    BRD-K54462405-003-03-3 BRD-K54462405-003-16-5 BSPBio_000106
    C06971 C19H21NO CAS-1229-29-4
    CCG-204434 CCRIS 9176 CHEMBL860
    Cidoxepin [INN] Cidoxepina Cidoxepinum
    D07875 DTXSID7022966 Deptran
    Dibenz(b,e)oxepin-delta(sup 11(6H)),gamma-propylamine, N,N-dimethyl- Doxepin (INN) Doxepin Hydrochloride,
    Doxepin [INN:BAN] Doxepin [USAN:INN:BAN] Doxepin [USAN]
    Doxepin hydrochloride;Doxepin;Doxepine Doxepin, (E)- Doxepina
    Doxepina [INN-Spanish] Doxepine Doxepinum
    Doxepinum [INN-Latin] E-DOXEPIN GTPL1225
    GTPL3958 HSDB 3069 L000699
    LS-174582 LS-61638 Lopac-D-4526
    Lopac0_000339 MF 10 N,N-Dimethyldibenz(b,e)oxepin-delta(11(6H),gamma)-propylamine
    NCGC00015344-01 NCGC00015344-02 NCGC00015344-03
    NCGC00015344-04 NCGC00024623-01 NCGC00162127-01
    Prestwick2_000263 Prestwick3_000263 Q27077103
    SCHEMBL116895 SDCCGSBI-0050327.P002 Sinequan
    Sinequan (TN) Tocris-0508 UNII-5ASJ6HUZ7D component ODQWQRRAPPTVAG-GZTJUZNOSA-N
    UNII-851NLB57HQ US8629135, SW-07 ZINC1331
    [11C]-doxepin [11C]doxepin cis-N-(3-(6H-Dibenz(b,e)oxepin-11-yliden)propyl)-N,N-dimethylamin
    curatin, lindo, doxepin, doxepinbiomo, stada, doxepin, quitaxon, doxepin teva, doxepin rph, espadox, doxepin hcl, prudoxin doxepin trans-doxepin

    DrugBank DB01142
    CAS Number 1229-29-4, 1668-19-5, 3607-34-9
    PubChem Compound 667477