Doxepin hydrochlorideProduct ingredient for Doxepin

Name
Doxepin hydrochloride
Drug Entry
Doxepin

Doxepin is a psychotropic agent with antidepressant and anxiolytic properties.9 It is a tertiary amine that can be presented as (E) and (Z) stereoisomers with the (Z) stereoisomer corresponding to cidoxepin. Doxepin commonly produces a 5:1 (E):(Z) racemic mixture.8

In a strict sense, doxepin is not a tricyclic antidepressant but it is commonly associated with the class since it shares a lot of properties with members of the drug family including amitriptyline, clomipramine, desipramine, imipramine, nortriptyline, protriptyline and trimipramine.13

Doxepin was developed by Pfizer and FDA approved in 1969 as an antidepressant.11 However, in 2010 it was approved for the treatment of insomnia. The latter indication was presented by Pernix Therapeutics.12

Accession Number
DBSALT000059
Structure
Thumb
Synonyms
Doxepin HCl
UNII
3U9A0FE9N5
CAS Number
1229-29-4
Weight
Average: 315.837
Monoisotopic: 315.138992038
Chemical Formula
C19H22ClNO
InChI Key
MHNSPTUQQIYJOT-UHFFFAOYSA-N
InChI
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
IUPAC Name
dimethyl(3-{9-oxatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene}propyl)amine hydrochloride
SMILES
Cl.[H]C(CCN(C)C)=C1C2=CC=CC=C2COC2=CC=CC=C12
PubChem Compound
14675
ChemSpider
14007
ChEBI
1151125
ChEMBL
CHEMBL1628234
Wikipedia
Doxepin
Predicted Properties
PropertyValueSource
Water Solubility0.0319 mg/mLALOGPS
logP4.08ALOGPS
logP3.84ChemAxon
logS-3.9ALOGPS
pKa (Strongest Basic)9.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity98.24 m3·mol-1ChemAxon
Polarizability32.47 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon