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
Structure for Doxepin hydrochloride (DBSALT000059)
- 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
- External Links
- PubChem Compound
- 14675
- ChemSpider
- 14007
- ChEBI
- 1151125
- ChEMBL
- CHEMBL1628234
- Wikipedia
- Doxepin
- Predicted Properties
Property Value Source Water Solubility 0.0319 mg/mL ALOGPS logP 4.08 ALOGPS logP 3.84 Chemaxon logS -3.9 ALOGPS pKa (Strongest Basic) 9.76 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 12.47 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 98.24 m3·mol-1 Chemaxon Polarizability 32.47 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon