doxepin   Click here for help

GtoPdb Ligand ID: 1225

Synonyms: Deptran® | P-3693A | Sinequan®
Approved drug PDB Ligand
doxepin is an approved drug (FDA (1969))
Compound class: Synthetic organic
Comment: Doxepin inhibits the sodium-dependent noradrenaline transporter SLC6A2.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 12.47
Molecular weight 279.16
XLogP 3.99
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CN(CCC=C1c2ccccc2OCc2c1cccc2)C
Isomeric SMILES CN(CC/C=C\1/c2ccccc2OCc2c1cccc2)C
InChI InChI=1S/C19H21NO/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/b17-11+
InChI Key ODQWQRRAPPTVAG-GZTJUZNOSA-N
Bioactivity Comments
Doxepin inhibits [3H]QNB binding to muscarinic acetylcholine receptors in bovine brain preparations with a Ki of 40nM [3].
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
H1 receptor Hs Antagonist Antagonist 9.5 – 10.0 pKi - 2
pKi 9.5 – 10.0 [2]
Selectivity at transporters
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
NET Primary target of this compound Hs Inhibitor Inhibition 7.5 pKi - 1
pKi 7.5 (Ki 2.9x10-8 M) [1]
SERT Primary target of this compound Hs Inhibitor Inhibition 7.2 pKi - 4
pKi 7.2 (Ki 6.8x10-8 M) [4]