DOXEPIN

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Synonyms
Status
Molecule Category Free-form
ATC D04AX01 N06AA12
UNII 5ASJ6HUZ7D

Structure

InChI Key ODQWQRRAPPTVAG-UHFFFAOYSA-N
Smiles CN(C)CCC=C1c2ccccc2COc2ccccc21
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C19H21NO
Molecular Weight 279.38
AlogP 3.96
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 3.0
Polar Surface Area 12.47
Molecular species BASE
Aromatic Rings 2.0
Heavy Atoms 21.0
Assay Description Organism Bioactivity Reference
Compound was tested for its inhibitory activity against 5-hydroxytryptamine receptor Rattus norvegicus 200.0 nM
Compound was tested for its binding affinity towards brain (Hippocampus) Adenylate cyclase Cavia porcellus 170.0 nM
Compound was tested for its binding affinity towards brain (neocortex) Adenylate cyclase Cavia porcellus 190.0 nM
Compound was tested for its inhibitory activity against Alpha-1 adrenergic receptor None 0.01 nM
Compound tested for its inhibitory activity against Histamine H1 receptor None 0.003 nM
Compound was tested for its inhibitory activity against Noradrenaline receptor Rattus norvegicus 65.0 nM
Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on voltage dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex at 10 uM Cavia porcellus 67.7 %
DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine) None 77.0 nM DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine) None 18.0 nM
DRUGMATRIX: Muscarinic M2 radioligand binding (ligand: [3H] N-Methylscopolamine) None 258.0 nM DRUGMATRIX: Muscarinic M2 radioligand binding (ligand: [3H] N-Methylscopolamine) None 92.0 nM
DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine) None 69.0 nM DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine) None 15.0 nM
DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) None 42.0 nM DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) None 5.842 nM
DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) None 26.0 nM DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) None 19.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: [3H] 8-OH-DPAT) None 868.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: [3H] Ketanserin) None 38.0 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: [3H] Ketanserin) None 11.0 nM
DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 107.0 nM DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 43.0 nM
DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 60.0 nM DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 33.0 nM
DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) None 118.0 nM DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) None 58.0 nM
DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) None 501.0 nM
DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscine) None 71.0 nM DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscine) None 32.0 nM
DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) None 150.0 nM
DRUGMATRIX: Norepinephrine Transporter radioligand binding (ligand: [125I] RTI-55) None 29.0 nM DRUGMATRIX: Norepinephrine Transporter radioligand binding (ligand: [125I] RTI-55) None 29.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 89.0 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 56.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: [3H] Mesulergine) None 46.0 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: [3H] Mesulergine) None 24.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT6 radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 320.0 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT6 radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 149.0 nM
DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand binding (ligand: [3H] Paroxetine) None 42.0 nM DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand binding (ligand: [3H] Paroxetine) None 22.0 nM
DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) None 631.0 nM DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) None 265.0 nM
DRUGMATRIX: Calcium Channel Type L, Phenylalkylamine radioligand binding (ligand: [3H] (-)-Desmethoxyverapamil (D-888)) Rattus norvegicus 535.0 nM DRUGMATRIX: Calcium Channel Type L, Phenylalkylamine radioligand binding (ligand: [3H] (-)-Desmethoxyverapamil (D-888)) Rattus norvegicus 520.0 nM
DRUGMATRIX: Dopamine D1 radioligand binding (ligand: [3H] SCH-23390) None 688.0 nM DRUGMATRIX: Dopamine D1 radioligand binding (ligand: [3H] SCH-23390) None 344.0 nM
DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) None 473.0 nM
DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) None 0.57 nM DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) None 0.066 nM
Displacement of [3H]mepyramine from human histamine H1 receptor expressed in HEK293 cells after 1 to 1.5 hrs by scintillation counting Homo sapiens 0.1778 nM
TP_TRANSPORTER: increase in Calcein-AM intracellular accumulation (Calcein-AM: ? uM, Doxepin: 100 uM) in MDR1-expressing MDCKII cells None 15.3 %
Displacement of [3H]LSD from human 5HT6 receptor expressed in HEK293 cells after 1.5 hrs by liquid scintillation counting Homo sapiens 105.0 nM
Displacement of [3H]mepyramine from human wild type N-terminal hemagglutinin-tagged histamine H1 receptor expressed in HEK293T cells after 4 hrs by microbeta liquid scintillation counting analysis Homo sapiens 0.2512 nM

Related Entries

Environmental Exposure

Environmental Exposure Map
Countries
Germany
Romania

Cross References

Resources Reference
ChEBI 4710
ChEMBL CHEMBL1628227
DrugBank DB01142
DrugCentral 956
FDA SRS 5ASJ6HUZ7D
Human Metabolome Database HMDB0015273
Guide to Pharmacology 1225
KEGG C06971
SureChEMBL SCHEMBL28054
CONTENTS