Compound Detail
CHEMBL1628227
DOXEPIN 💊 Approved Drug
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💊 Approved Drug
Basic Information
| ChEMBL ID | CHEMBL1628227 |
| Name | DOXEPIN |
| Phase | Approved |
| Structure Type | MOL |
| InChI Key | ODQWQRRAPPTVAG-UHFFFAOYSA-N |
| Therapeutic | ✓ Yes |
27
Targets
65
Activities
2
Assay Types
9
PK Parameters
20
Publications
5
Known Names
10
Indications
1
Mechanisms
Molecular Properties
279.4
MW (Da)
3.96
ALogP
2
HBA
0
HBD
12.5
PSA (Ų)
0.84
QED
0
Ro5 Violations
3
Rot. Bonds
Drug Information
| Molecule Type | Small molecule |
| First Approval | 1969 |
| Availability | Prescription |
| Chirality | Achiral |
Mechanism of Action
| Mechanism | Action Type | Target | Direct | Efficacy |
|---|---|---|---|---|
| Histamine H1 receptor antagonist | ANTAGONIST | Histamine H1 receptor | ✓ | ✓ |
Indications
Depressive Disorder Depressive Disorder Pruritus Anxiety Dementia Schizophrenia Urticaria Breast Neoplasms Irritable Bowel Syndrome Sleep Wake Disorders
ATC Classification
D04AX01
doxepin
Level 1: DERMATOLOGICALS
Level 2: ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
N06AA12
doxepin
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS
Activity Summary
IC50 33 meas. best 11.0
Ki 32 meas. best 10.18
Target Activity Profile
| Target | Type | Best pChEMBL | Mean pChEMBL | Best (nM) | # Data |
|---|---|---|---|---|---|
| Alpha-1A adrenergic receptor CHEMBL319 | IC50 | 11.0 | 8.985 | 0.0 | 2 |
| Histamine H1 receptor CHEMBL231 | Ki | 10.18 | 9.8433 | 0.1 | 3 |
| Histamine H1 receptor CHEMBL231 | IC50 | 9.24 | 9.24 | 0.6 | 1 |
| Muscarinic acetylcholine receptor M4 CHEMBL1821 | Ki | 8.23 | 8.23 | 5.8 | 1 |
| 5-hydroxytryptamine receptor 2A CHEMBL224 | Ki | 7.96 | 7.96 | 11.0 | 1 |
| Muscarinic acetylcholine receptor M3 CHEMBL245 | Ki | 7.82 | 7.82 | 15.0 | 1 |
| Muscarinic acetylcholine receptor M1 CHEMBL216 | Ki | 7.75 | 7.75 | 18.0 | 1 |
| Muscarinic acetylcholine receptor M5 CHEMBL2035 | Ki | 7.72 | 7.72 | 19.0 | 1 |
| Sodium-dependent serotonin transporter CHEMBL228 | Ki | 7.66 | 7.66 | 22.0 | 1 |
| 5-hydroxytryptamine receptor 2C CHEMBL225 | Ki | 7.62 | 7.62 | 24.0 | 1 |
| Muscarinic acetylcholine receptor M5 CHEMBL2035 | IC50 | 7.58 | 7.58 | 26.0 | 1 |
| Sodium-dependent noradrenaline transporter CHEMBL222 | Ki | 7.54 | 7.54 | 29.0 | 1 |
| Sodium-dependent noradrenaline transporter CHEMBL222 | IC50 | 7.54 | 7.54 | 29.0 | 1 |
| Alpha-2B adrenergic receptor CHEMBL1942 | Ki | 7.5 | 7.5 | 32.0 | 1 |
| Alpha-1B adrenergic receptor CHEMBL315 | Ki | 7.48 | 7.48 | 33.0 | 1 |
| 5-hydroxytryptamine receptor 2A CHEMBL224 | IC50 | 7.42 | 7.42 | 38.0 | 1 |
| Sodium-dependent serotonin transporter CHEMBL228 | IC50 | 7.38 | 7.38 | 42.0 | 1 |
| Muscarinic acetylcholine receptor M4 CHEMBL1821 | IC50 | 7.38 | 7.38 | 42.0 | 1 |
| Alpha-1A adrenergic receptor CHEMBL319 | Ki | 7.37 | 7.37 | 43.0 | 1 |
| 5-hydroxytryptamine receptor 2C CHEMBL225 | IC50 | 7.34 | 7.34 | 46.0 | 1 |
| 5-hydroxytryptamine receptor 2B CHEMBL1833 | Ki | 7.25 | 7.25 | 56.0 | 1 |
| Alpha-1D adrenergic receptor CHEMBL223 | Ki | 7.24 | 7.24 | 58.0 | 1 |
| Alpha-1B adrenergic receptor CHEMBL315 | IC50 | 7.22 | 7.22 | 60.0 | 1 |
| Unchecked CHEMBL612545 | IC50 | 7.19 | 6.092 | 65.0 | 5 |
| Muscarinic acetylcholine receptor M3 CHEMBL245 | IC50 | 7.16 | 7.16 | 69.0 | 1 |
| Alpha-2B adrenergic receptor CHEMBL1942 | IC50 | 7.15 | 7.15 | 71.0 | 1 |
| Muscarinic acetylcholine receptor M1 CHEMBL216 | IC50 | 7.11 | 7.11 | 77.0 | 1 |
| 5-hydroxytryptamine receptor 2B CHEMBL1833 | IC50 | 7.05 | 7.05 | 89.0 | 1 |
| Muscarinic acetylcholine receptor M2 CHEMBL211 | Ki | 7.04 | 7.04 | 92.0 | 1 |
| 5-hydroxytryptamine receptor 6 CHEMBL3371 | Ki | 6.98 | 6.905 | 105.0 | 2 |
| Alpha-1D adrenergic receptor CHEMBL223 | IC50 | 6.93 | 6.93 | 118.0 | 1 |
| Alpha-2C adrenergic receptor CHEMBL1916 | Ki | 6.82 | 6.82 | 150.0 | 1 |
| Unchecked CHEMBL612545 | Ki | 6.77 | 6.1983 | 170.0 | 6 |
| Serotonin (5-HT) receptor CHEMBL2094123 | IC50 | 6.7 | 6.7 | 200.0 | 1 |
| Muscarinic acetylcholine receptor M2 CHEMBL211 | IC50 | 6.59 | 6.59 | 258.0 | 1 |
| Sigma non-opioid intracellular receptor 1 CHEMBL287 | Ki | 6.58 | 6.58 | 265.0 | 1 |
| 5-hydroxytryptamine receptor 6 CHEMBL3371 | IC50 | 6.5 | 6.5 | 320.0 | 1 |
| D(1A) dopamine receptor CHEMBL2056 | Ki | 6.46 | 6.46 | 344.0 | 1 |
| D(3) dopamine receptor CHEMBL234 | Ki | 6.33 | 6.33 | 473.0 | 1 |
| Alpha-2A adrenergic receptor CHEMBL1867 | Ki | 6.3 | 6.3 | 501.0 | 1 |
| Sigma non-opioid intracellular receptor 1 CHEMBL287 | IC50 | 6.2 | 6.2 | 631.0 | 1 |
| D(1A) dopamine receptor CHEMBL2056 | IC50 | 6.16 | 6.16 | 688.0 | 1 |
| 5-hydroxytryptamine receptor 1A CHEMBL273 | Ki | 6.06 | 6.06 | 868.0 | 1 |
| Alpha-2C adrenergic receptor CHEMBL1916 | IC50 | 5.99 | 5.99 | 1029.0 | 1 |
| Alpha-2A adrenergic receptor CHEMBL1867 | IC50 | 5.88 | 5.88 | 1335.0 | 1 |
| D(3) dopamine receptor CHEMBL234 | IC50 | 5.86 | 5.86 | 1393.0 | 1 |
| 5-hydroxytryptamine receptor 1A CHEMBL273 | IC50 | 5.82 | 5.82 | 1519.0 | 1 |
| Histamine H2 receptor CHEMBL2882 | IC50 | 5.8 | 5.8 | 1600.0 | 1 |
| Histamine H2 receptor CHEMBL1941 | Ki | 5.74 | 5.74 | 1836.0 | 1 |
| Histamine H2 receptor CHEMBL1941 | IC50 | 5.73 | 5.73 | 1867.0 | 1 |
Pharmacokinetic Data
| Parameter | Value | Units | Species |
|---|---|---|---|
| CL | 14.0 | mL.min-1.kg-1 | Homo sapiens |
| CL | 14.0 | mL.min-1.kg-1 | Homo sapiens |
| F | 49.0 | % | Homo sapiens |
| Fu | 0.025 | - | Rattus norvegicus |
| Fu | 0.2 | - | Homo sapiens |
| MRT | 15.0 | hr | Homo sapiens |
| T1/2 | 16.5 | hr | - |
| T1/2 | 15.0 | hr | Homo sapiens |
| T1/2 | 18.0 | hr | Homo sapiens |
Activity Data Samples
Top measurements by pChEMBL value
Literature References
Data from ChEMBL 36 via Core Engine