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Compound Detail

CHEMBL1113

AMOXAPINE
💊 Approved Drug
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💊 Approved Drug
Clc1ccc2c(c1)C(N1CCNCC1)=Nc1ccccc1O2

Basic Information

ChEMBL ID CHEMBL1113
Name AMOXAPINE
Phase Approved
Structure Type MOL
InChI Key QWGDMFLQWFTERH-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Amoxapina Amoxapine Asendin Asendis CL 67,772 CL 67772 CL-67,772 CL-67772 Defanyl NSC-759559
32
Targets
71
Activities
3
Assay Types
1
PK Parameters
20
Publications
10
Known Names
1
Indications
3
Mechanisms

Molecular Properties

313.8
MW (Da)
3.43
ALogP
4
HBA
1
HBD
36.9
PSA (Ų)
0.81
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1980
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -pine
USAN Year 1971

Extended Properties

Molecular Formula C17H16ClN3O
MW 313.79
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness -0.58

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Serotonin transporter inhibitor INHIBITOR Sodium-dependent serotonin transporter
Norepinephrine transporter inhibitor INHIBITOR Sodium-dependent noradrenaline transporter
Dopamine receptor antagonist ANTAGONIST Dopamine receptor

Indications

Depressive Disorder

ATC Classification

N06AA17
amoxapine
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Drug Warnings

Black Box Warning
psychiatric toxicity
Country: United States

Activity Summary

IC50 41 meas. best 8.81
Ki 29 meas. best 9.35
EC50 1 meas. best 5.14

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 9.35 9.05 0.4 2
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 8.81 8.81 1.6 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 8.7 8.7 2.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 8.42 8.42 3.8 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 8.18 8.18 6.6 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 8.0 8.0 10.0 1
Histamine H1 receptor
CHEMBL231
Ki 7.96 7.96 11.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 7.89 7.89 13.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
IC50 7.89 7.89 13.0 1
Sodium-dependent serotonin transporter
CHEMBL228
Ki 7.75 7.75 18.0 1
Sodium-dependent serotonin transporter
CHEMBL228
IC50 7.47 7.47 34.0 1
D(4) dopamine receptor
CHEMBL219
Ki 7.47 7.47 34.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
Ki 7.46 7.46 35.0 1
D(3) dopamine receptor
CHEMBL234
Ki 7.34 7.34 46.0 1
Unchecked
CHEMBL612545
Ki 7.3 6.245 50.0 4
Alpha-1B adrenergic receptor
CHEMBL315
Ki 7.22 7.22 60.0 1
D(2) dopamine receptor
CHEMBL217
Ki 7.17 7.17 67.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
IC50 7.12 7.12 76.0 1
Unchecked
CHEMBL612545
IC50 7.08 6.04 83.0 5
Histamine H1 receptor
CHEMBL231
IC50 7.0 7.0 99.0 1
Alpha-1B adrenergic receptor
CHEMBL315
IC50 6.96 6.96 109.0 1
D(3) dopamine receptor
CHEMBL234
IC50 6.87 6.87 134.0 1
Alpha-1A adrenergic receptor
CHEMBL319
Ki 6.84 6.84 144.0 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 6.82 6.82 150.0 1
D(1A) dopamine receptor
CHEMBL2056
Ki 6.71 6.71 196.0 1
D(2) dopamine receptor
CHEMBL217
IC50 6.7 6.7 200.0 1
5-hydroxytryptamine receptor 1A
CHEMBL214
Ki 6.66 6.66 221.0 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
Ki 6.62 6.62 242.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 6.59 6.59 255.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
Ki 6.54 6.54 287.0 1
Alpha-1D adrenergic receptor
CHEMBL223
IC50 6.51 6.51 306.0 1
Alpha-1A adrenergic receptor
CHEMBL319
IC50 6.45 6.45 357.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
Ki 6.42 6.42 378.0 1
D(1A) dopamine receptor
CHEMBL2056
IC50 6.41 6.41 392.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 6.34 6.34 461.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 6.31 6.31 493.0 1
5-hydroxytryptamine receptor 7
CHEMBL3155
Ki 6.3 6.3 500.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
IC50 6.25 6.25 558.0 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
Ki 6.21 6.21 615.0 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
IC50 6.07 6.07 856.0 1
Muscarinic acetylcholine receptor M2
CHEMBL211
Ki 6.03 6.03 933.0 1
Plasmodium falciparum
CHEMBL364
IC50 5.94 5.1425 1140.0 8
Muscarinic acetylcholine receptor M1
CHEMBL216
IC50 5.92 5.92 1192.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 5.88 5.88 1314.0 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
IC50 5.76 5.76 1737.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
IC50 5.75 5.75 1781.0 1
Trypanosoma brucei rhodesiense
CHEMBL612348
IC50 5.73 5.73 1870.0 1
Muscarinic acetylcholine receptor M2
CHEMBL211
IC50 5.58 5.58 2623.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
IC50 5.5 5.5 3174.0 1
Salmonella typhimurium
CHEMBL351
EC50 5.14 5.14 7250.0 1

Pharmacokinetic Data

Parameter Value Units Species
Fu 0.01 - Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 2A Ki = 0.444 nM 9.35 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2A IC50 = 1.552 nM 8.81 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2A Ki = 1.77 nM 8.75 Displacement of [3H]ketanserin from human recombinant 5HT2A receptor expressed i... 22268448
5-hydroxytryptamine receptor 2C Ki = 1.984 nM 8.7 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2C IC50 = 3.787 nM 8.42 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2B Ki = 6.569 nM 8.18 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2B IC50 = 10.0 nM 8.0 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -
Histamine H1 receptor Ki = 11.0 nM 7.96 DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) -
Sodium-dependent noradrenaline transporter Ki = 13.0 nM 7.89 DRUGMATRIX: Norepinephrine Transporter radioligand binding (ligand: [125I] RTI-5... -
Sodium-dependent noradrenaline transporter IC50 = 13.0 nM 7.89 DRUGMATRIX: Norepinephrine Transporter radioligand binding (ligand: [125I] RTI-5... -
Sodium-dependent serotonin transporter Ki = 18.0 nM 7.75 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
Sodium-dependent serotonin transporter IC50 = 34.0 nM 7.47 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
D(4) dopamine receptor Ki = 34.0 nM 7.47 Displacement of [3H]-YM09151-2 from human cloned dopamine D4 receptor expressed ... 22268448
5-hydroxytryptamine receptor 6 Ki = 35.0 nM 7.46 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT6 radioligand binding (ligand: [... -
D(3) dopamine receptor Ki = 46.0 nM 7.34 DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) -
Unchecked Ki = 50.0 nM 7.3 Uncompetitive inhibition of recombinant Escherichia coli beta-glucosidase expres... 33652353
Alpha-1B adrenergic receptor Ki = 60.0 nM 7.22 DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) -
D(2) dopamine receptor Ki = 67.0 nM 7.17 DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone) -
5-hydroxytryptamine receptor 6 IC50 = 76.0 nM 7.12 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT6 radioligand binding (ligand: [... -
Unchecked IC50 = 83.0 nM 7.08 Inhibition of Escherichia coli beta-glucosidase expressed in Escherichia coli BL... 33652353

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 436
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
19734910 10.1038/nchembio.215 Plasmodium falciparum 7
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
19256501 10.1021/jm801441s No relevant target 4
33652353 10.1016/j.ejmech.2021.113322 Unchecked 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 3
37468498 10.1038/s41467-023-40064-9 Histamine H1 receptor 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
10447960 10.1021/jm9910369 No relevant target 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Histamine H2 receptor 2

Data from ChEMBL 36 via Core Engine