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Compound Detail

CHEMBL21731

MAPROTILINE
💊 Approved Drug
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💊 Approved Drug
CNCCCC12CCC(c3ccccc31)c1ccccc12

Basic Information

ChEMBL ID CHEMBL21731
Name MAPROTILINE
Phase Approved
Structure Type MOL
InChI Key QSLMDECMDJKHMQ-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

BA-34,276 FREE BASE BA-34,276 [AS HYDROCHLORIDE] BA-34276 FREE BASE Maprotilina Maprotiline
30
Targets
67
Activities
4
Assay Types
7
PK Parameters
20
Publications
5
Known Names
7
Indications

Molecular Properties

277.4
MW (Da)
4.21
ALogP
1
HBA
1
HBD
12.0
PSA (Ų)
0.83
QED
0
Ro5 Violations
4
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 Year 1971

Extended Properties

Molecular Formula C20H23N
MW 277.41
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness 0.83

Indications

Depressive Disorder Depressive Disorder Anxiety Dementia Schizophrenia Brain Neoplasms Glioblastoma

ATC Classification

N06AA21
maprotiline
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Activity Summary

Ki 31 meas. best 8.99
IC50 30 meas. best 8.06
Kd 4 meas. best 4.43
EC50 2 meas. best 4.8

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histamine H1 receptor
CHEMBL231
Ki 8.99 8.885 1.0 2
Histamine H1 receptor
CHEMBL231
IC50 8.06 8.06 8.8 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 7.92 7.72 12.0 2
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 7.75 7.75 18.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
IC50 7.52 7.52 30.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 7.39 7.39 41.0 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
Ki 7.24 7.24 58.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 7.19 7.19 64.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 7.11 7.11 78.0 1
Alpha-1B adrenergic receptor
CHEMBL315
Ki 7.05 7.05 90.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
Ki 7.0 7.0 100.0 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
Ki 6.94 6.94 115.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 6.88 6.88 133.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
Ki 6.84 6.84 143.0 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
IC50 6.8 6.8 160.0 1
Alpha-1B adrenergic receptor
CHEMBL315
IC50 6.79 6.79 163.0 1
D(1A) dopamine receptor
CHEMBL2056
Ki 6.73 6.565 187.0 2
Alpha-1D adrenergic receptor
CHEMBL223
Ki 6.71 6.71 195.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 6.67 6.67 214.0 1
D(3) dopamine receptor
CHEMBL234
Ki 6.66 6.48 219.0 2
Alpha-1A adrenergic receptor
CHEMBL319
Ki 6.64 6.64 230.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
IC50 6.54 6.54 292.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 6.47 6.47 336.0 1
D(1A) dopamine receptor
CHEMBL2056
IC50 6.43 6.43 373.0 1
Histamine H2 receptor
CHEMBL1941
Ki 6.41 6.41 393.0 1
Alpha-1D adrenergic receptor
CHEMBL223
IC50 6.4 6.4 397.0 1
Histamine H2 receptor
CHEMBL1941
IC50 6.4 6.4 400.0 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
IC50 6.38 6.38 413.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
Ki 6.38 6.38 414.0 1
D(1B) dopamine receptor
CHEMBL1850
Ki 6.37 6.37 429.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 6.36 6.36 442.0 1
Unchecked
CHEMBL612545
Ki 6.36 5.84 434.0 3
Unchecked
CHEMBL612545
IC50 6.35 5.8067 446.0 3
Muscarinic acetylcholine receptor M3
CHEMBL245
IC50 6.33 6.33 473.0 1
Alpha-1A adrenergic receptor
CHEMBL319
IC50 6.25 6.25 567.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
IC50 6.23 6.23 593.0 1
D(3) dopamine receptor
CHEMBL234
IC50 6.19 6.19 645.0 1
D(2) dopamine receptor
CHEMBL217
Ki 6.18 6.06 665.0 2
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 6.17 6.17 684.0 1
Muscarinic acetylcholine receptor M2
CHEMBL211
Ki 6.16 6.16 685.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
IC50 6.05 6.05 892.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 5.74 5.74 1824.0 1
Muscarinic acetylcholine receptor M2
CHEMBL211
IC50 5.71 5.71 1927.0 1
Sodium-dependent dopamine transporter
CHEMBL238
Ki 5.64 5.64 2312.0 1
Sodium-dependent dopamine transporter
CHEMBL238
IC50 5.54 5.54 2910.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
IC50 5.52 5.52 3044.0 1
D(2) dopamine receptor
CHEMBL217
IC50 5.46 5.46 3463.0 1
Cytochrome P450 3A4
CHEMBL340
IC50 5.36 5.36 4322.0 1
Voltage-dependent N-type calcium channel subunit alpha-1B
CHEMBL4478
IC50 5.0 5.0 10000.0 1
NON-PROTEIN TARGET
CHEMBL3879801
EC50 4.8 4.615 15800.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 31.0 mL.min-1.g-1 Homo sapiens
CL 14.0 mL.min-1.kg-1 Homo sapiens
Fu 0.12 - Homo sapiens
Fu 0.006 - Rattus norvegicus
Fu 0.11 - Homo sapiens
MRT 54.0 hr Homo sapiens
T1/2 51.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histamine H1 receptor Ki = 1.021 nM 8.99 DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) -
Histamine H1 receptor Ki = 1.67 nM 8.78 Displacement of [3H]pyrilamine from human histamine H1 receptor expressed in CHO... 19091563
Histamine H1 receptor IC50 = 8.792 nM 8.06 DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) -
Sodium-dependent noradrenaline transporter Ki = 12.0 nM 7.92 Inhibition of norepinephrine reuptake at NET 19836247
5-hydroxytryptamine receptor 2A Ki = 18.0 nM 7.75 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
Sodium-dependent noradrenaline transporter IC50 = 30.0 nM 7.52 DRUGMATRIX: Norepinephrine Transporter radioligand binding (ligand: [125I] RTI-5... -
Sodium-dependent noradrenaline transporter Ki = 30.0 nM 7.52 DRUGMATRIX: Norepinephrine Transporter radioligand binding (ligand: [125I] RTI-5... -
5-hydroxytryptamine receptor 2C Ki = 41.0 nM 7.39 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ... -
Muscarinic acetylcholine receptor M4 Ki = 58.0 nM 7.24 DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) -
5-hydroxytryptamine receptor 2A IC50 = 64.0 nM 7.19 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2C IC50 = 78.0 nM 7.11 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ... -
Alpha-1B adrenergic receptor Ki = 90.0 nM 7.05 DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) -
Muscarinic acetylcholine receptor M3 Ki = 100.0 nM 7.0 DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M5 Ki = 115.0 nM 6.94 DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Alpha-2B adrenergic receptor Ki = 133.0 nM 6.88 DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin... -
Muscarinic acetylcholine receptor M1 Ki = 143.0 nM 6.84 DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M5 IC50 = 160.0 nM 6.8 DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Alpha-1B adrenergic receptor IC50 = 163.0 nM 6.79 DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) -
D(1A) dopamine receptor Ki = 187.0 nM 6.73 DRUGMATRIX: Dopamine D1 radioligand binding (ligand: [3H] SCH-23390) -
Alpha-1D adrenergic receptor Ki = 195.0 nM 6.71 DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 202
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
35074589 10.1016/j.ejmech.2022.114102 Unchecked 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
18426954 10.1124/dmd.108.020479 ADMET 4
19256501 10.1021/jm801441s No relevant target 3
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
22931300 10.1021/tx300075j Cytochrome P450 3A4 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
36854648 10.1021/acs.jmedchem.2c01663 Urokinase plasminogen activator surface receptor 2
14971904 10.1021/jm030408h ADMET 2
24333581 10.1016/j.ejmech.2013.10.076 NON-PROTEIN TARGET 2
- 10.6019/CHEMBL3301361 ADMET 2
18027916 10.1021/jm070524a No relevant target 2
22931300 10.1021/tx300075j Liver microsomes 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
10447960 10.1021/jm9910369 No relevant target 2
10447960 10.1021/jm9910369 ADMET 2

Data from ChEMBL 36 via Core Engine