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Compound Detail

CHEMBL1237135

MAPROTILINE HYDROCHLORIDE
💊 Approved Drug
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💊 Approved Drug
CNCCCC12CCC(c3ccccc31)c1ccccc12.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1237135
Name MAPROTILINE HYDROCHLORIDE
Phase Approved
Structure Type MOL
InChI Key NZDMFGKECODQRY-UHFFFAOYSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL21731
Active Moiety CHEMBL21731

Known Names

BA-34,276 BA-34276 BA-34276 HYDROCHLORIDE Ludiomil Maprotiline hcl Maprotiline hydrochloride NSC-757085
3
Targets
13
Activities
2
Assay Types
0
PK Parameters
18
Publications
7
Known Names
1
Indications
1
Mechanisms

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

Extended Properties

Molecular Formula C20H24ClN
MW 313.87
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness 0.83

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Norepinephrine transporter inhibitor INHIBITOR Sodium-dependent noradrenaline transporter ✓ ✓

Indications

Depressive Disorder

Drug Warnings

Black Box Warning
psychiatric toxicity
Country: United States

Activity Summary

IC50 12 meas. best 7.3
EC50 1 meas. best 4.67

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent noradrenaline transporter
CHEMBL222
 IC50 7.3 7.3 50.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.3 5.0286 5011.9 7
Unchecked
CHEMBL612545
 IC50 5.07 4.67 8580.0 2
Unchecked
CHEMBL612545
 EC50 4.67 4.67 21310.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent noradrenaline transporter IC50 = 50.0 nM 7.3 Inhibition of the Norepinephrine transporter (NET, SLC6A2) as assessed by GPCR-m... 34112854
Plasmodium falciparum IC50 = 5011.87 nM 5.3 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
Unchecked IC50 = 8580.0 nM 5.07 PubChem BioAssay. Dry powder dose response confirmation of uHTS inhibitor hits ... -
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum Dd2 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR g... 19734910
Unchecked EC50 = 21310.0 nM 4.67 PUBCHEM_BIOASSAY: A cytotoxicity screen of small molecule inhibitors of the PhoP... -
Unchecked IC50 = 53520.0 nM 4.27 PUBCHEM_BIOASSAY: A counter screen for small molecule screen for inhibitors of t... -

Literature References

PubMed DOI Target Context # Activities
19734910 10.1038/nchembio.215 Plasmodium falciparum 7
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
16302826 10.1021/jm050645f No relevant target 2
- 10.6019/CHEMBL4513141 Cryptococcus neoformans 1
- 10.6019/EOS300108 HepG2 1
34112854 10.1038/s41598-021-91700-7 Sodium-dependent noradrenaline transporter 1
- 10.6019/CHEMBL4513141 Staphylococcus aureus 1
- 10.6019/CHEMBL4513141 Acinetobacter baumannii 1
- 10.6019/CHEMBL4513141 Pseudomonas aeruginosa 1
- 10.6019/CHEMBL4513141 Klebsiella pneumoniae 1
- 10.6019/CHEMBL4513141 Escherichia coli 1
- 10.6019/CHEMBL4513141 Candida albicans 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B3 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B1 1
17417631 10.1038/nchembio873 Unchecked 1

Data from ChEMBL 36 via Core Engine