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Compound Detail

CHEMBL1696

DESIPRAMINE HYDROCHLORIDE
💊 Approved Drug
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💊 Approved Drug
CNCCCN1c2ccccc2CCc2ccccc21.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1696
Name DESIPRAMINE HYDROCHLORIDE
Phase Approved
Structure Type MOL
InChI Key XAEWZDYWZHIUCT-UHFFFAOYSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL72
Active Moiety CHEMBL72

Known Names

18-8181 Desipramine hcl Desipramine hydrochloride DMI EX 4355 EX-4355 G-35020 JB-8181 Norpramin NSC-114901 Pertofran Pertofrane +2 more
6
Targets
16
Activities
3
Assay Types
0
PK Parameters
20
Publications
14
Known Names
4
Indications
1
Mechanisms

Molecular Properties

266.4
MW (Da)
3.53
ALogP
2
HBA
1
HBD
15.3
PSA (Ų)
0.85
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1964
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning
USAN Stem -pramine
USAN Year 1962

Extended Properties

Molecular Formula C18H23ClN2
MW 302.85
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness -0.44

Mechanism of Action

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

Indications

Depression Back Pain Small Cell Lung Carcinoma Depressive Disorder

Drug Warnings

Black Box Warning
psychiatric toxicity
Country: United States

Activity Summary

IC50 11 meas. best 8.6
Ki 4 meas. best 9.19
EC50 1 meas. best 4.39

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Norepinephrine transporter
CHEMBL304
 Ki 9.19 9.19 0.7 1
Sodium-dependent noradrenaline transporter
CHEMBL222
 Ki 9.1 9.1 0.8 1
Sodium-dependent serotonin transporter
CHEMBL313
 IC50 8.6 8.6 2.5 1
Sodium-dependent noradrenaline transporter
CHEMBL222
 IC50 8.2 8.2 6.3 1
Sodium-dependent serotonin transporter
CHEMBL313
 Ki 6.74 6.74 182.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.9 5.2714 1258.9 7
Sodium-dependent dopamine transporter
CHEMBL338
 Ki 5.18 5.18 6532.0 1
Unchecked
CHEMBL612545
 EC50 4.39 4.39 40390.0 1
Unchecked
CHEMBL612545
 IC50 4.11 4.11 77640.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Norepinephrine transporter Ki = 0.65 nM 9.19 Inhibition of norepinephrine (NE) into rat brain synaptosomes 6747993
Sodium-dependent noradrenaline transporter Ki = 0.8 nM 9.1 Displacement of [3H]nisoxetine from human NET 20597489
Sodium-dependent serotonin transporter IC50 = 2.5 nM 8.6 Compound was tested for its ability to inhibit the neurotransmitter serotonin-5-... -
Sodium-dependent noradrenaline transporter IC50 = 6.3 nM 8.2 Inhibition of the Norepinephrine transporter (NET, SLC6A2) as assessed by GPCR-m... 34112854
Sodium-dependent serotonin transporter Ki = 182.0 nM 6.74 Inhibition of serotonin (5-HT) uptake into rat brain synaptosomes 6747993
Plasmodium falciparum IC50 = 1258.93 nM 5.9 Antiplasmodial activity against Plasmodium falciparum Dd2 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 1584.89 nM 5.8 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
Plasmodium falciparum IC50 = 5011.87 nM 5.3 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Sodium-dependent dopamine transporter Ki = 6532.0 nM 5.18 Inhibition of dopamine (DA) uptake into rat brain synaptosomes 6747993
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 D10 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 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910
Unchecked EC50 = 40390.0 nM 4.39 PUBCHEM_BIOASSAY: A cytotoxicity screen of small molecule inhibitors of the PhoP... -
Unchecked IC50 = 77640.0 nM 4.11 PUBCHEM_BIOASSAY: A counter screen for small molecule screen for inhibitors of t... -

Literature References

PubMed DOI Target Context # Activities
9836611 10.1021/jm9810102 No relevant target 8
19734910 10.1038/nchembio.215 Plasmodium falciparum 7
22115837 10.1016/j.bmc.2011.10.075 No relevant target 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
22115837 10.1016/j.bmc.2011.10.075 ADMET 2
6747993 10.1021/jm00374a001 Mus musculus 2
20597489 10.1021/jm100269c Sodium-dependent noradrenaline transporter 1
- 10.6019/EOS300108 HepG2 1
- 10.1101/2020.04.03.023846 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
20597489 10.1021/jm100269c Sodium-dependent serotonin transporter 1
20597489 10.1021/jm100269c Sodium-dependent dopamine transporter 1
- 10.1016/S0960-894X(97)10053-1 Sodium-dependent serotonin transporter 1
3941416 10.1021/jm00151a002 Mus musculus 1
9836611 10.1021/jm9810102 Homo sapiens 1
6747993 10.1021/jm00374a001 Sodium-dependent serotonin transporter 1
6747993 10.1021/jm00374a001 Norepinephrine transporter 1

Data from ChEMBL 36 via Core Engine