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Compound Detail

CHEMBL1692

IMIPRAMINE HYDROCHLORIDE
💊 Approved Drug
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💊 Approved Drug
CN(C)CCCN1c2ccccc2CCc2ccccc21.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1692
Name IMIPRAMINE HYDROCHLORIDE
Phase Approved
Structure Type MOL
InChI Key XZZXIYZZBJDEEP-UHFFFAOYSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL11
Active Moiety CHEMBL11

Known Names

G-22355 Imidobenzyle Imipramine hcl Imipramine hydrochloride Imipramine hydrochloride rs Imipramini hydrochloridum Imizine Janimine NSC-114900 Pramine Praminil Presamine +3 more
3
Targets
9
Activities
2
Assay Types
15
PK Parameters
20
Publications
15
Known Names
3
Indications
2
Mechanisms

Molecular Properties

280.4
MW (Da)
3.88
ALogP
2
HBA
0
HBD
6.5
PSA (Ų)
0.84
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1959
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral

Flags

Black Box Warning
USAN Stem -pramine

Extended Properties

Molecular Formula C19H25ClN2
MW 316.88
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness -0.77

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 ✓ ✓

Indications

Enuresis Depressive Disorder Glioblastoma

Drug Warnings

Black Box Warning
psychiatric toxicity
Country: United States

Activity Summary

IC50 7 meas. best 8.59
Ki 2 meas. best 7.92

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Norepinephrine transporter
CHEMBL304
 IC50 8.59 8.59 2.6 1
Norepinephrine transporter
CHEMBL304
 Ki 7.92 7.92 12.0 1
Sodium-dependent serotonin transporter
CHEMBL313
 Ki 7.38 7.38 41.8 1
Plasmodium falciparum
CHEMBL364
 IC50 5.9 5.1167 1258.9 6

Pharmacokinetic Data

Parameter Value Units Species
CL 31.0 mL.min-1.kg-1 Homo sapiens
CL 13.0 mL.min-1.kg-1 Homo sapiens
CL 13.0 mL.min-1.kg-1 Homo sapiens
Cmax 713.22 nM Homo sapiens
Excretion 2.0 % Homo sapiens
F 42.0 % Homo sapiens
Fu 0.106 - Rattus norvegicus
Fu 0.104 - Homo sapiens
Fu 0.063 - Mus musculus
Fu 0.053 - Canis lupus familiaris
Fu 0.03 - Macaca mulatta
T1/2 10.7 hr Homo sapiens
T1/2 16.0 hr Homo sapiens
Tmax 2.0 hr Homo sapiens
Vd 18.0 L.kg-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Norepinephrine transporter IC50 = 2.6 nM 8.59 Norepinephrine transporter activity was determined by the ability of compound to... -
Norepinephrine transporter Ki = 12.0 nM 7.92 Inhibition of norepinephrine (NE) into rat brain synaptosomes 6747993
Sodium-dependent serotonin transporter Ki = 41.8 nM 7.38 Inhibition of serotonin (5-HT) uptake into rat brain synaptosomes 6747993
Plasmodium falciparum IC50 = 1258.93 nM 5.9 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
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 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
Plasmodium falciparum IC50 = 15848.93 nM 4.8 Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR g... 19734910

Literature References

PubMed DOI Target Context # Activities
42799 10.1021/jm00197a021 Mus musculus 10
- 10.6019/CHEMBL4689842 HEK-293T 9
- 10.6019/CHEMBL4689842 Fibroblast 9
19734910 10.1038/nchembio.215 Plasmodium falciparum 6
21282406 10.1124/dmd.110.037457 Nucleic Acid 5
21282406 10.1124/dmd.110.037457 Plasma 5
- 10.6019/CHEMBL4689842 U2OS 5
21282406 10.1124/dmd.110.037457 ADMET 5
1676756 10.1021/jm00111a013 Mus musculus 4
21282406 10.1124/dmd.110.037457 Homo sapiens 4
423198 10.1021/jm00188a012 Mus musculus 4
7328583 10.1021/jm00142a020 Mus musculus 3
- 10.6019/CHEMBL5209801 Beta-2 adrenergic receptor 2
25965777 10.1016/j.ejmech.2015.04.046 Mus musculus 2
5607 10.1021/jm00227a010 Mus musculus 2
- 10.6019/CHEMBL5209801 Apelin receptor 2
22277589 10.1016/j.bmc.2011.12.039 Mus musculus 2
6747993 10.1021/jm00374a001 Mus musculus 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2

Data from ChEMBL 36 via Core Engine