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Compound Detail

CHEMBL6067650

PAROXETINE HYDROCHLORIDE
💊 Approved Drug
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💊 Approved Drug
Cl.Cl.Fc1ccc([C@@H]2CCNC[C@H]2COc2ccc3c(c2)OCO3)cc1.Fc1ccc([C@@H]2CCNC[C@H]2COc2ccc3c(c2)OCO3)cc1.O

Basic Information

ChEMBL ID CHEMBL6067650
Name PAROXETINE HYDROCHLORIDE
Phase Approved
Structure Type MOL
InChI Key MQZOATSIFWSKKT-OASXIEIISA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL490
Active Moiety CHEMBL490

Known Names

Aropax BRL29060A Deroxat NSC-758654 Paroxetine hydrochloride Paroxetine hydrochloride anhydrous Paroxetine hydrochloride hemihydrate Paroxetine hydrochloride hydrate Paxil Paxil cr Seroxat
10
Targets
18
Activities
2
Assay Types
0
PK Parameters
20
Publications
11
Known Names
9
Indications
2
Mechanisms

Molecular Properties

329.4
MW (Da)
3.33
ALogP
4
HBA
1
HBD
39.7
PSA (Ų)
0.93
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1992
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning
USAN Stem -oxetine

Extended Properties

Molecular Formula C38H44Cl2F2N2O7
MW 749.68
Aromatic Rings 2
Heavy Atoms 24
NP-Likeness -0.12

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Serotonin transporter inhibitor INHIBITOR Sodium-dependent serotonin transporter
Serotonin transporter inhibitor INHIBITOR Sodium-dependent serotonin transporter

Indications

Anxiety Disorders Depressive Disorder, Major Obsessive-Compulsive Disorder Panic Disorder Phobia, Social Stress Disorders, Post-Traumatic Premature Ejaculation Anxiety Depressive Disorder

Activity Summary

IC50 14 meas. best 6.02
Ki 4 meas. best 10.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent serotonin transporter
CHEMBL313
Ki 10.3 10.3 0.1 1
Transporter
CHEMBL6184
Ki 7.23 7.23 59.0 1
Sodium-dependent dopamine transporter
CHEMBL338
Ki 7.01 7.01 98.0 1
Cytochrome P450 2D6
CHEMBL289
IC50 6.02 6.02 960.0 1
Beta-adrenergic receptor kinase 1
CHEMBL3711550
IC50 5.89 5.89 1300.0 1
Unchecked
CHEMBL612545
Ki 5.7 5.7 2000.0 1
Beta-adrenergic receptor kinase 1
CHEMBL4079
IC50 5.6 5.15 2500.0 2
Cytochrome P450 1A2
CHEMBL3356
IC50 5.27 5.27 5330.0 1
Cytochrome P450 3A4
CHEMBL340
IC50 4.62 4.62 24100.0 1
Bile salt export pump
CHEMBL6020
IC50 4.16 4.16 68910.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent serotonin transporter Ki = 0.05 nM 10.3 Displacement of [3H]citalopram from serotonin transporter in Sprague-Dawley rat ... 20980153
Transporter Ki = 59.0 nM 7.23 Displacement of [3H]nisoxetine from norepinephrine transporter in Sprague-Dawley... 20980153
Sodium-dependent dopamine transporter Ki = 98.0 nM 7.01 Displacement of [3H]WIN 35428 from dopamine transporter in Sprague-Dawley rat br... 20980153
Cytochrome P450 2D6 IC50 = 960.0 nM 6.02 Inhibition of CYP2D6 in human liver microsomes using dextromethorphan as substra... 22328583
Beta-adrenergic receptor kinase 1 IC50 = 1300.0 nM 5.89 Inhibition of bovine GRK2 S670A mutant assessed as decrease in phosphorylation o... 27362616
Unchecked Ki = 2000.0 nM 5.7 Selectivity ratio of Ki for dopamine transporter in Sprague-Dawley rat brain to ... 20980153
Beta-adrenergic receptor kinase 1 IC50 = 2500.0 nM 5.6 Inhibition of human GRK2 S670A mutant assessed as decrease in phosphorylation of... 27362616
Cytochrome P450 1A2 IC50 = 5330.0 nM 5.27 Inhibition of CYP1A2 in human liver microsomes using phenacetin as substrate aft... 22328583
Beta-adrenergic receptor kinase 1 IC50 = 19900.0 nM 4.7 Inhibition of human GRK2 S670A mutant assessed as decrease in phosphorylation of... 27362616
Cytochrome P450 3A4 IC50 = 24100.0 nM 4.62 Inhibition of CYP3A4 in human liver microsomes using midazolam as substrate afte... 22328583
Bile salt export pump IC50 = 68910.0 nM 4.16 Inhibition of human BSEP expressed in baculovirus transfected fall armyworm Sf21... 22961681

Literature References

PubMed DOI Target Context # Activities
27362616 10.1021/acs.jmedchem.5b01939 Unchecked 9
- 10.6019/CHEMBL5303304 Fibroblast 6
- 10.6019/CHEMBL5303304 U2OS 6
27362616 10.1021/acs.jmedchem.5b01939 Beta-adrenergic receptor kinase 1 4
20980153 10.1016/j.bmc.2010.09.060 Unchecked 3
27362616 10.1021/acs.jmedchem.5b01939 Rhodopsin kinase GRK1 3
27362616 10.1021/acs.jmedchem.5b01939 G protein-coupled receptor kinase 5 3
16464584 10.1016/j.bmcl.2006.01.078 Spermatozoa 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL5303304 HEK-293T 2
22328583 10.1124/dmd.111.043505 Cytochrome P450 2J2 2
22328583 10.1124/dmd.111.043505 Cytochrome P450 2C9 1
22328583 10.1124/dmd.111.043505 Cytochrome P450 2C8 1
22328583 10.1124/dmd.111.043505 Cytochrome P450 2C19 1
- 10.6019/EOS300108 HepG2 1
22328583 10.1124/dmd.111.043505 Cytochrome P450 2D6 1
22328583 10.1124/dmd.111.043505 Cytochrome P450 3A4 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B3 1
20980153 10.1016/j.bmc.2010.09.060 Transporter 1
20980153 10.1016/j.bmc.2010.09.060 Sodium-dependent serotonin transporter 1

Data from ChEMBL 36 via Core Engine