Compound Detail

CHEMBL490

PAROXETINE

💊 Approved Drug

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💊 Approved Drug

Fc1ccc([C@@H]2CCNC[C@H]2COc2ccc3c(c2)OCO3)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL490
Name	PAROXETINE
Phase	Approved
Structure Type	MOL
InChI Key	AHOUBRCZNHFOSL-YOEHRIQHSA-N
Therapeutic	✓ Yes

Known Names

(-)3s,4r-paroxetine Arketis Arotin Besitram BRL 29060 BRL-29060 Casbol Daparox Fg-7051 Frosinor Motivan Parogen +4 more

Targets

132

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

329.4

MW (Da)

3.33

ALogP

HBA

HBD

39.7

PSA (Å²)

0.93

QED

Ro5 Violations

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
USAN Year	1989

Extended Properties

Molecular Formula	C19H20FNO3
MW	329.37
Aromatic Rings	2
Heavy Atoms	24
NP-Likeness	-0.12

Indications

Depressive Disorder Depressive Disorder Depressive Disorder, Major Agoraphobia Alcoholism Anxiety Anxiety Disorders Arthritis, Rheumatoid Bipolar Disorder Dementia Diabetes Mellitus, Type 2 Hepatitis C, Chronic Neuralgia Obsessive-Compulsive Disorder Panic Disorder Parkinson Disease Phobia, Social Premature Ejaculation Schizophrenia Stress Disorders, Post-Traumatic

ATC Classification

N06AB05

paroxetine

Level 1: NERVOUS SYSTEM

Level 2: PSYCHOANALEPTICS

Activity Summary

IC50 69 meas. best 10.1

Ki 47 meas. best 10.4

EC50 8 meas. best 5.57

Kd 8 meas. best 9.89

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Sodium-dependent serotonin transporter CHEMBL228	Ki	10.4	9.79	0.0	11
Sodium-dependent serotonin transporter CHEMBL228	IC50	10.1	9.09	0.1	5
Sodium-dependent serotonin transporter CHEMBL228	Kd	9.89	9.89	0.1	1
Sodium-dependent serotonin transporter CHEMBL313	Kd	9.82	9.82	0.1	1
Sodium-dependent serotonin transporter CHEMBL313	IC50	9.55	8.87	0.3	2
Unchecked CHEMBL612545	Ki	9.51	6.71	0.3	7
Sodium-dependent serotonin transporter CHEMBL4642	Ki	9.36	9.36	0.4	1
Sodium-dependent serotonin transporter CHEMBL313	Ki	9.28	9.2125	0.5	4
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	9.22	9.22	0.6	1
Rattus norvegicus CHEMBL376	IC50	8.19	6.7033	6.4	3
5-hydroxytryptamine receptor 6 CHEMBL3371	IC50	8.15	8.15	7.0	1
Myeloperoxidase CHEMBL2439	IC50	7.7	7.7	20.0	1
Sodium-dependent noradrenaline transporter CHEMBL2370	Ki	7.7	7.7	20.0	1
Norepinephrine transporter CHEMBL304	Ki	7.48	6.83	33.0	2
Muscarinic acetylcholine receptor M4 CHEMBL1821	Ki	7.47	7.47	34.0	1
Muscarinic acetylcholine receptor M1 CHEMBL216	Ki	7.46	7.46	35.0	1
Muscarinic acetylcholine receptor M3 CHEMBL245	Ki	7.42	7.42	38.0	1
Cytochrome P450 2D6 CHEMBL289	IC50	7.4	6.4757	40.0	7
Sodium-dependent noradrenaline transporter CHEMBL222	Kd	7.4	7.4	40.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	Ki	7.07	6.9867	86.0	3
Sodium-dependent noradrenaline transporter CHEMBL222	IC50	7.07	7.035	86.0	2
Unchecked CHEMBL612545	IC50	7.05	6.0233	90.0	6
Muscarinic acetylcholine receptor M5 CHEMBL2035	Ki	7.05	7.05	89.0	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	IC50	6.91	6.91	123.0	1
Muscarinic acetylcholine receptor M1 CHEMBL216	IC50	6.84	6.84	145.0	1
Muscarinic acetylcholine receptor M3 CHEMBL245	IC50	6.75	6.75	179.0	1
Muscarinic acetylcholine receptor M2 CHEMBL211	Ki	6.72	6.72	189.0	1
Muscarinic acetylcholine receptor M4 CHEMBL1821	IC50	6.61	6.61	244.0	1
Sodium-dependent dopamine transporter CHEMBL238	Ki	6.41	6.36	388.0	3
Sodium-dependent dopamine transporter CHEMBL338	Ki	6.4	6.085	400.0	2
Sodium-dependent dopamine transporter CHEMBL2799	Ki	6.34	6.34	460.0	1
Sodium-dependent dopamine transporter CHEMBL238	Kd	6.31	6.31	490.0	1
Norepinephrine transporter CHEMBL304	IC50	6.27	6.27	535.0	1
Muscarinic acetylcholine receptor M2 CHEMBL211	IC50	6.27	6.27	532.0	1
Sodium-dependent dopamine transporter CHEMBL338	IC50	6.21	6.21	623.0	1
Sodium-dependent dopamine transporter CHEMBL238	IC50	6.17	6.17	672.0	1
Beta-adrenergic receptor kinase 1 CHEMBL3711550	IC50	6.11	5.985	780.0	2
Substance-P receptor CHEMBL249	IC50	6.05	6.05	900.0	1
Beta-adrenergic receptor kinase 1 CHEMBL4079	IC50	5.96	5.9	1100.0	5
Trypanosoma brucei rhodesiense CHEMBL612348	IC50	5.95	5.95	1130.0	1
Ebolavirus CHEMBL4434621	IC50	5.86	5.3733	1380.0	3
P2X purinoceptor 4 CHEMBL2104	IC50	5.73	5.5475	1870.0	4
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	5.65	5.65	2255.0	1
P2X purinoceptor 4 CHEMBL2818	IC50	5.61	5.61	2450.0	2
Schistosoma mansoni CHEMBL612893	IC50	5.6	5.6	2500.0	1
Schistosoma mansoni CHEMBL612893	EC50	5.57	5.0663	2700.0	8
Beta-adrenergic receptor kinase 1 CHEMBL4079	Kd	5.53	5.53	2980.0	1
Voltage-gated L-type calcium channel CHEMBL2095229	IC50	5.41	5.41	3900.0	1
Cytochrome P450 2D6 CHEMBL289	Ki	5.31	5.31	4850.0	1
Adrenergic receptor alpha-1 CHEMBL1907610	Ki	5.27	5.27	5320.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	270.0	ng.hr.mL-1	Homo sapiens
AUC	590.0	ng.hr.mL-1	Homo sapiens
CL	18.0	mL.min-1.kg-1	Homo sapiens
CL	18.0	mL.min-1.kg-1	Homo sapiens
Cmax	103.23	nM	Homo sapiens
Cmax	51.61	nM	Homo sapiens
F	79.0	%	Homo sapiens
Fu	0.05	-	Homo sapiens
Fu	0.06	-	Homo sapiens
Fu	0.25	-	Homo sapiens
Fu	0.005	-	Homo sapiens
Fu	0.0039	-	Rattus norvegicus
Fu	0.0026	-	Sus scrofa
Fu	0.006	-	Macaca fascicularis
Fu	0.004	-	Canis lupus familiaris
Fu	0.003	-	Cavia porcellus
Fu	0.004	-	Mus musculus
Fu	0.006	-	Rattus norvegicus
Fu	0.074	-	Not specified
Fu	0.089	-	Not specified
Fu	0.099	-	Not specified
Fu	0.136	-	Not specified
Fu	0.004	-	Rattus norvegicus
MRT	17.0	hr	Homo sapiens
T1/2	21.1	hr	Homo sapiens
T1/2	15.9	hr	Homo sapiens
T1/2	13.0	hr	Homo sapiens
T1/2	0.405	hr	Mus musculus
Vd	8.7	L.kg-1	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Sodium-dependent serotonin transporter	Ki	=	0.04	nM	10.4	Binding inhibition towards human serotonin transporter	16162005
Sodium-dependent serotonin transporter	Ki	=	0.043	nM	10.37	DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind...	-
Sodium-dependent serotonin transporter	Ki	=	0.077	nM	10.11	Evaluated for affinity at 5-HT uptake site using [3H]paroxetine as radioligand i...	-
Sodium-dependent serotonin transporter	Ki	=	0.08	nM	10.1	Displacement of [125I]RTI55 binding from human wild type SERT	34049262
Sodium-dependent serotonin transporter	IC50	=	0.08	nM	10.1	DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind...	-
Sodium-dependent serotonin transporter	Ki	=	0.09	nM	10.05	Displacement of [3H]paroxetine from SERT receptor in human platelet membrane	17900912
Sodium-dependent serotonin transporter	Ki	=	0.11	nM	9.96	Displacement of [3H]citalopram from human SERT expressed in HEK293 cell membrane...	27865645
Sodium-dependent serotonin transporter	Kd	=	0.13	nM	9.89	Equilibrium dissociation constant (KD) for Competitive binding between [3H]- imi...	9871604
Sodium-dependent serotonin transporter	Kd	=	0.15	nM	9.82	The potency of the [3H]paroxetine for 5-HT transporters	8176704
Sodium-dependent serotonin transporter	IC50	=	0.2	nM	9.7	Displacement of [125I]RTI-55 from human recombinant SERT expressed in HEK293 cel...	23477943
Sodium-dependent serotonin transporter	IC50	=	0.28	nM	9.55	Inhibition of [3H]paroxetine (0.2 nM) binding to 5-HT transporter	9457247
Unchecked	Ki	=	0.31	nM	9.51	Displacement of [3H]-paroxetine from SERT in rabbit cortical membrane	21272963
Sodium-dependent serotonin transporter	Ki	=	0.38	nM	9.42	Displacement of [3H]paroxetine from human SERT expressed in HEK293 cells	18644726
Sodium-dependent serotonin transporter	Ki	=	0.38	nM	9.42	Displacement of [3H]paroxetine from human SERT expressed in HEK293 cells	18487050
Sodium-dependent serotonin transporter	Ki	=	0.42	nM	9.38	Displacement of [3H]citalopram from human SERT expressed in HEK293 cells	18644726
Sodium-dependent serotonin transporter	Ki	=	0.42	nM	9.38	Displacement of [3H]citalopram from human SERT expressed in HEK293 cells	18487050
Sodium-dependent serotonin transporter	Ki	=	0.44	nM	9.36	Tested in vitro for serotonin(5-HT) neuronal uptake inhibition	2213832
Sodium-dependent serotonin transporter	Ki	=	0.53	nM	9.28	Displacement of [3H]citalopram from rat cortical serotonin transporter (SERT)	11859009
Sodium-dependent serotonin transporter	Ki	=	0.53	nM	9.28	Inhibition of [3H]citalopram binding to Serotonin transporter of rat cerebral co...	10915050
Sodium-dependent serotonin transporter	IC50	=	0.56	nM	9.25	Inhibition of human SERT expressed in CHO cell membranes assessed as reduction i...	27865645

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	439
-	10.5281/zenodo.13943903	ADMET	89
16472241	10.2174/1570163043334794	Hepatotoxicity	18
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
17846135	10.1128/aac.01243-06	Homo sapiens	13
-	10.1039/C5MD00596E	Schistosoma mansoni	11
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
28399372	10.1021/acs.jmedchem.7b00156	Unchecked	8
21751791	10.1021/jm200370y	Staphylococcus aureus	7
38901106	10.1016/j.ejmech.2024.116601	5-hydroxytryptamine receptor 6	5
-	10.1039/C2MD20101A	Staphylococcus aureus	5
21474681	10.1124/dmd.111.038778	Brain	5
37468498	10.1038/s41467-023-40064-9	5-hydroxytryptamine receptor 2B	5
37934858	10.1021/acs.jmedchem.3c01669	Cytochrome P450 2D6	5
21098647	10.1124/dmd.110.036988	ADMET	5
21272963	10.1016/j.ejmech.2010.12.018	Unchecked	5
18426954	10.1124/dmd.108.020479	ADMET	4
22432682	10.1021/jm201446h	Staphylococcus aureus	4
28323425	10.1021/acs.jmedchem.7b00112	Beta-adrenergic receptor kinase 1	4

Data from ChEMBL 36 via Core Engine