Compound Detail

CHEMBL809

SERTRALINE

💊 Approved Drug

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💊 Approved Drug

CN[C@H]1CC[C@@H](c2ccc(Cl)c(Cl)c2)c2ccccc21

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL809
Name	SERTRALINE
Phase	Approved
Structure Type	MOL
InChI Key	VGKDLMBJGBXTGI-SJCJKPOMSA-N
Therapeutic	✓ Yes

Known Names

Sertralina Sertraline

Targets

104

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

306.2

MW (Da)

5.18

ALogP

HBA

HBD

12.0

PSA (Å²)

0.81

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1991
Availability	Prescription
Chirality	Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Natural Product

USAN Stem	-traline
USAN Year	1983

Extended Properties

Molecular Formula	C17H17Cl2N
MW	306.24
Aromatic Rings	2
Heavy Atoms	20
NP-Likeness	0.12

Indications

Depressive Disorder Depressive Disorder Depressive Disorder, Major Anxiety Anxiety Disorders Autistic Disorder Bipolar Disorder Dementia Meningitis, Cryptococcal Obsessive-Compulsive Disorder Phobia, Social Schizophrenia Sleep Initiation and Maintenance Disorders Stress Disorders, Post-Traumatic Alcoholism Alcoholism Brain Injuries Child Development Disorders, Pervasive Cocaine-Related Disorders Coccidioidomycosis

ATC Classification

N06AB06

sertraline

Level 1: NERVOUS SYSTEM

Level 2: PSYCHOANALEPTICS

Activity Summary

IC50 68 meas. best 9.85

Ki 31 meas. best 10.12

Kd 4 meas. best 9.54

EC50 1 meas. best 4.94

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Sodium-dependent serotonin transporter CHEMBL228	Ki	10.12	10.12	0.1	1
Sodium-dependent serotonin transporter CHEMBL228	IC50	9.85	9.1525	0.1	4
Sodium-dependent serotonin transporter CHEMBL228	Kd	9.54	9.54	0.3	1
Sodium-dependent serotonin transporter CHEMBL313	Ki	9.07	8.77	0.8	2
Sodium-dependent dopamine transporter CHEMBL238	Kd	7.6	7.6	25.0	1
Sodium-dependent dopamine transporter CHEMBL238	Ki	7.59	7.59	25.8	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	7.53	7.385	29.3	2
Sodium-dependent dopamine transporter CHEMBL238	IC50	7.49	6.8367	32.4	3
Sigma non-opioid intracellular receptor 1 CHEMBL3602	Ki	7.24	7.24	57.0	1
Rattus norvegicus CHEMBL376	IC50	7.22	6.57	60.0	2
Sodium-dependent serotonin transporter CHEMBL313	IC50	7.22	6.78	60.0	2
Sigma non-opioid intracellular receptor 1 CHEMBL287	IC50	7.16	7.16	69.7	1
Sodium-dependent dopamine transporter CHEMBL338	Ki	7.11	6.845	78.3	2
Alpha-2B adrenergic receptor CHEMBL1942	Ki	7.08	7.08	82.8	1
Alpha-2A adrenergic receptor CHEMBL1867	Ki	6.96	6.96	108.3	1
Norepinephrine transporter CHEMBL304	Ki	6.8	6.73	159.0	2
Alpha-2B adrenergic receptor CHEMBL1942	IC50	6.74	6.74	181.4	1
Alpha-2A adrenergic receptor CHEMBL1867	IC50	6.54	6.54	288.8	1
Norepinephrine transporter CHEMBL304	IC50	6.52	6.22	300.0	2
Muscarinic acetylcholine receptor M1 CHEMBL216	Ki	6.51	6.51	310.2	1
Cytochrome P450 2C19 CHEMBL3622	IC50	6.51	5.72	310.0	3
Sodium-dependent dopamine transporter CHEMBL338	IC50	6.5	6.195	320.0	2
Alpha-1B adrenergic receptor CHEMBL315	Ki	6.47	6.47	334.9	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	Ki	6.44	6.44	364.5	1
Muscarinic acetylcholine receptor M4 CHEMBL1821	Ki	6.43	6.43	366.9	1
Sodium-dependent noradrenaline transporter CHEMBL222	Kd	6.38	6.38	420.0	1
Plasmodium falciparum CHEMBL364	IC50	6.29	6.29	510.0	1
Muscarinic acetylcholine receptor M5 CHEMBL2035	IC50	6.29	6.29	507.3	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	6.25	6.25	567.3	1
Alpha-1B adrenergic receptor CHEMBL315	IC50	6.22	6.22	605.0	1
Alpha-2C adrenergic receptor CHEMBL1916	Ki	6.19	6.19	650.5	1
Unchecked CHEMBL612545	IC50	6.16	5.3133	700.0	9
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	6.11	6.11	783.1	1
Trypanosoma brucei rhodesiense CHEMBL612348	IC50	6.11	6.11	770.0	1
Cytochrome P450 3A4 CHEMBL340	IC50	6.1	5.485	800.0	2
Sodium-dependent noradrenaline transporter CHEMBL222	IC50	6.08	6.0567	825.0	3
Sodium-dependent noradrenaline transporter CHEMBL222	Ki	6.01	6.01	976.6	1
Muscarinic acetylcholine receptor M2 CHEMBL211	Ki	6.01	6.01	984.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	IC50	5.96	5.96	1083.0	1
Muscarinic acetylcholine receptor M1 CHEMBL216	IC50	5.89	5.89	1288.2	1
Unchecked CHEMBL612545	Ki	5.88	5.67	1304.0	5
Cytochrome P450 2D6 CHEMBL289	IC50	5.85	5.695	1400.0	2
Ebolavirus CHEMBL4434621	IC50	5.84	5.5675	1440.0	4
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	5.67	5.67	2159.5	1
Voltage-dependent L-type calcium channel subunit alpha-1C CHEMBL3762	IC50	5.64	5.61	2310.0	2
Marburgvirus CHEMBL4296577	IC50	5.61	5.61	2430.0	1
Muscarinic acetylcholine receptor M4 CHEMBL1821	IC50	5.58	5.58	2630.9	1
5-hydroxytryptamine receptor 2A CHEMBL224	IC50	5.56	5.56	2740.9	1
Muscarinic acetylcholine receptor M2 CHEMBL211	IC50	5.56	5.56	2767.5	1
5-hydroxytryptamine receptor 2B CHEMBL1833	IC50	5.47	5.47	3393.5	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	71.0	mL.min-1.kg-1	Rattus norvegicus
CL	131590.0	mL.min-1.g-1	Mus musculus
F	51.0	%	Rattus norvegicus
Fu	0.00066	-	Mus musculus
Fu	0.001	-	Homo sapiens
Fu	0.001	-	Macaca fascicularis
Fu	0.001	-	Canis lupus familiaris
Fu	0.001	-	Cavia porcellus
Fu	0.001	-	Mus musculus
Fu	0.001	-	Rattus norvegicus
Fu	0.001	-	Rattus norvegicus
T1/2	2.0	hr	Homo sapiens
T1/2	0.3833	hr	Rattus norvegicus
T1/2	5.0	hr	Rattus norvegicus
T1/2	2.0	hr	Homo sapiens
t1/2	-	-	Mus musculus
T1/2	0.6912	hr	Mus musculus
Tmax	4.0	hr	Rattus norvegicus
Vd	1900.0	L.kg-1	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Sodium-dependent serotonin transporter	Ki	=	0.075	nM	10.12	DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind...	-
Sodium-dependent serotonin transporter	IC50	=	0.141	nM	9.85	DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind...	-
Sodium-dependent serotonin transporter	IC50	=	0.19	nM	9.72	Inhibition of SERT (unknown origin)	33111525
Sodium-dependent serotonin transporter	Kd	=	0.29	nM	9.54	Equilibrium dissociation constant (KD) for Competitive binding between [3H]- imi...	9871604
Sodium-dependent serotonin transporter	Ki	=	0.85	nM	9.07	Inhibition the uptake of tritiated serotonin (5-HT) by the serotonin transporter...	3039136
Sodium-dependent serotonin transporter	IC50	=	3.0	nM	8.52	Inhibition of serotonin re-uptake at human serotonin transporter expressed in HE...	16314097
Sodium-dependent serotonin transporter	IC50	=	3.0	nM	8.52	Inhibition of [3H]serotonin reuptake at human SERT expressed in HEK293 cells by ...	21093273
Sodium-dependent serotonin transporter	Ki	=	3.4	nM	8.47	Inhibition of [3H]5-HT reuptake into rat frontal cortex synaptosomes	9871604
Sodium-dependent dopamine transporter	Kd	=	25.0	nM	7.6	Equilibrium dissociation constant (KD) for Competitive binding between [3H]WIN-3...	9871604
Sodium-dependent dopamine transporter	Ki	=	25.8	nM	7.59	DRUGMATRIX: Dopamine Transporter radioligand binding (ligand: [125I] RTI-55)	-
Sigma non-opioid intracellular receptor 1	Ki	=	29.3	nM	7.53	DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol)	-
Sodium-dependent dopamine transporter	IC50	=	32.4	nM	7.49	DRUGMATRIX: Dopamine Transporter radioligand binding (ligand: [125I] RTI-55)	-
Sigma non-opioid intracellular receptor 1	Ki	=	57.0	nM	7.24	Binding affinity to sigma 1 receptor	23641311
Sigma non-opioid intracellular receptor 1	Ki	=	57.0	nM	7.24	Displacement of [3H]-(+)-pentazocine from sigma 1 receptor in Sprague-Dawley rat...	33111525
Rattus norvegicus	IC50	=	60.0	nM	7.22	In vitro inhibition of serotonin (5-HT) uptake in crude rat brain synaptosomes	3257267
Sodium-dependent serotonin transporter	IC50	=	60.0	nM	7.22	Inhibition of 5-HT uptake in synaptosomal preparation from rat corpus striatum, ...	6492080
Sigma non-opioid intracellular receptor 1	IC50	=	69.7	nM	7.16	DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol)	-
Sodium-dependent dopamine transporter	Ki	=	78.3	nM	7.11	Inhibition of the uptake of tritiated dopamine (DA) in rat synaptosomes	3039136
Alpha-2B adrenergic receptor	Ki	=	82.8	nM	7.08	DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin...	-
Alpha-2A adrenergic receptor	Ki	=	108.3	nM	6.96	DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912)	-

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	419
-	10.5281/zenodo.13943903	ADMET	87
16472241	10.2174/1570163043334794	Hepatotoxicity	18
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
36948129	10.1016/j.ejmech.2023.115273	Cortical neurone	14
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
33775839	10.1016/j.bmcl.2021.127997	Molecular identity unknown	9
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
33775839	10.1016/j.bmcl.2021.127997	SGC-7901	8
35253435	10.1021/acs.jmedchem.1c01845	Cryptococcus neoformans	7
16314097	10.1016/j.bmcl.2005.11.031	Rattus norvegicus	6
21474681	10.1124/dmd.111.038778	Brain	5
36948129	10.1016/j.ejmech.2023.115273	ADMET	4
35253435	10.1021/acs.jmedchem.1c01845	Unchecked	4
36846366	10.1039/d2md00243d	Mus musculus	4
35253435	10.1021/acs.jmedchem.1c01845	ADMET	3
35253435	10.1021/acs.jmedchem.1c01845	Candida albicans	3
37468498	10.1038/s41467-023-40064-9	Histamine H1 receptor	3
32905862	10.1016/j.ejmech.2020.112726	Unchecked	3
37468498	10.1038/s41467-023-40064-9	Alpha-1A adrenergic receptor	3

Data from ChEMBL 36 via Core Engine