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Compound Detail

CHEMBL1709

SERTRALINE HYDROCHLORIDE
💊 Approved Drug
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💊 Approved Drug
CN[C@H]1CC[C@@H](c2ccc(Cl)c(Cl)c2)c2ccccc21.Cl

Basic Information

ChEMBL ID CHEMBL1709
Name SERTRALINE HYDROCHLORIDE
Phase Approved
Structure Type MOL
InChI Key BLFQGGGGFNSJKA-XHXSRVRCSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL809
Active Moiety CHEMBL809

Known Names

Aremis Besitron CP-51,974-1 CP-51974-1 Lustral NSC-746308 NSC-758948 Sertraline (as hydrochloride) Sertraline hcl Sertraline hydrochloride Zoloft
5
Targets
22
Activities
2
Assay Types
0
PK Parameters
20
Publications
11
Known Names
9
Indications
1
Mechanisms

Molecular Properties

306.2
MW (Da)
5.18
ALogP
1
HBA
1
HBD
12.0
PSA (Ų)
0.81
QED
1
Ro5 Violations
2
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 C17H18Cl3N
MW 342.70
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness 0.12

Mechanism of Action

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

Indications

Depressive Disorder, Major Headache Obsessive-Compulsive Disorder Phobia, Social Stress Disorders, Post-Traumatic Depressive Disorder Intellectual Disability Panic Disorder Huntington Disease

Drug Warnings

Black Box Warning
psychiatric toxicity
Country: United States

Activity Summary

IC50 21 meas. best 7.16
EC50 1 meas. best 5.09

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent serotonin transporter
CHEMBL313
IC50 7.16 7.16 70.0 1
Sodium-dependent dopamine transporter
CHEMBL338
IC50 6.28 6.28 520.0 1
Norepinephrine transporter
CHEMBL304
IC50 6.14 6.14 720.0 1
Plasmodium falciparum
CHEMBL364
IC50 5.4 5.0857 3981.1 7
Unchecked
CHEMBL612545
IC50 5.33 4.8355 4711.3 11
Unchecked
CHEMBL612545
EC50 5.09 5.09 8180.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent serotonin transporter IC50 = 70.0 nM 7.16 Inhibition of 5-HT uptake in synaptosomal preparation from rat corpus striatum, ... 6492080
Sodium-dependent dopamine transporter IC50 = 520.0 nM 6.28 Inhibition of dopamine uptake in synaptosomal preparation in rat corpus striatum... 6492080
Norepinephrine transporter IC50 = 720.0 nM 6.14 Inhibition of norepinephrine uptake in synaptosomal preparation fro rat hypothal... 6492080
Plasmodium falciparum IC50 = 3981.07 nM 5.4 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 3981.07 nM 5.4 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
Unchecked IC50 = 4711.3 nM 5.33 PubChem BioAssay. SW480 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Unchecked IC50 = 4902.7 nM 5.31 PubChem BioAssay. SNU-C1 viability from Cell TiterGlo-IC50. (Class of assay: c... -
Unchecked EC50 = 8180.0 nM 5.09 PUBCHEM_BIOASSAY: A cytotoxicity screen of small molecule inhibitors of the PhoP... -
Unchecked IC50 = 8607.3 nM 5.07 PubChem BioAssay. GSK3B-pretreated HCT116 viability from Cell TiterGlo-IC50. (... -
Unchecked IC50 = 9344.3 nM 5.03 PubChem BioAssay. HT-29 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum Dd2 after 72 hrs by SYBR g... 19734910
Unchecked IC50 = 10207.2 nM 4.99 PubChem BioAssay. Colo320 viability from Cell TiterGlo-IC50. (Class of assay: ... -
Unchecked IC50 = 11015.2 nM 4.96 PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: conf... -
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 D10 after 72 hrs by SYBR g... 19734910
Unchecked IC50 = 19330.0 nM 4.71 PUBCHEM_BIOASSAY: A counter screen for small molecule screen for inhibitors of t... -
Unchecked IC50 = 25210.0 nM 4.6 PUBCHEM_BIOASSAY: High Throughput Screening Assay used to Identify Novel Compoun... -
Unchecked IC50 = 27450.0 nM 4.56 PUBCHEM_BIOASSAY: A High Throughput Confirmatory Assay used to Identify Novel Co... -

Literature References

PubMed DOI Target Context # Activities
19734910 10.1038/nchembio.215 Plasmodium falciparum 7
16464584 10.1016/j.bmcl.2006.01.078 Trichomonas vaginalis 2
16464584 10.1016/j.bmcl.2006.01.078 Spermatozoa 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/EOS300108 HepG2 1
6492080 10.1021/jm00377a021 Sodium-dependent dopamine transporter 1
35253435 10.1021/acs.jmedchem.1c01845 Cryptococcus neoformans 1
- 10.6019/CHEMBL4513141 Staphylococcus aureus 1
- 10.6019/CHEMBL4513141 Acinetobacter baumannii 1
- 10.6019/CHEMBL4513141 Pseudomonas aeruginosa 1
- 10.6019/CHEMBL4513141 Klebsiella pneumoniae 1
- 10.6019/CHEMBL4513141 Escherichia coli 1
- 10.6019/CHEMBL4513141 Cryptococcus neoformans 1
- 10.6019/CHEMBL4513141 Candida albicans 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B1 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B3 1
6492080 10.1021/jm00377a021 Norepinephrine transporter 1
6492080 10.1021/jm00377a021 Sodium-dependent serotonin transporter 1

Data from ChEMBL 36 via Core Engine