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Compound Detail

CHEMBL2104993

VORTIOXETINE
💊 Approved Drug
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💊 Approved Drug
Cc1ccc(Sc2ccccc2N2CCNCC2)c(C)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2104993
Name VORTIOXETINE
Phase Approved
Structure Type MOL
InChI Key YQNWZWMKLDQSAC-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Brintellix LU AA21004 LU-AA21004 LUAA21004 Vortioxetina Vortioxetine
8
Targets
20
Activities
2
Assay Types
13
PK Parameters
20
Publications
6
Known Names
8
Indications

Molecular Properties

298.5
MW (Da)
3.86
ALogP
3
HBA
1
HBD
15.3
PSA (Ų)
0.93
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2013
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product First in Class
USAN Stem -oxetine
USAN Year 2011

Extended Properties

Molecular Formula C18H22N2S
MW 298.46
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness -1.11

Indications

Anxiety Disorders Depressive Disorder Depressive Disorder Depressive Disorder, Major Attention Deficit Disorder with Hyperactivity Bipolar Disorder Feeding and Eating Disorders Liver Diseases

ATC Classification

N06AX26
vortioxetine
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Activity Summary

Ki 12 meas. best 8.8
IC50 8 meas. best 8.54

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent serotonin transporter
CHEMBL228
 Ki 8.8 8.8 1.6 1
Sodium-dependent serotonin transporter
CHEMBL313
 IC50 8.54 8.54 2.9 4
Monocyte
CHEMBL614076
 IC50 8.54 8.54 2.9 1
Prostaglandin G/H synthase 2
CHEMBL230
 IC50 8.51 8.51 3.1 1
5-hydroxytryptamine receptor 3A
CHEMBL1899
 Ki 8.43 8.43 3.7 1
Prostaglandin G/H synthase 1
CHEMBL221
 IC50 8.29 8.29 5.2 1
Sodium-dependent serotonin transporter
CHEMBL228
 IC50 8.27 8.27 5.4 1
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 8.02 7.98 9.5 5
5-hydroxytryptamine receptor 7
CHEMBL3155
 Ki 7.72 7.608 19.0 5

Pharmacokinetic Data

Parameter Value Units Species
CL 153.2 mL.min-1.g-1 Rattus norvegicus
CL 153.2 mL.min-1.g-1 Rattus norvegicus
CL 153200.0 mL.min-1.g-1 Rattus norvegicus
CL 6470.0 mL.min-1.g-1 Homo sapiens
CL 153.2 mL.min-1.g-1 Rattus norvegicus
CL 6.5 mL.min-1.g-1 Homo sapiens
F 75.0 % Homo sapiens
T1/2 0.15 hr Rattus norvegicus
T1/2 0.15 hr Rattus norvegicus
T1/2 0.15 hr Rattus norvegicus
T1/2 3.572 hr Homo sapiens
T1/2 0.15 hr Rattus norvegicus
T1/2 3.572 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent serotonin transporter Ki = 1.6 nM 8.8 Binding affinity to human SERT assessed as inhibition constant 34311086
Sodium-dependent serotonin transporter IC50 = 2.9 nM 8.54 Inhibition of [3H]serotonin reuptake in rat brain synaptosomes SERT after 15 min... 29291438
Sodium-dependent serotonin transporter IC50 = 2.9 nM 8.54 Inhibition of rat synaptosomes 5HT transporter assessed as reduction in [3H]sero... 31627993
Sodium-dependent serotonin transporter IC50 = 2.9 nM 8.54 Inhibition of rat synaptosomes 5HT transporter assessed as reduction in [3H]sero... 31699607
Monocyte IC50 = 2.9 nM 8.54 Inhibition of PMA-induced oxidative burst in human monocytes preincubated for 1 ... 32992247
Sodium-dependent serotonin transporter IC50 = 2.9 nM 8.54 Inhibition of SERT in rat brain synaptosomes assessed as reduction in [3H]-5-HT ... 29138029
Prostaglandin G/H synthase 2 IC50 = 3.11 nM 8.51 Inhibition of human COX-2 by spectrophotometer analysis 32992247
5-hydroxytryptamine receptor 3A Ki = 3.7 nM 8.43 Binding affinity to human 5-HT3R assessed as inhibition constant 34311086
Prostaglandin G/H synthase 1 IC50 = 5.19 nM 8.29 Inhibition of human COX-1 by spectrophotometer analysis 32992247
Sodium-dependent serotonin transporter IC50 = 5.4 nM 8.27 Inhibition of SERT receptor (unknown origin) 36598095
5-hydroxytryptamine receptor 1A Ki = 9.5 nM 8.02 Displacement of [3H]8-OH-DPAT from recombinant human 5-HT1A receptor expressed i... 29138029
5-hydroxytryptamine receptor 1A Ki = 9.5 nM 8.02 Displacement of [3H]-8-OH-DPAT from 5HT1A receptor (unknown origin) expressed in... 31699607
5-hydroxytryptamine receptor 1A Ki = 9.5 nM 8.02 Displacement of [3H]-8-OH-DPAT from 5HT1A receptor (unknown origin) expressed in... 31627993
5-hydroxytryptamine receptor 1A Ki = 9.5 nM 8.02 Displacement of [3H]8-OH-DPAT from recombinant human 5-HT1A receptor expressed i... 29291438
5-hydroxytryptamine receptor 1A Ki = 15.0 nM 7.82 Binding affinity to human 5-HT1A assessed as inhibition constant 34311086
5-hydroxytryptamine receptor 7 Ki = 19.0 nM 7.72 Binding affinity to human 5-HT7R assessed as inhibition constant 34311086
5-hydroxytryptamine receptor 7 Ki = 26.0 nM 7.58 Displacement of [3H]-LSD from recombinant human 5-HT7 receptor expressed in CHO ... 29138029
5-hydroxytryptamine receptor 7 Ki = 26.0 nM 7.58 Displacement of [3H]LSD from recombinant human 5-HT7 receptor expressed in CHO c... 29291438
5-hydroxytryptamine receptor 7 Ki = 26.0 nM 7.58 Displacement of [3H]-LSD from 5HT7 receptor (unknown origin) expressed in CHO ce... 31627993
5-hydroxytryptamine receptor 7 Ki = 26.0 nM 7.58 Displacement of [3H]-LSD from 5HT7 receptor (unknown origin) expressed in CHO ce... 31699607

Literature References

PubMed DOI Target Context # Activities
32992247 10.1016/j.bmc.2020.115760 Unchecked 11
32992247 10.1016/j.bmc.2020.115760 Monocyte 4
31699607 10.1016/j.bmcl.2019.126769 ADMET 4
31627993 10.1016/j.bmcl.2019.126703 ADMET 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
31699607 10.1016/j.bmcl.2019.126769 Mus musculus 2
29138029 10.1016/j.bmcl.2017.11.007 ADMET 2
31699607 10.1016/j.bmcl.2019.126769 Sodium-dependent serotonin transporter 2
31699607 10.1016/j.bmcl.2019.126769 5-hydroxytryptamine receptor 7 2
29291438 10.1016/j.ejmech.2017.12.063 ADMET 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
31699607 10.1016/j.bmcl.2019.126769 5-hydroxytryptamine receptor 1A 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
- 10.1101/2020.04.21.054387 SARS-CoV-2 1
31627993 10.1016/j.bmcl.2019.126703 5-hydroxytryptamine receptor 7 1
31627993 10.1016/j.bmcl.2019.126703 5-hydroxytryptamine receptor 1A 1
38552597 10.1016/j.bmc.2024.117698 Mus musculus 1
29291438 10.1016/j.ejmech.2017.12.063 5-hydroxytryptamine receptor 1A 1
29291438 10.1016/j.ejmech.2017.12.063 Sodium-dependent serotonin transporter 1
29138029 10.1016/j.bmcl.2017.11.007 Mus musculus 1

Data from ChEMBL 36 via Core Engine