Compound Detail

CHEMBL439849

VILAZODONE

💊 Approved Drug

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💊 Approved Drug

N#Cc1ccc2[nH]cc(CCCCN3CCN(c4ccc5oc(C(N)=O)cc5c4)CC3)c2c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL439849
Name	VILAZODONE
Phase	Approved
Structure Type	MOL
InChI Key	SGEGOXDYSFKCPT-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

EMD 515259 EMD 68843 BASE EMD-515259 EMD-68-843 Emd-68843 base Vilazodona Vilazodone

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

441.5

MW (Da)

4.03

ALogP

HBA

HBD

102.3

PSA (Å²)

0.42

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	2011
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product

USAN Year

2009

Extended Properties

Molecular Formula	C26H27N5O2
MW	441.54
Aromatic Rings	4
Heavy Atoms	33
NP-Likeness	-1.20

Indications

Depressive Disorder Anxiety Disorders Marijuana Abuse Memory Disorders

ATC Classification

N06AX24

vilazodone

Level 1: NERVOUS SYSTEM

Level 2: PSYCHOANALEPTICS

Activity Summary

IC50 38 meas. best 9.96

Ki 8 meas. best 9.7

EC50 5 meas. best 9.92

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
5-hydroxytryptamine receptor 1A CHEMBL214	IC50	9.96	9.83	0.1	2
5-hydroxytryptamine receptor 1A CHEMBL214	EC50	9.92	9.49	0.1	5
5-hydroxytryptamine receptor 1A CHEMBL214	Ki	9.7	8.695	0.2	4
5-hydroxytryptamine receptor 1A CHEMBL273	IC50	9.52	8.94	0.3	2
Sodium-dependent serotonin transporter CHEMBL228	IC50	9.4	9.338	0.4	5
Sodium-dependent serotonin transporter CHEMBL228	Ki	9.3	9.01	0.5	2
Sodium-dependent serotonin transporter CHEMBL313	IC50	9.3	8.99	0.5	7
D(3) dopamine receptor CHEMBL3138	IC50	7.15	7.15	71.0	1
D(2) dopamine receptor CHEMBL339	IC50	7.02	6.6	95.0	2
Sodium-dependent noradrenaline transporter CHEMBL222	IC50	6.8	6.8	158.1	1
5-hydroxytryptamine receptor 4 CHEMBL4317	IC50	6.6	6.6	252.0	1
Sodium-dependent dopamine transporter CHEMBL238	IC50	6.53	6.53	295.0	1
Unchecked CHEMBL612545	IC50	6.5	6.5	317.0	1
D(2) dopamine receptor CHEMBL217	Ki	6.18	6.18	666.0	1
5-hydroxytryptamine receptor 2A CHEMBL322	IC50	5.82	5.82	1510.0	1
5-hydroxytryptamine receptor 2C CHEMBL324	IC50	5.7	5.7	2000.0	1
Adrenergic receptor alpha-1 CHEMBL2094251	IC50	5.7	5.7	1980.0	1
5-hydroxytryptamine receptor 7 CHEMBL3223	IC50	5.52	5.52	3000.0	1
5-hydroxytryptamine receptor 6 CHEMBL3372	IC50	5.52	5.52	3000.0	1
D(4) dopamine receptor CHEMBL3361	IC50	5.47	5.47	3400.0	1
5-hydroxytryptamine receptor 7 CHEMBL3155	Ki	5.41	5.41	3900.0	1
5-hydroxytryptamine receptor 1D CHEMBL5450	IC50	5.4	5.4	4000.0	1
Serotonin 3 (5-HT3) receptor CHEMBL2094116	IC50	5.37	5.37	4300.0	1
5-hydroxytryptamine receptor 1B CHEMBL3459	IC50	5.3	5.3	5000.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	5.26	5.255	5550.0	2
Adrenergic receptor alpha-2 CHEMBL2095158	IC50	5.22	5.22	6000.0	1
Acetylcholinesterase CHEMBL3198	IC50	4.67	4.67	21300.0	1
Acetylcholinesterase CHEMBL3199	IC50	4.67	4.67	21300.0	2

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	409.0	ng.hr.mL-1	Rattus norvegicus
AUC	791.0	ng.hr.mL-1	Canis lupus familiaris
AUC	443.0	ng.hr.mL-1	Rattus norvegicus
AUC	2020.0	ng.hr.mL-1	Canis lupus familiaris
AUC	1645.0	ng.hr.mL-1	Homo sapiens
CL	48590.0	mL.min-1.g-1	Rattus norvegicus
CL	26000.0	mL.min-1.g-1	Homo sapiens
CL	77.3	mL.min-1.kg-1	Rattus norvegicus
CL	31.6	mL.min-1.g-1	Rattus norvegicus
CL	30.1	mL.min-1.g-1	Mus musculus
CL	49.3	mL.min-1.g-1	Mus musculus
CL	51.59	mL.min-1.g-1	Homo sapiens
CL	60.6	mL.min-1.g-1	Mus musculus
CL	40.17	mL.min-1.kg-1	Rattus norvegicus
CL	346.67	mL.min-1.kg-1	Canis lupus familiaris
Cmax	0.488	ug.mL-1	Canis lupus familiaris
Cmax	0.173	ug.mL-1	Rattus norvegicus
Cmax	0.454	ug.mL-1	Canis lupus familiaris
Cmax	0.156	ug.mL-1	Homo sapiens
F	47.45	%	Rattus norvegicus
F	52.5	%	Rattus norvegicus
T1/2	0.4753	hr	Rattus norvegicus
T1/2	0.8887	hr	Homo sapiens
T1/2	0.2983	hr	Rattus norvegicus
T1/2	0.73	hr	Rattus norvegicus
T1/2	0.6633	hr	Mus musculus
T1/2	0.4683	hr	Mus musculus
T1/2	0.4478	hr	Homo sapiens
T1/2	0.3847	hr	Mus musculus
T1/2	1.45	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
5-hydroxytryptamine receptor 1A	IC50	=	0.11	nM	9.96	Inhibition of 5-HT1a (unknown origin)	34182358
5-hydroxytryptamine receptor 1A	EC50	=	0.12	nM	9.92	Agonist activity at human 5H1A receptor expressed in HEK293 cells incubated for ...	30744931
5-hydroxytryptamine receptor 1A	EC50	=	0.12	nM	9.92	Agonist activity at human 5-HT1A receptor expressed in HEK293 cells after 60 min...	29729987
5-hydroxytryptamine receptor 1A	IC50	=	0.2	nM	9.7	Agonist activity at human 5HT1A expressed in CHO cell membranes assessed as incr...	29400967
5-hydroxytryptamine receptor 1A	Ki	=	0.2	nM	9.7	Displacement of [3H]-8-OH-DPAT from 5HT1A receptor (unknown origin) expressed in...	31627993
5-hydroxytryptamine receptor 1A	Ki	=	0.3	nM	9.52	Displacement of [3H]8-OH-DPAT from human 5HT1A receptor by liquid scintillation ...	22520153
5-hydroxytryptamine receptor 1A	EC50	=	0.3	nM	9.52	Agonist activity at recombinant human 5-HT1AR extracted from CHO cell membrane i...	38875810
5-hydroxytryptamine receptor 1A	IC50	=	0.3	nM	9.52	Inhibition of 8-OH DPAT binding to rat hydroxytryptamine 1A receptor expressed i...	15341484
Sodium-dependent serotonin transporter	IC50	=	0.4	nM	9.4	Inhibition of SERT (unknown origin) expressed in human HEK293 cells	35430560
Sodium-dependent serotonin transporter	IC50	=	0.4	nM	9.4	Inhibition of SERT (unknown origin) in HEK293 cells assessed as inhibition of 5-...	34922191
Sodium-dependent serotonin transporter	IC50	=	0.4	nM	9.4	Inhibition of SERT (unknown origin) expressed in HEK293 cells assessed as reduct...	29729987
Sodium-dependent serotonin transporter	IC50	=	0.48	nM	9.32	Inhibition of SERT receptor (unknown origin)	36598095
Sodium-dependent serotonin transporter	Ki	=	0.5	nM	9.3	Displacement of [3H]Citalopram from human SERT by liquid scintillation counting	22520153
Sodium-dependent serotonin transporter	IC50	=	0.5	nM	9.3	inhibition of rat cerebral 5HT transporter assessed as reduction in [3H]5HT reup...	29400967
Sodium-dependent serotonin transporter	IC50	=	0.5	nM	9.3	Inhibition of SERT in rat cerebral synaptosomes assessed as reduction in [3H]5-H...	38875810
Sodium-dependent serotonin transporter	IC50	=	0.5	nM	9.3	Inhibition of [3H]5-HT re-uptake in rat synaptosomes	15341484
Sodium-dependent serotonin transporter	IC50	=	0.5	nM	9.3	Inhibition of rat synaptosomes 5HT transporter assessed as reduction in [3H]sero...	31627993
Sodium-dependent serotonin transporter	IC50	=	0.67	nM	9.17	Inhibition of human SERT expressed in HEK293 cells incubated for 30 mins	38875810
Sodium-dependent serotonin transporter	IC50	=	0.67	nM	9.17	Inhibition of serotonin transporter expressed in rat brain tissue assessed as in...	34182358
5-hydroxytryptamine receptor 1A	EC50	=	0.79	nM	9.1	Agonist activity at human 5-HT1A receptor expressed in HEK293 cells incubated fo...	34922191

Literature References

PubMed	DOI	Target Context	# Activities
-	10.5281/zenodo.13943903	ADMET	80
31158845	10.1038/s41586-019-1291-3	ADMET	65
36598095	10.1021/acs.jmedchem.2c01339	ADMET	26
34922191	10.1016/j.ejmech.2021.114045	ADMET	5
31627993	10.1016/j.bmcl.2019.126703	ADMET	4
36202190	10.1016/j.bmcl.2022.129006	ADMET	4
38875810	10.1016/j.ejmech.2024.116564	5-hydroxytryptamine receptor 1A	3
38516587	10.1039/d3md00677h	ADMET	3
15341484	10.1021/jm040793q	Unchecked	3
15341484	10.1021/jm040793q	Rattus norvegicus	2
15341484	10.1021/jm040793q	5-hydroxytryptamine receptor 1A	2
34182358	10.1016/j.ejmech.2021.113644	ADMET	2
36598095	10.1021/acs.jmedchem.2c01339	Hypothalamus	2
38875810	10.1016/j.ejmech.2024.116564	Sodium-dependent serotonin transporter	2
35430560	10.1016/j.ejmech.2022.114347	ADMET	2
-	10.6019/CHEMBL4808148	Histone deacetylase 6	2
15341484	10.1021/jm040793q	D(2) dopamine receptor	2
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
15341484	10.1021/jm040793q	Sodium-dependent serotonin transporter	2
15341484	10.1021/jm040793q	5-hydroxytryptamine receptor 2A	1

Data from ChEMBL 36 via Core Engine