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Compound Detail

CHEMBL1201066

VENLAFAXINE HYDROCHLORIDE
💊 Approved Drug
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💊 Approved Drug
COc1ccc(C(CN(C)C)C2(O)CCCCC2)cc1.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1201066
Name VENLAFAXINE HYDROCHLORIDE
Phase Approved
Structure Type MOL
InChI Key QYRYFNHXARDNFZ-UHFFFAOYSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL637
Active Moiety CHEMBL637

Known Names

Effexor Effexor xr NSC-745751 Venlafaxine (as hydrochloride) Venlafaxine hcl Venlafaxine hydrochloride WY-45,030 WY-45030
3
Targets
18
Activities
1
Assay Types
4
PK Parameters
20
Publications
8
Known Names
20
Indications
2
Mechanisms

Molecular Properties

277.4
MW (Da)
3.04
ALogP
3
HBA
1
HBD
32.7
PSA (Ų)
0.90
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1993
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Black Box Warning
USAN Stem -faxine
USAN Year 1989

Extended Properties

Molecular Formula C17H28ClNO2
MW 313.87
Aromatic Rings 1
Heavy Atoms 20
NP-Likeness 0.13

Mechanism of Action

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

Indications

Anxiety Disorders Anxiety Disorders Depressive Disorder Depressive Disorder Depressive Disorder Depressive Disorder, Major Panic Disorder Phobia, Social Anxiety Bipolar Disorder Breast Neoplasms Dementia Depressive Disorder, Treatment-Resistant Hot Flashes Obsessive-Compulsive Disorder Parkinson Disease Prostatic Neoplasms Schizophrenia Cocaine-Related Disorders Meniere Disease

Drug Warnings

Black Box Warning
psychiatric toxicity
Country: United States
Black Box Warning
gastrointestinal toxicity
Country: United States
Black Box Warning
cardiotoxicity
Country: United States

Activity Summary

IC50 18 meas. best 7.44

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent serotonin transporter
CHEMBL228
 IC50 7.44 6.7913 36.1 8
Sodium-dependent noradrenaline transporter
CHEMBL222
 IC50 5.59 5.5463 2550.0 8
Sodium-dependent dopamine transporter
CHEMBL238
 IC50 5.59 5.195 2550.0 2

Pharmacokinetic Data

Parameter Value Units Species
Fu 0.18 - Mus musculus
Fu 0.99 - Mus musculus
Fu 0.092 - Rattus norvegicus
Fu 0.64 - Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent serotonin transporter IC50 = 36.1 nM 7.44 Inhibition of human SERT expressed in HEK293 cells at incubated for 15 mins by n... 25221656
Sodium-dependent serotonin transporter IC50 = 200.0 nM 6.7 Inhibition of [3H]-5-HT reuptake in human SERT transfected into HEK293 cells by ... 27041397
Sodium-dependent serotonin transporter IC50 = 200.0 nM 6.7 Inhibition of [3H]-5-hydroxytryptamine reuptake in human SERT expressed in HEK29... 28274674
Sodium-dependent serotonin transporter IC50 = 200.0 nM 6.7 Inhibition of re-uptake of [3H]-5-HT at human SERT expressed in HEK293 cells by ... 28807575
Sodium-dependent serotonin transporter IC50 = 200.0 nM 6.7 Inhibition of human SERT expressed in HEK293 cells assessed as reduction in [3H]... 30007567
Sodium-dependent serotonin transporter IC50 = 200.0 nM 6.7 Inhibition of [3H]serotonin uptake at human SERT expressed in HEK293 cells after... 30293797
Sodium-dependent serotonin transporter IC50 = 200.0 nM 6.7 Inhibition of [3H]-5-hydroxytryptamine reuptake in human SERT expressed in HEK29... 27647372
Sodium-dependent serotonin transporter IC50 = 204.0 nM 6.69 Inhibition of human SERT expressed in HEK293 cells assessed as reduction of sero... 26337019
Sodium-dependent noradrenaline transporter IC50 = 2550.0 nM 5.59 Inhibition of [3H]-NE reuptake in human NET transfected into HEK293 cells by liq... 27041397
Sodium-dependent dopamine transporter IC50 = 2550.0 nM 5.59 Inhibition of [3H]-5-dopamine reuptake in human DAT expressed in HEK293 cells by... 27647372
Sodium-dependent noradrenaline transporter IC50 = 2550.0 nM 5.59 Inhibition of [3H]-5-norepinephrine reuptake in human NET expressed in HEK293 ce... 27647372
Sodium-dependent noradrenaline transporter IC50 = 2550.0 nM 5.59 Inhibition of [3H]norepinephrine uptake at human NET expressed in HEK293 cells a... 30293797
Sodium-dependent noradrenaline transporter IC50 = 2550.0 nM 5.59 Inhibition of human NET expressed in HEK293 cells assessed as reduction in [3H]-... 30007567
Sodium-dependent noradrenaline transporter IC50 = 2550.0 nM 5.59 Inhibition of re-uptake of [3H]-NE at human NET expressed in HEK293 cells by liq... 28807575
Sodium-dependent noradrenaline transporter IC50 = 2550.0 nM 5.59 Inhibition of [3H]-5-norepinephrine reuptake in human NET expressed in HEK293 ce... 28274674
Sodium-dependent noradrenaline transporter IC50 = 2553.0 nM 5.59 Inhibition of human NET expressed in HEK293 cells assessed as reduction of serot... 26337019
Sodium-dependent noradrenaline transporter IC50 = 5720.0 nM 5.24 Inhibition of human NET expressed in HEK293 cells at incubated for 15 mins by ne... 25221656
Sodium-dependent dopamine transporter IC50 = 15700.0 nM 4.8 Inhibition of human DAT expressed in HEK293 cells at incubated for 15 mins by ne... 25221656

Literature References

PubMed DOI Target Context # Activities
22112383 10.1124/dmd.111.043083 ADMET 8
22112383 10.1124/dmd.111.043083 Plasma 6
22112383 10.1124/dmd.111.043083 Brain 4
25221656 10.1021/ml500187a Sodium-dependent noradrenaline transporter 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
30293797 10.1016/j.bmc.2018.09.033 Sodium-dependent noradrenaline transporter 2
30293797 10.1016/j.bmc.2018.09.033 Sodium-dependent serotonin transporter 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
22112383 10.1124/dmd.111.043083 Molecular identity unknown 2
25221656 10.1021/ml500187a Unchecked 2
25221656 10.1021/ml500187a Sodium-dependent dopamine transporter 2
25221656 10.1021/ml500187a Sodium-dependent serotonin transporter 2
26337019 10.1016/j.bmc.2015.08.022 Sodium-dependent serotonin transporter 1
26337019 10.1016/j.bmc.2015.08.022 Sodium-dependent noradrenaline transporter 1
27041397 10.1016/j.bmc.2016.03.044 Sodium-dependent serotonin transporter 1
27041397 10.1016/j.bmc.2016.03.044 Sodium-dependent noradrenaline transporter 1
28274674 10.1016/j.bmc.2017.02.051 Sodium-dependent serotonin transporter 1
28274674 10.1016/j.bmc.2017.02.051 Sodium-dependent noradrenaline transporter 1
28807575 10.1016/j.bmc.2017.07.046 Sodium-dependent serotonin transporter 1
- 10.6019/CHEMBL5724796 Bromodomain-containing protein 4 1

Data from ChEMBL 36 via Core Engine