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Compound Detail

CHEMBL1118

DESVENLAFAXINE
💊 Approved Drug
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💊 Approved Drug
CN(C)CC(c1ccc(O)cc1)C1(O)CCCCC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1118
Name DESVENLAFAXINE
Phase Approved
Structure Type MOL
InChI Key KYYIDSXMWOZKMP-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

D-veniz Desvenlafaxina Desvenlafaxine Khedezla Mdd-xr Newven O-desmethylvenlafaxine O-desmethylvenlafaxine (odv) Odv
6
Targets
16
Activities
2
Assay Types
5
PK Parameters
20
Publications
9
Known Names
5
Indications
2
Mechanisms

Molecular Properties

263.4
MW (Da)
2.73
ALogP
3
HBA
2
HBD
43.7
PSA (Ų)
0.88
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2008
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -faxine
USAN Year 2003

Extended Properties

Molecular Formula C16H25NO2
MW 263.38
Aromatic Rings 1
Heavy Atoms 19
NP-Likeness 0.44

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

Depressive Disorder Depressive Disorder Depressive Disorder, Major Fibromyalgia Hepatitis C, Chronic

ATC Classification

N06AX23
desvenlafaxine
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Drug Warnings

Black Box Warning
psychiatric toxicity
Country: United States

Activity Summary

IC50 12 meas. best 7.77
Ki 4 meas. best 8.39

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent serotonin transporter
CHEMBL228
 Ki 8.39 8.105 4.1 2
Sodium-dependent serotonin transporter
CHEMBL228
 IC50 7.77 7.525 17.0 2
Alpha-1A adrenergic receptor
CHEMBL319
 IC50 7.22 7.22 60.0 1
Sodium-dependent serotonin transporter
CHEMBL313
 IC50 6.75 6.75 180.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
 IC50 6.27 6.045 538.0 2
Sodium-dependent noradrenaline transporter
CHEMBL222
 Ki 6.17 6.17 668.0 1
Norepinephrine transporter
CHEMBL304
 IC50 5.94 5.94 1160.0 1
Sodium-dependent dopamine transporter
CHEMBL238
 Ki 5.43 5.43 3726.0 1

Pharmacokinetic Data

Parameter Value Units Species
Fu 0.45 - Mus musculus
Fu 0.99 - Mus musculus
Fu 0.35 - Rattus norvegicus
Fu 0.89 - Rattus norvegicus
T1/2 11.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent serotonin transporter Ki = 4.1 nM 8.39 Uptake Assay Protocol: SERT: This protocol was designed to measure inhibition of... -
Sodium-dependent serotonin transporter Ki = 15.0 nM 7.82 Displacement of [3H]citalopram from human SERT transfected in HEK293 cells after... 24900709
Sodium-dependent serotonin transporter IC50 = 17.0 nM 7.77 Displacement of [3H]citalopram from human SERT transfected in HEK293 cells after... 24900709
Sodium-dependent serotonin transporter IC50 = 53.0 nM 7.28 Inhibition of human SERT expressed in CHO cells assessed as reduction of [3H]-5-... 28731336
Alpha-1A adrenergic receptor IC50 = 60.0 nM 7.22 Inhibition of binding of [3H]imipramine to imipramine receptor in rat brain 1976813
Sodium-dependent serotonin transporter IC50 = 180.0 nM 6.75 Inhibition of uptake of tritiated serotonin (5-HT) into rat brain synaptosomes 1976813
Sodium-dependent noradrenaline transporter IC50 = 538.0 nM 6.27 Inhibition of human NET expressed in CHO cells assessed as reduction of [3H]-NE ... 28731336
Sodium-dependent noradrenaline transporter Ki = 668.0 nM 6.17 Uptake Assay Protocol: NET: This protocol was designed to measure inhibition of ... -
Norepinephrine transporter IC50 = 1160.0 nM 5.94 Inhibition of uptake of tritiated norepinephrine (NE) into rat brain synaptosome... 1976813
Sodium-dependent noradrenaline transporter IC50 = 1500.0 nM 5.82 Displacement of [3H]Nisoxetine from human NET transfected in HEK293 cells after ... 24900709
Sodium-dependent dopamine transporter Ki = 3726.0 nM 5.43 Uptake Assay Protocol: DAT: This protocol was designed to measure inhibition of ... -

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 65
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
22112383 10.1124/dmd.111.043083 ADMET 8
22112383 10.1124/dmd.111.043083 Plasma 6
22112383 10.1124/dmd.111.043083 Brain 4
24900709 10.1021/ml400049p Unchecked 3
24900709 10.1021/ml400049p Sodium-dependent serotonin transporter 3
25087753 10.1016/j.vascn.2014.07.002 Voltage-gated inwardly rectifying potassium channel KCNH2 3
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
22112383 10.1124/dmd.111.043083 Molecular identity unknown 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
25087753 10.1016/j.vascn.2014.07.002 Voltage-gated potassium channel, IKs; KCNQ1(Kv7.1)/KCNE1(MinK) 2
25087753 10.1016/j.vascn.2014.07.002 Sodium channel protein type 5 subunit alpha 2
25087753 10.1016/j.vascn.2014.07.002 Voltage-dependent L-type calcium channel subunit alpha-1C 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
24900709 10.1021/ml400049p Sodium-dependent noradrenaline transporter 2

Data from ChEMBL 36 via Core Engine