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Compound Detail

CHEMBL814

FLUVOXAMINE
💊 Approved Drug
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💊 Approved Drug
COCCCC/C(=N\OCCN)c1ccc(C(F)(F)F)cc1

Basic Information

ChEMBL ID CHEMBL814
Name FLUVOXAMINE
Phase Approved
Structure Type MOL
InChI Key CJOFXWAVKWHTFT-XSFVSMFZSA-N
Therapeutic ✓ Yes

Known Names

Fluvoxamina Fluvoxamine N06AB08
15
Targets
20
Activities
2
Assay Types
10
PK Parameters
20
Publications
3
Known Names
16
Indications

Molecular Properties

318.3
MW (Da)
3.20
ALogP
4
HBA
1
HBD
56.8
PSA (Ų)
0.43
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1994
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning
USAN Year 1995

Extended Properties

Molecular Formula C15H21F3N2O2
MW 318.34
Aromatic Rings 1
Heavy Atoms 22
NP-Likeness -0.69

Indications

Depressive Disorder Depressive Disorder Depressive Disorder Anxiety Anxiety Disorders Anxiety, Separation Autistic Disorder Dementia Obsessive-Compulsive Disorder Phobia, Social Schizophrenia Severe Acute Respiratory Syndrome Severe Acute Respiratory Syndrome Panic Disorder Post-Acute COVID-19 Syndrome Neoplasms

ATC Classification

N06AB08
fluvoxamine
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Activity Summary

Ki 12 meas. best 8.84
IC50 8 meas. best 8.42

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent dopamine transporter
CHEMBL238
Ki 8.84 8.84 1.5 1
Sodium-dependent serotonin transporter
CHEMBL228
Ki 8.51 7.425 3.1 2
Sodium-dependent serotonin transporter
CHEMBL228
IC50 8.42 8.42 3.8 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
Ki 7.44 7.44 36.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL3602
Ki 7.44 7.44 36.0 2
Sodium-dependent serotonin transporter
CHEMBL313
IC50 6.27 6.27 540.0 1
Norepinephrine transporter
CHEMBL304
IC50 5.72 5.72 1900.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 5.51 5.51 3100.0 1
Voltage-dependent L-type calcium channel subunit alpha-1C
CHEMBL2366456
IC50 5.31 5.31 4900.0 2
Cytochrome P450 2D6
CHEMBL289
Ki 5.1 4.935 8000.0 2
Cytochrome P450 2C9
CHEMBL3397
Ki 5.07 5.07 8500.0 1
Sigma intracellular receptor 2
CHEMBL4105864
Ki 5.07 5.07 8439.0 1
Unchecked
CHEMBL612545
Ki 5.07 5.07 8439.0 1
Sodium channel protein type 5 subunit alpha
CHEMBL1980
IC50 4.41 4.41 39400.0 1
Sodium-dependent dopamine transporter
CHEMBL338
IC50 4.35 4.35 45000.0 1
Cytochrome P450 1A2
CHEMBL1075125
Ki 4.24 4.24 57400.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 79.0 % Homo sapiens
Fu 0.022 - Homo sapiens
Fu 0.0084 - Rattus norvegicus
Fu 0.0074 - Sus scrofa
Fu 0.044 - Macaca fascicularis
Fu 0.038 - Canis lupus familiaris
Fu 0.011 - Cavia porcellus
Fu 0.034 - Mus musculus
Fu 0.009 - Rattus norvegicus
Fu 0.013 - Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent dopamine transporter Ki = 1.46 nM 8.84 In vitro competitive binding versus [N-methyl-3H]WIN-35428 in murine kidney cell... 12620070
Sodium-dependent serotonin transporter Ki = 3.08 nM 8.51 Inhibition constant against [3H]citalopram in murine kidney cells transfected wi... 10691690
Sodium-dependent serotonin transporter IC50 = 3.8 nM 8.42 Inhibition of SERT (unknown origin) 33111525
Sigma non-opioid intracellular receptor 1 Ki = 36.0 nM 7.44 Displacement of [3H]-(+)-pentazocine from sigma 1 receptor in Sprague-Dawley rat... 33111525
Sigma non-opioid intracellular receptor 1 Ki = 36.0 nM 7.44 Binding affinity to sigma 1 receptor 23641311
Sigma non-opioid intracellular receptor 1 Ki = 36.0 nM 7.44 Displacement of [3H]-(+)pentazocine from rat brain sigma 1-type opioid receptor 22515405
Sodium-dependent serotonin transporter Ki = 458.0 nM 6.34 Displacement of [3H]citalopram from human SERT in HEK293 cells by Topcount scint... 34049262
Sodium-dependent serotonin transporter IC50 = 540.0 nM 6.27 Inhibition of 5-HT uptake in synaptosomal preparation from rat corpus striatum, ... 6492080
Norepinephrine transporter IC50 = 1900.0 nM 5.72 Inhibition of norepinephrine uptake in synaptosomal preparation fro rat hypothal... 6492080
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 3100.0 nM 5.51 Inhibition of hERG K channel 21300721
Voltage-dependent L-type calcium channel subunit alpha-1C IC50 = 4900.0 nM 5.31 Inhibition of L-type calcium channel measured using whole-cell patch clamp in gu... 22761000
Voltage-dependent L-type calcium channel subunit alpha-1C IC50 = 4900.0 nM 5.31 Inhibition of calcium current (ICaL) measured using whole-cell patch clamp exper... 21300721
Cytochrome P450 2D6 Ki = 8000.0 nM 5.1 Inhibition of CYP2D6 (unknown origin) assessed as sparteine oxidation 22688609
Cytochrome P450 2C9 Ki = 8500.0 nM 5.07 Binding affinity towards cytochrome P450 2C9 14761192
Unchecked Ki = 8439.0 nM 5.07 Binding affinity to sigma 2 receptor 23641311
Sigma intracellular receptor 2 Ki = 8439.0 nM 5.07 Displacement of [3H]DTG from sigma 2 receptor in Sprague-Dawley rat brain membra... 33111525
Cytochrome P450 2D6 Ki = 17000.0 nM 4.77 Inhibition of CYP2D6 (unknown origin) assessed as desipramine oxidation 22688609
Sodium channel protein type 5 subunit alpha IC50 = 39400.0 nM 4.41 Inhibition of sodium current measured using whole-cell patch clamp experiments i... 21300721
Sodium-dependent dopamine transporter IC50 = 45000.0 nM 4.35 Inhibition of dopamine uptake in synaptosomal preparation in rat corpus striatum... 6492080
Cytochrome P450 1A2 Ki = 57400.0 nM 4.24 Mechanism based inhibition of rat cytochrome P450 CYP1A2 measured by zolmitripta... 16248836

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
21474681 10.1124/dmd.111.038778 Brain 5
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
10691690 10.1021/jm9902234 Sodium-dependent serotonin transporter 3
20014752 10.1021/tx900326k Hepatotoxicity 3
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 3
16248836 10.2174/138920005774330639 Cytochrome P450 1A2 2
22328583 10.1124/dmd.111.043505 Cytochrome P450 2J2 2
22931300 10.1021/tx300075j Cytochrome P450 3A4 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
20384344 10.1021/jm901890s Mus musculus 2
17725338 10.1021/jm070375w No relevant target 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
22688609 10.1124/dmd.112.045237 Cytochrome P450 2D6 2
10691690 10.1021/jm9902234 Unchecked 2
10891117 10.1021/jm0000564 ADMET 2
10891117 10.1021/jm0000564 No relevant target 2

Data from ChEMBL 36 via Core Engine