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Compound Detail

CHEMBL641

ATOMOXETINE
💊 Approved Drug
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💊 Approved Drug
CNCC[C@@H](Oc1ccccc1C)c1ccccc1

Basic Information

ChEMBL ID CHEMBL641
Name ATOMOXETINE
Phase Approved
Structure Type MOL
InChI Key VHGCDTVCOLNTBX-QGZVFWFLSA-N
Therapeutic ✓ Yes

Known Names

Atomoxetina Atomoxetine Atomoxetine component of ad-109 Atomoxetine component of ad-313 Atomoxetine component of ad109 Atomoxetine component of ad313
13
Targets
58
Activities
3
Assay Types
23
PK Parameters
20
Publications
6
Known Names
20
Indications

Molecular Properties

255.4
MW (Da)
3.72
ALogP
2
HBA
1
HBD
21.3
PSA (Ų)
0.85
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2002
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -oxetine
USAN Year 2001

Extended Properties

Molecular Formula C17H21NO
MW 255.36
Aromatic Rings 2
Heavy Atoms 19
NP-Likeness -0.06

Indications

Attention Deficit Disorder with Hyperactivity Autistic Disorder Neoplasms Schizophrenia Alcoholism Cognitive Dysfunction Hypotension, Orthostatic Marijuana Abuse Opioid-Related Disorders Phobia, Social Sleep Apnea Syndromes Sleep Apnea, Obstructive Substance-Related Disorders Substance-Related Disorders Syncope, Vasovagal Tourette Syndrome Amphetamine-Related Disorders Cocaine-Related Disorders Orthostatic Intolerance Tobacco Use Disorder

ATC Classification

N06BA09
atomoxetine
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Activity Summary

IC50 43 meas. best 8.52
Ki 12 meas. best 9.15
Kd 3 meas. best 8.69

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Norepinephrine transporter
CHEMBL304
Ki 9.15 8.725 0.7 2
Sodium-dependent noradrenaline transporter
CHEMBL222
Kd 8.69 8.69 2.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
IC50 8.52 8.3883 3.0 12
Transporter
CHEMBL6184
Ki 8.4 8.4 4.0 1
Rattus norvegicus
CHEMBL376
Ki 8.4 6.64 4.0 3
Rattus norvegicus
CHEMBL376
IC50 8.4 7.11 4.0 2
Sodium-dependent serotonin transporter
CHEMBL228
Kd 8.05 8.05 8.9 1
Sodium-dependent serotonin transporter
CHEMBL313
Ki 7.37 6.7667 43.0 3
Sodium-dependent serotonin transporter
CHEMBL228
IC50 7.32 6.912 48.0 10
Sodium-dependent dopamine transporter
CHEMBL338
Ki 6.15 5.9467 708.0 3
Sodium-dependent dopamine transporter
CHEMBL238
Kd 5.97 5.97 1080.0 1
Plasmodium falciparum
CHEMBL364
IC50 5.8 5.25 1584.9 4
Cytochrome P450 2D6
CHEMBL289
IC50 5.7 5.7 2000.0 2
Sodium-dependent dopamine transporter
CHEMBL338
IC50 5.7 5.7 2000.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 5.68 5.68 2100.0 1
Sodium-dependent dopamine transporter
CHEMBL238
IC50 5.52 5.5157 3000.0 7
Unchecked
CHEMBL612545
IC50 5.38 5.37 4186.0 2
Krueppel-like factor 10
CHEMBL3407312
IC50 4.0 4.0 100000.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 910.0 ng.hr.mL-1 Rattus norvegicus
CL 14.3 mL.min-1.kg-1 Homo sapiens
CL 50.0 mL.min-1.kg-1 Homo sapiens
CL 14.3 mL.min-1.kg-1 Homo sapiens
CL - - Rattus norvegicus
CL 36.4 mL.min-1.kg-1 Rattus norvegicus
CL 9.3 mL.min-1.kg-1 Homo sapiens
CL 9.0 mL.min-1.kg-1 Homo sapiens
CL 9.3 mL.min-1.kg-1 Homo sapiens
CL 9.3 mL.min-1.kg-1 Homo sapiens
Cmax 665.73 nM Rattus norvegicus
F 63.0 % Homo sapiens
F 85.0 % Homo sapiens
F 1.5 % Rattus norvegicus
Fu 0.02 - Homo sapiens
Fu 0.02 - Homo sapiens
Fu 0.02 - Homo sapiens
MRT 1.5 hr Homo sapiens
T1/2 8.0 hr Homo sapiens
T1/2 3.0 hr Homo sapiens
T1/2 2.8 hr Rattus norvegicus
T1/2 5.2 hr Homo sapiens
Tmax 2.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Norepinephrine transporter Ki = 0.7 nM 9.15 Inhibition of [3H]- NE reuptake into rat hippocampal synaptosomes 9871604
Sodium-dependent noradrenaline transporter Kd = 2.03 nM 8.69 Equilibrium dissociation constant (KD) for Competitive binding between [3H]- nis... 9871604
Sodium-dependent noradrenaline transporter IC50 = 3.0 nM 8.52 Inhibition of norepinephrine uptake at human NET expressed in MDCK cells 18771916
Sodium-dependent noradrenaline transporter IC50 = 3.0 nM 8.52 Inhibition of norepinephrine uptake at human NET expressed in MDCK-Net6 cells 19329313
Sodium-dependent noradrenaline transporter IC50 = 3.0 nM 8.52 Inhibition of norepinephrine uptake at human NET expressed in MDCK-Net6 cells 20153188
Sodium-dependent noradrenaline transporter IC50 = 3.0 nM 8.52 Inhibition of norepinephrine uptake at human NET expressed in MDCK-Net6 cells 18951020
Sodium-dependent noradrenaline transporter IC50 = 3.1 nM 8.51 Inhibition of [3H]norepinephrine uptake at human NET expressed in MDCK-Net6 cell... 19722525
Transporter Ki = 4.0 nM 8.4 Displacement of [3H]nisoxetine from Sprague-dawley rat NET by liquid scintillati... 19038547
Rattus norvegicus Ki = 4.0 nM 8.4 Inhibition of norepinephrine uptake into rat synaptosomes 14643350
Rattus norvegicus IC50 = 4.0 nM 8.4 In vitro inhibition of norepinephrine (NE) uptake in crude rat brain synaptosome... 3257267
Sodium-dependent noradrenaline transporter IC50 = 5.0 nM 8.3 Inhibition of norepinephrine uptake at human NET expressed in HEK cells 18667309
Sodium-dependent noradrenaline transporter IC50 = 5.0 nM 8.3 Inhibition of norepinephrine uptake at human NET expressed in HEK293 cells 18672364
Sodium-dependent noradrenaline transporter IC50 = 5.0 nM 8.3 Inhibition of norepinephrine uptake at human NET in human HEK293 cells 18550369
Sodium-dependent noradrenaline transporter IC50 = 5.0 nM 8.3 Inhibition of norepinephrine uptake at human NET transfected in HEK cells 18954981
Norepinephrine transporter Ki = 5.0 nM 8.3 Ability to inhibit reuptake of norepinephrine ([3H]NE) at norepinephrine transpo... 14505672
Sodium-dependent noradrenaline transporter IC50 = 5.1 nM 8.29 Inhibition of human NET 18445525
Sodium-dependent noradrenaline transporter IC50 = 5.1 nM 8.29 Inhibition of human NET 18207394
Sodium-dependent noradrenaline transporter IC50 = 5.1 nM 8.29 Displacement of Levo[ring-2,5,6-3H]norepinephrine from human cloned NET expresse... 18954038
Sodium-dependent serotonin transporter Kd = 8.9 nM 8.05 Equilibrium dissociation constant (KD) for Competitive binding between [3H]- imi... 9871604
Sodium-dependent serotonin transporter Ki = 43.0 nM 7.37 Inhibition of [3H]5-HT reuptake into rat frontal cortex synaptosomes 9871604

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
20070106 10.1021/jm901371v Homo sapiens 8
18954038 10.1021/jm8009537 Rattus norvegicus 6
19734910 10.1038/nchembio.215 Plasmodium falciparum 4
18426954 10.1124/dmd.108.020479 ADMET 4
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
18445525 10.1016/j.bmcl.2008.04.025 No relevant target 3
18954038 10.1021/jm8009537 No relevant target 3
15225731 10.1016/j.bmcl.2004.05.018 Unchecked 3
14643350 10.1016/j.bmcl.2003.08.079 Rattus norvegicus 3
9871604 10.1016/s0960-894x(98)00062-6 Sodium-dependent serotonin transporter 2
3257267 10.1021/jm00396a030 Rattus norvegicus 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
25581017 10.1021/jm5018187 Krueppel-like factor 10 2
19445515 10.1021/jm900403j Homo sapiens 2
18954038 10.1021/jm8009537 Caco-2 2
14971904 10.1021/jm030408h ADMET 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
9871604 10.1016/s0960-894x(98)00062-6 Sodium-dependent dopamine transporter 2
18445525 10.1016/j.bmcl.2008.04.025 Homo sapiens 2

Data from ChEMBL 36 via Core Engine