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Compound Detail

CHEMBL14370

REBOXETINE
💊 Approved Drug
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💊 Approved Drug
CCOc1ccccc1OC(c1ccccc1)C1CNCCO1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL14370
Name REBOXETINE
Phase Approved
Structure Type MOL
InChI Key CBQGYUDMJHNJBX-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Edronax Reboxetina Reboxetine
7
Targets
26
Activities
2
Assay Types
15
PK Parameters
20
Publications
3
Known Names
12
Indications
1
Mechanisms

Molecular Properties

313.4
MW (Da)
3.19
ALogP
4
HBA
1
HBD
39.7
PSA (Ų)
0.89
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1997
Availability Unknown
Chirality Racemic

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -oxetine
USAN Year 1997

Extended Properties

Molecular Formula C19H23NO3
MW 313.40
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness -0.17

Mechanism of Action

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

Indications

Depressive Disorder Depressive Disorder Anxiety Dementia Fatigue Fibromyalgia Schizophrenia Attention Deficit Disorder with Hyperactivity Depressive Disorder, Major Diabetic Neuropathies Pain Stress Disorders, Post-Traumatic

ATC Classification

N06AX18
reboxetine
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Activity Summary

IC50 13 meas. best 8.52
Ki 13 meas. best 9.16

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Transporter
CHEMBL6184
 Ki 9.16 9.16 0.7 1
Unchecked
CHEMBL612545
 Ki 9.08 9.08 0.8 1
Sodium-dependent noradrenaline transporter
CHEMBL222
 Ki 8.96 8.52 1.1 3
Sodium-dependent noradrenaline transporter
CHEMBL222
 IC50 8.52 8.3514 3.0 7
Sodium-dependent serotonin transporter
CHEMBL228
 Ki 8.05 6.66 9.0 4
Norepinephrine transporter
CHEMBL304
 Ki 7.86 7.86 13.7 1
Sodium-dependent dopamine transporter
CHEMBL238
 Ki 7.22 7.22 60.0 1
Sodium-dependent serotonin transporter
CHEMBL228
 IC50 6.62 6.49 242.0 6
Sodium-dependent serotonin transporter
CHEMBL313
 Ki 6.3 6.3 503.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 0.82 mL.min-1.kg-1 Homo sapiens
CL 0.8 mL.min-1.kg-1 Homo sapiens
CL 0.82 mL.min-1.kg-1 Homo sapiens
CL 0.82 mL.min-1.kg-1 Homo sapiens
Fu 0.019 - Homo sapiens
Fu 0.019 - Homo sapiens
Fu 0.046 - Homo sapiens
Fu 0.074 - Macaca fascicularis
Fu 0.058 - Canis lupus familiaris
Fu 0.043 - Cavia porcellus
Fu 0.051 - Mus musculus
Fu 0.033 - Rattus norvegicus
Fu 0.042 - Rattus norvegicus
MRT 13.0 hr Homo sapiens
T1/2 10.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Transporter Ki = 0.69 nM 9.16 Displacement of [3H]-dopamine from rat cerebral cortex NET after 7 mins 24315194
Unchecked Ki = 0.826 nM 9.08 Inhibition of NET in rat cerebral cortex assessed as [3H]norepinephrine accumula... 21446715
Sodium-dependent noradrenaline transporter Ki = 1.1 nM 8.96 In vitro binding affinity against human norepinephrine transporter in human embr... 14971892
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 cells 18771916
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 = 3.2 nM 8.49 Inhibition of norepinephrine uptake at human NET expressed in MDCK-Net6 cells 20131864
Sodium-dependent noradrenaline transporter IC50 = 3.2 nM 8.49 Inhibition of [3H]norepinephrine uptake at human NET expressed in MDCK-Net6 cell... 19722525
Sodium-dependent noradrenaline transporter Ki = 5.0 nM 8.3 Inhibition of [3H]nisoxetine reuptake at human NET expressed in HEK293 cells 18387300
Sodium-dependent noradrenaline transporter Ki = 5.0 nM 8.3 Inhibition of [3H]Nisoxetine uptake in human noradrenaline transporter transfect... 18313294
Sodium-dependent serotonin transporter Ki = 9.0 nM 8.05 In vitro competitive binding versus [3H]-citalopram in murine kidney cells trans... 12620070
Sodium-dependent noradrenaline transporter IC50 = 11.0 nM 7.96 Inhibition of [3H]NA reuptake at NA transporter in HEK293 cells 16750363
Sodium-dependent noradrenaline transporter IC50 = 11.0 nM 7.96 Inhibition of [3H]NA uptake at NA transporter expressed in HEK293 cells 16750359
Norepinephrine transporter Ki = 13.7 nM 7.86 Binding affinity against norepinephrine transporter (NET) by displacement of [3H... 14640559
Sodium-dependent dopamine transporter Ki = 60.0 nM 7.22 In vitro competitive binding versus [N-methyl-3H]WIN-35428 in murine kidney cell... 12620070
Sodium-dependent serotonin transporter Ki = 129.0 nM 6.89 Inhibition of [125I]RTI-55 binding to human serotonin transporter expressed in h... 14971892
Sodium-dependent serotonin transporter IC50 = 242.0 nM 6.62 Inhibition of serotonin uptake at human SERT expressed in human JAR cells 20131864
Sodium-dependent serotonin transporter IC50 = 242.0 nM 6.62 Inhibition of serotonin uptake at human SERT expressed in JAR cells 18951020
Sodium-dependent serotonin transporter IC50 = 242.0 nM 6.62 Inhibition of serotonin uptake at human SERT expressed in human JAR cells 19329313
Sodium-dependent serotonin transporter IC50 = 242.0 nM 6.62 Inhibition of serotonin uptake at human SERT expressed in JAR cells 18771916

Literature References

PubMed DOI Target Context # Activities
20070106 10.1021/jm901371v Homo sapiens 8
21474681 10.1124/dmd.111.038778 Brain 5
18426954 10.1124/dmd.108.020479 ADMET 4
19445515 10.1021/jm900403j Homo sapiens 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 2
37468498 10.1038/s41467-023-40064-9 Androgen receptor 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
14971892 10.1021/jm030384e Sodium-dependent noradrenaline transporter 1
16750363 10.1016/j.bmcl.2006.05.049 Sodium-dependent noradrenaline transporter 1
16750363 10.1016/j.bmcl.2006.05.049 Sodium-dependent dopamine transporter 1
14640559 10.1021/jm0309349 Sodium-dependent serotonin transporter 1
14640559 10.1021/jm0309349 5-hydroxytryptamine receptor 2A 1

Data from ChEMBL 36 via Core Engine