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Compound Detail

CHEMBL180101

ESREBOXETINE
🧪 Phase III
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🧪 Phase III
CCOc1ccccc1O[C@@H](c1ccccc1)[C@@H]1CNCCO1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL180101
Name ESREBOXETINE
Phase Phase III
Structure Type MOL
InChI Key CBQGYUDMJHNJBX-OALUTQOASA-N

Known Names

(S,S)-RBX (s,s)-reboxetine Esreboxetina Esreboxetine REBOXETINE S,s-reboxetine Ss-rbx
7
Targets
12
Activities
2
Assay Types
0
PK Parameters
20
Publications
7
Known Names
4
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
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -oxetine
USAN Year 2007

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

Fibromyalgia Diabetic Neuropathies Pain Urinary Incontinence

Activity Summary

IC50 7 meas. best 8.7
Ki 5 meas. best 9.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent noradrenaline transporter
CHEMBL222
 Ki 9.52 9.25 0.3 2
Unchecked
CHEMBL612545
 Ki 8.72 8.72 1.9 1
Sodium-dependent noradrenaline transporter
CHEMBL222
 IC50 8.7 8.5767 2.0 3
Transporter
CHEMBL6184
 IC50 8.51 8.51 3.1 1
Sodium-dependent serotonin transporter
CHEMBL228
 Ki 6.18 6.18 661.0 1
Sodium-dependent serotonin transporter
CHEMBL228
 IC50 5.5 5.5 3162.3 1
Cytochrome P450 2D6
CHEMBL289
 IC50 5.5 5.5 3162.3 1
Sodium-dependent serotonin transporter
CHEMBL313
 IC50 5.28 5.28 5200.0 1
Sodium-dependent dopamine transporter
CHEMBL238
 Ki 4.7 4.7 19952.6 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent noradrenaline transporter Ki = 0.3 nM 9.52 Inhibition of norepinephrine reuptake at NET 19836247
Sodium-dependent noradrenaline transporter Ki = 1.04 nM 8.98 Displacement of [3H]nisoxetine from human NET receptor expressed in HEK293 cells 19067522
Unchecked Ki = 1.9 nM 8.72 Inhibitory constant determined against Norepinephrine transporter 15664840
Sodium-dependent noradrenaline transporter IC50 = 1.995 nM 8.7 Inhibition of human recombinant NET expressed in HEK293 cells assessed as inhibi... 23347683
Sodium-dependent noradrenaline transporter IC50 = 3.0 nM 8.52 Inhibition of norepinephrine uptake at human NET expressed in HEK293 cells 18672364
Transporter IC50 = 3.1 nM 8.51 Inhibition of norepinephrine uptake at NET in rat brain synaptosome 18539031
Sodium-dependent noradrenaline transporter IC50 = 3.1 nM 8.51 Inhibition of [3H]norepinephrine uptake at human NET expressed in MDCK-Net6 cell... 19722525
Sodium-dependent serotonin transporter Ki = 661.0 nM 6.18 Displacement of [3H]citalopram from human SERT receptor expressed in HEK293 cell... 19067522
Sodium-dependent serotonin transporter IC50 = 3162.28 nM 5.5 Inhibition of human recombinant SERT expressed in HEK293 cells assessed as inhib... 23347683
Cytochrome P450 2D6 IC50 = 3162.28 nM 5.5 Inhibition of human recombinant CYP2D6 by luminescence assay 23347683
Sodium-dependent serotonin transporter IC50 = 5200.0 nM 5.28 Inhibition of serotonin uptake at SERT in rat brain synaptosome 18539031
Sodium-dependent dopamine transporter Ki = 19952.62 nM 4.7 Displacement of [3H]WIN35428 from human recombinant DAT transfected in HEK293 ce... 23347683

Literature References

PubMed DOI Target Context # Activities
23347683 10.1016/j.bmcl.2012.12.061 Rattus norvegicus 4
23347683 10.1016/j.bmcl.2012.12.061 ADMET 2
23347683 10.1016/j.bmcl.2012.12.061 Liver microsomes 2
19067522 10.1021/jm800817h Unchecked 2
23347683 10.1016/j.bmcl.2012.12.061 Unchecked 2
19067522 10.1021/jm800817h Sodium-dependent noradrenaline transporter 1
19722525 10.1021/jm900888c Sodium-dependent dopamine transporter 1
19722525 10.1021/jm900888c Sodium-dependent serotonin transporter 1
19144451 10.1016/j.ejmech.2008.12.003 5-hydroxytryptamine receptor 3A 1
18539031 10.1016/j.bmcl.2008.05.077 Mus musculus 1
18539031 10.1016/j.bmcl.2008.05.077 Sodium-dependent dopamine transporter 1
18539031 10.1016/j.bmcl.2008.05.077 Transporter 1
18539031 10.1016/j.bmcl.2008.05.077 Sodium-dependent serotonin transporter 1
15664840 10.1016/j.bmcl.2004.11.025 Unchecked 1
19067522 10.1021/jm800817h Sodium-dependent dopamine transporter 1
18672364 10.1016/j.bmcl.2008.07.049 Sodium-dependent dopamine transporter 1
18672364 10.1016/j.bmcl.2008.07.049 Sodium-dependent serotonin transporter 1
18672364 10.1016/j.bmcl.2008.07.049 Sodium-dependent noradrenaline transporter 1
26051602 10.1016/j.bmc.2015.05.017 Rattus norvegicus 1
15664840 10.1016/j.bmcl.2004.11.025 Sodium-dependent dopamine transporter 1

Data from ChEMBL 36 via Core Engine