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Compound Detail

CHEMBL99946

LEVOMILNACIPRAN
💊 Approved Drug
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💊 Approved Drug
CCN(CC)C(=O)[C@@]1(c2ccccc2)C[C@H]1CN
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL99946
Name LEVOMILNACIPRAN
Phase Approved
Structure Type MOL
InChI Key GJJFMKBJSRMPLA-DZGCQCFKSA-N
Therapeutic ✓ Yes

Known Names

(1s,2r)-milnacipran F 2695 F-2695 F2695 Levomilnacipran Milnacipran, (1s,2r)-
5
Targets
15
Activities
2
Assay Types
7
PK Parameters
20
Publications
6
Known Names
2
Indications

Molecular Properties

246.3
MW (Da)
1.77
ALogP
2
HBA
1
HBD
46.3
PSA (Ų)
0.86
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2013
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Year 2010

Extended Properties

Molecular Formula C15H22N2O
MW 246.35
Aromatic Rings 1
Heavy Atoms 18
NP-Likeness -0.10

Indications

Depressive Disorder Tobacco Use Disorder

ATC Classification

N06AX28
levomilnacipran
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Activity Summary

IC50 13 meas. best 7.98
Ki 2 meas. best 8.07

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent serotonin transporter
CHEMBL313
 Ki 8.07 8.07 8.5 2
Sodium-dependent noradrenaline transporter
CHEMBL222
 IC50 7.98 7.5933 10.5 3
Sodium-dependent serotonin transporter
CHEMBL228
 IC50 6.5 5.9067 320.0 3
Sodium-dependent dopamine transporter
CHEMBL238
 IC50 5.5 5.5 3200.0 3
Glutamate NMDA receptor
CHEMBL1907608
 IC50 5.2 5.2 6300.0 4

Pharmacokinetic Data

Parameter Value Units Species
AUC 566.0 ng.hr.mL-1 Rattus norvegicus
CL 5.0 mL.min-1.kg-1 Homo sapiens
CL 5.0 mL.min-1.kg-1 Homo sapiens
CL 24.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 941.75 nM Rattus norvegicus
T1/2 12.0 hr Rattus norvegicus
Tmax 0.3 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent serotonin transporter Ki = 8.5 nM 8.07 Inhibition of [3H]-paroxetine binding on serotonin transporter of rat cerebral c... 8941398
Sodium-dependent serotonin transporter Ki = 8.5 nM 8.07 Inhibition of Serotonin transporter in cerebral cortical synaptic membrane of ra... 9719604
Sodium-dependent noradrenaline transporter IC50 = 10.5 nM 7.98 Inhibition of NET (unknown origin) 38360418
Sodium-dependent noradrenaline transporter IC50 = 40.0 nM 7.4 Inhibition of human NET 18445525
Sodium-dependent noradrenaline transporter IC50 = 40.0 nM 7.4 Inhibition of norepinephrine uptake at human NET expressed in HEK293 cells 18468895
Sodium-dependent serotonin transporter IC50 = 320.0 nM 6.5 Inhibition of human SERT 18445525
Sodium-dependent serotonin transporter IC50 = 320.0 nM 6.5 Inhibition of serotonin uptake at human SERT expressed in HEK293 cells 18468895
Sodium-dependent dopamine transporter IC50 = 3200.0 nM 5.5 Inhibition of human DAT 18445525
Sodium-dependent dopamine transporter IC50 = 3200.0 nM 5.5 Inhibition of dopamine uptake at human DAT expressed in HEK293 cells 18468895
Sodium-dependent dopamine transporter IC50 = 3200.0 nM 5.5 Inhibition of DAT (unknown origin) 38360418
Glutamate NMDA receptor IC50 = 6300.0 nM 5.2 Binding affinity for N-methyl-D-aspartate glutamate receptor of cerebral cortica... 14640541
Glutamate NMDA receptor IC50 = 6300.0 nM 5.2 Inhibition of [3H]-MK-801 binding to NMDA receptor from rat cerebral cortical sy... 8941398
Glutamate NMDA receptor IC50 = 6300.0 nM 5.2 Inhibition of [3H]MK-801 binding to N-methyl-D-aspartate glutamate receptor of r... 9719604
Glutamate NMDA receptor IC50 = 6300.0 nM 5.2 Inhibition of [3H]MK-801 binding to NMDA receptor of rat cerebral cortical synap... 7636857
Sodium-dependent serotonin transporter IC50 = 19000.0 nM 4.72 Inhibition of SERT (unknown origin) 38360418

Literature References

PubMed DOI Target Context # Activities
18468895 10.1016/j.bmcl.2008.04.045 No relevant target 3
18468895 10.1016/j.bmcl.2008.04.045 Rattus norvegicus 3
18468895 10.1016/j.bmcl.2008.04.045 Caco-2 2
18468895 10.1016/j.bmcl.2008.04.045 Liver microsomes 2
18468895 10.1016/j.bmcl.2008.04.045 Brain 2
18468895 10.1016/j.bmcl.2008.04.045 Nucleic Acid 2
7636857 10.1021/jm00015a019 Mus musculus 2
38360418 10.1016/j.bmcl.2024.129654 Mus musculus 2
18445525 10.1016/j.bmcl.2008.04.025 Caco-2 2
18445525 10.1016/j.bmcl.2008.04.025 No relevant target 2
18445525 10.1016/j.bmcl.2008.04.025 Sodium-dependent serotonin transporter 1
18445525 10.1016/j.bmcl.2008.04.025 Liver microsomes 1
18445525 10.1016/j.bmcl.2008.04.025 Sodium-dependent dopamine transporter 1
38360418 10.1016/j.bmcl.2024.129654 Sodium-dependent dopamine transporter 1
7636857 10.1021/jm00015a019 Glutamate NMDA receptor 1
9719604 10.1021/jm980238m Sodium-dependent serotonin transporter 1
9719604 10.1021/jm980238m Glutamate NMDA receptor 1
8941398 10.1021/jm960495w Unchecked 1
8941398 10.1021/jm960495w Sodium-dependent serotonin transporter 1
8941398 10.1021/jm960495w Glutamate receptor ionotropic, NMDA 2C 1

Data from ChEMBL 36 via Core Engine