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Compound Detail

CHEMBL259209

MILNACIPRAN
💊 Approved Drug
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💊 Approved Drug
CCN(CC)C(=O)C1(c2ccccc2)CC1CN
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL259209
Name MILNACIPRAN
Phase Approved
Structure Type MOL
InChI Key GJJFMKBJSRMPLA-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Impulsor Milnacipran Milnacipran pierre fabre medicament
8
Targets
30
Activities
2
Assay Types
19
PK Parameters
20
Publications
3
Known Names
7
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 2009
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Year 2007

Extended Properties

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

Indications

Depressive Disorder Depressive Disorder Fibromyalgia Peripheral Nervous System Diseases Irritable Bowel Syndrome Low Back Pain Neuralgia

ATC Classification

N06AX17
milnacipran
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Activity Summary

IC50 25 meas. best 9.1
Ki 5 meas. best 8.19

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent noradrenaline transporter
CHEMBL222
 IC50 9.1 6.9057 0.8 7
Sodium-dependent serotonin transporter
CHEMBL228
 Ki 8.19 7.925 6.5 2
Unchecked
CHEMBL612545
 Ki 7.8 7.8 16.0 1
Sodium-dependent serotonin transporter
CHEMBL228
 IC50 7.66 6.5789 22.0 9
Sodium-dependent serotonin transporter
CHEMBL313
 Ki 7.57 7.57 27.0 1
Transporter
CHEMBL6184
 IC50 7.52 7.26 30.0 2
Sodium-dependent serotonin transporter
CHEMBL313
 IC50 7.33 7.01 47.0 2
Sodium-dependent noradrenaline transporter
CHEMBL222
 Ki 7.07 7.07 85.0 1
Sodium-dependent dopamine transporter
CHEMBL238
 IC50 5.21 5.21 6100.0 3
Cytochrome P450 2D6
CHEMBL289
 IC50 4.5 4.5 31622.8 1
Sodium-dependent dopamine transporter
CHEMBL338
 IC50 4.43 4.43 37000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 2342.6 ng.hr.mL-1 Homo sapiens
AUC 2766.5 ng.hr.mL-1 Homo sapiens
CL 2.6 mL.min-1.kg-1 Homo sapiens
CL 18.0 mL.min-1.kg-1 Rattus norvegicus
CL 3.1 mL.min-1.kg-1 Homo sapiens
CL 24.0 mL.min-1.kg-1 Rattus norvegicus
CL 150.6 mL.min-1.g-1 Homo sapiens
Cmax 0.2396 ug.mL-1 Homo sapiens
F 84.0 % Homo sapiens
F 85.0 % Homo sapiens
F 85.0 % Homo sapiens
Fu 0.828 - Not specified
Fu 0.777 - Not specified
Fu 0.837 - Not specified
Fu 0.809 - Not specified
T1/2 8.0 hr Homo sapiens
T1/2 8.9 hr Homo sapiens
Tmax 2.0 hr Homo sapiens
Tmax 3.5 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent noradrenaline transporter IC50 = 0.7943 nM 9.1 Inhibition of human recombinant NET expressed in HEK293 cells assessed as inhibi... 23347683
Sodium-dependent serotonin transporter Ki = 6.5 nM 8.19 Displacement of [3H]citalopram from human SERT transfected in HEK293 cells after... 24900709
Unchecked Ki = 16.0 nM 7.8 Displacement of [3H]-nisoxetine from Sprague-Dawley rat brain NET after 1 hr 24900709
Sodium-dependent serotonin transporter IC50 = 22.0 nM 7.66 Displacement of [3H]citalopram from human SERT transfected in HEK293 cells after... 24900709
Sodium-dependent serotonin transporter Ki = 22.0 nM 7.66 Displacement of [3H]citalopram from human SERT expressed in HEK293 cell membrane... 27865645
Sodium-dependent serotonin transporter Ki = 27.0 nM 7.57 Displacement of [3H]-citalopram from Sprague-Dawley rat brain SERT after 1 hr 24900709
Transporter IC50 = 30.0 nM 7.52 Displacement of Levo[ring-2,5,6-3H]norepinephrine from rat synaptosomal NET expr... 18954038
Sodium-dependent noradrenaline transporter IC50 = 41.0 nM 7.39 Displacement of [3H]Nisoxetine from human NET transfected in HEK293 cells after ... 24900709
Sodium-dependent serotonin transporter IC50 = 47.0 nM 7.33 Displacement of [alpha,beta-3H(N)]-5-hydroxytryptamine from rat synaptosomal SER... 18954038
Sodium-dependent serotonin transporter IC50 = 50.12 nM 7.3 Inhibition of human recombinant SERT expressed in HEK293 cells assessed as inhib... 23347683
Sodium-dependent serotonin transporter IC50 = 64.0 nM 7.19 Inhibition of human SERT expressed in CHO cell membranes assessed as reduction i... 27865645
Sodium-dependent noradrenaline transporter IC50 = 77.0 nM 7.11 Inhibition of human NET 18207394
Sodium-dependent noradrenaline transporter IC50 = 77.0 nM 7.11 Inhibition of human NET 18445525
Sodium-dependent noradrenaline transporter IC50 = 77.0 nM 7.11 Displacement of Levo[ring-2,5,6-3H]norepinephrine from human cloned NET expresse... 18954038
Sodium-dependent noradrenaline transporter Ki = 85.0 nM 7.07 Displacement of [3H]Nisoxetine from human NET transfected in HEK293 cells after ... 24900709
Transporter IC50 = 100.0 nM 7.0 Inhibition of radiolabeled noradrenaline uptake from rat brain NET 18954038
Sodium-dependent serotonin transporter IC50 = 100.0 nM 7.0 Inhibitory concentration against serotonin transporter 16220969
Sodium-dependent serotonin transporter IC50 = 203.0 nM 6.69 Inhibition of radiolabeled serotonin uptake from rat brain SERT 18954038
Sodium-dependent serotonin transporter IC50 = 420.0 nM 6.38 Displacement of [alpha,beta-3H(N)]-5-hydroxytryptamine from human cloned SERT ex... 18954038
Sodium-dependent serotonin transporter IC50 = 420.0 nM 6.38 Inhibition of human SERT 18445525

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 71
22653299 10.1124/dmd.112.045120 ADMET 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
22653299 10.1124/dmd.112.045120 Plasma 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
22653299 10.1124/dmd.112.045120 Homo sapiens 7
21098647 10.1124/dmd.110.036988 ADMET 5
24900709 10.1021/ml400049p Unchecked 4
23347683 10.1016/j.bmcl.2012.12.061 Rattus norvegicus 4
27865645 10.1016/j.bmc.2016.10.034 Sodium-dependent serotonin transporter 3
24900709 10.1021/ml400049p Sodium-dependent serotonin transporter 3
18954038 10.1021/jm8009537 Sodium-dependent serotonin transporter 3
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
33606526 10.1021/acs.jmedchem.0c02047 POU domain, class 2, transcription factor 1 3
18954038 10.1021/jm8009537 No relevant target 3
18468895 10.1016/j.bmcl.2008.04.045 Caco-2 2
18468895 10.1016/j.bmcl.2008.04.045 Liver microsomes 2
23347683 10.1016/j.bmcl.2012.12.061 Unchecked 2
18445525 10.1016/j.bmcl.2008.04.025 Sodium-dependent serotonin transporter 2

Data from ChEMBL 36 via Core Engine