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Compound Detail

CHEMBL273575

NOMIFENSINE
💊 Approved Drug
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💊 Approved Drug
CN1Cc2c(N)cccc2C(c2ccccc2)C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL273575
Name NOMIFENSINE
Phase Approved
Structure Type MOL
InChI Key XXPANQJNYNUNES-UHFFFAOYSA-N

Known Names

Linamiphen Nomifensin Nomifensina Nomifensine
9
Targets
64
Activities
3
Assay Types
16
PK Parameters
20
Publications
4
Known Names
1
Indications

Molecular Properties

238.3
MW (Da)
2.85
ALogP
2
HBA
1
HBD
29.3
PSA (Ų)
0.77
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1984
Availability Withdrawn
Chirality Racemic

Routes of Administration

Oral

Flags

Withdrawn Natural Product
USAN Stem -fensine
USAN Year 1975

Extended Properties

Molecular Formula C16H18N2
MW 238.33
Aromatic Rings 2
Heavy Atoms 18
NP-Likeness 0.22

Indications

Depressive Disorder

ATC Classification

N06AX04
nomifensine
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Activity Summary

IC50 36 meas. best 8.18
Ki 26 meas. best 8.42
EC50 2 meas. best 8.51

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Rattus norvegicus
CHEMBL376
 EC50 8.51 8.01 3.1 2
Sodium-dependent noradrenaline transporter
CHEMBL222
 Ki 8.42 7.822 3.8 5
Norepinephrine transporter
CHEMBL304
 Ki 8.42 8.42 3.8 2
Transporter
CHEMBL6184
 Ki 8.4 8.05 4.0 2
Norepinephrine transporter
CHEMBL304
 IC50 8.18 8.02 6.6 3
Sodium-dependent dopamine transporter
CHEMBL238
 Ki 8.0 7.3567 10.0 6
Sodium-dependent dopamine transporter
CHEMBL238
 IC50 7.82 6.8614 15.0 7
Rattus norvegicus
CHEMBL376
 IC50 7.75 6.562 18.0 10
Sodium-dependent dopamine transporter
CHEMBL338
 Ki 7.58 7.2875 26.0 4
Sodium-dependent dopamine transporter
CHEMBL338
 IC50 7.47 6.8967 34.0 9
Dopamine receptor
CHEMBL2093868
 IC50 7.32 7.32 48.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
 IC50 6.2 6.2 631.0 1
Sodium-dependent serotonin transporter
CHEMBL313
 IC50 6.08 5.81 830.0 3
Sodium-dependent serotonin transporter
CHEMBL228
 Ki 6.06 5.868 874.0 5
Sodium-dependent serotonin transporter
CHEMBL313
 Ki 6.06 6.06 874.0 2
Sodium-dependent serotonin transporter
CHEMBL228
 IC50 5.06 5.06 8709.6 1

Pharmacokinetic Data

Parameter Value Units Species
CL 22.0 mL.min-1.kg-1 Homo sapiens
CL 9.5 mL.min-1.kg-1 Homo sapiens
CL 22.0 mL.min-1.kg-1 Homo sapiens
CL 22.0 mL.min-1.kg-1 Homo sapiens
CL 37.0 mL.min-1.g-1 Homo sapiens
Fu 0.4 - Homo sapiens
Fu 0.4 - Homo sapiens
Fu 0.071 - Homo sapiens
Fu 0.068 - Macaca fascicularis
Fu 0.072 - Canis lupus familiaris
Fu 0.068 - Cavia porcellus
Fu 0.078 - Mus musculus
Fu 0.064 - Rattus norvegicus
Fu 0.066 - Rattus norvegicus
MRT 4.5 hr Homo sapiens
T1/2 6.5 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Rattus norvegicus EC50 = 3.1 nM 8.51 In vivo NET occupancy in sc dosed Long Evans rat thalamus assessed as unbound pl... 24900562
Norepinephrine transporter Ki = 3.8 nM 8.42 Inhibition of uptake of tritiated norepinephrine (NE) in rat synaptosomes 3039136
Sodium-dependent noradrenaline transporter Ki = 3.8 nM 8.42 Binding affinity to NET (unknown origin) 28731336
Norepinephrine transporter Ki = 3.8 nM 8.42 Inhibition of norepinephrine (NE) into rat brain synaptosomes 6747993
Transporter Ki = 4.0 nM 8.4 Inhibition of NET in rat synaptosomal membrane 24900562
Sodium-dependent noradrenaline transporter Ki = 5.0 nM 8.3 Inhibition of human recombinant NET expressed in HEK cells 24900562
Norepinephrine transporter IC50 = 6.6 nM 8.18 Effect on synaptosomal uptake inhibition of Noradrenaline (NA) 6134833
Norepinephrine transporter IC50 = 6.6 nM 8.18 Inhibition of noradrenaline uptake in rat synaptosomal fraction 2999402
Sodium-dependent dopamine transporter Ki = 10.0 nM 8.0 Inhibition of human recombinant DAT expressed in HEK cells 24900562
Sodium-dependent dopamine transporter IC50 = 15.0 nM 7.82 Inhibition of full-length recombinant human DAT expressed in CHOK1 cells assesse... 28958625
Rattus norvegicus IC50 = 18.0 nM 7.75 In vitro inhibition of [14C]norepinephrine uptake into rat hypothalamus 3572969
Norepinephrine transporter IC50 = 20.0 nM 7.7 Inhibition of norepinephrine uptake in synaptosomal preparation fro rat hypothal... 6492080
Transporter Ki = 20.0 nM 7.7 Inhibition of rat NET 23084899
Sodium-dependent noradrenaline transporter Ki = 21.5 nM 7.67 Inhibition of human NET 23084899
Sodium-dependent noradrenaline transporter Ki = 23.0 nM 7.64 Inhibition of human NET 23084899
Sodium-dependent dopamine transporter Ki = 23.5 nM 7.63 Displacement of [3H]WIN-from cocaine site of dopamine transporter 8496700
Sodium-dependent dopamine transporter Ki = 26.0 nM 7.58 Inhibition of DAT in rat synaptosomal membrane 24900562
Sodium-dependent dopamine transporter IC50 = 30.2 nM 7.52 Inhibition of [3H]dopamine reuptake at human DAT expressed in CHOK1 cells by sci... 21093273
Rattus norvegicus EC50 = 31.0 nM 7.51 In vivo DAT occupancy in sc dosed Long Evans rat striatum assessed as unbound pl... 24900562
Rattus norvegicus IC50 = 32.0 nM 7.5 In vitro inhibition of [14C]norepinephrine uptake into rat hypothalamus 3572969

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
3572969 10.1021/jm00388a009 Mus musculus 9
3572969 10.1021/jm00388a009 Rattus norvegicus 9
20070106 10.1021/jm901371v Homo sapiens 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
24900562 10.1021/ml300262e Rattus norvegicus 7
3806569 10.1021/jm00157a012 Mus musculus 6
1552510 10.1021/jm00084a001 Sodium-dependent dopamine transporter 6
21474681 10.1124/dmd.111.038778 Brain 5
8558500 10.1021/jm950630p Rattus norvegicus 4
18426954 10.1124/dmd.108.020479 ADMET 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
3039136 10.1021/jm00391a028 Mus musculus 3
37468498 10.1038/s41467-023-40064-9 Histamine H1 receptor 3
2563772 10.1021/jm00123a004 Mus musculus 3
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
23084899 10.1016/j.bmcl.2012.09.050 Unchecked 2
38830007 10.1021/acs.jmedchem.4c00159 Sodium-dependent dopamine transporter 2
2999402 10.1021/jm00150a012 Sodium-dependent serotonin transporter 2
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 2

Data from ChEMBL 36 via Core Engine