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Compound Detail

CHEMBL305187

IFENPRODIL
🧪 Phase II
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🧪 Phase II
CC(C(O)c1ccc(O)cc1)N1CCC(Cc2ccccc2)CC1

Basic Information

ChEMBL ID CHEMBL305187
Name IFENPRODIL
Phase Phase II
Structure Type MOL
InChI Key UYNVMODNBIQBMV-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Ifenprodil NP-120 RC 61-91 RC-61-91
23
Targets
103
Activities
3
Assay Types
4
PK Parameters
20
Publications
4
Known Names
4
Indications

Molecular Properties

325.4
MW (Da)
3.77
ALogP
3
HBA
2
HBD
43.7
PSA (Ų)
0.88
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Racemic

Flags

Natural Product
USAN Stem -dil

Extended Properties

Molecular Formula C21H27NO2
MW 325.45
Aromatic Rings 2
Heavy Atoms 24
NP-Likeness 0.06

Indications

Cardiovascular Diseases Idiopathic Pulmonary Fibrosis Multiple Sclerosis, Relapsing-Remitting Severe Acute Respiratory Syndrome

ATC Classification

C04AX28
ifenprodil
Level 1: CARDIOVASCULAR SYSTEM
Level 2: PERIPHERAL VASODILATORS

Activity Summary

Ki 65 meas. best 8.99
IC50 35 meas. best 9.14
EC50 3 meas. best 6.69

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
SH-SY5Y
CHEMBL614910
IC50 9.14 9.14 0.7 1
Translocator protein
CHEMBL4552
IC50 9.14 9.14 0.7 1
Sigma non-opioid intracellular receptor 1
CHEMBL4153
Ki 8.99 7.1288 1.0 17
Sigma non-opioid intracellular receptor 1
CHEMBL3602
Ki 8.7 8.505 2.0 2
Unchecked
CHEMBL612545
Ki 8.64 7.491 2.3 10
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase
CHEMBL5525
Ki 8.57 8.0333 2.7 6
Sigma non-opioid intracellular receptor 1
CHEMBL287
IC50 8.41 8.41 3.9 1
Glutamate receptor ionotropic, NMDA 2B
CHEMBL1904
Ki 8.24 8.0267 5.8 9
Glutamate NMDA receptor; GRIN1/GRIN2B
CHEMBL1907603
Ki 8.0 8.0 10.0 2
Glutamate receptor ionotropic, NMDA 2B
CHEMBL311
Ki 7.96 7.74 11.0 5
Glutamate receptor ionotropic, NMDA 2B
CHEMBL1904
IC50 7.88 7.118 13.3 5
Glutamate receptor ionotropic, NMDA 2B
CHEMBL311
IC50 7.7 7.605 20.0 4
PC-3
CHEMBL390
Ki 7.59 7.59 25.8 1
Glutamate NMDA receptor; GRIN1/GRIN2B
CHEMBL1907603
IC50 7.18 6.7771 66.0 7
Glutamate NMDA receptor; Grin1/Grin2b
CHEMBL2096666
IC50 7.14 7.14 73.0 1
Sigma intracellular receptor 2
CHEMBL4105864
Ki 7.01 7.01 98.0 12
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 7.0 7.0 100.0 1
Adrenergic receptor alpha-1
CHEMBL1907610
IC50 7.0 6.98 100.0 2
Glutamate NMDA receptor
CHEMBL1907608
Ki 6.84 6.84 143.2 1
NON-PROTEIN TARGET
CHEMBL3879801
EC50 6.69 6.2567 206.0 3
5-hydroxytryptamine receptor 1A
CHEMBL3737
IC50 6.62 6.62 238.0 1
Unchecked
CHEMBL612545
IC50 6.6 6.3533 250.0 3
Glutamate NMDA receptor
CHEMBL1907608
IC50 6.58 6.58 263.0 1
5-hydroxytryptamine receptor 2A
CHEMBL3446
IC50 6.21 6.21 610.0 1
Histamine H1 receptor
CHEMBL231
IC50 6.0 6.0 1000.0 1
NON-PROTEIN TARGET
CHEMBL3879801
IC50 5.46 5.46 3500.0 1
Glutamate receptor ionotropic, NMDA 2C
CHEMBL4109
IC50 4.54 4.54 29100.0 1
Glutamate receptor ionotropic, NMDA 2A
CHEMBL1972
IC50 4.4 4.4 39500.0 1
Glutamate receptor ionotropic, NMDA 2D
CHEMBL2591
IC50 4.12 4.12 75900.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.08333 hr Mus musculus
T1/2 0.01667 hr Rattus norvegicus
T1/2 0.08333 hr Homo sapiens
T1/2 4.818 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
SH-SY5Y IC50 = 0.73 nM 9.14 Neuroprotective activity in human SH-SY5Y cells assessed as protection against N... 23033965
Translocator protein IC50 = 0.73 nM 9.14 Inhibition of rat TSPO 38295689
Sigma non-opioid intracellular receptor 1 Ki = 1.02 nM 8.99 Displacement of [3H]-(+)-pentazocine from guinea pig brain sigma1 receptor after... 24290063
Sigma non-opioid intracellular receptor 1 Ki = 2.0 nM 8.7 Displacement of [3H](+)-pentazocine from sigma1 receptor in rat liver membrane b... 19673530
Sigma non-opioid intracellular receptor 1 Ki = 2.0 nM 8.7 Displacement of [3H](+)-pentazocine from sigma 1 receptor in guinea pig brain me... 19053780
Unchecked Ki = 2.3 nM 8.64 Displacement of [3H]-DTG from sigma 2-type opioid receptor in rat liver membrane... 19053780
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase Ki = 2.71 nM 8.57 Inhibition of [3H]-emopamil binding to Sterol delta 8-delta 7 isomerase in guine... 12747784
Sigma non-opioid intracellular receptor 1 IC50 = 3.9 nM 8.41 Compound was tested for the binding affinity against sigma receptor by using [3H... 1681106
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase Ki = 4.7 nM 8.33 Displacement of [3H](+/-)-emopamil from delta8-delta7 sterol isomerase (SI) site... 16366605
Sigma non-opioid intracellular receptor 1 Ki = 4.9 nM 8.31 Inhibition of [3H]- ifenprodil binding against Sigma opioid receptor type 2 from... 10602703
Glutamate receptor ionotropic, NMDA 2B Ki = 5.8 nM 8.24 Displacement of [3H]ifenprodil from human GluN2B expressed in mouse L-M(TK-) cel... 37580890
Glutamate receptor ionotropic, NMDA 2B Ki = 10.0 nM 8.0 Displacement of [3H]ifenprodil from human GluN2B expressed in mouse L(tk-) cells... 25458498
Glutamate receptor ionotropic, NMDA 2B Ki = 10.0 nM 8.0 Displacement of [3H]ifenprodil from human GluN2B expressed in mouse L(tk-) cell ... 32070917
Glutamate receptor ionotropic, NMDA 2B Ki = 10.07 nM 8.0 Displacement of [3H]ifenprodil from recombinant human GluN2B NMDA receptor (unkn... 36084304
Glutamate receptor ionotropic, NMDA 2B Ki = 10.0 nM 8.0 Displacement of [3H]ifenprodil from GluN2B (unknown origin) expressed in mouse L... 32435366
Glutamate receptor ionotropic, NMDA 2B Ki = 10.0 nM 8.0 Displacement of [3H]ifenprodil from human recombinant GluN2B expressed in mouse ... 31843460
Glutamate receptor ionotropic, NMDA 2B Ki = 10.0 nM 8.0 Displacement of [3H]-ifenprodil from GluN2B (unknown origin) expressed in rat L(... 30881618
Unchecked Ki = 10.0 nM 8.0 Displacement of [3H]ifenprodil from GluN1A/GluN2B (unknown origin) expressed in ... 31648876
Glutamate NMDA receptor; GRIN1/GRIN2B Ki = 10.0 nM 8.0 Displacement of [3H]-ifenprodil from GluN1a/GluN2B (unknown origin) expressed in... 30103189
Unchecked Ki = 10.0 nM 8.0 Displacement of [3H]ifenprodil from recombinant human GluN1A/GluN2B receptor exp... 28704758

Literature References

PubMed DOI Target Context # Activities
38413367 10.1021/acs.jmedchem.3c01524 Rattus norvegicus 11
37037139 10.1016/j.ejmech.2023.115318 ADMET 6
28704758 10.1016/j.ejmech.2017.06.068 Unchecked 5
38413367 10.1021/acs.jmedchem.3c01524 Unchecked 4
17417631 10.1038/nchembio873 NON-PROTEIN TARGET 4
36934527 10.1016/j.bmc.2023.117236 PC-12 4
34547896 10.1021/acs.jmedchem.1c00823 Transthyretin 4
34710748 10.1016/j.ejmech.2021.113876 Unchecked 3
19053780 10.1021/jm800965b Unchecked 3
20692832 10.1016/j.bmcl.2010.07.043 Glutamate NMDA receptor; GRIN1/GRIN2B 3
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
37037139 10.1016/j.ejmech.2023.115318 SH-SY5Y 3
36870623 10.1016/j.bmcl.2023.129213 SH-SY5Y 3
23458846 10.1021/jm3015926 Unchecked 3
24411196 10.1016/j.bmc.2013.12.040 Glutamate receptor ionotropic, NMDA 2B 3
23140383 10.1021/jm301508d Glutamate receptor ionotropic, NMDA 2B 3
21453995 10.1016/j.ejmech.2011.03.013 Glutamate NMDA receptor; GRIN1/GRIN2B 3
17417631 10.1038/nchembio873 Unchecked 3
30108812 10.1039/C6MD00621C Unchecked 2
30223122 10.1016/j.ejmech.2018.09.010 Unchecked 2

Data from ChEMBL 36 via Core Engine