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Compound Detail

CHEMBL19449

IBUDILAST
💊 Approved Drug
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💊 Approved Drug
CC(C)C(=O)c1c(C(C)C)nn2ccccc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL19449
Name IBUDILAST
Phase Approved
Structure Type MOL
InChI Key ZJVFLBOZORBYFE-UHFFFAOYSA-N

Known Names

AV-411 AV411 Ibudilast Ketas MN-166
9
Targets
25
Activities
4
Assay Types
0
PK Parameters
20
Publications
5
Known Names
14
Indications
4
Mechanisms

Molecular Properties

230.3
MW (Da)
3.30
ALogP
3
HBA
0
HBD
34.4
PSA (Ų)
0.76
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1989
Availability Unknown
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -ast; -dil-

Extended Properties

Molecular Formula C14H18N2O
MW 230.31
Aromatic Rings 2
Heavy Atoms 17
NP-Likeness -0.71

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Phosphodiesterase 4 inhibitor INHIBITOR Phosphodiesterase 4 ✓ ✓
Phosphodiesterase 3A inhibitor INHIBITOR cGMP-inhibited 3',5'-cyclic phosphodiesterase 3A ✓ ✓
Phosphodiesterase 10A inhibitor INHIBITOR cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A ✓ ✓
Phosphodiesterase 5A inhibitor INHIBITOR cGMP-specific 3',5'-cyclic phosphodiesterase ✓ ✓

Indications

Lung Diseases, Obstructive Spinal Cord Diseases Alcoholism Amphetamine-Related Disorders Amyotrophic Lateral Sclerosis Multiple Sclerosis, Chronic Progressive Opioid-Related Disorders Pneumonia, Viral Post-Acute COVID-19 Syndrome Diabetic Neuropathies Glioblastoma Migraine Disorders Pain Substance-Related Disorders

ATC Classification

R03DC04
ibudilast
Level 1: RESPIRATORY SYSTEM
Level 2: DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES

Activity Summary

IC50 22 meas. best 7.27
EC50 1 meas. best 6.05
Kd 1 meas. best 5.85
Ki 1 meas. best 4.51

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
3',5'-cyclic-AMP phosphodiesterase 4A
CHEMBL254
 IC50 7.27 6.925 54.0 4
3',5'-cyclic-AMP phosphodiesterase 4B
CHEMBL275
 IC50 7.19 6.7175 65.0 4
3',5'-cyclic-AMP phosphodiesterase 4D
CHEMBL288
 IC50 6.78 6.78 166.0 3
3',5'-cyclic-AMP phosphodiesterase 4C
CHEMBL291
 IC50 6.62 6.62 239.0 3
3',5'-cyclic-AMP phosphodiesterase 4A
CHEMBL254
 EC50 6.05 6.05 900.0 1
Macrophage migration inhibitory factor
CHEMBL2085
 Kd 5.85 5.85 1400.0 1
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3A
CHEMBL241
 IC50 5.8 5.8 1600.0 1
Blood
CHEMBL613416
 IC50 5.6 5.405 2500.0 2
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B
CHEMBL290
 IC50 5.57 5.57 2700.0 1
cGMP-specific 3',5'-cyclic phosphodiesterase
CHEMBL1827
 IC50 5.46 5.46 3510.0 2
Macrophage migration inhibitory factor
CHEMBL2085
 Ki 4.51 4.51 30900.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
3',5'-cyclic-AMP phosphodiesterase 4A IC50 = 54.0 nM 7.27 Inhibition of human PDE4A 18686943
3',5'-cyclic-AMP phosphodiesterase 4A IC50 = 54.0 nM 7.27 Inhibition of human PDE4A expressed in insect sf9 cells using [3H]-cAMP as subst... 32255344
3',5'-cyclic-AMP phosphodiesterase 4A IC50 = 54.0 nM 7.27 Affinity Biochemical interaction: (Inhibition of radiolabelled [3H]cAMP cleavage... -
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 65.0 nM 7.19 Inhibition of human PDE4B 18686943
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 65.0 nM 7.19 Inhibition of human PDE4B expressed in insect sf9 cells using [3H]-cAMP as subst... 32255344
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 65.0 nM 7.19 Affinity Biochemical interaction: (Inhibition of radiolabelled [3H]cAMP cleavage... -
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 166.0 nM 6.78 Inhibition of human PDE4D 18686943
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 166.0 nM 6.78 Inhibition of human PDE4D expressed in insect sf9 cells using [3H]-cAMP as subst... 32255344
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 166.0 nM 6.78 Affinity Biochemical interaction: (Inhibition of radiolabelled [3H]cAMP cleavage... -
3',5'-cyclic-AMP phosphodiesterase 4C IC50 = 239.0 nM 6.62 Inhibition of human PDE4C expressed in insect sf9 cells using [3H]-cAMP as subst... 32255344
3',5'-cyclic-AMP phosphodiesterase 4C IC50 = 239.0 nM 6.62 Affinity Biochemical interaction: (Inhibition of radiolabelled [3H]cAMP cleavage... -
3',5'-cyclic-AMP phosphodiesterase 4C IC50 = 239.0 nM 6.62 Inhibition of human PDE4C 18686943
3',5'-cyclic-AMP phosphodiesterase 4A EC50 = 900.0 nM 6.05 Induction of SQSTM1-dependent intracellular redistribution of GFP-tagged PDE4A4 ... 21456625
3',5'-cyclic-AMP phosphodiesterase 4A IC50 = 1300.0 nM 5.89 Inhibition of full-length PDE4A4 using cAMP as substrate by two-step radiochemic... 21456625
Macrophage migration inhibitory factor Kd = 1400.0 nM 5.85 Binding affinity to recombinant biotinylated human MIF expressed in Escherichia ... 33062162
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3A IC50 = 1600.0 nM 5.8 Selectivity interaction (Enzymatic assay) EUB0002598a PDE3A -
Blood IC50 = 2500.0 nM 5.6 Inhibition of fMLP-induced LTB4 biosynthesis in human whole blood 18686943
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B IC50 = 2700.0 nM 5.57 Selectivity interaction (Enzymatic assay) EUB0002598a PDE3B -
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 3510.0 nM 5.46 Selectivity interaction (Enzymatic assay) EUB0002598a PDE5A -
cGMP-specific 3',5'-cyclic phosphodiesterase IC50 = 3510.0 nM 5.46 Selectivity interaction (Enzymatic assay) EUB0002598a PDE5A -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
21456625 10.1021/jm200070e 3',5'-cyclic-AMP phosphodiesterase 4A 3
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
37468498 10.1038/s41467-023-40064-9 Beta-1 adrenergic receptor 2
33062162 10.1021/acsmedchemlett.9b00351 Macrophage migration inhibitory factor 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 2
- 10.6019/CHEMBL5715260 cGMP-specific 3',5'-cyclic phosphodiesterase 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 2
37468498 10.1038/s41467-023-40064-9 Beta-2 adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 2
18686943 10.1021/jm800582j Blood 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
21530250 10.1016/j.bmcl.2011.04.021 cGMP-inhibited 3',5'-cyclic phosphodiesterase 3A 1

Data from ChEMBL 36 via Core Engine