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Compound Detail

CHEMBL514800

APREMILAST
💊 Approved Drug
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💊 Approved Drug
CCOc1cc([C@@H](CS(C)(=O)=O)N2C(=O)c3cccc(NC(C)=O)c3C2=O)ccc1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL514800
Name APREMILAST
Phase Approved
Structure Type MOL
InChI Key IMOZEMNVLZVGJZ-QGZVFWFLSA-N
Therapeutic ✓ Yes

Known Names

Apremilast Apremilast accord CC-10004 CC10004 Otezla
6
Targets
24
Activities
1
Assay Types
9
PK Parameters
20
Publications
5
Known Names
20
Indications
1
Mechanisms

Molecular Properties

460.5
MW (Da)
2.43
ALogP
7
HBA
1
HBD
119.1
PSA (Ų)
0.60
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2014
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product First in Class
USAN Stem -ast
USAN Year 2005

Extended Properties

Molecular Formula C22H24N2O7S
MW 460.51
Aromatic Rings 2
Heavy Atoms 32
NP-Likeness -1.10

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Phosphodiesterase 4 inhibitor INHIBITOR Phosphodiesterase 4 ✓ ✓

Indications

Arthritis, Psoriatic Behcet Syndrome Immune System Diseases Oral Ulcer Psoriasis Psoriasis Psoriasis Influenza, Human Pneumonia Severe Acute Respiratory Syndrome Spondylitis, Ankylosing Acne Vulgaris Alcoholism Arthritis, Rheumatoid Colitis, Ulcerative Dermatitis Dermatitis, Allergic Contact Dermatitis, Atopic Dermatomyositis Eczema

ATC Classification

L04AA32
apremilast
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: IMMUNOSUPPRESSANTS

Activity Summary

IC50 24 meas. best 8.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
3',5'-cyclic-AMP phosphodiesterase 4D
CHEMBL288
 IC50 8.0 7.1813 10.0 8
3',5'-cyclic-AMP phosphodiesterase 4B
CHEMBL275
 IC50 7.78 7.524 16.5 5
Unchecked
CHEMBL612545
 IC50 7.68 7.502 21.0 5
Phosphodiesterase 4
CHEMBL2093863
 IC50 7.13 7.0875 74.0 4
PBMC
CHEMBL613107
 IC50 7.11 7.11 77.0 1
Blood
CHEMBL613416
 IC50 6.96 6.96 110.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 11000.0 ng.hr.mL-1 Rattus norvegicus
AUC 14000.0 ng.hr.mL-1 Rattus norvegicus
CL 8.333 mL.min-1.kg-1 Rattus norvegicus
Cmax 14331.94 nM Rattus norvegicus
Cmax 2388.66 nM Rattus norvegicus
F 64.0 % Rattus norvegicus
T1/2 3.0 hr Rattus norvegicus
T1/2 5.0 hr Rattus norvegicus
T1/2 1.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 10.0 nM 8.0 Inhibition of human N-terminal GST-tagged PDE4D7 (2 to 748 residues) expressed i... 38861808
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 16.5 nM 7.78 Inhibitory Effect on the Enzyme In Vitro Assay: The enzyme activity was indicate... -
Unchecked IC50 = 21.0 nM 7.68 Inhibition of recombinant human His6-tagged PDE4D UCR2 deletion mutant catalytic... 31013090
Unchecked IC50 = 23.0 nM 7.64 Inhibition of recombinant human His6-tagged PDE4D3 UCR1 S54D mutant expressed in... 31013090
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 24.0 nM 7.62 Inhibition of recombinant human His6-tagged PDE4B1 UCR1 S133D mutant expressed i... 31013090
Unchecked IC50 = 26.0 nM 7.58 Inhibition of recombinant human His6-tagged PDE4D7 UCR1 S129D mutant expressed i... 31013090
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 27.0 nM 7.57 Inhibition of PDE4B (unknown origin) 31035240
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 30.0 nM 7.52 Inhibition of recombinant human PDE4B2 expressed in African green monkey COS7 ce... 29502405
Unchecked IC50 = 32.0 nM 7.5 Inhibition of recombinant human wild-type His6-tagged PDE4D7 UCR1 domain (S129 r... 31013090
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 32.44 nM 7.49 Inhibition of his-tagged recombinant human PDE4D catalytic domain (T86 to S413 r... 37918035
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 33.0 nM 7.48 Inhibition of PDE4D (unknown origin) 31035240
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 35.0 nM 7.46 Inhibition of recombinant human His6-tagged PDE4D2 expressed in baculovirus infe... 31013090
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 47.6 nM 7.32 Inhibition of human PDE4D catalytic domain (86 to 413 residues) expressed in Esc... 32100544
Phosphodiesterase 4 IC50 = 74.0 nM 7.13 Inhibition of human PDE4 19256507
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 74.0 nM 7.13 Inhibition of PDE4D (unknown origin) using cAMP as substrate 31099559
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 74.0 nM 7.13 Inhibition of human PDE4B using [3H]cAMP as substrate incubated for 5 mins follo... 27713015
Phosphodiesterase 4 IC50 = 74.0 nM 7.13 Inhibition of PDE4 (unknown origin) 32255344
Phosphodiesterase 4 IC50 = 74.0 nM 7.13 Inhibition of PDE4 (unknown origin) 39098133
PBMC IC50 = 77.0 nM 7.11 Inhibition of TNFalpha production in LPS-stimulated human PBMC preincubated befo... 19256507
Unchecked IC50 = 77.0 nM 7.11 Inhibition of PDE-4 in human PBMC assessed as LPS-induced TNFalpha production in... 27713015

Literature References

PubMed DOI Target Context # Activities
19256507 10.1021/jm900210d Rattus norvegicus 12
31013090 10.1021/acs.jmedchem.9b00193 Unchecked 8
31099559 10.1021/acs.jmedchem.9b00518 ADMET 6
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
31099559 10.1021/acs.jmedchem.9b00518 Mus musculus 4
27713015 10.1016/j.bmc.2016.09.011 3',5'-cyclic-AMP phosphodiesterase 4B 3
27713015 10.1016/j.bmc.2016.09.011 Unchecked 3
31035240 10.1016/j.ejmech.2019.04.020 3',5'-cyclic-AMP phosphodiesterase 4A 3
31035240 10.1016/j.ejmech.2019.04.020 Unchecked 3
37468498 10.1038/s41467-023-40064-9 Estrogen receptor 2
31013090 10.1021/acs.jmedchem.9b00193 3',5'-cyclic-AMP phosphodiesterase 4B 2
31013090 10.1021/acs.jmedchem.9b00193 3',5'-cyclic-AMP phosphodiesterase 4D 2
37468498 10.1038/s41467-023-40064-9 Glucocorticoid receptor 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
37468498 10.1038/s41467-023-40064-9 Peroxisome proliferator-activated receptor gamma 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 2
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 2

Data from ChEMBL 36 via Core Engine