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Compound Detail

CHEMBL42126

PICLAMILAST
🧪 Phase II
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🧪 Phase II
COc1ccc(C(=O)Nc2c(Cl)cncc2Cl)cc1OC1CCCC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL42126
Name PICLAMILAST
Phase Phase II
Structure Type MOL
InChI Key RRRUXBQSQLKHEL-UHFFFAOYSA-N

Known Names

Piclamilast RP 73401 RP-73041 RP-73401 RP73401 RPR-73401
14
Targets
54
Activities
3
Assay Types
1
PK Parameters
20
Publications
6
Known Names

Molecular Properties

381.3
MW (Da)
4.97
ALogP
4
HBA
1
HBD
60.5
PSA (Ų)
0.79
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Stem -ast
USAN Year 1996

Extended Properties

Molecular Formula C18H18Cl2N2O3
MW 381.26
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness -0.72

Activity Summary

IC50 42 meas. best 10.7
Ki 10 meas. best 9.4
EC50 2 meas. best 7.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
3',5'-cyclic-AMP phosphodiesterase 4D
CHEMBL288
 IC50 10.7 10.09 0.0 6
3',5'-cyclic-AMP phosphodiesterase 4B
CHEMBL275
 IC50 10.39 9.5843 0.0 7
Phosphodiesterase 4
CHEMBL2093863
 IC50 9.52 8.8746 0.3 13
Phosphodiesterase 4
CHEMBL2093863
 Ki 9.4 9.0413 0.4 8
Phosphodiesterase 4A
CHEMBL3333
 IC50 9.0 9.0 1.0 1
Unchecked
CHEMBL612545
 Ki 9.0 9.0 1.0 1
Homo sapiens
CHEMBL372
 IC50 8.89 8.395 1.3 4
3',5'-cyclic-AMP phosphodiesterase 4A
CHEMBL254
 IC50 8.8 8.6 1.6 2
3',5'-cyclic-AMP phosphodiesterase 4C
CHEMBL291
 IC50 8.42 8.135 3.8 2
ADMET
CHEMBL612558
 IC50 8.3 8.3 5.0 1
Unchecked
CHEMBL612545
 IC50 8.05 6.5525 9.0 4
Cavia porcellus
CHEMBL369
 IC50 7.62 7.62 24.0 1
Phosphodiesterase 4
CHEMBL2094267
 Ki 7.58 7.58 26.0 1
U-937
CHEMBL612794
 EC50 7.4 7.4 40.0 1
Rattus norvegicus
CHEMBL376
 IC50 7.16 7.16 70.0 1
Trypanosoma brucei brucei
CHEMBL612851
 EC50 5.02 5.02 9570.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 5.0 % Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 0.02 nM 10.7 Inhibition of human PDE4D catalytic domain using [3H]-cAMP or [3H]-cGMP incubate... -
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 0.021 nM 10.68 Inhibition of human PDE4D 20188577
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 0.021 nM 10.68 Inhibition of human His-tagged PDE4D catalytic domain expressed in Escherichia c... 26908025
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 0.021 nM 10.68 Inhibition of human PDE4D by scintillation counting method 32255344
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 0.041 nM 10.39 Inhibition of human PDE4B 20188577
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 0.041 nM 10.39 Inhibition of human His-tagged PDE4B catalytic domain expressed in Escherichia c... 26908025
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 0.041 nM 10.39 Inhibition of human PDE4B by scintillation counting method 32255344
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 0.2 nM 9.7 Inhibitory activity against recombinant phosphodiesterase 4B (PDE4B) of human mo... 11844693
Phosphodiesterase 4 IC50 = 0.3 nM 9.52 Inhibition of phosphodiesterase 4 12824031
Phosphodiesterase 4 Ki = 0.4 nM 9.4 Binding affinity against PDE4 was determined using [3H]- rolipram in guinea pig ... 9873449
Phosphodiesterase 4 Ki = 0.4 nM 9.4 Affinity for rolipram binding site of phosphodiesterase type IV (PDE4) 9873675
Phosphodiesterase 4 IC50 = 0.8 nM 9.1 Inhibition of solubilized eosinophil PDE IV 8201604
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 0.8 nM 9.1 In vitro inhibitory activity on unpurified recombinant Phosphodiesterase 4D 9464356
Phosphodiesterase 4 Ki = 0.85 nM 9.07 Inhibition of rolipram binding to phosphodiesterase 4 12824031
Phosphodiesterase 4 Ki = 1.0 nM 9.0 Inhibition of Rolipram binding to Phosphodiesterase 4 9873613
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 1.0 nM 9.0 Inhibition of recombinant human Phosphodiesterase 4B 9464356
Phosphodiesterase 4 Ki = 1.0 nM 9.0 Binding affinity at Phosphodiesterase 4 by measuring displacement of (+/-)-[3H]-... 9784096
Phosphodiesterase 4 IC50 = 1.0 nM 9.0 Inhibition of human Phosphodiesterase 4 11738561
Phosphodiesterase 4 IC50 = 1.0 nM 9.0 Inhibition of Phosphodiesterase type 4 (PDE4) from guinea-pig macrophage 9873449
Phosphodiesterase 4 IC50 = 1.0 nM 9.0 Inhibition of Phosphodiesterase 4 (PDE4) from guinea pig macrophages 9873613

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 175
8201604 10.1021/jm00037a021 Cavia porcellus 7
24984230 10.1021/jm500378a No relevant target 4
22023548 10.1021/jm201148s Unchecked 3
11738561 10.1016/s0960-894x(01)00668-0 Phosphodiesterase 4 3
12824031 10.1016/s0960-894x(03)00438-4 Phosphodiesterase 4 3
9873613 10.1016/s0960-894x(98)00497-1 Phosphodiesterase 4 3
11140727 10.1016/s0960-894x(00)00587-4 Phosphodiesterase 4 2
9464356 10.1021/jm970685m Homo sapiens 2
11012037 10.1016/s0960-894x(00)00449-2 Phosphodiesterase 4 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
9873675 10.1016/s0960-894x(98)00572-1 Phosphodiesterase 4 2
8201604 10.1021/jm00037a021 Phosphodiesterase 4 2
9873449 10.1016/s0960-894x(98)00324-2 Phosphodiesterase 4 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
9784096 10.1021/jm970575f Phosphodiesterase 4 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
11844693 10.1016/s0960-894x(01)00817-4 Mus musculus 2
12824031 10.1016/s0960-894x(03)00438-4 Mus musculus 1
9632360 10.1021/jm9800090 U-937 1

Data from ChEMBL 36 via Core Engine