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Compound Detail

CHEMBL511115

CILOMILAST
🧪 Phase III
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🧪 Phase III
COc1ccc([C@]2(C#N)CC[C@@H](C(=O)O)CC2)cc1OC1CCCC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL511115
Name CILOMILAST
Phase Phase III
Structure Type MOL
InChI Key CFBUZOUXXHZCFB-OYOVHJISSA-N

Known Names

Ariflo Cilomilast SB 207499 SB-207499 SB207499
17
Targets
89
Activities
3
Assay Types
12
PK Parameters
20
Publications
5
Known Names
1
Indications
1
Mechanisms

Molecular Properties

343.4
MW (Da)
4.05
ALogP
4
HBA
1
HBD
79.5
PSA (Ų)
0.87
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -ast
USAN Year 1999

Extended Properties

Molecular Formula C20H25NO4
MW 343.42
Aromatic Rings 1
Heavy Atoms 25
NP-Likeness 0.16

Mechanism of Action

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

Indications

Pulmonary Disease, Chronic Obstructive

Activity Summary

IC50 84 meas. best 8.0
EC50 3 meas. best 8.46
Ki 2 meas. best 7.42

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 EC50 8.46 8.46 3.5 1
Phosphodiesterase 4
CHEMBL2093863
 IC50 8.0 6.8939 10.0 18
3',5'-cyclic-AMP phosphodiesterase 4D
CHEMBL288
 IC50 7.96 7.4264 11.0 11
3',5'-cyclic-AMP phosphodiesterase 4B
CHEMBL275
 IC50 7.6 7.0617 25.0 12
Phosphodiesterase 4
CHEMBL2093863
 Ki 7.42 7.42 38.0 2
3',5'-cyclic-AMP phosphodiesterase 4A
CHEMBL254
 IC50 7.42 6.6233 38.0 9
Phosphodiesterase 4
CHEMBL2094267
 IC50 7.31 6.35 49.0 8
Unchecked
CHEMBL612545
 IC50 7.19 6.6633 65.0 6
Homo sapiens
CHEMBL372
 IC50 6.96 5.5367 110.0 6
ADMET
CHEMBL612558
 IC50 6.54 6.54 290.0 1
3',5'-cyclic-AMP phosphodiesterase 4B
CHEMBL3382
 IC50 6.51 6.51 310.0 1
3',5'-cyclic-AMP phosphodiesterase 4C
CHEMBL291
 IC50 6.21 5.906 610.0 5
Oryctolagus cuniculus
CHEMBL374
 EC50 6.1 6.1 800.0 1
Blood
CHEMBL613416
 IC50 6.08 6.08 840.0 1
Rattus norvegicus
CHEMBL376
 IC50 6.0 6.0 1000.0 1
PBMC
CHEMBL613107
 IC50 5.46 5.46 3467.0 1
U-937
CHEMBL612794
 EC50 5.44 5.44 3630.0 1
U-937
CHEMBL612794
 IC50 5.44 5.44 3630.0 1
Cavia porcellus
CHEMBL369
 IC50 5.35 5.35 4500.0 1
Class 1 phosphodiesterase PDEB1
CHEMBL2010636
 IC50 4.8 4.8 16000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 9.2 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 0.5 mL.min-1.kg-1 Homo sapiens
CL 0.5 mL.min-1.kg-1 Homo sapiens
CL 0.5 mL.min-1.kg-1 Homo sapiens
CL 0.5 mL.min-1.kg-1 Homo sapiens
CL 13.0 mL.min-1.g-1 Homo sapiens
CL 28.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
F 35.0 % Rattus norvegicus
Fu 0.006 - Homo sapiens
Fu 0.006 - Homo sapiens
MRT 8.5 hr Homo sapiens
T1/2 7.9 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked EC50 = 3.47 nM 8.46 Anti-inflammatory activity against human PBMCs assessed as reduction in LPS-indu... 33569941
Phosphodiesterase 4 IC50 = 10.0 nM 8.0 Inhibition of PDE4 from U937 monocytic cells 14980691
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 11.0 nM 7.96 Inhibition of human PDE4D 20188577
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 11.0 nM 7.96 Inhibition of human PDE4D catalytic domain using [3H]-cAMP or [3H]-cGMP incubate... -
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 11.0 nM 7.96 Inhibition of human His-tagged PDE4D catalytic domain expressed in Escherichia c... 26908025
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 13.0 nM 7.89 Inhibition of PDE4D (unknown origin) 32717478
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 25.0 nM 7.6 Inhibition of human PDE4B 20188577
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 25.0 nM 7.6 Inhibition of human His-tagged PDE4B catalytic domain expressed in Escherichia c... 26908025
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 27.0 nM 7.57 Inhibition of human PDE4D3 incubated for 10 mins using cAMP and [3H]cAMP substra... 19447034
Phosphodiesterase 4 IC50 = 30.0 nM 7.52 Inhibition of phosphodiesterase type 4 isozyme (PDE4) from the U937 human cell l... 11123995
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 37.0 nM 7.43 Inhibition of human PDE4B1 incubated for 10 mins using cAMP and [3H]cAMP substra... 19447034
Phosphodiesterase 4 Ki = 38.0 nM 7.42 Inhibition of rolipram binding to Phosphodiesterase 4 11738561
3',5'-cyclic-AMP phosphodiesterase 4A IC50 = 38.0 nM 7.42 Inhibitory concentration against human PDE4A isoform using a construct represent... 12031319
3',5'-cyclic-AMP phosphodiesterase 4A IC50 = 38.0 nM 7.42 Inhibition of human Phosphodiesterase 4A isoform using construct representing th... 12270195
Phosphodiesterase 4 Ki = 38.0 nM 7.42 Inhibition of rolipram binding to PDE4 11140727
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 39.0 nM 7.41 Inhibition of human recombinant PDE4D 17228876
Phosphodiesterase 4 IC50 = 40.0 nM 7.4 Inhibition of [3H]rolipram binding in human peripheral blood mononuclear cells 11755362
Phosphodiesterase 4 IC50 = 49.0 nM 7.31 Inhibition of [3H]rolipram binding to Wistar rat brain membranes 11123995
3',5'-cyclic-AMP phosphodiesterase 4A IC50 = 62.0 nM 7.21 Inhibition of human full length PDE4A4 expressed in baculovirus infected sf21 ce... 23806553
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 63.0 nM 7.2 Inhibition of human Phosphodiesterase 4D from peripheral blood mononuclear cells 11755362

Literature References

PubMed DOI Target Context # Activities
9526558 10.1021/jm970090r Phosphodiesterase 4 8
11266153 10.1016/s0960-894x(00)00681-8 Phosphodiesterase 4 8
20070106 10.1021/jm901371v Homo sapiens 8
10691693 10.1021/jm991094u Rattus norvegicus 5
9526558 10.1021/jm970090r Unchecked 4
19447034 10.1016/j.bmcl.2009.04.121 Mustela putorius furo 4
- 10.6019/CHEMBL3301361 ADMET 4
18426954 10.1124/dmd.108.020479 ADMET 4
18686943 10.1021/jm800582j Unchecked 4
32717478 10.1016/j.ejmech.2020.112492 3',5'-cyclic-AMP phosphodiesterase 4D 4
11123995 10.1021/jm000315p Phosphodiesterase 4 3
11123995 10.1021/jm000315p Unchecked 3
11140727 10.1016/s0960-894x(00)00587-4 Rattus norvegicus 3
11738561 10.1016/s0960-894x(01)00668-0 Phosphodiesterase 4 3
32717478 10.1016/j.ejmech.2020.112492 Unchecked 3
14684291 10.1016/j.bmcl.2003.10.025 Mustela putorius furo 3
22891752 10.1021/jm300514y Mus musculus 3
12036360 10.1021/jm0110340 Unchecked 2
14684329 10.1016/j.bmcl.2003.09.087 Rattus norvegicus 2
12031319 10.1016/s0960-894x(02)00190-7 3',5'-cyclic-AMP phosphodiesterase 4A 2

Data from ChEMBL 36 via Core Engine