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Compound Detail

CHEMBL217899

TOFIMILAST
🧪 Phase II
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🧪 Phase II
CCc1nn(C2CCCC2)c2c1CCn1c(-c3cccs3)nnc1-2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL217899
Name TOFIMILAST
Phase Phase II
Structure Type MOL
InChI Key DHCOPPHTVOXDKU-UHFFFAOYSA-N

Known Names

CP-325,366 CP-325366 Tofimilast
9
Targets
11
Activities
2
Assay Types
25
PK Parameters
20
Publications
3
Known Names
2
Indications
1
Mechanisms

Molecular Properties

339.5
MW (Da)
4.10
ALogP
6
HBA
0
HBD
48.5
PSA (Ų)
0.72
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Stem -ast
USAN Year 2000

Extended Properties

Molecular Formula C18H21N5S
MW 339.47
Aromatic Rings 3
Heavy Atoms 24
NP-Likeness -1.41

Mechanism of Action

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

Indications

Asthma Pulmonary Disease, Chronic Obstructive

Activity Summary

IC50 10 meas. best 7.89
EC50 1 meas. best 6.64

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
3',5'-cyclic-AMP phosphodiesterase 4B
CHEMBL275
 IC50 7.89 7.89 13.0 1
3',5'-cyclic-AMP phosphodiesterase 4D
CHEMBL288
 IC50 7.89 7.89 13.0 1
3',5'-cyclic-AMP phosphodiesterase 4A
CHEMBL254
 IC50 7.64 7.64 23.0 1
Monocyte
CHEMBL614076
 IC50 7.23 7.2 59.0 2
Unchecked
CHEMBL612545
 IC50 6.85 6.85 140.0 1
U-937
CHEMBL612794
 EC50 6.64 6.64 230.0 1
Adenosine receptor A1
CHEMBL226
 IC50 5.89 5.585 1300.0 2
Adenosine receptor A2a
CHEMBL251
 IC50 5.36 5.36 4400.0 1
Adenosine receptor A3
CHEMBL256
 IC50 5.32 5.32 4800.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 3200.0 ng.hr.mL-1 Rattus norvegicus
AUC 76.0 ng.hr.mL-1 Rattus norvegicus
AUC 649.0 ng.hr.mL-1 Canis lupus familiaris
AUC 23.2 ng.hr.mL-1 Canis lupus familiaris
AUC 263.0 ng.hr.mL-1 Canis lupus familiaris
CL 29.5 mL.min-1.kg-1 Rattus norvegicus
CL 26.8 mL.min-1.kg-1 Canis lupus familiaris
CL 6.0 uL.min-1.(10^6cells)-1 Homo sapiens
CL 22.0 mL.min-1.g-1 Homo sapiens
CL 73.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
Cmax 447.76 nM Mustela putorius furo
Cmax 1154.74 nM Mustela putorius furo
Cmax 123.72 nM Rattus norvegicus
Cmax 35.35 nM Canis lupus familiaris
Cmax 288.69 nM Canis lupus familiaris
F 1.2 % Rattus norvegicus
F 3.2 % Canis lupus familiaris
F 8.1 % Canis lupus familiaris
F 1.2 % Rattus norvegicus
F 3.0 % Canis lupus familiaris
Fu 0.02 - Homo sapiens
T1/2 2.1 hr Rattus norvegicus
T1/2 1.7 hr Canis lupus familiaris
T1/2 1.2 hr Canis lupus familiaris
T1/2 1.8 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 13.0 nM 7.89 Inhibition of human recombinant PDE4B 17228876
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 13.0 nM 7.89 Inhibition of human recombinant PDE4D 17228876
3',5'-cyclic-AMP phosphodiesterase 4A IC50 = 23.0 nM 7.64 Inhibition of human recombinant PDE4A 17228876
Monocyte IC50 = 59.0 nM 7.23 Inhibition of LPS-stimulated TNF alpha release in human monocytes 17228876
Monocyte IC50 = 67.0 nM 7.17 Inhibition of PDE-mediated cAMP catabolism in human monocytes 17228876
Unchecked IC50 = 140.0 nM 6.85 Inhibition of human eosinophil phosphodiesterase 17228876
U-937 EC50 = 230.0 nM 6.64 Increase in cAMP levels in PGE1-stimulated U937 cells 17228876
Adenosine receptor A1 IC50 = 1300.0 nM 5.89 Inhibition of adenosine A1 receptor 17228876
Adenosine receptor A2a IC50 = 4400.0 nM 5.36 Inhibition of adenosine A2A receptor 17228876
Adenosine receptor A3 IC50 = 4800.0 nM 5.32 Inhibition of adenosine A3 receptor 17228876
Adenosine receptor A1 IC50 = 5200.0 nM 5.28 Inhibition of human adenosine A1 receptor expressed in CHO cells 17228876

Literature References

PubMed DOI Target Context # Activities
17228876 10.1021/jm060904g Canis familiaris 12
17228876 10.1021/jm060904g Unchecked 7
17228876 10.1021/jm060904g Rattus norvegicus 7
- 10.6019/CHEMBL3301361 ADMET 5
17228876 10.1021/jm060904g Mustela putorius furo 4
- 10.6019/CHEMBL3301361 No relevant target 2
17228876 10.1021/jm060904g Adenosine receptor A1 2
17228876 10.1021/jm060904g Monocyte 2
17228876 10.1021/jm060904g Plasma 1
17228876 10.1021/jm060904g Adenosine receptor A2a 1
17228876 10.1021/jm060904g Adenosine receptor A3 1
17228876 10.1021/jm060904g U-937 1
17228876 10.1021/jm060904g 3',5'-cyclic-AMP phosphodiesterase 4D 1
17228876 10.1021/jm060904g 3',5'-cyclic-AMP phosphodiesterase 4C 1
18686943 10.1021/jm800582j Mustela putorius furo 1
18686943 10.1021/jm800582j Rattus norvegicus 1
18686943 10.1021/jm800582j Canis familiaris 1
24400806 10.1021/jm401549m No relevant target 1
17228876 10.1021/jm060904g 3',5'-cyclic-AMP phosphodiesterase 4A 1
17228876 10.1021/jm060904g 3',5'-cyclic-AMP phosphodiesterase 4B 1

Data from ChEMBL 36 via Core Engine