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Compound Detail

CHEMBL193240

ROFLUMILAST
💊 Approved Drug
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💊 Approved Drug
O=C(Nc1c(Cl)cncc1Cl)c1ccc(OC(F)F)c(OCC2CC2)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL193240
Name ROFLUMILAST
Phase Approved
Structure Type MOL
InChI Key MNDBXUUTURYVHR-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Arq-151 ARQ-154 (ROFLUMILAST FOAM) B-9302-107 B9302-107 BY-217 BY217 BYK-20869 BYK20869 Daliresp Daxas Libertek Roflumilast +1 more
11
Targets
78
Activities
3
Assay Types
28
PK Parameters
20
Publications
13
Known Names
20
Indications
1
Mechanisms

Molecular Properties

403.2
MW (Da)
5.03
ALogP
4
HBA
1
HBD
60.5
PSA (Ų)
0.70
QED
1
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2010
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Topical

Flags

First in Class
USAN Stem -ast
USAN Year 2002

Extended Properties

Molecular Formula C17H14Cl2F2N2O3
MW 403.21
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness -1.56

Mechanism of Action

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

Indications

Bronchitis, Chronic Lung Diseases, Obstructive Psoriasis Pulmonary Disease, Chronic Obstructive Asthma Bronchiectasis Dermatitis, Atopic Diabetic Nephropathies Cognitive Dysfunction Dementia Dermatitis Dermatitis, Seborrheic Diabetes Mellitus, Type 2 Fragile X Syndrome Non-alcoholic Fatty Liver Disease Respiratory Distress Syndrome Rosacea Brain Diseases Depressive Disorder, Major Lymphoma

ATC Classification

D05AX06
roflumilast
Level 1: DERMATOLOGICALS
Level 2: ANTIPSORIATICS
R03DX07
roflumilast
Level 1: RESPIRATORY SYSTEM
Level 2: DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES

Activity Summary

IC50 75 meas. best 10.7
Ki 2 meas. best 9.4
EC50 1 meas. best 7.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
PBMC
CHEMBL613107
 IC50 10.7 9.645 0.0 2
3',5'-cyclic-AMP phosphodiesterase 4D
CHEMBL288
 IC50 9.89 8.893 0.1 20
3',5'-cyclic-AMP phosphodiesterase 4B
CHEMBL275
 IC50 9.82 9.0004 0.1 28
3',5'-cyclic-AMP phosphodiesterase 4A
CHEMBL254
 IC50 9.68 9.38 0.2 4
Phosphodiesterase 4
CHEMBL2093863
 IC50 9.52 9.224 0.3 5
3',5'-cyclic-AMP phosphodiesterase 4B
CHEMBL275
 Ki 9.4 9.4 0.4 1
Unchecked
CHEMBL612545
 IC50 9.22 8.338 0.6 10
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.92 8.92 1.2 1
Splenocyte
CHEMBL612422
 IC50 8.92 8.92 1.2 1
3',5'-cyclic-AMP phosphodiesterase 4C
CHEMBL291
 IC50 8.77 8.645 1.7 2
Blood
CHEMBL613416
 IC50 7.7 7.68 19.9 2
Unchecked
CHEMBL612545
 EC50 7.3 7.3 50.0 1
Class 1 phosphodiesterase PDEB1
CHEMBL2010636
 Ki 5.5 5.5 3162.3 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 95.0 ng.hr.mL-1 Mustela putorius furo
AUC - - Mustela putorius furo
AUC - - Mustela putorius furo
AUC 35.0 ng.hr.mL-1 Homo sapiens
AUC 337.85 ng.hr.mL-1 Homo sapiens
AUC 449.43 ng.hr.mL-1 Rattus norvegicus
AUC 499.51 ng.hr.mL-1 Rattus norvegicus
CL 5.0 mL.min-1.g-1 Homo sapiens
CL 150.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 114.19 mL.min-1.kg-1 Rattus norvegicus
CL 0.03337 mL.min-1.kg-1 Rattus norvegicus
Cmax 138.89 nM Mustela putorius furo
Cmax - - Mustela putorius furo
Cmax - - Mustela putorius furo
Cmax 13.1 nM Homo sapiens
Cmax 22.4 nM Homo sapiens
Cmax 269.83 nM Rattus norvegicus
Fu 0.02 - Homo sapiens
T1/2 4.2 hr Mustela putorius furo
t1/2 - - Mustela putorius furo
t1/2 - - Mustela putorius furo
T1/2 0.2048 hr Rattus norvegicus
T1/2 6.938 hr Rattus norvegicus
Tmax 4.4 hr Mustela putorius furo
Tmax - - Mustela putorius furo
Tmax - - Mustela putorius furo
Tmax 1.0 hr Rattus norvegicus
Vd 0.02004 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
PBMC IC50 = 0.02 nM 10.7 Inhibition of TNFalpha production in LPS-stimulated human PBMC preincubated befo... 19256507
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 0.13 nM 9.89 Inhibition of human recombinant PDE4D using [3H]cAMP as substrate preincubated w... 32717478
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 0.15 nM 9.82 Inhibition of human recombinant PDE4B using [3H]cAMP as substrate preincubated w... 32717478
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 0.2 nM 9.7 Inhibition of PDE4D (unknown origin) 31035240
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 0.2 nM 9.7 Inhibition of human PDE4B using [3H]cAMP as substrate incubated for 5 mins follo... 27713015
3',5'-cyclic-AMP phosphodiesterase 4A IC50 = 0.21 nM 9.68 Inhibition of human recombinant PDE4A using [3H]cAMP as substrate preincubated w... 32717478
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 0.27 nM 9.57 Inhibition of human PDE4D3 assessed as inhibition of [3H]cAMP hydrolysis to [3H]... 21871695
Phosphodiesterase 4 IC50 = 0.3 nM 9.52 Inhibition of human PDE4 19256507
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 0.3 nM 9.52 Inhibition of human recombinant PDE4D 33569941
3',5'-cyclic-AMP phosphodiesterase 4A IC50 = 0.35 nM 9.46 Inhibition of human full length PDE4A4 expressed in baculovirus infected sf21 ce... 23806553
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 0.39 nM 9.41 Inhibition of his-tagged recombinant human PDE4D catalytic domain (T86 to S413 r... 37918035
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 0.4 nM 9.4 Inhibition of PDE4D2 (unknown origin) 32115956
3',5'-cyclic-AMP phosphodiesterase 4B Ki = 0.3981 nM 9.4 Inhibition of full length recombinant human PDE4B1 expressed in Sf21 insect cell... 29672041
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 0.4 nM 9.4 Inhibition of PDE4D2 (unknown origin) 35985255
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 0.4 nM 9.4 Inhibition of PDE4D (unknown origin) 35188767
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 0.3981 nM 9.4 Inhibition of human recombinant PDE4B by scintillation proximity assay 19656678
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 0.3981 nM 9.4 Inhibition of human recombinant PDE4B by scintillation proximity assay 19195882
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 0.4 nM 9.4 Inhibition of PDE4D (unknown origin) using cAMP as substrate 31099559
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 0.4 nM 9.4 Inhibition of human recombinant PDE4B1 activity assessed as residual cAMP concen... 25149511
3',5'-cyclic-AMP phosphodiesterase 4B IC50 = 0.49 nM 9.31 Inhibition of human recombinant PDE4B (152 to 564 amino acids) using cAMP as sub... 23602400

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 175
22889281 10.1021/jm300459a Mustela putorius furo 9
30553143 10.1016/j.ejmech.2018.12.013 Mus musculus 8
29477888 10.1016/j.ejmech.2018.02.038 Rattus norvegicus 7
27933955 10.1021/acs.jmedchem.6b00829 Rattus norvegicus 6
34046629 10.1039/d0md00423e Macrophage 6
21871695 10.1016/j.ejmech.2011.07.054 Mustela putorius furo 5
37561958 10.1021/acs.jmedchem.3c01012 ADMET 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
28613871 10.1021/acs.jmedchem.6b01647 Homo sapiens 4
39098133 10.1016/j.ejmech.2024.116710 Mus musculus 4
- 10.6019/CHEMBL3301361 ADMET 4
34046629 10.1039/d0md00423e Mus musculus 4
29477888 10.1016/j.ejmech.2018.02.038 3',5'-cyclic-AMP phosphodiesterase 4B 3
32088124 10.1016/j.bmc.2020.115372 Histone-lysine N-methyltransferase SETD7 3
27933955 10.1021/acs.jmedchem.6b00829 Unchecked 3
29502405 10.1021/acs.jmedchem.7b01751 Rattus norvegicus 3
29477888 10.1016/j.ejmech.2018.02.038 ADMET 3
27713015 10.1016/j.bmc.2016.09.011 Unchecked 3
32717478 10.1016/j.ejmech.2020.112492 ADMET 3

Data from ChEMBL 36 via Core Engine