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Compound Detail

CHEMBL1473

FLUTICASONE PROPIONATE
💊 Approved Drug
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💊 Approved Drug
CCC(=O)O[C@]1(C(=O)SCF)[C@H](C)C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C

Basic Information

ChEMBL ID CHEMBL1473
Name FLUTICASONE PROPIONATE
Phase Approved
Structure Type MOL
InChI Key WMWTYOKRWGGJOA-CENSZEJFSA-N
Therapeutic ✓ Yes

Known Names

Aerivio spiromax Airflusal forspiro Armonair digihaler Armonair respiclick CCI 18781 CCI-18781 CCI18781 Cutivate Flixonase Flixotide Flonase Flonase allergy relief +18 more
7
Targets
15
Activities
2
Assay Types
23
PK Parameters
20
Publications
30
Known Names
20
Indications
1
Mechanisms

Molecular Properties

500.6
MW (Da)
4.43
ALogP
6
HBA
1
HBD
80.7
PSA (Ų)
0.58
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1990
Availability OTC
Chirality Single Enantiomer

Routes of Administration

Topical
USAN Year 1985

Extended Properties

Molecular Formula C25H31F3O5S
MW 500.58
Aromatic Rings 0
Heavy Atoms 34
NP-Likeness 1.62

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Glucocorticoid receptor agonist AGONIST Glucocorticoid receptor

Indications

Asthma Bronchitis, Chronic Dermatitis, Atopic Emphysema Lung Diseases, Obstructive Nasal Obstruction Nasal Polyps Nasal Polyps Pulmonary Disease, Chronic Obstructive Rhinitis, Allergic, Seasonal Rhinitis, Allergic, Seasonal Skin Diseases Bronchiolitis Obliterans Chronic Disease Eosinophilic Esophagitis Respiratory Sounds Rhinitis, Allergic, Perennial Sinusitis Adenomatous Polyposis Coli Blepharitis

ATC Classification

D07AC17
fluticasone
Level 1: DERMATOLOGICALS
Level 2: CORTICOSTEROIDS, DERMATOLOGICAL PREPARATIONS
R01AD08
fluticasone
Level 1: RESPIRATORY SYSTEM
Level 2: NASAL PREPARATIONS
R01AD58
fluticasone, combinations
Level 1: RESPIRATORY SYSTEM
Level 2: NASAL PREPARATIONS
R03BA05
fluticasone
Level 1: RESPIRATORY SYSTEM
Level 2: DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES

Activity Summary

IC50 12 meas. best 10.4
EC50 3 meas. best 9.15

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Glucocorticoid receptor
CHEMBL2034
IC50 10.4 9.846 0.0 5
PBMC
CHEMBL613107
IC50 10.0 10.0 0.1 1
Glucocorticoid receptor
CHEMBL3368
IC50 9.85 9.075 0.1 2
Unchecked
CHEMBL612545
IC50 9.82 9.82 0.1 1
Glucocorticoid receptor
CHEMBL2034
EC50 9.15 9.055 0.7 2
Glucocorticoid receptor
CHEMBL3368
EC50 9.12 9.12 0.8 1
Blood
CHEMBL613416
IC50 8.03 8.03 9.3 1
Progesterone receptor
CHEMBL208
IC50 7.68 7.68 21.0 1
Mineralocorticoid receptor
CHEMBL1994
IC50 6.83 6.83 149.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 100116.0 ng.hr.mL-1 Rattus norvegicus
CL 17.0 mL.min-1.kg-1 Homo sapiens
CL 51.0 mL.min-1.g-1 Homo sapiens
CL 300.0 mL.min-1.g-1 Homo sapiens
CL 56000.0 mL.min-1.g-1 Rattus norvegicus
CL 1800000.0 mL.min-1.g-1 Rattus norvegicus
CL 107.15 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 150.0 uL.min-1.(10^6cells)-1 Homo sapiens
CL 103.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 24.0 nM Rattus norvegicus
F 2.0 % Rattus norvegicus
F 0.1 % Rattus norvegicus
Fu 0.1 - Homo sapiens
MRT 3.9 hr Homo sapiens
MRT 6.0 hr Rattus norvegicus
T1/2 6.0 hr Homo sapiens
T1/2 1.1 hr Rattus norvegicus
T1/2 9.067 hr Homo sapiens
T1/2 0.01433 hr Homo sapiens
T1/2 0.2667 hr Homo sapiens
T1/2 0.9667 hr Homo sapiens
T1/2 3.3 hr Rattus norvegicus
T1/2 4.5 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Glucocorticoid receptor IC50 = 0.04 nM 10.4 Transrepression of glucocorticoid receptor in PMA-stimulated human ChaGoK1 cells... 28937774
Glucocorticoid receptor IC50 = 0.044 nM 10.36 Transrepression of glucocorticoid receptor in human PBMC assessed as inhibition ... 28937774
Glucocorticoid receptor IC50 = 0.075 nM 10.12 Transrepression activity at glucocorticoid receptor in human H292 cells assessed... 21944381
PBMC IC50 = 0.1 nM 10.0 Inhibition of TNFalpha release in human PBMC by ELISA assay 21880489
Glucocorticoid receptor IC50 = 0.14 nM 9.85 Transrepression of glucocorticoid receptor in Wistar rat PBMC assessed as inhibi... 28937774
Unchecked IC50 = 0.15 nM 9.82 GILZ gene assays: HUT78 cells were cultured in IMEM plus 20% heat inactivated FB... -
Glucocorticoid receptor IC50 = 0.5 nM 9.3 Inhibition of [3H]dexamethasone binding to human Glucocorticoid Receptor 10633034
Glucocorticoid receptor EC50 = 0.7 nM 9.15 Transactivation activity at glucocorticoid receptor in human HepG2 cells assesse... 21944381
Glucocorticoid receptor EC50 = 0.76 nM 9.12 Transactivation activity at glucocorticoid receptor in rat H4II-E cells assessed... 21944381
Glucocorticoid receptor IC50 = 0.9 nM 9.05 Displacement of fluormone labelled GS Red from human recombinant glucocorticoid ... 28937774
Glucocorticoid receptor EC50 = 1.09 nM 8.96 Agonist activity at GR in human SW1353 cells transfected with luciferase gene li... 21880489
Glucocorticoid receptor IC50 = 5.0 nM 8.3 Steroid binding against the rat thymus glucocorticoid receptor 8960547
Blood IC50 = 9.3 nM 8.03 Inhibition of TNFalpha release in LPS-stimulated human whole blood by ELISA assa... 21880489
Progesterone receptor IC50 = 21.0 nM 7.68 Displacement of fluormone labelled PL Red from human recombinant progesterone re... 28937774
Mineralocorticoid receptor IC50 = 149.0 nM 6.83 Displacement of [3H]-aldosterone from N terminal maltose binding protein tagged ... 28937774

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4689842 HEK-293T 344
- 10.6019/CHEMBL4689842 U2OS 344
- 10.6019/CHEMBL4689842 Fibroblast 341
28937774 10.1021/acs.jmedchem.7b01215 Rattus norvegicus 10
25740159 10.1016/j.bmcl.2015.02.013 No relevant target 9
28937774 10.1021/acs.jmedchem.7b01215 Glucocorticoid receptor 7
11170650 10.1021/jm001035c Rattus norvegicus 7
24755427 10.1016/j.bmcl.2014.03.070 Rattus norvegicus 7
21944381 10.1016/j.bmcl.2011.08.108 Rattus norvegicus 6
21944381 10.1016/j.bmcl.2011.08.108 Glucocorticoid receptor 6
21880489 10.1016/j.bmcl.2011.07.106 Rattus norvegicus 6
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 6
28937774 10.1021/acs.jmedchem.7b01215 Lung 5
- 10.6019/CHEMBL3301361 ADMET 5
18426954 10.1124/dmd.108.020479 ADMET 4
37468498 10.1038/s41467-023-40064-9 Androgen receptor 4
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 4
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 4
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 4
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 4

Data from ChEMBL 36 via Core Engine