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Compound Detail

CHEMBL1159650

CLOBETASOL PROPIONATE
💊 Approved Drug
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💊 Approved Drug
CCC(=O)O[C@]1(C(=O)CCl)[C@@H](C)C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C

Basic Information

ChEMBL ID CHEMBL1159650
Name CLOBETASOL PROPIONATE
Phase Approved
Structure Type MOL
InChI Key CBGUOGMQLZIXBE-XGQKBEPLSA-N
Therapeutic ✓ Yes

Known Names

CCI 4725 CCI-4725 Clarelux Clobaderm Clobecort amex Clobetasol Clobetasol 17-propionate Clobetasol propionate Clobetasol propionate (emollient) Clobex Cormax Dermovate +15 more
11
Targets
20
Activities
4
Assay Types
1
PK Parameters
20
Publications
27
Known Names
17
Indications
1
Mechanisms

Molecular Properties

467.0
MW (Da)
4.10
ALogP
5
HBA
1
HBD
80.7
PSA (Ų)
0.50
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1985
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Topical

Flags

Black Box Warning
USAN Year 1983

Extended Properties

Molecular Formula C25H32ClFO5
MW 466.98
Aromatic Rings 0
Heavy Atoms 32
NP-Likeness 1.95

Mechanism of Action

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

Indications

Psoriasis Psoriasis Skin Diseases Alopecia Areata Arthritis, Rheumatoid Cataract Dermatitis, Seborrheic Lichen Sclerosus et Atrophicus Pemphigoid, Bullous Vulvar Lichen Sclerosus Colorectal Neoplasms Colorectal Neoplasms Lichen Planus Lichen Planus, Oral Pulmonary Disease, Chronic Obstructive Rectal Neoplasms Dermatitis, Atopic

ATC Classification

D07AD01
clobetasol
Level 1: DERMATOLOGICALS
Level 2: CORTICOSTEROIDS, DERMATOLOGICAL PREPARATIONS

Drug Warnings

Black Box Warning
General Warning
Country: United States

Activity Summary

IC50 14 meas. best 8.84
Ki 3 meas. best 9.18
EC50 2 meas. best 4.6
Kd 1 meas. best 7.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Glucocorticoid receptor
CHEMBL2034
Ki 9.18 9.18 0.7 1
Glucocorticoid receptor
CHEMBL2034
IC50 8.84 8.84 1.5 1
Progesterone receptor
CHEMBL1909044
Ki 8.82 8.82 1.5 1
Glucocorticoid receptor
CHEMBL3368
IC50 8.5 8.5 3.2 1
Progesterone receptor
CHEMBL1909044
IC50 7.92 7.92 12.0 1
Cytochrome P450 3A5
CHEMBL3019
IC50 7.68 6.79 21.0 5
Cytochrome P450 3A5
CHEMBL3019
Kd 7.0 7.0 100.0 1
Cytochrome P450 3A4
CHEMBL340
IC50 6.69 6.69 206.0 1
Plasmodium falciparum
CHEMBL364
IC50 6.1 6.1 797.0 1
Androgen receptor
CHEMBL3072
Ki 5.6 5.6 2517.0 1
Androgen receptor
CHEMBL3072
IC50 5.42 5.42 3775.0 1
Bile salt export pump
CHEMBL6020
IC50 5.07 5.07 8500.0 2
Trypanosoma cruzi
CHEMBL368
EC50 4.6 4.6 25000.0 1
Bile salt export pump
CHEMBL2073674
IC50 4.46 4.46 35000.0 1
ADMET
CHEMBL612558
EC50 4.39 4.39 41000.0 1

Pharmacokinetic Data

Parameter Value Units Species
Cmax 43.0 nM Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Glucocorticoid receptor Ki = 0.662 nM 9.18 DRUGMATRIX: Glucocorticoid radioligand binding (ligand: [3H] Dexamethasone) -
Glucocorticoid receptor IC50 = 1.456 nM 8.84 DRUGMATRIX: Glucocorticoid radioligand binding (ligand: [3H] Dexamethasone) -
Progesterone receptor Ki = 1.519 nM 8.82 DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020) -
Glucocorticoid receptor IC50 = 3.17 nM 8.5 Competitive displacement of [3H]dexamethasone from glucocorticoid receptor of ra... 1875343
Progesterone receptor IC50 = 12.0 nM 7.92 DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020) -
Cytochrome P450 3A5 IC50 = 21.0 nM 7.68 Inhibition of CYP3A5 in doxycycline-induced CYP3A5 overexpressing wild type huma... 31965799
Cytochrome P450 3A5 IC50 = 44.0 nM 7.36 Inhibition of CYP3A5 in wild type human AsPC1 cells assessed as decrease in 1-hy... 31965799
Cytochrome P450 3A5 IC50 = 78.0 nM 7.11 Inhibition of CYP3A5 in lentiviral pLVX-TRE3G-ZsGreen1-CYP3A5 transduced wild ty... 31965799
Cytochrome P450 3A5 Kd = 100.0 nM 7.0 Binding affinity to heme in His-tagged CYP3A5 (unknown origin) expressed in Esch... 31965799
Cytochrome P450 3A5 IC50 = 103.0 nM 6.99 Inhibition of CYP3A5 in CRISPR/Cas9-mediated CYP3A5 knock-out and doxycycline-in... 31965799
Cytochrome P450 3A4 IC50 = 206.0 nM 6.69 Inhibition of human recombinant CYP3A4 expressed in supersomes assessed as decre... 31965799
Plasmodium falciparum IC50 = 797.0 nM 6.1 Antiplasmodial activity against Plasmodium falciparum 3D7 infected in RBCs by fi... 20547797
Androgen receptor Ki = 2517.0 nM 5.6 DRUGMATRIX: Androgen (Testosterone) AR radioligand binding (ligand: [3H] Miboler... -
Androgen receptor IC50 = 3775.0 nM 5.42 DRUGMATRIX: Androgen (Testosterone) AR radioligand binding (ligand: [3H] Miboler... -
Bile salt export pump IC50 = 8500.0 nM 5.07 Inhibition of recombinant human BSEP expressed in baculovirus infected sf21 cell... 24799086
Bile salt export pump IC50 = 8500.0 nM 5.07 Inhibition of human BSEP expressed in plasma membrane vesicles of Sf21 cells ass... 21965623
Cytochrome P450 3A5 IC50 = 15600.0 nM 4.81 Inhibition of human recombinant CYP3A5 expressed in supersomes assessed as decre... 31965799
Trypanosoma cruzi EC50 = 25000.0 nM 4.6 Antitrypanosomal activity against Trypanosoma cruzi amastigotes infected in BESM... 20547819
Bile salt export pump IC50 = 35000.0 nM 4.46 Inhibition of Sprague-Dawley rat Bsep expressed in plasma membrane vesicles of S... 21965623
ADMET EC50 = 41000.0 nM 4.39 Cytotoxicity against BESM cells after 88 hrs by HTS assay 20547819

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 312
31965799 10.1021/acs.jmedchem.9b02067 Cytochrome P450 3A5 10
31965799 10.1021/acs.jmedchem.9b02067 Cytochrome P450 3A4 9
31965799 10.1021/acs.jmedchem.9b02067 ASPC1 9
- 10.6019/CHEMBL5303304 U2OS 8
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
24799086 10.1002/hep.27206 Homo sapiens 2
37468498 10.1038/s41467-023-40064-9 Peroxisome proliferator-activated receptor gamma 2
37468498 10.1038/s41467-023-40064-9 Estrogen receptor 2
21965623 10.1124/dmd.111.040758 Bile salt export pump 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
18066055 10.1038/nchembio.2007.53 HeLa 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 2

Data from ChEMBL 36 via Core Engine