CLOBETASOL PROPIONATE

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Trade Names
Synonyms
Status
Molecule Category Free-form
UNII 779619577M
EPA CompTox DTXSID6045907
Parent Compound: CLOBETASOL

Structure

InChI Key CBGUOGMQLZIXBE-XGQKBEPLSA-N
Smiles 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
InChI
InChI=1S/C25H32ClFO5/c1-5-21(31)32-25(20(30)13-26)14(2)10-18-17-7-6-15-11-16(28)8-9-22(15,3)24(17,27)19(29)12-23(18,25)4/h8-9,11,14,17-19,29H,5-7,10,12-13H2,1-4H3/t14-,17-,18-,19-,22-,23-,24-,25-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C25H32ClFO5
Molecular Weight 466.98
AlogP 4.1
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 4.0
Polar Surface Area 80.67
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 32.0

Bioactivity

Mechanism of Action Action Reference
Glucocorticoid receptor agonist AGONIST PubMed
Protein: Glucocorticoid receptor
Description: Glucocorticoid receptor
Organism : Homo sapiens
P04150 ENSG00000113580
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 206 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A5
- 21-15600 100 - 90
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 1
- 3 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 20
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 8500-8500 - - -
Assay Description Organism Bioactivity Reference
Competitive displacement of [3H]dexamethasone from glucocorticoid receptor of rat liver cytosol Rattus norvegicus 3.17 nM
Antiplasmodial activity against Plasmodium falciparum 3D7 infected in RBCs by firefly luciferase reporter gene assay Plasmodium falciparum 797.0 nM
DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020) Bos taurus 12.0 nM DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020) Bos taurus 1.519 nM
DRUGMATRIX: Glucocorticoid radioligand binding (ligand: [3H] Dexamethasone) None 1.456 nM DRUGMATRIX: Glucocorticoid radioligand binding (ligand: [3H] Dexamethasone) None 0.662 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 20.25 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 21.34 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus -12.08 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli -1.37 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae -2.85 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 1.19 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 5.15 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 0.73 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans 4.34 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens -10.38 %
Inhibition of human recombinant CYP3A4 expressed in supersomes assessed as decrease in formation of D-luciferin using luciferin-IPA as substrate incubated for 10 mins in presence of NADPH by P450-Glo luminescence assay Homo sapiens 206.0 nM
Inhibition of human recombinant CYP3A5 expressed in supersomes assessed as decrease in formation of D-luciferin at 1.89 uM using luciferin-IPA as substrate incubated for 10 mins in presence of NADPH by P450-Glo luminescence assay relative to control Homo sapiens 90.0 %
Inhibition of CYP3A5 in wild type human AsPC1 cells assessed as decrease in 1-hydroxymidazolam formation using midazolam as substrate after 24 hrs by LC-MS/MS analysis Homo sapiens 44.0 nM
Inhibition of CYP3A5 in lentiviral pLVX-TRE3G-ZsGreen1-CYP3A5 transduced wild type human AsPC1 cells overexpressing CYP3A5 assessed as decrease in 1-hydroxymidazolam formation using midazolam as substrate after 24 hrs by LC-MS/MS analysis Homo sapiens 78.0 nM
Inhibition of CYP3A5 in doxycycline-induced CYP3A5 overexpressing wild type human AsPC1 cells assessed as decrease in 1-hydroxymidazolam formation using midazolam as substrate pretreated with doxycycline for 24 hrs followed by incubation with compound for 24 hrs by LC-MS/MS analysis Homo sapiens 21.0 nM
Inhibition of CYP3A5 in CRISPR/Cas9-mediated CYP3A5 knock-out and doxycycline-induced CYP3A5 overexpressing human AsPC1 cells assessed as decrease in 1-hydroxymidazolam formation using midazolam as substrate pretreated with doxycycline for 24 hrs followed by incubation with compound for 24 hrs by LC-MS/MS analysis Homo sapiens 103.0 nM
Binding affinity to heme in His-tagged CYP3A5 (unknown origin) expressed in Escherichia coli DH5alpha assessed as changes in absorbance spectra of heme-compound complex by measuring dissociation constant by UV-vis spectrophotometric titration analysis Homo sapiens 100.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 14.32 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 11.22 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.28 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.48 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.48 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.28 %

Cross References

Resources Reference
ChEBI 31414
ChEMBL CHEMBL1159650
DrugBank DB01013
DrugCentral 4452
FDA SRS 779619577M
Guide to Pharmacology 7062
PharmGKB PA164744375
PubChem 32798
SureChEMBL SCHEMBL3997
ZINC ZINC000003977767
CONTENTS