ciclesonide   Click here for help

GtoPdb Ligand ID: 7469

Synonyms: Alvesco® | Omnaris® | RPR-251526
Approved drug Immunopharmacology Ligand
ciclesonide is an approved drug (FDA (2006))
Compound class: Synthetic organic
Comment: Ciclesonide is a prodrug. The active metabolite is desisobutyrylciclesonide (PubChem CID 6918281). It is a clinically used inhalation corticosteroid/glucocorticoid drug.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 99.13
Molecular weight 540.31
XLogP 4.29
No. Lipinski's rules broken 0
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Isomeric SMILES O=C(C(C)C)OCC(=O)[C@@]12O[C@@H](O[C@@H]1C[C@@H]1[C@]2(C)C[C@H](O)[C@H]2[C@H]1CCC1=CC(=O)C=C[C@]21C)C1CCCCC1
InChI InChI=1S/C32H44O7/c1-18(2)28(36)37-17-25(35)32-26(38-29(39-32)19-8-6-5-7-9-19)15-23-22-11-10-20-14-21(33)12-13-30(20,3)27(22)24(34)16-31(23,32)4/h12-14,18-19,22-24,26-27,29,34H,5-11,15-17H2,1-4H3/t22-,23-,24-,26+,27+,29+,30-,31-,32+/m0/s1
Bioactivity Comments
The IC50 for ciclesonide at the human glucocorticoid receptor is 210 nM, compared to 1.75 nM for the active metabolite, desisobutyrylciclesonide. Ki values show the same pattern of higher affinity of desisobutyrylciclesonide (37 nM for ciclesonide vs 0.31 nM for desisobutyrylciclesonide) [1].

SARS-CoV-2: Ciclesonide is able to block SARS-CoV-2 replication in vitro, with an EC90 concentration of 6.3 μM [2] (note that this data is from a preprint article posted to bioRxiv, so has not been certified by peer review). This effect is predicted to occur through inhibition of the virus' nonstructural protein (NSP) 15. In the same assay mometasone, mifepristone and algestone also inhibited SARS-CoV-2 replication, whereas cortisone, prednisolone, dexamethasone and fluticasone did not.
Selectivity at nuclear hormone receptors
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Glucocorticoid receptor Primary target of this compound Hs Agonist Agonist 7.4 pKi - 1
pKi 7.4 (Ki 3.7x10-8 M) [1]