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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES O=C(C(C)C)OCC(=O)C12OC(OC1CC1C2(C)CC(O)C2C1CCC1=CC(=O)C=CC21C)C1CCCCC1
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
InChI Key LUKZNWIVRBCLON-GXOBDPJESA-N
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
Key to terms and symbols Click column headers to sort
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]