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
SMILES / InChI / InChIKey
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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
References
1. Belvisi MG, Bundschuh DS, Stoeck M, Wicks S, Underwood S, Battram CH, Haddad el-B, Webber SE, Foster ML. (2005)
Preclinical profile of ciclesonide, a novel corticosteroid for the treatment of asthma.
J. Pharmacol. Exp. Ther., 314 (2): 568-74. [PMID:15878996]
2. Matsuyama S, Kawase M, Nao N, Shirato K, Ujike M, Kamitani W, Shimojima M, Fukushi S. (2020)
The inhaled corticosteroid ciclesonide blocks coronavirus RNA replication by targeting viral NSP15.
bioRxiv, Preprint. DOI: 10.1101/2020.03.11.987016