Ciclesonide

• CAT Number: A000036
• CAS Number: 126544-47-6
• Molecular Formula: C32H44O7
• Molecular Weight: 540.7
• Purity: ≥95%
• Synonyms: Ciclesonide, Alvesco, Omnaris, RPR251526, Zetonna
• Target: Vitamin D Related/Nuclear Receptor
• Solubility: >15.8mg/mL in DMSO
• Storage: Store at -20°C
• IUPAC Name: [2-[(1S,2S,4R,6R,8S,9S,11S,12S,13R)-6-cyclohexyl-11-hydroxy-9,13-dimethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-8-yl]-2-oxoethyl] 2-methylpropanoate
• 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
• InChIKey: LUKZNWIVRBCLON-ROPSEAAASA-N
• SMILES: O=C1C=C[C@@]2(C)C(CC[C@]3([H])[C@]2([H])[C@@H](O)C[C@@]4(C)[C@@]3([H])C[C@]5([H])[C@@]4(C(COC(C(C)C)=O)=O)O[C@H](C6CCCCC6)O5)=C1

Ciclesonide (CAS 126544-47-6) is an inhaled corticosteroids, used to ameliorate symptoms of airway inflammatory diseases, such as asthma, allergic rhinitis, and chronic obstructive pulmonary disease. Ciclesonide is a corticosteroid prodrug that is converted to its active form, desisobutyryl-CIC. Des-CIC is a glucocorticoid receptor agonist.

Overview of Clinical Research

Ciclesonide is a Glucocorticoid receptor agonist. The US FDA approved IND application for ciclesonide in COVID-2019 infections in 2020.

Reference

1: Pedersen SE, Prasad N, Goehring UM, Andersson H, Postma DS. Control of moderate-to-severe asthma with randomized ciclesonide doses of 160, 320 and 640 μg/day. J Asthma Allergy. 2017 Mar 7;10:35-46. doi: 10.2147/JAA.S111712. eCollection 2017. PubMed PMID: 28331346; PubMed Central PMCID: PMC5349703.
2: Barthwal MS, Meshram S. A randomized, double-blind study comparing the efficacy and safety of a combination of formoterol and ciclesonide with ciclesonide alone in asthma subjects with moderate-to-severe airflow limitation. Lung India. 2017 Jan-Feb;34(1):111-112. doi: 10.4103/0970-2113.197102. PubMed PMID: 28144080; PubMed Central PMCID: PMC5234188.
3: Postma DS, Dekhuijzen R, van der Molen T, Martin RJ, van Aalderen W, Roche N, Guilbert TW, Israel E, van Eickels D, Khalid JM, Herings RM, Overbeek JA, Miglio C, Thomas V, Hutton C, Hillyer EV, Price DB. Asthma-Related Outcomes in Patients Initiating Extrafine Ciclesonide or Fine-Particle Inhaled Corticosteroids. Allergy Asthma Immunol Res. 2017 Mar;9(2):116-125. doi: 10.4168/aair.2017.9.2.116. PubMed PMID: 28102056; PubMed Central PMCID: PMC5266109.
4: Mukker JK, Singh RS, Derendorf H. Ciclesonide: A Pro-Soft Drug Approach for Mitigation of Side Effects of Inhaled Corticosteroids. J Pharm Sci. 2016 Sep;105(9):2509-14. doi: 10.1016/j.xphs.2016.05.004. Epub 2016 Jun 21. PubMed PMID: 27339407.
5: Liddell BS, Oberlin JM, Hsu DP. Inhaled corticosteroid related adrenal suppression detected by poor growth and reversed with ciclesonide. J Asthma. 2017 Jan 2;54(1):99-104. doi: 10.1080/02770903.2016.1196370. Epub 2016 Jun 10. PubMed PMID: 27284755.
6: Salvi SS, Vaidya AJ, Kodgule RR, Gogtay JA. A randomized, double-blind study comparing the efficacy and safety of a combination of formoterol and ciclesonide with ciclesonide alone in asthma subjects with moderate-to-severe airflow limitation. Lung India. 2016 May-Jun;33(3):272-7. doi: 10.4103/0970-2113.180803. PubMed PMID: 27185990; PubMed Central PMCID: PMC4857562.
7: Mandaliya PH, Kennedy B, van Asperen P, Robinson PD. Ciclesonide-induced bronchospasm: an important but preventable side effect. Med J Aust. 2015 Sep 7;203(5):233-3e.1. PubMed PMID: 26852062.