Ciclesonide

Base Information

• Chemical Name: Ciclesonide
• CAS No.: 141845-82-1
• Deprecated CAS: 141845-82-1
• Molecular Formula: C32H45O7
• Molecular Weight: 540.69
• Hs Code.: 2937229000
• European Community (EC) Number: 685-344-5
• UNII: S59502J185
• DSSTox Substance ID: DTXSID9046659
• Nikkaji Number: J561.842H
• Wikipedia: Ciclesonide
• Wikidata: Q5119448
• NCI Thesaurus Code: C65326
• RXCUI: 274964
• Pharos Ligand ID: U92GRBX86HV5
• Metabolomics Workbench ID: 146070
• ChEMBL ID: CHEMBL2040682
• Mol file: 141845-82-1.mol

Synonyms:(R)-11beta,16alpha,17,21-Tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with cyclohexanecarboxaldehyde, 21-isobutyrate;Alvesco;Omnaris;Pregna-1,4-diene-3,20-dione, 16,17-(((R)-cyclohexylmethylene)bis(oxy))-11-hydroxy-21-(2-methyl-1-oxopropoxy)-, (11beta,16alpha)-;Pregna-1,4-diene-3,20-dione, 16,17-((cyclohexylmethylene)bis(oxy))-11-hydroxy-21-(2-methyl-1-oxopropoxy)-, (11beta,16alpha(R))-;Rpr 251526;Unii-S59502J185;

Chemical Property of Ciclesonide

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 1.61E-20mmHg at 25°C
• Refractive Index: 1.575
• Boiling Point: 665°C at 760 mmHg
• Flash Point: 210°C
• PSA: 99.13000
• Density: 1.23g/cm³
• LogP: 4.70390
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 540.30870374
• Heavy Atom Count: 39
• Complexity: 1100

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(=O)OCC(=O)C12C(CC3C1(CC(C4C3CCC5=CC(=O)C=CC45C)O)C)OC(O2)C6CCCCC6
• Isomeric SMILES: CC(C)C(=O)OCC(=O)[C@@]12[C@@H](C[C@@H]3[C@@]1(C[C@@H]([C@H]4[C@H]3CCC5=CC(=O)C=C[C@]45C)O)C)O[C@H](O2)C6CCCCC6
• Recent ClinicalTrials: Comparison Between Systemic Exposure to Ciclesonide Nasal Spray, Ciclesonide HFA Nasal Aerosol and Orally Inhaled Ciclesonide (BY9010/M1-422)
• Recent EU Clinical Trials: The CIMMCov-study: A Single-center, Double-blinded, Randomized, 28-days, Parallel-group, study to evaluate the effect of Ciclesonide 320 mcg inhalation twice daily versus placebo on healthcare utilization, disease progression and symptoms in the treatment of mild-to-moderate COVID-19.
• Recent NIPH Clinical Trials: Combination therapy of favipiravir, camostat mesilate and inhaled ciclesonide for COVID-19 pneumonia
• Uses: Treatment of asthma as prophylactic therapy in adults and adolescents.

Technology Process of Ciclesonide

There total 27 articles about Ciclesonide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.3%

16,17-[(cyclohexylmethylene)bis(oxy)]-11,21-dihydroxypregna-1,4-diene-3,20-dione[11beta, 16alpha(R,S)] + 2-Methylpropionic anhydride (97-72-3) → 16,17-[(cyclohexylmethylene)bis(oxy)]-11-hydroxy-21-(2-methyl-1-oxopropoxy)pregna-1,4-diene-3,20-dione[11beta, 16alpha(R,S)] (848439-16-7,141845-82-1)

Guidance literature:

With potassium carbonate; In acetone; for 2.5h; Heating / reflux;

Reference yield: 88.0%

11β,16α,17α-trihydroxypregna-21-(2-methyl-1-oxopropoxy)-1,4-diene-3,20-dione (886861-17-2) + cyclohexanecarbaldehyde (2043-61-0) → ciclesonide (126544-47-6,141845-82-1)

Guidance literature:

With boron trifluoride; In tetrahydrofuran; dichloromethane; at 5 - 20 ℃; for 4h;

Reference yield: 84.0%

C21H28O6 + isobutyryl chloride (79-30-1) + cyclohexanecarbaldehyde (2043-61-0) → ciclesonide (141845-82-1)

Guidance literature:

C₂₁H₂₈O₆; cyclohexanecarbaldehyde; With sodium metabisulfite; perchloric acid; In chloroform; at -5 - 5 ℃;

isobutyryl chloride; With triethylamine; at -5 - 5 ℃;

upstream raw materials:

11β,16α,17α-trihydroxypregna-21-(2-methyl-1-oxopropoxy)-1,4-diene-3,20-dione

cyclohexanecarbaldehyde

desonide 21-isobutyrate

desisobutyryl ciclesonide

Downstream raw materials:

ciclesonide

Refernces

• 1、 -. "Ciclesonide preparation method". Paragraph 0016; 0017; 0021-0023; 0026-0028; 0031; 0032. . Retrieved 2019/02/13.
• 2、 -. "Pregnane derivatives 16, 17 - acetal (ketone) preparation method". Paragraph 0043-0045. . Retrieved 2017/08/31.