Desisobutyryl-ciclesonide

Modify Date: 2024-01-07 12:02:30

Desisobutyryl-ciclesonide Structure
Desisobutyryl-ciclesonide structure
Common Name Desisobutyryl-ciclesonide
CAS Number 161115-59-9 Molecular Weight 470.59800
Density 1.284g/cm3 Boiling Point 640.778ºC at 760 mmHg
Molecular Formula C28H38O6 Melting Point 129-132ºC
MSDS N/A Flash Point 211.522ºC

 Use of Desisobutyryl-ciclesonide


Desisobutyryl-ciclesonide is the active metabolite of Ciclesonide. Desisobutyryl-ciclesonide has affinity for the glucocorticoid receptor.

 Names

Name Desisobutyrylciclesonide
Synonym More Synonyms

 Desisobutyryl-ciclesonide Biological Activity

Description Desisobutyryl-ciclesonide is the active metabolite of Ciclesonide. Desisobutyryl-ciclesonide has affinity for the glucocorticoid receptor.
Related Catalog
Target

Glucocorticoid receptor[1]

In Vitro Ciclesonide, an inhaled corticosteroid with almost no affinity for the glucocorticoid receptor, is highly effective in downregulating in vitro pro-inflammatory activities of airway parenchymal cells when converted into the active metabolite Desisobutyryl-ciclesonide. Peripheral blood mononuclear cell proliferation to C. albicans is dose-dependently inhibited by 0.3-3.0 μM Ciclesonide and Desisobutyryl-ciclesonide but inhibition by Desisobutyryl-ciclesonide is higher. A significant proliferation to PhlP5 is observed only in cultures from atopic subjects: an effective downregulation is already detected at 0.03 μM Ciclesonide and 0.003 μM Desisobutyryl-ciclesonide (complete inhibition at 3 μM Ciclesonide and 0.03 μM Desisobutyryl-ciclesonide). 3 μM Ciclesonide and Desisobutyryl-ciclesonide reduce the PhlP5-specific T-cell blast proliferation and interleukin 4-producing cell proportion. In PBMCs cultures from atopic patients, both Ciclesonide (CIC) and Desisobutyryl-ciclesonide (des-CIC) induce a dose-dependent downregulation of PhlP5-induced proliferation. The effect is already significantat 0.03 μM Ciclesonide and at 0.003 μM Desisobutyryl-ciclesonide (p<0.001, each comparison),with an early complete inhibition observed at 3μM Ciclesonide and at 0.03 μM Desisobutyryl-ciclesonide. The inhibitory activity toward PhlP5-induced PBMC proliferation is higher for Desisobutyryl-ciclesonide than for Ciclesonide at 0.003 μM (p<0.05), 0.03 μM (p<0.001) and 0.3 μM (p<0.05)[1].
Cell Assay Peripheral blood mononuclear cells are isolated from non atopic and atopic asthmatic children sensitized to Phleum pratense (PhlP5). Proliferation toward Candida albicans or PhlP5 in the presence of Ciclesonide or Desisobutyryl-ciclesonide (0.003-3.0 μM) is evaluated as [3H]thymidine incorporation. Modulation of PhlP5-specific T-cell blasts proliferation and PhlP5-induced interleukin 4 expression by Ciclesonide and Desisobutyryl-ciclesonide are measured[1].
References

[1]. Silvestri M, et al. Ciclesonide modulates in vitro allergen-driven activation of blood mononuclear cells and allergen-specific T-cell blasts. Immunol Lett. 2012 Jan 30;141(2):190-6.

 Chemical & Physical Properties

Density 1.284g/cm3
Boiling Point 640.778ºC at 760 mmHg
Melting Point 129-132ºC
Molecular Formula C28H38O6
Molecular Weight 470.59800
Flash Point 211.522ºC
Exact Mass 470.26700
PSA 93.06000
LogP 3.49700
Storage condition -20°C Freezer

 Synthetic Route

~60%

Desisobutyryl-ciclesonide Structure

Desisobutyryl-c...

CAS#:161115-59-9

Literature: CORUS PHARMA, INC. Patent: WO2006/138212 A1, 2006 ; Location in patent: Page/Page column 42-43 ;

~99%

Desisobutyryl-ciclesonide Structure

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CAS#:161115-59-9

Literature: MIKASA SEIYAKU CO., LTD. Patent: US2012/59158 A1, 2012 ; Location in patent: Page/Page column 3 ;

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Desisobutyryl-ciclesonide Structure

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CAS#:161115-59-9

Literature: WO2005/63777 A1, ; Page/Page column 18; 49 ;

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Desisobutyryl-ciclesonide Structure

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CAS#:161115-59-9

Literature: WO2009/112557 A2, ; Page/Page column 6; 7 ;

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Desisobutyryl-ciclesonide Structure

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CAS#:161115-59-9

Literature: EP2392584 A1, ;

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Desisobutyryl-ciclesonide Structure

Desisobutyryl-c...

CAS#:161115-59-9

Literature: EP2392584 A1, ;

 Synonyms

desisobutyryl-ciclesonide
Des-CIC
Ciclesonide active principle
B-9207-021
CIC-AP
Ciclesonide impurity B