Ciclesonide

Names

[ Name ]:
Ciclesonide

[Synonym ]:
2-[(4aR,4bS,5S,6aS,6bS,8R,9aR,10aS,10bS)-8-Cyclohexyl-5-hydroxy-4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,9a,10,10a,10b,11,12-dodecahydro-6bH-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-6b-yl]-2-oxoethyl-2-methylpropanoat
(R)-11b,16a,17,21-Tetrahydroxypregna-1,4-diene-3,20-dione Cyclic 16,17-Acetal with Cyclohexanecarboxaldehyde 21-Isobutyrate
2-méthylpropanoate de 2-[(4aR,4bS,5S,6aS,6bS,8R,9aR,10aS,10bS)-8-cyclohexyl-5-hydroxy-4a,6a-diméthyl-2-oxo-2,4a,4b,5,6,6a,9a,10,10a,10b,11,12-dodécahydro-6bH-naphto[2',1':4,5]indéno[1,2-d][1,3]dioxol-6b-yl]-2-oxoéthyle
Propanoic acid, 2-methyl-, 2-[(4aR,4bS,5S,6aS,6bS,8R,9aR,10aS,10bS)-8-cyclohexyl-2,4a,4b,5,6,6a,9a,10,10a,10b,11,12-dodecahydro-5-hydroxy-4a,6a-dimethyl-2-oxo-6bH-naphth[2',1':4,5]indeno[1,2-d][1,3]dioxol-6b-yl]-2-oxoethyl ester
2-[(4aR,4bS,5S,6aS,6bS,8R,9aR,10aS,10bS)-8-Cyclohexyl-5-hydroxy-4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,9a,10,10a,10b,11,12-dodecahydro-6bH-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-6b-yl]-2-oxoethyl 2-methylpropanoate
2-méthylpropanoate de 2-[(4aR,4bS,5S,6aS,6bS,8R,9aR,10aS,10bS)-8-cyclohexyl-5-hydroxy-4a,6a-diméthyl-2-oxo-2,4a,4b,5,6,6a,9a,10,10a,10b,11,12-dodécahydro-6bH-naphto[2',1':4,5]indéno[1,2-d][1,3]dioxol-
Alvesco
Ciclesonide
propanoic acid, 2-methyl-, 2-[(4aR,4bS,5S,6aS,6bS,8R,9aR,10aS,10bS)-8-cyclohexyl-2,4a,4b,5,6,6a,9a,10,10a,10b,11,12-dodecahydro-5-hydroxy-4a,6a-dimethyl-2-oxo-6bH-naphth[2',1':4,5]indeno[1,2-d][1,3]di

Biological Activity

[Description]:

Ciclesonide(RPR251526) is a glucocorticoid used to treat obstructive airway diseases.Target: Glucocorticoid ReceptorCiclesonide (CIC) is an inhaled glucocorticosteroid. CIC (5 microM) was rapidly hydrolyzed by NHBE cells (approximately 30% conversion at 4h), with almost complete conversion by 24h. In liver and NHBE cells, major involvement of cytosolic carboxylesterases, with some contribution by cholinesterases, was indicated. The highest level of conversion was found in the liver, the site of inactivation of des-CIC through rapid oxidation by cytochrome P450. Carboxylesterases in bronchial epithelial cells probably contribute significantly to the conversion to des-CIC in the target organ, whereas low systemic levels of des-CIC are a result of the high metabolic clearance by the liver following CIC inhalation [1]. Ciclesonide may have some advantage although it is not as yet licensed in all countries for paediatric use [2].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Glucocorticoid Receptor

Research Areas >> Inflammation/Immunology

[References]

[1]. Mutch, E., et al., The role of esterases in the metabolism of ciclesonide to desisobutyryl-ciclesonide in human tissue. Biochem Pharmacol, 2007. 73(10): p. 1657-64.

[2]. Barnes, N.C., The properties of inhaled corticosteroids: similarities and differences. Prim Care Respir J, 2007. 16(3): p. 149-54.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.23 g/cm3

[ Boiling Point ]:
665ºC at 760 mmHg

[ Melting Point ]:
202-209?C

[ Molecular Formula ]:
C₃₂H₄₄O₇

[ Molecular Weight ]:
540.68800

[ Flash Point ]:
210ºC

[ Exact Mass ]:
540.30900

[ PSA ]:
99.13000

[ LogP ]:
4.70390

[ Vapour Pressure ]:
1.61E-20mmHg at 25°C

[ Index of Refraction ]:
1.575

[ Storage condition ]:
Refrigerator

Safety Information

[ HS Code ]:
2937229000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2937229000