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Merck
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Key Documents

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SML1955

Sigma-Aldrich

Ciclesonide

≥98% (HPLC)

Sinónimos:

(11,16)-16,17-[[(R)-Cyclohexylmethylene]bis(oxy)]-11-hydroxy-21-(2-methyl-1-oxopropoxy)pregna-1,4-diene-3,20-dione

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About This Item

Fórmula empírica (notación de Hill):
C32H44O7
Número de CAS:
126544-47-6
Peso molecular:
540.69
MDL number:
MFCD00866004
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

SMILES string

C[C@@]12C(CC[C@]3([H])[C@]2([H])[C@@H](O)C[C@@]4(C)[C@@]3([H])C[C@]5([H])[C@]4(O[C@@](C6CCCCC6)([H])O5)C(COC(C(C)C)=O)=O)=CC(C=C1)=O

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

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Biochem/physiol Actions

Ciclesonide is a glucocorticoid antiasthmatic prodrug. It is de-esterified in the lung to the active metabolite.
Ciclesonide is a glucocorticoid antiasthmatic prodrug; it is de-esterified in the lung to the active metabolite.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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D S Postma et al.
The European respiratory journal, 17(6), 1083-1088 (2001-08-09)
The study addressed the question whether the novel inhaled prodrug corticosteroid ciclesonide is equally effective when inhaled in the morning compared to the evening. For this purpose a double-blind, randomized, parallel group study was initiated in which 209 asthmatic patients
Wheezing in older children asthma
Respiratory medicine case reports, 686-721 (2019)
Brian S Liddell et al.
The Journal of asthma : official journal of the Association for the Care of Asthma, 54(1), 99-104 (2016-06-11)
This case series intends to highlight the association between decreased linear growth velocity and adrenal suppression in patients receiving inhaled corticosteroids for asthma. A potential treatment option is also discussed. Adrenal suppression secondary to inhaled corticosteroids has previously been reported
Michael Stoeck et al.
The Journal of pharmacology and experimental therapeutics, 309(1), 249-258 (2004-01-14)
The glucocorticoid ciclesonide is the 2'R-epimer of 2'-cyclohexyl-11beta-hydroxy-21-isobutyryloxy-16bH-dioxolo[5',4':16,17]pregna-1,4-diene-3,20-dione. The active metabolite desisobutyryl-ciclesonide (des-CIC) is derived from ciclesonide by esterase cleavage of isobutyrate at the C21 position. The relative binding affinities at the rat glucocorticoid receptor were dexamethasone, 100; ciclesonide, 12;
Jatinder Kaur Mukker et al.
Journal of pharmaceutical sciences, 105(9), 2509-2514 (2016-06-25)
Inhaled corticosteroids are used as one of the first-line drug therapy in patients with asthma. However, their long-term use is associated with various oropharyngeal and systemic side and adverse effects. Design of pro-soft drug is one of the strategies, which

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