A glucocorticoid receptor agonist and the active metabolite of ciclesonide
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Pro-drug Form(s)
18227Ciclesonide
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Desisobutyryl Ciclesonide

Item No. 34819

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
16α,17-[[(R)-cyclohexylmethylene]bis(oxy)]-11β,21-dihydroxy-pregna-1,4-diene-3,20-dione
CAS Number
161115-59-9
Synonyms
  • CIC-AP
  • des-CIC
Molecular Formula
C28H38O6
Formula Weight
470.6
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Methanol: Soluble
SMILES
C[C@@]12[C@@]3(C(CO)=O)[C@@](O[C@](C4CCCCC4)([H])O3)([H])C[C@@]1([H])[C@@]5([H])[C@]([C@@]6(C(CC5)=CC(C=C6)=O)C)([H])[C@H](C2)O
InChi Code
InChI=1S/C28H38O6/c1-26-11-10-18(30)12-17(26)8-9-19-20-13-23-28(22(32)15-29,27(20,2)14-21(31)24(19)26)34-25(33-23)16-6-4-3-5-7-16/h10-12,16,19-21,23-25,29,31H,3-9,13-15H2,1-2H3/t19-,20-,21-,23+,24+,25+,26-,27-,28+/m0/s1
InChi Key
OXPLANUPKBHPMS-ZXBNPROVSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $213

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    Product Description

    Desisobutyryl ciclesonide is a glucocorticoid receptor agonist and the active metabolite of the prodrug ciclesonide (Item No. 18227).1,2 It is formed from inhaled ciclesonide by intracellular esterases in the lung. Desisobutyryl ciclesonide binds to the glucocorticoid receptor (IC50 = 1.75 nM for the human receptor) and induces glucocorticoid receptor-mediated gene transactivation in a reporter assay. It inhibits concanavalin A-induced proliferation of primary rat spleen cells and human peripheral blood mononuclear cells (PBMCs; IC50s = 1.5 and 1.3 nM, respectively). Desisobutyryl ciclesonide also inhibits CD3-induced proliferation of human CD4+ lymphocytes (IC50 = 0.2 nM) and the production of cytokines in the same cells (IC50s = 0.5-1.5 nM).3 It reduces eosinophil, TNF-α, and total protein accumulation in bronchoalveolar lavage fluid (BALF) of rats sensitized and challenged with ovalbumin (ED50s = 0.7, 0.4, and 0.5 mg/kg, respectively).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Belvisi, M.G., Bundschuh, D.S., Stoeck, M., et al. Preclinical profile of ciclesonide, a novel corticosteroid for the treatment of asthma. J. Pharmacol. Exp. Ther. 314(2), 568-574 (2005).

    2. Joshi, T., Johnson, M., Newton, R., et al. An analysis of glucocorticoid receptor-mediated gene expression in BEAS-2B human airway epithelial cells identifies distinct, ligand-directed, transcription profiles with implications for asthma therapeutics. Br. J. Pharmacol. 172(5), 1360-1378 (2015).

    3. Stoeck, M., Riedel, R.T., Hochhaus, G., et al. In vitro and in vivo anti-inflammatory activity of the new glucocorticoid ciclesonide. J. Pharmacol. Exp. Ther. 309(1), 249-258 (2004).