Ciclesonide

Ciclesonide

Catalog Number:
FC01365651APE
Mfr. No.:
APE-B3477
Price:
$204
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      • Overview
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          Background

          Ciclesonide is a prodrug of the potent glucocorticoid receptor agonist desisobutyryl-ciclesonide. Ciclesonide undergoes the hydrolysis process by ester cleavage at the C21 position to desisobutyryl-ciclesonide, followed by reversible formation of fatty acid esters in lung cells. Although both ciclesonide and desisobutyryl-ciclesonide are able to bind to the glucocorticoid receptor, the active metabolite desisobutyryl-ciclesonide (IC50 = 210 nM) is about 100-fold more potent than the parent compound ciclesonide (IC50 = 1.75 nM). Formulations containing ciclesonide have been used in the maintenance treatment of asthma and in the treatment of allergic rhinitis.

          1. Derendorf H, Nave R, Drollmann A, et al. Relevance of pharmacokinetics and pharmacodynamics of inhaled corticosteroids to asthma. European Respiratory Journal, 2006, 28(5): 1042-1050.
          2. Mutch E, Nave R, McCracken N, et al. The role of esterases in the metabolism of ciclesonide to desisobutyryl-ciclesonide in human tissue. Biochemical Pharmacology, 2007, 73(10): 1657-1664.
          3. Belvisi MG, Bundschuh DS, Stoeck M, et al. Preclinical profile of ciclesonide, a novel corticosteroid for the treatment of asthma. Journal of Pharmacology and Experimental Therapeutics, 2005, 314(2): 568-574.

      • Properties
        • Categories
          A glucocorticoid
          Alternative Name
          2-((6aR,6bS,7S,8aS,8bS,10R,11aR,12aS,12bS)-10-cyclohexyl-7-hydroxy-6a,8a-dimethyl-4-oxo-2,4,6a,6b,7,8,8a,8b,11a,12,12a,12b-dodecahydro-1H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-8b-yl)-2-oxoethyl isobutyrate
          CAS Number
          126544-47-6
          Molecular Formula
          C32H44O7
          Molecular Weight
          540.69
          Appearance
          A solid
          Purity
          98.00%
          Solubility
          insoluble in H2O; ≥15.8 mg/mL in DMSO; ≥50.6 mg/mL in EtOH
          Storage
          Store at -20°C
          SMILES
          CC(C(OCC([[email protected]@]12[[email protected]@](O[[email protected]@](O2)([H])C3CCCCC3)([H])C[[email protected]@]4([H])[[email protected]]([[email protected]]5([H])[[email protected]](O)([H])C[[email protected]@]41C)([H])CCC6=CC(C=C[[email protected]@]65C)=O)=O)=O)C

          * For Research Use Only

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