Ciclesonide active principle
Desisobutyryl Ciclesonide
CAS: 161115-59-9
Molecular Formula: C28H38O6
Ciclesonide active principle - Names and Identifiers
Ciclesonide active principle - Physico-chemical Properties
| Molecular Formula | C28H38O6 |
| Molar Mass | 470.61 |
| Density | 1.28±0.1 g/cm3(Predicted) |
| Melting Point | 129-132?C |
| Boling Point | 640.8±55.0 °C(Predicted) |
| Solubility | Chloroform (Slightly), Methanol (Slightly) |
| Appearance | neat |
| Color | White to Off-White |
| pKa | 12.87±0.10(Predicted) |
| Storage Condition | -20°C Freezer |
| In vitro study | 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). |
Ciclesonide active principle - References
| Introduction | ciclesonide, 16α,17α-22R-cyclohexylmethylene -11 β-hydroxy -1, 4-pregnadiene-3, 20-diketo-21-isobutyrate is a new generation of inhaled non-halogenated enzyme glucocorticosteroids with high local anti-inflammatory ability, can effectively relieve the patient's lung and respiratory tract inflammation. It is a kind of ester prodrug, basically without oral bioavailability, activated by endogenous esterase, and has very low systemic side effects and pharyngeal side effects. |
| preparation | (I) acetal reaction: 16α,17α-22R,S-cyclohexylmethylene -11 β-hydroxy-1, 4-pregnanediene-3, 20-diketo-21-acetate (R/S = 99:10) add 10g of 11 β,16 α,17 α-trihydroxy-1, 4-pregnadiene -3, 20-diketo-21-acetate to the reaction flask, 30ml of isopropyl alcohol and 30ml of 70% hydrofluoric acid, stirred and dissolved, temperature control to 0±2 ℃, Dropwise Add 10ml of cyclohexyl formaldehyde, heat preservation 0±2 ℃ for 2 hours, thin layer analysis to no raw material, diluted in ice water, filtration and drying gave 11.8g of acetal (1). (Ii) purification 1:16 α,17α-22R,S-cyclohexylmethylene-11 β-hydroxy-1, 4-pregnadiene-3, 20-diketo-21-acetate (R/S = 99:1) into the reaction bottle, 20g of acetal (1), 30ml of chloroform and 40ml of ethanol were added, and the mixture was heated to 55 ° C., stirred and dissolved, upon cooling to -5 °c, a large amount of a white crystalline solid was precipitated, and 15.8g of compound (2) was obtained by filtration. (3) hydrolysis reaction: 16α,17α-22R,S-cyclohexylmethylene-11 β,21-dihydroxy-1, 4-pregnadiene-3, 20-diketone (R/S = 99:1, to isobutyl ciclesonide) reaction bottle was added 30ml methanol and 30ml dichloromethane, 10g compound (2) was added, drop 20ml of 2% KOH/methanol solution within one hour, keep the temperature 0-5 ℃ and react for 2 hours. After thin layer analysis to no raw material, add appropriate amount of acetic acid and neutralize to PH = 7, concentration under reduced pressure and recrystallization from methanol gave 7.5g of the hydrolysate (3) desisobutylciclesonide. |
| biological activity | Desisobutyryl-ciclesonide is an active metabolite of ciclesonate. Desisobutyryl-ciclesonide has an affinity for the glucocorticoid receptor. |
| Target | Glucocorticoid receptor |
Last Update：2024-04-09 21:21:28
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