去异丁基环索奈德
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- CAS号:
- 161115-59-9
- 英文名:
- Desisobutyryl Ciclesonide
- 英文别名:
- CIC-AP;Ciclesonide impurity B;Norpropionyl cyclosonide;Ciclesonide EP Impurity B;Desisobutyryl Ciclesonide;Ciclesonide impurity B CRS;21-Desisobutyryl Ciclesonide;Ciclesonide active principle;Desisobutyryl-ciclesonide (CIC-AP;Desisobutyryl Ciclesonide (10mM in DMSO)
- 中文名:
- 去异丁基环索奈德
- 中文别名:
- 环索奈德杂质;环索奈德杂质B;去异丁酰环索奈德;去异丁基环索奈德;去甲丙酰基环索奈德;环索奈德EP杂质B;去异丁酸酯环索奈德;去异丁酰基环索奈德;化合物 T13646;环索奈德杂质B(EP)
- CBNumber:
- CB62487016
- 分子式:
- C28H38O6
- 分子量:
- 470.61
- MOL File:
- 161115-59-9.mol
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去异丁基环索奈德化学性质
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熔点:
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129-132?C
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沸点:
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640.8±55.0 °C(Predicted)
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密度:
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1.28±0.1 g/cm3(Predicted)
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储存条件:
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-20°C Freezer
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溶解度:
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Chloroform (Slightly), Methanol (Slightly)
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酸度系数(pKa):
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12.87±0.10(Predicted)
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颜色:
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White to Off-White
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去异丁基环索奈德性质、用途与生产工艺
环索奈德，16α，17α-22R-环己基亚甲基-11β-羟基-1，4-孕甾二烯-3，20-二酮-21-异丁酸酯，是新一代的吸入性非卤代酶糖皮质甾体，具有较高局部抗炎能力，能够有效缓解患者肺部和呼吸道的炎症。它是一种酯类前药，基本无口服的生物利用度，通过内源性酯酶而活化，对全身副作用和咽部副作用极低。
(一）缩醛反应：16α，17α-22R，S-环己基亚甲基-11β-羟基-1，4-孕甾二烯-3，20-二酮-21-醋酸酯（R/S=99：10） 反应瓶中加入10g11β，16α，17α-三羟基-1，4-孕甾二烯-3，20-二酮-21-醋酸酯，30ml异丙醇和30ml70%氢氟酸，搅拌溶解，控温至0±2℃，滴加10ml环己基甲醛，保温0±2℃反应2小时，薄层分析至无原料后，稀释于冰水中，过滤，干燥得到11.8g缩醛物(1)。 （二）提纯1：16α，17α-22R，S-环己基亚甲基-11β-羟基-1，4-孕甾二烯-3，20-二酮-21-醋酸酯（R/S=99：1） 反应瓶中加入缩醛物(1)20g，氯仿30ml，乙醇40ml，加热至55℃搅拌溶解，冷却至-5℃，析出大量白色晶状固体，过滤得15.8g化合物(2)。 （三）水解反应：16α，17α-22R，S-环己基亚甲基-11β，21-二羟基-1，4-孕甾二烯-3，20-二酮（R/S=99：1，去异丁基环索奈德） 反应瓶中加入30ml甲醇和30ml二氯甲烷，加入10g化合物(2)，通氮气，降温至0℃，于一小时内滴入20ml2%KOH/甲醇溶液，保温0-5℃反应2小时，薄层分析至无原料后，加入适量醋酸中和至PH=7，减压浓缩，甲醇中重结晶，得到7.5g水解物(3)去异丁基环索奈德。
Desisobutyryl-ciclesonide 是 Ciclesonide 的活性代谢产物。Desisobutyryl-ciclesonide 对糖皮质激素受体 (glucocorticoid receptor) 具有亲和力。
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).
去异丁基环索奈德
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| 更新日期 | 产品编号 | 产品名称 | CAS编号 | 包装 | 价格 |
|---|
| 2024/04/30 | HY-111490 | 去异丁基环索奈德
Desisobutyryl-ciclesonide | 161115-59-9 | 5mg | 900元 |
| 2024/04/30 | HY-111490 | 去异丁基环索奈德
Desisobutyryl-ciclesonide | 161115-59-9 | 10mM * 1mLin DMSO | 932元 |
161115-59-9, 去异丁基环索奈德 相关搜索:
- Steroids
- Pharmaceuticals
- Intermediates & Fine Chemicals
- 高端化学
- 去异丁酰基环索奈德
- 环索奈德 EP 杂质 B(21-去异丁酰环索奈德)
- 去异丁基环索奈德(环索奈德杂质)
- 去甲丙酰基环索奈德
- 环索奈德杂质
- 去异丁酰环索奈德
- 环索奈德杂质B(EP)
- 化合物 T13646
- 环索奈德杂质B EP标准品
- 环索奈德EP杂质B
- 环索奈德杂质B
- 去异丁酸酯环索奈德
- 去异丁基环索奈德
- 161115-59-9
- (6aR,6bS,7S,8aS,8bS,10R,11aR,12aS,12bS)-10-cyclohexyl-7-hydroxy-8b-(2-hydroxyacetyl)-6a,8a-dimethyl-1,2,6a,6b,7,8,8a,8b,11a,12,12a,12b-dodecahydro-4H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-4-one
- Ciclesonide Impurity 2 (Ciclesonide EP Impurity B) (21-Desisobutyryl Ciclesonide)
- Desisobutyryl ciclesonide,Desisobutyrylciclesonide
- Norpropionyl cyclosonide
- Desisobutyryl-ciclesonide (CIC-AP
- Desisobutyryl Ciclesonide (10mM in DMSO)
- Pregna-1,4-diene-3,20-dione, 16,17-[[(R)-cyclohexylmethylene]bis(oxy)]-11,21-dihydroxy-, (11β,16α)-
- Ciclesonide EP Impurity B (21-DesisobutyrylCiclesonide)
- Ciclesonide impurity B CRS
- Ciclesonide EP Impurity B
- Ciclesonide active principle
- CIC-AP
- (11β,16α)-16,17-[[(R)-CyclohexylMethylene]bis(oxy)]-11,21-dihydroxypregna-1,4-diene-3,20-dione
- Desisobutyryl Ciclesonide
- Ciclesonide impurity B
- (2′R)-2′-Cyclohexyl-11b,21-dihydroxy-16bH-[1,3]dioxolo[4′,5′:16,17]pregna-1,4-diene-3,20-dione
- 21-Desisobutyryl Ciclesonide