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141845-82-1 分子结构
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2-[(1S,2S,4R,8S,9S,11S,12S,13R)-6-cyclohexyl-11-hydroxy-9,13-dimethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-8-yl]-2-oxoethyl 2-methylpropanoate

ChemBase编号:1219
分子式:C32H44O7
平均质量:540.68756
单一同位素质量:540.30870375
SMILES和InChIs

SMILES:
O1[C@]2([C@@]3([C@H]([C@H]4[C@H]([C@@H](O)C3)[C@@]3(C(=CC(=O)C=C3)CC4)C)C[C@H]2OC1C1CCCCC1)C)C(=O)COC(=O)C(C)C
Canonical SMILES:
O=C(C(C)C)OCC(=O)[C@@]12OC(O[C@@H]1C[C@@H]1[C@]2(C)C[C@H](O)[C@H]2[C@H]1CCC1=CC(=O)C=C[C@]21C)C1CCCCC1
InChI:
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
InChIKey:
LUKZNWIVRBCLON-FOMURGDPSA-N

引用这个纪录

CBID:1219 http://www.chembase.cn/molecule-1219.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
2-[(1S,2S,4R,8S,9S,11S,12S,13R)-6-cyclohexyl-11-hydroxy-9,13-dimethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-8-yl]-2-oxoethyl 2-methylpropanoate
IUPAC传统名
ciclesonide
商标名
Alvesco
别名
ciclesonide
Ciclesonide
CAS号
141845-82-1
PubChem SID
160964679
46508553
PubChem CID
444033

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID
DrugBank DB01410 external link
PubChem 444033 external link
数据来源 数据ID 价格

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 14.7785225  质子受体
质子供体 LogD (pH = 5.5) 5.3232727 
LogD (pH = 7.4) 5.3232727  Log P 5.3232727 
摩尔折射率 146.2789 cm3 极化性 57.75212 Å3
极化表面积 99.13 Å2 可自由旋转的化学键
里宾斯基五规则 false 
Log P 4.08  LOG S -5.54 
溶解度 1.57e-03 g/l 

分子性质

分子性质

生物活性(PubChem)

详细说明

详细说明

DrugBank DrugBank
DrugBank -  DB01410 external link
Item Information
Drug Groups approved; investigational
Description Ciclesonide is a glucocorticoid used to treat obstructive airway diseases. It is marketed under the brand name Alvesco.
Indication For the treatment of nasal symptoms associated with seasonal and perennial allergic rhinitis in adults and adolescents 12 years of age and older.
Pharmacology Ciclesonide is a pro-drug that is enzymatically hydrolyzed to a pharmacologically active metabolite, C21-desisobutyryl-ciclesonide (des-ciclesonide or RM1) following intranasal application. Des-ciclesonide has anti-inflammatory activity with affinity for the glucocorticoid receptor that is 120 times higher than the parent compound. The precise mechanism through which ciclesonide affects allergic rhinitis symptoms is not known. Corticosteroids have been shown to have a wide range of effects on multiple cell types (e.g., mast cells, eosinophils, neutrophils, macrophages, and lymphocytes) and mediators (e.g., histamine, eicosanoids, leukotrienes, and cytokines) involved in allergic inflammation.
Affected Organisms
Humans and other mammals
Biotransformation Des-ciclesonide undergoes metabolism in the liver to additional metabolites mainly by the cytochrome P450 (CYP) 3A4 isozyme and to a lesser extent by CYP 2D6.
Absorption Ciclesonide and des-ciclesonide have negligible oral bioavailability (both less than 1%) due to low gastrointestinal absorption and high first-pass metabolism. The intranasal administration of ciclesonide at recommended doses results in negligible serum concentrations of ciclesonide.
Protein Binding The percentage of ciclesonide and des-ciclesonide bound to human plasma proteins averaged ≥ 99% each, with ≤ 1% of unbound drug detected in the systemic circulation.
Clearance * 152 L/hr [Following IV administration of 800 mcg of ciclesonide]
References
Mutch E, Nave R, McCracken N, Zech K, Williams FM: The role of esterases in the metabolism of ciclesonide to desisobutyryl-ciclesonide in human tissue. Biochem Pharmacol. 2007 May 15;73(10):1657-64. Epub 2007 Jan 28. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Mutch E, Nave R, McCracken N, Zech K, Williams FM: The role of esterases in the metabolism of ciclesonide to desisobutyryl-ciclesonide in human tissue. Biochem Pharmacol. 2007 May 15;73(10):1657-64. Epub 2007 Jan 28. Pubmed
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专利

专利

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