Tìm theo
Ciclesonide
Thuốc Gốc
Small Molecule
CAS: 141845-82-1
ATC: R03BA08
ĐG : 3M Health Care , http://www.3m.com
CTHH: C32H44O7
PTK: 540.6876
Ciclesonide is a glucocorticoid used to treat obstructive airway diseases. It is marketed under the brand name Alvesco.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C32H44O7
Phân tử khối
540.6876
Monoisotopic mass
540.308703762
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
InChI Key
InChIKey=LUKZNWIVRBCLON-FOMURGDPSA-N
IUPAC Name
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
Traditional IUPAC Name
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
SMILES
[H][C@@]12C[C@@]3([H])[C@]4([H])CCC5=CC(=O)C=C[C@]5(C)[C@@]4([H])[C@@H](O)C[C@]3(C)[C@@]1(OC(O2)C1CCCCC1)C(=O)COC(=O)C(C)C
Độ hòa tan
1.57e-03 g/l
logP
5.32
logS
-5.5
pKa (strongest acidic)
14.78
pKa (Strongest Basic)
-2.9
PSA
99.13 Å2
Refractivity
146.28 m3·mol-1
Polarizability
60.21 Å3
Rotatable Bond Count
6
H Bond Acceptor Count
6
H Bond Donor Count
1
Physiological Charge
0
Number of Rings
6
Bioavailability
0
MDDR-Like Rule
true
Dược Lực Học : 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.
Cơ Chế Tác Dụng : Ciclesonide is a glucocorticoid used to treat obstructive airway diseases. It is marketed under the brand name Alvesco. Glucocorticoids such as ciclesonide can inhibit leukocyte infiltration at the site of inflammation, interfere with mediators of inflammatory response, and suppress humoral immune responses. The antiinflammatory actions of glucocorticoids are thought to involve phospholipase A2 inhibitory proteins, lipocortins, which control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes. Ciclesonide reduces inflammatory reaction by limiting the capillary dilatation and permeability of the vascular structures. These compounds restrict the accumulation of polymorphonuclear leukocytes and macrophages and reduce the release of vasoactive kinins. Recent research suggests that corticosteroids may inhibit the release of arachidonic acid from phospholipids, thereby reducing the formation of prostaglandins. Ciclesonide is a glucocorticoid receptor agonist. On binding, the corticoreceptor-ligand complex translocates itself into the cell nucleus, where it binds to many glucocorticoid response elements (GRE) in the promoter region of the target genes. The DNA bound receptor then interacts with basic transcription factors, causing an increase or decrease in expression of specific target genes, including suppression of IL2 (interleukin 2) expression.
Dược Động Học :
▧ 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.
▧ Metabolism :
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.
▧ Clearance :
* 152 L/hr [Following IV administration of 800 mcg of ciclesonide]
Chỉ Định : For the treatment of nasal symptoms associated with seasonal and perennial allergic rhinitis in adults and adolescents 12 years of age and older.
Tương Tác Thuốc :
  • Itraconazole Increased effects/toxicity of ciclesonide
  • Ketoconazole Increased effects/toxicity of ciclesonide
  • Nelfinavir Increased effects/toxicity of ciclesonide
  • Ritonavir Increased effects/toxicity of ciclesonide
  • Telithromycin Telithromycin may reduce clearance of Ciclesonide. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Ciclesonide if Telithromycin is initiated, discontinued or dose changed.
  • Voriconazole Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of ciclesonide by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of ciclesonide if voriconazole is initiated, discontinued or dose changed.
Liều Lượng & Cách Dùng : Aerosol, metered - Nasal
Aerosol, metered - Respiratory (inhalation)
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Alvesco
  • Công ty :
    Sản phẩm biệt dược : Omnaris
  • Công ty :
    Sản phẩm biệt dược : Omniair
  • Công ty :
    Sản phẩm biệt dược : Zetonna
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB01410
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=444033
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46508553
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D01703
ChemSpider
http://www.chemspider.com/Chemical-Structure.392056.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/63402-711-01
PharmGKB
http://www.pharmgkb.org/drug/PA164781399
Wikipedia
http://en.wikipedia.org/wiki/Ciclesonide
RxList
http://www.rxlist.com/cgi/generic/omnaris.htm
Drugs.com
http://www.drugs.com/cdi/ciclesonide-spray.html
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