Search summary:
Session ID: f4fad9367f200b168ce1b715bbb88813
Search Type: drug
Started at: 2010-07-01 11:33:52
Finished at: 2010-07-01 11:36:06
| Field | Result | Source |
|---|---|---|
| Name | ||
| ciclesonide | External | |
| Drugbank ID | ||
| DB01410 | DrugBank | |
| Description | ||
| Ciclesonide is a glucocorticoid used to treat obstructive airway diseases. It is marketed under the brand name Alvesco for asthma and Omnaris/Omniair for hayfever in the US & Canada. Phase 3 trials for the hayfever indication outside the US are ongoing. | Wikipedia | |
| 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. | DrugBank | |
| Chemical Kingdom | ||
| Organic | BioSpider | |
| Chemical Class | ||
| Not Available | Not Applicable | |
| Chemical Species | ||
| acetal | Checkmol | |
| alkene | Checkmol | |
| carboxylic acid ester | Checkmol | |
| heterocyclic compound | Checkmol | |
| ketone | Checkmol | |
| secondary alcohol | Checkmol | |
| Synonym | ||
| Alvesco | DPD | |
| Ciclesonide [inn] | Pubchem | |
| Brand Mixture | ||
| Not Available | Not Applicable | |
| CAS | ||
| 141845-82-1 | DrugBank | |
| InChI Identifier | ||
InChI=1/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 |
ChemSpider | |
| IUPAC | ||
| Not Available | Not Applicable | |
| Chemical Formula | ||
| C32H44O7 | PubChem | |
| Chemical Structure | ||
 |
Molconvert | |
| Average Molecular Weight (g/mol) | ||
| 540.687560 | BioSpider | |
| Monoisotopic Molecular Weight (g/mol) | ||
| 540.308700 | BioSpider | |
| SMILES (Isomeric) | ||
O=C(OCC(=O)[C@]25O[C@@H](O[C@@H]5C[C@H]1[C@H]4[C@H]([C@@H](O)C[C@ @]12C)[C@]/3(/C=C\C(=O)\C=C\3CC4)C)C6CCCCC6)C(C)C |
ChemSpider | |
| SMILES (Canonical) | ||
CC(C)C(=O)OCC(=O)C12C(CC3C1(CC(C4C3CCC5=CC(=O)C=CC45C)O)C)OC(O2)C 6CCCCC6 |
PubChem | |
| Kegg Drug | ||
| D01703 | DrugBank | |
| Kegg Compound | ||
| Not Available | Not Applicable | |
| Pubchem Compound ID | ||
| 444033 | DrugBank | |
| Pubchem Substance ID | ||
| 10299472 | Pubchem | |
| 16432537 | Pubchem | |
| 36887146 | Pubchem | |
| 46508553 | Pubchem | |
| 57404595 | Pubchem | |
| 75476863 | Pubchem | |
| OMIM ID | ||
| Not Available | Not Applicable | |
| ChEBI | ||
| Not Available | Not Applicable | |
| BioCyc | ||
| Not Available | Not Applicable | |
| PharmGKB | ||
| Not Available | Not Applicable | |
| HET ID | ||
| Not Available | Not Applicable | |
| DPD ID | ||
| 02285606 | DPD | |
| 02285614 | DPD | |
| Rxlist Link | ||
| http://www.rxlist.com/cgi/generic/omnaris.htm | DrugBank | |
| Wikipedia | ||
| ciclesonide | Wikipedia | |
| Pdr Health Link | ||
| http://www.pdrhealth.com/drugs/rx/rx-mono.aspx?contentFileName=alv1949.html&contentName=Alvesco&contentId=46 | PDRHealth | |
| Melting Point | ||
| Not Available | Not Applicable | |
| State | ||
| Not Available | Not Applicable | |
| MSDS Link | ||
| Not Available | Not Applicable | |
| FDA Label | ||
| Not Available | Not Applicable | |
| Experimental Water Solubility | ||
| Not Available | Not Applicable | |
| Predicted Water Solubility | ||
| 0.00157 mg/mL [Predicted by ALOGPS] | Alogps | |
| Experimental LogP | ||
| Not Available | Not Applicable | |
| Predicted LogP | ||
| 4.08 [Predicted by ALOGPS] | Alogps | |
| pKa | ||
| Not Available | Not Applicable | |
| SDF File | ||
| 1278005644.sdf | Pubchem | |
| Mol File | ||
| 1278005635.mol | Molconvert | |
| Pdb File | ||
| 1278005755.pdb | Molconvert | |
| Mass Spec File | ||
| Not Available | Not Applicable | |
| Associated Disorder | ||
| Not Available | Not Applicable | |
| Pathway | ||
| Not Available | Not Applicable | |
| Category | ||
| Not Available | Not Applicable | |
| ATC Code | ||
| R03BA08 | DPD | |
| AHFS Code | ||
| 68:04.00 | DPD | |
| Schedule | ||
| SCHEDULE F RECOMMENDED (Canada) | DPD | |
| Indication | ||
| Ciclesonide is a glucocorticoid used to treat obstructive airway diseases. It is marketed under the brand name Alvesco for asthma and Omnaris/Omniair for hayfever in the US & Canada. Phase 3 trials for the hayfever indication outside the US are ongoing. | Wikipedia | |
| For the treatment of nasal symptoms associated with seasonal and perennial allergic rhinitis in adults and adolescents 12 years of age and older. | DrugBank | |
| 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. | DrugBank | |
| Mechanism Of Action | ||
| 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. | DrugBank | |
| Absorption | ||
| "A novel approach to minimizing the risk of toxicity from systemic absorption of an inhaled corticosteroid underlay the development of ciclesonide | Wikipedia | |
| 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. | DrugBank | |
| When absorbed into the circulation, the active product is tightly bound to serum protiens, and so has little access to glucocorticoid receptors in skin, eye, and bone, minimizing its risk of causing cutaneous thinning, cataracts, osteoporosis, or temporary slowing of growth" // Maintenance treatment in persistent asthma; hayfever | Wikipedia | |
| Protein Binding | ||
| The percentage of ciclesonide and des-ciclesonide bound to human plasma proteins averaged &ge | DrugBank | |
| Half Life | ||
| Not Available | Not Applicable | |
| 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. | DrugBank | |
| Toxicity | ||
| Phase 3 trials for the hayfever indication outside the US are ongoing. "A novel approach to minimizing the risk of toxicity from systemic absorption of an inhaled corticosteroid underlay the development of ciclesonide | Wikipedia | |
| Dosage | ||
| Metered-Dose [Aerosol] (Inhalation) | DPD | |
| Patient Information | ||
| 1278005764.html | RxList | |
| Interactions | ||
| Not Available | Not Applicable | |
| Contraindications | ||
| Not Available | Not Applicable | |
| Targets | ||
P08185[ UniProt | Analyze ] |
DrugBank |