ciclesonide

{{Short description|Chemical compound}}

{{Use dmy dates|date=June 2024}}

{{cs1 config |name-list-style=vanc |display-authors=6}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 460035585

| image = Ciclesonide.svg

| alt =

| image2 = Ciclesonide ball-and-stick from crystal.png

| alt2 =

| tradename = Omnaris, others

| Drugs.com = {{drugs.com|monograph|ciclesonide}}

| MedlinePlus = a607008

| pregnancy_AU = B3

| pregnancy_category =

| routes_of_administration = Nasal inhalation

| ATC_prefix = R01

| ATC_suffix = AD13

| ATC_supplemental = {{ATC|R03|BA08}}

| legal_AU = S4

| legal_UK = POM

| legal_US = Rx-only

| legal_US_comment = {{cite web | title=Omnaris- ciclesonide spray | website=DailyMed | date=8 November 2022 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=15fefd46-ac7e-40d0-b635-e6c3d653c666 | access-date=29 June 2024}}{{cite web | title=Alvesco- ciclesonide aerosol, metered | website=DailyMed | date=16 February 2023 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=9f6112fb-78ef-43cf-8ae3-36370eb45468 | access-date=29 June 2024}}{{cite web | title=Zetonna- ciclesonide aerosol, metered | website=DailyMed | date=16 February 2023 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f0316d1b-9ba8-4ef3-9802-4cfed5d91d55 | access-date=29 June 2024}}{{cite web | title=Aservo Equihaler- ciclesonide spray, metered | website=DailyMed | date=16 September 2021 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=aa0d984b-4fff-4698-a78b-f21ee008956a | access-date=29 June 2024}}

| legal_EU = Rx-only

| legal_EU_comment = {{cite web | website=European Medicines Agency | title=Aservo Equihaler EPAR | date=28 February 2020 | url=https://www.ema.europa.eu/en/medicines/veterinary/EPAR/aservo-equihaler | access-date=29 June 2024}}

| legal_status =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| IUPHAR_ligand = 7469

| CAS_number_Ref = {{cascite|changed|CAS}}

| CAS_number = 126544-47-6

| PubChem = 6918155

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB01410

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 5293368

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = S59502J185

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D01703

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1201164

| 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

| C=32 | H=44 | O=7

| smiles = 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

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = LUKZNWIVRBCLON-GXOBDPJESA-N

| synonyms = (11β, 16α)-16, 17-[[(R)-cyclohexylmethylene]bis(oxy)]-11-hydroxy-21- (2-methyl-1-oxopropoxy)- pregna-1, 4-diene-3, 20-dione

}}

Ciclesonide, sold under the brand name Omnaris among others, is a glucocorticoid used to treat asthma and allergic rhinitis.

Side effects of the medication include headache, nosebleeds, and inflammation of the nose and throat linings.{{cite journal | vauthors = Mutch E, Nave R, McCracken N, Zech K, Williams FM | title = The role of esterases in the metabolism of ciclesonide to desisobutyryl-ciclesonide in human tissue | journal = Biochemical Pharmacology | volume = 73 | issue = 10 | pages = 1657–1664 | date = May 2007 | pmid = 17331475 | doi = 10.1016/j.bcp.2007.01.031 }}

It was patented in 1990 and approved for medical use in 2005.{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=488 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA488 |language=en}} The drug was approved for adults and children 12 and over by the US Food and Drug Administration in October 2006.{{cite web|url=https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/2006/ucm108773.htm|title=FDA News Release. FDA Approves New Treatment for Allergies|date=23 October 2006|publisher=Food and Drug Administration|access-date=30 July 2009}} It is on the World Health Organization's List of Essential Medicines.{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 22nd list (2021) | year = 2021 | hdl = 10665/345533 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2021.02 | hdl-access=free }}