Ciclesonide

Ciclesonide

Clinical data
Trade names	Omnaris, others
Other names	(11β, 16α)-16, 17-[[(R)-cyclohexylmethylene]bis(oxy)]-11-hydroxy-21- (2-methyl-1-oxopropoxy)- pregna-1, 4-diene-3, 20-dione
AHFS/Drugs.com	Monograph
MedlinePlus	a607008
Pregnancy category	AU:B3
Routes of administration	Nasal inhalation
ATC code	R01AD13 ( WHO ) R03BA08 ( WHO )
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only [1] [2] [3] [4] EU:Rx-only [5]
Identifiers
IUPAC name 2-[(1S, 2S, 4R, 8S, 9S,11S, 12S, 13R)-6-cyclohexyl-11-hydroxy-9, 13-dimethyl-16-oxo-5, 7-dioxapentacyclo [10.8.0.02,9.04, 8.013,18] icosa-14, 17-dien-8-yl]- 2-oxoethyl 2-methylpropanoate
CAS Number	126544-47-6  N
PubChem CID	6918155
IUPHAR/BPS	7469
DrugBank	DB01410  Y
ChemSpider	5293368  Y
UNII	S59502J185
KEGG	D01703  Y
ChEMBL	ChEMBL1201164  N
CompTox Dashboard (EPA)	DTXSID9046659
ECHA InfoCard	100.210.908
Chemical and physical data
Formula	C32H44O7
Molar mass	540.697 g·mol−1
3D model (JSmol)	Interactive image
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
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 Y Key:LUKZNWIVRBCLON-GXOBDPJESA-N Y
NY  (what is this?)    (verify)

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. ^[6]

It was patented in 1990 and approved for medical use in 2005. ^[7] The drug was approved for adults and children 12 and over by the US Food and Drug Administration in October 2006. ^[8] It is on the World Health Organization's List of Essential Medicines. ^[9]

Society and culture

Brand names

It is marketed under the brand names Alvesco for asthma and Omnaris, Omniair, Zetonna, and Alvesco for hay fever in the US and Canada.

References

1. "Omnaris- ciclesonide spray". DailyMed. 8 November 2022. Retrieved 29 June 2024.
2. "Alvesco- ciclesonide aerosol, metered". DailyMed. 16 February 2023. Retrieved 29 June 2024.
3. "Zetonna- ciclesonide aerosol, metered". DailyMed. 16 February 2023. Retrieved 29 June 2024.
4. "Aservo Equihaler- ciclesonide spray, metered". DailyMed. 16 September 2021. Retrieved 29 June 2024.
5. "Aservo Equihaler EPAR". European Medicines Agency. 28 February 2020. Retrieved 29 June 2024.
6. Mutch E, Nave R, McCracken N, Zech K, Williams FM (May 2007). "The role of esterases in the metabolism of ciclesonide to desisobutyryl-ciclesonide in human tissue". Biochemical Pharmacology. 73 (10): 1657–1664. doi:10.1016/j.bcp.2007.01.031. PMID   17331475.
7. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 488. ISBN   9783527607495.
8. "FDA News Release. FDA Approves New Treatment for Allergies". Food and Drug Administration. 23 October 2006. Archived from the original on 9 July 2009. Retrieved 30 July 2009.
9. World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl: 10665/345533 . WHO/MHP/HPS/EML/2021.02.

Further reading

• Rossi S, ed. (2006). Australian Medicines Handbook. Adelaide: Australian Medicines Handbook. ISBN   0-9757919-2-3.