Ciclesonide

Ciclesonide

Systematic (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
Clinical data
AHFS/Drugs.com	monograph
MedlinePlus	a607008
Pregnancy cat.	B3(AU) C(US)
Legal status	Prescription Only (S4) (AU) POM (UK) ℞-only (US)
Identifiers
CAS number	141845-82-1 Y
ATC code	R03BA08
PubChem	CID 6918155
DrugBank	DB01410
ChemSpider	5293368 Y
UNII	S59502J185 Y
KEGG	D01703 Y
ChEMBL	CHEMBL1201164 N
Synonyms	(11β, 16α)-16, 17-[[(R)-cyclohexylmethylene]bis(oxy)]-11-hydroxy-21- (2-methyl-1-oxopropoxy)- pregna-1, 4-diene-3, 20-dione
Chemical data
Formula	C32H44O7
Mol. mass	540.688 g/mol
SMILES	eMolecules & PubChem
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
N(what is this?)  (verify)

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.

"A novel approach to minimizing the risk of toxicity from systemic absorption of an inhaled corticosteroid underlay the development of ciclesonide. This corticosteroid is inhaled as a prodrug activated by cleavage by esterases in bronchial epithelial cells. When absorbed into the circulation, the active product is tightly bound to serum proteins, 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"

Indications

Maintenance treatment in persistent asthma; hayfever.

Specific Considerations

Pregnancy

No data as yet exists, Other inhaled glucocorticoids are considered ADEC category B3.

Breastfeeding

Should be safe to use. Consult your medical professional.^{[citation needed]}

Practice Points

• Appears to be as effective as budesonide or fluticasone for maintenance treatment in persistent asthma although long term data on clinical outcomes are lacking.
• In short term studies ciclesonide had a minimal effect on markers of adrenal suppression but data with long term use is lacking. The US Food and Drug Administration (FDA) announced October 2006 the approval of ciclesonide nasal spray for the treatment of nasal symptoms associated with seasonal and perennial allergic rhinitis in adults and children 12 years of age and older.

The safety and efficacy of the nasal spray, manufactured by ALTANA Pharma US, Inc. of Florham Park, NJ, were studied in randomized placebo controlled clinical trials. The studies showed that patients treated with nasal spray had an 8-10 percent greater reduction in nasal symptoms compared to placebo, with difference between ciclesonide nasal spray and placebo significant, i.e. p<0.05.

The highest level of conversion was found in the liver, the site of inactivation of des-CIC through rapid oxidation by cytochrome P450. Carboxylesterases in bronchial epithelial cells probably contribute significantly to the conversion to des-CIC in the target organ, whereas low systemic levels of des-CIC are a result of the high metabolic clearance by the liver following CIC inhalation.

The most common side effects were headache, nosebleeds, and inflammation of the nose and throat linings.

References

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