Ciclesonide

Ciclesonide
Clinical data


AHFS/Drugs.com	Monograph
MedlinePlus	a607008
Pregnancy category	AU: B3 US: C (Risk not ruled out)
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
Identifiers
IUPAC name 2-[(1S, 2S, 4R, 8S, 9S,11S, 12S, 13R)-6-cyclohexyl-11-hydroxy-9, 13-dimethyl-16-oxo-5, 7-dioxapentacyclo [10.8.0.0^2,9.0^{4, 8}.0^13,18] icosa-14, 17-dien-8-yl]- 2-oxoethyl 2-methylpropanoate
Synonyms	(11β, 16α)-16, 17-[[(R)-cyclohexylmethylene]bis(oxy)]-11-hydroxy-21- (2-methyl-1-oxopropoxy)- pregna-1, 4-diene-3, 20-dione
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
Chemical and physical data
Formula	C₃₂H₄₄O₇
Molar mass	540.688 g/mol
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 is a glucocorticoid used to treat asthma and allergic rhinitis. It is marketed under the brand names Alvesco for asthma and Omnaris, Omniair, and Zetonna for hay fever in the US and Canada. Phase 3 trials for the hay fever indication outside of the US are ongoing.^[1] The drug was approved for adults and children 12 and over by the US Food and Drug Administration in October 2006.^[2] Side effects of the medication include headache, nosebleeds, and inflammation of the nose and throat linings.^[3]

References

↑ "OMNARIS/OMNAIR". Products. Nycomed International Management GmbH. 2009. Archived from the original on February 2, 2009. Retrieved 2009-07-30.
↑ "FDA NEWS RELEASE. FDA Approves New Treatment for Allergies.". Food and Drug Administration. 2006-10-23. Retrieved 2009-07-30.
↑ Mutch, Elaine; Nave, Ruediger; McCracken, Nigel; Zech, Karl; Williams, Faith M. (2007). "The role of esterases in the metabolism of ciclesonide to desisobutyryl-ciclesonide in human tissue". Biochemical Pharmacology. 73 (10): 1657–64. PMID 17331475. doi:10.1016/j.bcp.2007.01.031.

Cortisol-like and related (16-unsubstituted): Chloroprednisone
Cloprednol
Difluprednate
Fludrocortisone
Flugestone acetate (flurogestone acetate)
Fluocinolone
Fluorometholone
- Fluorometholone acetate
Fluperolone
- Fluperolone acetate
Fluprednisolone
- Fluprednisolone esters
Loteprednol
Medrysone
Methylprednisolone
- Methylprednisolone esters
Prednicarbate
Prednisolone
Prednisone
Tixocortol
- Tixocortol pivalate

Methasones and related (16-substituted): Alclometasone
Beclometasone
- Beclometasone esters
Betamethasone
- Betamethasone esters
Clobetasol
- Clobetasol propionate
Clobetasone
Clocortolone
- Clocortolone esters
Cortivazol
Desoximetasone
Dexamethasone
- Dexamethasone esters
Diflorasone
Diflucortolone
- Diflucortolone valerate
Fluclorolone
Flumetasone
Fluocortin
Fluocortolone
- Fluocortolone esters
Fluprednidene acetate
Fluticasone
- Fluticasone furoate
- Fluticasone propionate
Halometasone
Meprednisone
Mometasone
- Mometasone furoate
Paramethasone
Prednylidene
Rimexolone
Triamcinolone
Ulobetasol (halobetasol)

Cyclic ketals (16,17-cyclized): Amcinonide
Budesonide
Ciclesonide
Deflazacort
Desonide
Fluclorolone acetonide (flucloronide)
Fludroxycortide (flurandrenolone, flurandrenolide)
Flunisolide
Fluocinolone acetonide
Fluocinonide
Formocortal (fluoroformylone)
Halcinonide
Triamcinolone acetonide
- Triamcinolone acetonide esters

Antiglucocorticoids

Synthesis modifiers

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

See also: Androgens and antiandrogens • Estrogens and antiestrogens • Progestogens and antiprogestogens • Mineralocorticoids and antimineralocorticoids

Drugs for obstructive airway diseases: asthma/COPD (R03)

Adrenergics, inhalants

Short-acting β₂ agonists	Bitolterol Carbuterol Fenoterol Isoetarine Pirbuterol Procaterol Reproterol Rimiterol Salbutamol (albuterol)^#/Levosalbutamol (levalbuterol) Terbutaline Tulobuterol
Long-acting β₂ agonists	Bambuterol Clenbuterol Formoterol/Arformoterol Salmeterol Salmefamol
Ultra-long-acting β₂ agonists	Abediterol Carmoterol Indacaterol Olodaterol Vilanterol
Other	Epinephrine^# Hexoprenaline Isoprenaline (isoproterenol) Orciprenaline (metaproterenol)

Glucocorticoids

Anticholinergics/
muscarinic antagonist

Mast cell stabilizers

Xanthines

Eicosanoid inhibition

Leukotriene antagonists	Montelukast Pranlukast Zafirlukast
Arachidonate 5-lipoxygenase inhibitors	Zileuton
Thromboxane receptor antagonists	Ramatroban Seratrodast
Non-xanthine PDE4 inhibitors	Ibudilast Roflumilast

Others/unknown

Combination products

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Decongestants and other nasal preparations (R01)

Topical

Sympathomimetics, plain	Cyclopentamine Ephedrine Epinephrine Fenoxazoline Levomethamphetamine Metizoline Naphazoline Oxymetazoline Phenylephrine Propylhexedrine Tetryzoline Tramazoline Tuaminoheptane Tymazoline Xylometazoline
Antiallergic agents, excluding corticosteroids	Spaglumic acid histamine antagonists (Levocabastine Antazoline Thonzylamine) mast cell stabilizer (some are also antihistamines) (Cromoglicic acid Nedocromil Azelastine Olopatadine Lodoxamide)
Corticosteroids	Beclometasone dipropionate Betamethasone Budesonide Ciclesonide Dexamethasone Flunisolide Fluticasone Mometasone furoate Prednisolone Tixocortol Triamcinolone
Other nasal preparations	Cafaminol Calcium hexamine thiocyanate Eucalyptus oil Framycetin Hexamidine Hyaluronan Ipratropium bromide Mupirocin Retinol Ritiometan Saline water

Systemic use:
Sympathomimetics

Glucocorticoid receptor modulators

Agonists	Cortisol-like and related (16-unsubstituted): 3α,5α-Tetrahydrocorticosterone 5α-Dihydrocorticosterone 9α-Fluorocortisone (alfluorone) 11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone) 11-Dehydrocorticosterone acetate 11-Deoxycorticosterone (desoxycortone, deoxycortone, desoxycorticosterone) Desoxycortone esters 11-Deoxycortisol (cortodoxone, cortexolone) Cortifen (cortiphen, kortifen) Cortodoxone acetate 21-Deoxycortisol Δ⁷-Prednisolone Δ⁷-Prednisolone 21-acetate Amebucort Chloroprednisone Chloroprednisone acetate Cloprednol Cloprednol acetate Corticosterone Corticosterone acetate Corticosterone benzoate Cortisol (hydrocortisone) Benzodrocortisone (hydrocortisone benzoate) Hydrocortamate (hydrocortisone diethylaminoacetate) Hydrocortisone esters Cortisone Cortisone acetate Deprodone Deprodone propionate Dichlorisone Dichlorisone acetate Dichlorisone diacetate Difluprednate Endrisone (endrysone) Etiprednol Etiprednol dicloacetate (etiprednol dichloroacetate) Fludrocortisone (fludrocortone) Fludrocortisone acetate Fluorometholone Fluorometholone acetate Fluperolone Fluperolone acetate Fluprednisolone Fluprednisolone esters Halopredone Halopredone acetate (halopredone diacetate) Isoflupredone (9α-fluoroprednisolone) Isoflupredone acetate Loteprednol Loteprednol etabonate Mazipredone (depersolone) Medrysone Methylprednisolone Methylprednisolone esters Prebediolone Prebediolone acetate Prednisolone Prednazate Prednazoline Prednicarbate (prednisolone ethylcarbonate propionate) Prednimustine Prednisolamate (prednisolone diethylaminoacetate) Prednisolone esters Prednisone Prednisone esters Pregnenolone Pregnenolone acetate Pregnenolone succinate (pregnenolone hemisuccinate) Resocortol Tipredane Tixocortol Butixocort (tixocortol butyrate) Butixocort propionate Tixocortol pivalate Methasones and related (16-substituted): 16α-Methyl-11-oxoprednisolone Alclometasone Alclometasone dipropionate Amelometasone Beclometasone (beclomethasone) Beclometasone esters Betamethasone (betametasone) Betamethasone esters Cortobenzolone (betamethasone salicylate) Ciclometasone (ciclomethasone, cyclomethasone) Clobetasol Clobetasol propionate Clobetasone Clobetasone butyrate Clocortolone Clocortolone esters Cloticasone Cloticasone propionate Cormetasone (cormethasone) Cormetasone acetate Descinolone Desoximetasone (desoxymethasone) Dexamethasone (dexametasone) Dexamethasone esters Diflorasone Diflorasone diacetate Diflucortolone Diflucortolone pivalate Diflucortolone valerate Dimesone Dimesone acetate Doxibetasol (doxybetasol) Fluclorolone Flumetasone (flumethasone) Flumetasone acetate Flumetasone pivalate Fluocinolone Fluocortin Fluocortin butyl (fluocortin butylate) Fluocortolone Fluocortolone esters Fluprednidene (fluprednylidene) Fluprednidene acetate Fluticasone Fluticasone furoate Fluticasone propionate Halocortolone Halometasone Icometasone Icometasone enbutate (icometasone butyrate acetate) Isoprednidene Locicortolone (locicortone) Locicortolone dicibate (locicortone dicibate) Meclorisone Meclorisone dibutyrate Meprednisone (methylprednisone) Meprednisone acetate Meprednisone hydrogen succinate (methylprednisone hemisuccinate) Mometasone Mometasone furoate Paramethasone Paramethasone acetate Paramethasone disodium phosphate Paramethasone phosphate Prednylidene Prednylidene diethylaminoacetate Rimexolone Ticabesone Ticabesone propionate Timobesone Timobesone acetate Triamcinolone Triamcinolone diacetate Ulobetasol (halobetasol) Ulobetasol propionate Vamorolone Cyclic ketals (16,17-cyclized): Acrocinonide (triamcinolone acroleinide) Amcinafal (triamcinolone pentanonide) Amcinafide (triamcinolone acetophenide) Amcinonide (triamcinolone acetate cyclopentanonide) Budesonide Ciclesonide Cicortonide Deflazacort (azacort) Descinolone acetonide Desonide (hydroxyprednisolone acetonide) Desonide disodium phosphate Desonide pivalate Dexbudesonide Drocinonide Drocinonide phosphate Fluazacort Fluclorolone acetonide (flucloronide) Fludroxycortide (flurandrenolone, flurandrenolide) Flumoxonide Flunisolide Flunisolide acetate Fluocinolone acetonide Ciprocinonide (fluocinolone acetonide cyclopropylcarboxylate) Fluocinonide (fluocinolide, fluocinolone acetonide acetate) Procinonide (fluocinolone acetonide propionate) Formocortal Halcinonide Itrocinonide Rofleponide Rofleponide palmitate Tralonide Triamcinolone acetonide Flupamesone (triamcinolone acetonide metembonate) Triamcinolone acetonide esters Triamcinolone aminobenzal benzamidoisobutyrate (TBI-PAB) Triclonide Others/atypical (other expanded steroid ring systems, homosteroids, and non-pregnane steroids): Cortisuzol Cortivazol Domoprednate Naflocort Nicocortonide Nicocortonide acetate Nivacortol (nivazol) Oxisopred RU-28362 Non-corticosteroids with some glucocorticoid activity: 15β-Hydroxycyproterone acetate 17α-Hydroxyprogesterone Chlormadinone acetate Cyproterone Cyproterone acetate Delmadinone acetate Flugestone Flugestone acetate (flurogestone acetate) Fluoxymesterone Gestodene Medrogestone Medroxyprogesterone acetate Megestrol acetate Metribolone Norgestomet Osaterone acetate Progesterone Promegestone Quingestrone Segesterone acetate (nestorone) Tetrahydrogestrinone Nonsteroidal glucocorticoids: AZD-5423 GSK-9027
Mixed (SEGRMs)	Dagrocorat Fosdagrocorat Mapracorat
Antagonists	7α-Hydroxy-DHEA 17α-Methylprogesterone Aglepristone Asoprisnil Asoprisnil ecamate C108297 C113176 CORT-108297 Cyproterone acetate Guggulsterone Ketoconazole Lilopristone LLY-2707 Miconazole Mifepristone Onapristone ORG-34116 ORG-34517 (SCH-900636) ORG-34850 Pregnenolone 16α-carbonitrile RTI 3021–012 RTI 3021–022 Telapristone Tibolone Toripristone Ulipristal acetate

See also: Receptor/signaling modulators; Androgenics; Estrogenics; Mineralocorticoidics; Progestogenics; Steroid metabolism modulators; List of corticosteroids

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Ciclesonide

See also

References

Further reading