シクレソニド
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2013/09/21 16:21:21」(JST)
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Ciclesonide
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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) |
Routes |
nasal inhalation |
Identifiers |
CAS number |
141845-82-1 Y |
ATC code |
R01AD13 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
- 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
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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
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N (what is this?) (verify)
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Ciclesonide is a glucocorticoid used to treat asthma and allergic rhinitis. It is marketed under the brand name Alvesco for asthma and Omnaris/Omniair for hay fever in the US and Canada. Phase 3 trials for the hay fever indication outside 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[edit source | edit]
- ^ "OMNARIS/OMNAIR". Products. Nycomed International Management GmbH. 2009. Retrieved 2009-07-30. [dead link]
- ^ "FDA NEWS RELEASE. FDA Approves New Treatment for Allergies.". Food and Drug Administration. 2006-10-23. Retrieved 2009-07-30.
- ^ 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.". Biochem Pharmacol. (England: Elsevier Science) 73 (10): 1657–1664. doi:10.1016/j.bcp.2007.01.031. ISSN 0006-2952. PMID 17331475. Retrieved 2007-07-30.
- Rossi S (Ed.) (2006). Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook. ISBN 0-9757919-2-3
Drugs for obstructive airway diseases: asthma/COPD (R03)
|
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Adrenergics, inhalants |
Short acting β2-agonists |
- Bitolterol
- Carbuterol
- Fenoterol
- Pirbuterol
- Procaterol
- Reproterol
- Rimiterol
- Salbutamol#/Levosalbutamol
- Terbutaline
- Tulobuterol
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|
Long acting β2-agonists (LABA) |
- Arformoterol
- Bambuterol
- Clenbuterol
- Formoterol
- Olodaterol
- Salmeterol
- Ultra LABA: Indacaterol
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|
other |
- Epinephrine#
- Hexoprenaline
- Isoprenaline (Isoproterenol)
- Orciprenaline (Metaproterenol)
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|
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Glucocorticoids |
- Beclometasone#
- Betamethasone
- Budesonide
- Ciclesonide
- Flunisolide
- Fluticasone
- Mometasone
- Triamcinolone
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Anticholinergics/
muscarinic antagonist |
- Aclidinium bromide
- Glycopyrronium bromide
- Ipratropium bromide#
- Oxitropium bromide
- Tiotropium bromide
|
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Mast cell stabilizers |
|
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Xanthines |
- Doxofylline
- Enprofylline
- Theobromine
- Theophylline/Aminophylline/Choline theophyllinate
|
|
Eicosanoid inhibition |
Leukotriene antagonists |
- Montelukast
- Pranlukast
- Zafirlukast
|
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Lipoxygenase inhibitor |
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Thromboxane receptor antagonists |
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Combination products |
- Budesonide/formoterol
- Fluticasone/salmeterol
- Ipratropium bromide/salbutamol
- Mometasone/formoterol
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|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
anat (n, x, l, c)/phys/devp
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noco (c, p)/cong/tumr, sysi/epon, injr
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proc, drug (R1/2/3/5/6/7)
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Decongestants and other nasal preparations (R01)
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Topical |
Sympathomimetics, plain
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- Cyclopentamine
- Ephedrine
- Phenylephrine
- Oxymetazoline
- Tetryzoline
- Xylometazoline
- Naphazoline
- Tramazoline
- Metizoline
- Tuaminoheptane
- Fenoxazoline
- Tymazoline
- Epinephrine
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Antiallergic agents,
excluding corticosteroids
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- histamine antagonists (Levocabastine
- Antazoline
- Thonzylamine)
- mast cell stabilizer (some are also antihistamines) (Cromoglicic acid
- Nedocromil
- Azelastine
- Olopatadine
- Lodoxamide)
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Corticosteroids
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- Beclometasone
- Prednisolone
- Dexamethasone
- Flunisolide
- Budesonide
- Betamethasone
- Tixocortol
- Fluticasone
- Mometasone furoate
- Triamcinolone
- Ciclesonide
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Other nasal preparations
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- Cafaminol
- Calcium hexamine thiocyanate
- Retinol
- Ipratropium bromide
- Ritiometan
- Mupirocin
- Hexamidine
- Framycetin
- Hyaluronic acid
- Eucalyptus oil
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Systemic use:
Sympathomimetics |
- Phenylpropanolamine
- Pseudoephedrine (+loratadine)
- Phenylephrine
- Phenylpropylamine
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anat (n, x, l, c)/phys/devp
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noco (c, p)/cong/tumr, sysi/epon, injr
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proc, drug (R1/2/3/5/6/7)
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Corticosteroids – glucocorticoids and mineralocorticoids (H02)
(also A07EA, C05AA, D07, D10AA, R01AD, R03BA, S01BA, S02B, and S03B)
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Mineralocorticoids
(3-one, 4-ene,
no FG at 16) |
- Pregnenedione: ALDOSTERONE
- 11-DEOXYCORTICOSTERONE
- HALOGENATED AT 9: Fludrocortisone
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Glucocorticoids
(3-one, 4-ene,
11-FG,
17-hydroxy) |
Pregnene
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Pregnenedione
(+20-one)
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- HYDROCORTISONE/CORTISOL# (Hydrocortisone aceponate
- Hydrocortisone buteprate
- Hydrocortisone butyrate)
- Budesonide
- Ciclesonide
- Deflazacort
- Medrysone
- Tixocortol
- HALOGENATED AT 6: Cloprednol
- HALOGENATED, WITH FG AT 16: Halcinonide
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Pregnadiene (+1-ene)
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- Rimexolone
- HALOGENATED, WITH FG AT 16: Flunisolide
- Triamcinolone
- Amcinonide
- Fluocinolone acetonide (Fluocinonide)
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Pregnadienediol
(+21-hydroxy)
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- Prednisone (Meprednisone)
- HALOGENATED AT 9: Fluorometholone
- HALOGENATED, WITH FG AT 16: Fluocortolone (Clocortolone
- Diflucortolone
- Fluocortin)
- Desoximetasone
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Pregnadienetriol
(+11-hydroxy)
|
- Prednisolone# (Methylprednisolone
- Methylprednisolone aceponate
- Prednicarbate
- Prednylidene)
- Desonide
- HALOGENATED: Fluprednisolone (Difluprednate
- Fluperolone)
- HALOGENATED, WITH FG AT 16: Dexamethasone#
- Betamethasone (Clobetasol
- Clobetasone
- Diflorasone
- Halometasone
- Ulobetasol)
- Beclometasone
- Paramethasone
- Alclometasone
- Fluclorolone acetonide
- Flumetasone
- Fluprednidene
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Pregnatriene
(+2-ene)
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|
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Androstene
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- HALOGENATED, WITH FG AT 16: Fluticasone (Fluticasone propionate
- Fluticasone furoate)
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Other/ungrouped
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- HALOGENATED: Loteprednol
- HALOGENATED, WITH FG AT 16: Fludroxycortide
- Formocortal
- Mometasone furoate
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Aldosterone antagonists |
- Spironolactone
- Eplerenone
- Potassium canrenoate
- Canrenone
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Synthesis modifiers |
- Trilostane
- Carbenoxolone
- Aminoglutethimide
- Metyrapone
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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noco (d)/cong/tumr, sysi/epon
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proc, drug (A10/H1/H2/H3/H5)
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Glucocorticoids
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Receptor |
|
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Enzyme
(inhibitors) |
20,22-Desmolase
|
- 22-ABC
- 3,3′-Dimethoxybenzidine
- 3-Methoxybenzidine
- Aminoglutethimide
- Cyanoketone
- Danazol
- Etomidate
- Mitotane
- Trilostane
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|
17α-Hydroxylase,
17,20-Lyase
|
- 22-ABC
- 22-Oxime
- Abiraterone
- Bifonazole
- Clotrimazole
- Cyanoketone
- Cyproterone
- Danazol
- Econazole
- Galeterone
- Gestrinone
- Isoconazole
- Ketoconazole
- L-39
- Liarozole
- LY-207,320
- MDL-27,302
- Miconazole
- Mifepristone
- Orteronel
- Pioglitazone
- Rosiglitazone
- Spironolactone
- Stanozolol
- SU-10,603
- TGF-β
- Tioconazole
- Troglitazone
- VN/87-1
- YM116
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3β-HSD
|
- 4-MA
- Azastene
- Cyanoketone
- Danazol
- Epostane
- Genistein
- Gestrinone
- Metyrapone
- Norethisterone
- Oxymetholone
- Pioglitazone
- Rosiglitazone
- Trilostane
- Troglitazone
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|
21-Hydroxylase
|
- Aminoglutethimide
- Amphenone B
- Bifonazole
- Clotrimazole
- Diazepam
- Econazole
- Genistein
- Isoconazole
- Ketoconazole
- Metyrapone
- Miconazole
- Midazolam
- Tioconazole
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|
11β-Hydroxylase
|
- Aminoglutethimide
- Canrenone
- Etomidate
- Fadrozole
- FETO
- Ketoconazole
- Metomidate
- Metyrapone
- Mitotane
- Potassium canrenoate
- Spironolactone
- Trilostane
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18-Hydroxylase
|
- Aminoglutethimide
- Canrenone
- FAD286
- Fadrozole
- Ketoconazole
- LCI699
- Metyrapone
- Mespirenone
- Potassium canrenoate
- Spironolactone
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|
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Other |
Endogenous
|
- Glucocorticoids: Corticosterone
- Cortisone
- Cortodoxone/Deoxycortisol
- Hydrocortisone/Cortisol
- Antiglucocorticoids: 17-Hydroxyprogesterone
- Deoxycorticosterone
- Pregnenolone
- Progesterone
- Precursors: Cholesterol
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- Pregnenolone
- 17-Hydroxypregnenolone
- 17-Hydroxyprogesterone
- Progesterone
- Deoxycorticosterone
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Indirect
|
- ACTH/Corticotropin
- CRH
- DHEA
- DHEA sulfate
- Plasma proteins (Transcortin, Albumin)
- Vasopressin
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Procedures
|
- Adrenalectomy
- Hypophysectomy
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UpToDate Contents
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English Journal
- Differences in Adherence to Common Inhaled Medications in COPD.
- Huurne KK1, Movig K, van der Valk P, van der Palen J, Brusse-Keizer M.
- COPD.COPD.2015 Aug 19:1-6. [Epub ahead of print]
- OBJECTIVE: To study differences in adherence to common inhaled medications in COPD.METHODS: Adherence of 795 patients was recorded from pharmacy records over 3 years in the COMIC cohort. It was expressed as percentage and deemed good at ≥75-≤125%, sub-optimal ≥50-<75%, and poor <50% (un
- PMID 25775100
- Formoterol synergy with des-ciclesonide inhibits IL-4 expression in IgE/antigen-induced mast cells by inhibiting JNK activation.
- Sun YH1, Ge LT2, Jiang JX1, Shen HJ1, Jia YL1, Dong XW1, Sun Y2, Xie QM3.
- European journal of pharmacology.Eur J Pharmacol.2015 Aug 15;761:161-7. doi: 10.1016/j.ejphar.2015.05.008. Epub 2015 May 19.
- Inhaled corticosteroid (ICS) therapy in combination with long-acting β-adrenergic agonists (LABA) is the most important treatment for allergic asthma, although the mechanism still remains unclear. However, mast cells play a central role in the pathogenesis of asthma. In this study, we explored the
- PMID 26003274
- Evidence of hypothalamic-pituitary-adrenal axis suppression during moderate-to-high-dose inhaled corticosteroid use.
- Cavkaytar O1, Vuralli D, Arik Yilmaz E, Buyuktiryaki B, Soyer O, Sahiner UM, Kandemir N, Sekerel BE.
- European journal of pediatrics.Eur J Pediatr.2015 Aug 9. [Epub ahead of print]
- The possible risk of adverse effects due to regular use of inhaled corticosteroids (ICS) is a real concern. Our aim was to describe the factors that have an impact on hypothalamic-pituitary-adrenal axis suppression (HPA-AS) in children and adolescents taking ICS regularly. The HPA axis status of pat
- PMID 26255048
Japanese Journal
- 気管支喘息におけるシクレソニド(HFA-CIC)の末梢気道病変に対する治療効果の検討
- 血清IgE低値でアレルゲンが明瞭でない重症喘息にオマリズマブが奏効した1例
- 杉野 安輝,三田 亮,高木 康之,加藤 誠章,大田 亜希子,奥村 隼也,長井 秀明
- アレルギー 59(11), 1572-1579, 2010-11-30
- 症例は49歳女性.高用量吸入ステロイド(フルチカゾン1000μg/日+シクレソニド800μg/日),サルメテロール吸入(100μg/日),ベタメサゾン内服(1mg/日)を中心とする多剤併用療法にても喘息コントロールが得られない重症難治性喘息であった.血清総IgE値は9(IU/mL)と低値で,明らかな通年性アレルゲンも認められなかったが,患者同意のもと2009年8月からオマリズマブ150mgを投与し …
- NAID 110007989019
Related Links
- Ciclesonide is a prescription medication used to treat nasal symptoms from seasonal and year-round allergies. It is... ... Common side effects with ciclesonide nasal spray include: headache nose bleeds stuffy nose ear pain sore ...
- 吸入ステロイド喘息治療薬シクレソニド(ciclesonide : オルベスコ_【 !R】インヘラー)の薬理学的特徴と臨床効果 ... オルベスコ®インヘラーは新規のプロドラッグ型ステロイドであるシクレソニドを主薬とする定量噴霧式エアゾール剤 ...
★リンクテーブル★
[★]
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