フルオシノロン
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/02/08 10:44:21」(JST)
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Fluocinolone acetonide
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| Systematic (IUPAC) name |
| (1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one |
| Clinical data |
| AHFS/Drugs.com |
International Drug Names |
| Pregnancy cat. |
C |
| Legal status |
Prescription Only |
| Routes |
Topical |
| Pharmacokinetic data |
| Metabolism |
Hepatic, CYP3A4-mediated |
| Half-life |
1.3 to 1.7 hours |
| Identifiers |
| CAS number |
67-73-2 Y |
| ATC code |
C05AA10 D07AC04 S01BA15 S02BA08 |
| PubChem |
CID 6215 |
| DrugBank |
DB00591 |
| ChemSpider |
5980 Y |
| UNII |
0CD5FD6S2M Y |
| KEGG |
D01825 Y |
| ChEMBL |
CHEMBL989 Y |
| Chemical data |
| Formula |
C24H30F2O6 |
| Mol. mass |
452.488 g/mol |
SMILES
- O=C\1\C=C5/[C@@](/C=C/1)(C)[C@]2(F)[C@H]([C@H]3[C@](C[C@@H]2O)([C@@]4(OC(O[C@@H]4C3)(C)C)C(=O)CO)C)C[C@@H]5F
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InChI
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InChI=1S/C24H30F2O6/c1-20(2)31-19-9-13-14-8-16(25)15-7-12(28)5-6-21(15,3)23(14,26)17(29)10-22(13,4)24(19,32-20)18(30)11-27/h5-7,13-14,16-17,19,27,29H,8-11H2,1-4H3/t13-,14-,16-,17-,19+,21-,22-,23-,24+/m0/s1 Y
Key:FEBLZLNTKCEFIT-VSXGLTOVSA-N Y
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Y (what is this?) (verify)
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Fluocinolone acetonide is a corticosteroid primarily used in dermatology to reduce skin inflammation and relieve itching. It is a synthetic hydrocortisone derivative. The fluorine substitution at position 9 in the steroid nucleus greatly enhances its activity. A typical dosage strength used in dermatology is 0.01–0.025%. One such cream is sold under the brand name Flucort-N and includes the antibiotic neomycin.
See also
References
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Vasoprotectives (C05)
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| Antihemorrhoidals for topical use |
corticosteroids (Hydrocortisone, Prednisolone, Betamethasone, Fluorometholone, Fluocortolone, Dexamethasone, Fluocinolone acetonide, Fluocinonide)
local anesthetics (Lidocaine, Tetracaine, Benzocaine, Dibucaine, Procaine, Oxetacaine, Pramocaine)
other (Tribenoside)
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|
| Antivaricose therapy |
heparins or heparinoids for topical use (Organo-heparinoid, Sodium apolate, Heparin, Pentosan polysulfate)
sclerosing agents for local injection (Monoethanolamine oleate, Polidocanol, Invert sugar, Sodium tetradecyl sulfate, Phenol)
other (Calcium dobesilate)
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| Capillary stabilising agents |
bioflavonoids (Rutoside, Monoxerutin, Diosmin, Troxerutin, Hidrosmin) - other (Tribenoside, Etamsylate)
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anat (a:h/u/t/a/l,v:h/u/t/a/l)/phys/devp/cell/prot
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noco/syva/cong/lyvd/tumr, sysi/epon, injr
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proc, drug (C2s+n/3/4/5/7/8/9)
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Otologicals (S02)
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| Anti-infectives |
- Acetic acid
- Aluminium acetotartrate
- Boric acid
- Chloramphenicol
- Chlorhexidine
- Ciprofloxacin
- Clioquinol
- Gentamicin
- Hydrogen peroxide
- Miconazole
- Neomycin
- Nitrofurazone
- Ofloxacin
- Polymyxin B
- Rifamycin
- Tetracycline
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| Corticosteroids |
- Betamethasone
- Dexamethasone
- Fluocinolone acetonide
- Hydrocortisone
- Prednisolone
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| Analgesics and anesthetics |
- Lidocaine
- Cocaine
- Phenazone
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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) |
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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)
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- 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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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) |
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20,22-Desmolase
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- 22-ABC
- 3,3′-Dimethoxybenzidine
- 3-Methoxybenzidine
- Aminoglutethimide
- Cyanoketone
- Danazol
- Etomidate
- Mitotane
- Trilostane
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17α-Hydroxylase,
17,20-Lyase
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- 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
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- 4-MA
- Azastene
- Cyanoketone
- Danazol
- Epostane
- Genistein
- Gestrinone
- Metyrapone
- Norethisterone
- Oxymetholone
- Pioglitazone
- Rosiglitazone
- Trilostane
- Troglitazone
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21-Hydroxylase
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- Aminoglutethimide
- Amphenone B
- Bifonazole
- Clotrimazole
- Diazepam
- Econazole
- Genistein
- Isoconazole
- Ketoconazole
- Metyrapone
- Miconazole
- Midazolam
- Tioconazole
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11β-Hydroxylase
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- Aminoglutethimide
- Canrenone
- Etomidate
- Fadrozole
- FETO
- Ketoconazole
- Metomidate
- Metyrapone
- Mitotane
- Potassium canrenoate
- Spironolactone
- Trilostane
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18-Hydroxylase
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- Aminoglutethimide
- Canrenone
- FAD286
- Fadrozole
- Ketoconazole
- LCI699
- Metyrapone
- Mespirenone
- Potassium canrenoate
- Spironolactone
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| Other |
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Endogenous
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- 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
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- ACTH/Corticotropin
- CRH
- DHEA
- DHEA sulfate
- Plasma proteins (Transcortin, Albumin)
- Vasopressin
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Procedures
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- Adrenalectomy
- Hypophysectomy
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UpToDate Contents
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English Journal
- Fluocinolone Acetonide Is a Potent Synergistic Factor of TGF-β3-Associated Chondrogenesis of Bone Marrow-Derived Mesenchymal Stem Cells for Articular Surface Regeneration.
- Hara ES1,2, Ono M1, Pham HT1, Sonoyama W1, Kubota S3, Takigawa M4, Matsumoto T2, Young MF5, Olsen BR6, Kuboki T1.
- Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research.J Bone Miner Res.2015 Sep;30(9):1585-96. doi: 10.1002/jbmr.2502. Epub 2015 May 27.
- Articular cartilage repair remains a challenging problem. Based on a high-throughput screening and functional analysis, we found that fluocinolone acetonide (FA) in combination with transforming growth factor beta 3 (TGF-β3) strongly potentiated chondrogenic differentiation of human bone marrow-der
- PMID 25753754
- Design, characterization and skin permeating potential of Fluocinolone acetonide loaded nanostructured lipid carriers for topical treatment of psoriasis.
- Pradhan M1, Singh D2, Murthy SN3, Singh MR4.
- Steroids.Steroids.2015 Sep;101:56-63. doi: 10.1016/j.steroids.2015.05.012. Epub 2015 Jun 3.
- The aim of the current study was to develop and optimize Fluocinolone acetonide (FA) loaded nanostructured lipid carriers (NLC) and to evaluate its potential as topical delivery system for management of psoriasis. FA loaded NLCs were successfully developed by modified microemulsion method and optimi
- PMID 26049018
- Spontaneous Dissociation of Fluocinolone Acetonide Sustained Release Implant (Retisert) with Dislocation into the Anterior Chamber.
- Chang PY1, Kresch Z, Samson CM, Gentile RC.
- Ocular immunology and inflammation.Ocul Immunol Inflamm.2015 Aug 27:1-4. [Epub ahead of print]
- PURPOSE: To report two cases of spontaneous Retisert implant dissociation with dislocation of the medication reservoir into the anterior chamber.DESIGN AND METHODS: Case reports.RESULTS: Two patients with chronic, noninfectious uveitis following Retisert implantation between 6 and 7 years prior pres
- PMID 24724735
Japanese Journal
- Degradation of Corticosteroids during Activated Sludge Processing
- Miyamoto Aoi,Kitaichi Yuko,Uchikura Kazuo
- Chemical and Pharmaceutical Bulletin 62(1), 72-76, 2014
- … and 3) triamcinolone acetonide, and fluocinolone acetonide of which more than 50% remained after 24 h. …
- NAID 130003381810
- Pemphigus, discoid lupus erythematosus, and dermatomyositis during an 8-year follow-up period: a case report
- Thongprasom Kobkan,Prasongtanskul Suwan,Fongkhum Achara,Iamaroon Anak
- Journal of Oral Science 55(3), 255-258, 2013
- … There are no previous reports of pemphigus, discoid lupus erythematosus, and dermatomyositis in a Thai patient.Fluocinolone acetonide 0.1% in Orabase and systemic steroid were effective in treating oral PV in this patient. …
- NAID 130003366682
- 症例報告 尋常性痤瘡治療に用いられたフルオシノロンアセトニドによると考えられた酒皶様皮膚炎の1例
Related Links
- Fluocinolone acetonide is a corticosteroid primarily used in dermatology to reduce skin inflammation and relieve itching. It is a synthetic hydrocortisone derivative. The fluorine substitution at position 9 in the steroid nucleus greatly enhances its ...
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