フルオシノロンアセトニド
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2017/09/22 21:11:02」(JST)
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Fluocinolone acetonide
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Clinical data |
AHFS/Drugs.com |
International Drug Names |
Pregnancy
category |
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Routes of
administration |
Topical |
ATC code |
- C05AA10 (WHO) D07AC04 (WHO) S01BA15 (WHO) S02BA08 (WHO)
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Legal status |
Legal status |
- In general: ℞ (Prescription only)
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Pharmacokinetic data |
Metabolism |
Hepatic, CYP3A4-mediated |
Biological half-life |
1.3 to 1.7 hours |
Identifiers |
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
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CAS Number |
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PubChem CID |
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IUPHAR/BPS |
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DrugBank |
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ChemSpider |
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UNII |
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KEGG |
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ChEBI |
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ChEMBL |
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ECHA InfoCard |
100.000.607 |
Chemical and physical data |
Formula |
C24H30F2O6 |
Molar mass |
452.488 g/mol |
3D model (JSmol) |
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SMILES
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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
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Key:FEBLZLNTKCEFIT-VSXGLTOVSA-N Y
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NY (what is this?) (verify) |
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. It was first synthesized in 1959 in the Research Department of Syntex Laboratories S.A. Mexico City.[1] Preparations containing it were first marketed under the name Synalar. 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.
Fluocinolone acetonide was also found to strongly potentiate TGF-β-associated chondrogenesis of bone marrow mesenchymal stem/progenitor cells, by increasing the levels of collagen type II by more than 100 fold compared to the widely used dexamethasone.[2]
Fluocinolone acetonide intravitreal implants have been used to treat non-infectious uveitis. A systematic review could not determine whether fluocinolone acetonide implants are superior to standard of care treatment for uveitis.[3]
Flucinolone is a group V (0.025%) or group VI (0.01%) corticosteroid under US classification.
See also
- Topical steroid
- Fluocinonide
- Ciprocinonide
- Glucocorticoid
References
- ^ J S Mills, A. Bowers, Carl Djerassi and H.J. Ringold, Steroids CXXXVII. Synthesis of a New Class of Potent Cortical Hormones. 6α,9α-Difluoro-16α-Hydroxyprednisolone and its Acetonide, Journal of the American Chemical Society, 80, 3399-3404 (1960)
- ^ Hara ES, Ono M, Pham HT, Sonoyama W, Kubota S, Takigawa M, Matsumoto T, Young MF, Olsen BR, Kuboki T. Fluocinolone Acetonide is a Potent Synergistic Factor of TGF-β3-Associated Chondrogenesis of Bone Marrow-Derived Mesenchymal Stem Cells for Articular Surface Regeneration. J Bone Miner Res. 2015. http://onlinelibrary.wiley.com/doi/10.1002/jbmr.2502/abstract
- ^ Brady CJ, Villanti AC, Law HA, Rahimy E, Reddy R, Sieving PC, Garg SJ, Tang J (2016). "Corticosteroid implants for chronic non-infectious uveitis". Cochrane Database Syst Rev. 2: CD010469. PMID 26866343. doi:10.1002/14651858.CD010469.pub2.
Glucocorticoids and antiglucocorticoids (H02)
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Glucocorticoids |
Natural |
- Cortisone
- Cortodoxone (cortexolone, 11-deoxycortisol)
- Desoxycortone (deoxycortone, cortexone, 11-deoxycorticosterone)
- Hydrocortisone (cortisol)#
- Prebediolone acetate
- Pregnenolone
- Pregnenolone acetate
- Pregnenolone succinate
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Synthetic |
- Cortisol-like and related (16-unsubstituted): Chloroprednisone
- Cloprednol
- Difluprednate
- Fludrocortisone
- Flugestone acetate (flurogestone acetate)
- Fluocinolone
- Fluorometholone
- Fluperolone
- Fluprednisolone
- Loteprednol
- Medrysone
- Methylprednisolone
- Methylprednisolone esters
- Prednicarbate
- Prednisolone
- Prednisone
- Tixocortol
- Methasones and related (16-substituted): Alclometasone
- Beclometasone
- Betamethasone
- Clobetasol
- Clobetasone
- Clocortolone
- Cortivazol
- Desoximetasone
- Dexamethasone
- Diflorasone
- Diflucortolone
- Fluclorolone
- Flumetasone
- Fluocortin
- Fluocortolone
- Fluprednidene acetate
- Fluticasone
- Fluticasone furoate
- Fluticasone propionate
- Halometasone
- Meprednisone
- Mometasone
- 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
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Antiglucocorticoids |
- Antagonists: Aglepristone
- Ketoconazole
- Mifepristone
- Ulipristal acetate
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Synthesis modifiers |
- Acetoxolone
- Aminoglutethimide
- Carbenoxolone
- Enoxolone
- Ketoconazole
- Metyrapone
- Mitotane
- Trilostane
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
- See also
- Glucocorticoid receptor modulators
- Mineralocorticoids and antimineralocorticoids
- List of corticosteroids
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Vasoprotectives (C05)
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Antihemorrhoidals for topical use |
corticosteroids |
- Hydrocortisone
- Prednisolone
- Betamethasone
- Fluorometholone
- Fluocortolone
- Dexamethasone
- Fluocinolone acetonide
- Fluocinonide
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local anesthetics |
- Lidocaine
- Tetracaine
- Benzocaine
- Dibucaine
- Procaine
- Oxetacaine
- Pramocaine
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other |
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Antivaricose therapy |
heparins or heparinoids for topical use |
- Organo-heparinoid
- Sodium apolate
- Heparin
- Pentosan polysulfate
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sclerosing agents for local injection |
- Monoethanolamine oleate
- Polidocanol
- Inverted sugar syrup
- Sodium tetradecyl sulfate
- Phenol
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other |
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Capillary stabilising agents |
bioflavonoids |
- Rutoside
- Monoxerutin
- Diosmin
- Troxerutin
- Hidrosmin
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other |
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Drugs used for diseases of the ear (S02)
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Infection |
- Acetic acid
- Aluminium acetotartrate
- Aluminium triacetate (Burow's solution)
- 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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Glucocorticoid receptor modulators
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GR |
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)
- 11-Deoxycortisol (cortodoxone, cortexolone)
- Cortifen (cortiphen, kortifen)
- Cortodoxone acetate
- 21-Deoxycortisol
- Δ7-Prednisolone
- Δ7-Prednisolone 21-acetate
- Amebucort
- Chloroprednisone
- Cloprednol
- Corticosterone
- Corticosterone acetate
- Corticosterone benzoate
- Cortisol (hydrocortisone)
- Benzodrocortisone (hydrocortisone benzoate)
- Hydrocortamate (hydrocortisone diethylaminoacetate)
- Hydrocortisone esters
- Cortisone
- Deprodone
- Dichlorisone
- Dichlorisone acetate
- Dichlorisone diacetate
- Difluprednate
- Endrisone (endrysone)
- Etiprednol
- Etiprednol dicloacetate (etiprednol dichloroacetate)
- Fludrocortisone (fludrocortone)
- Fluorometholone
- Fluperolone
- Fluprednisolone
- Halopredone
- Halopredone acetate (halopredone diacetate)
- Isoflupredone (9α-fluoroprednisolone)
- Loteprednol
- Mazipredone (depersolone)
- Medrysone
- Methylprednisolone
- Methylprednisolone esters
- Prebediolone
- Prednisolone
- Prednazate
- Prednazoline
- Prednicarbate (prednisolone ethylcarbonate propionate)
- Prednimustine
- Prednisolamate (prednisolone diethylaminoacetate)
- Prednisolone esters
- Prednisone
- Pregnenolone
- Pregnenolone acetate
- Pregnenolone succinate (pregnenolone hemisuccinate)
- Resocortol
- Tipredane
- Tixocortol
- Butixocort (tixocortol butyrate)
- Tixocortol pivalate
- Methasones and related (16-substituted): 16α-Methyl-11-oxoprednisolone
- Alclometasone
- Alclometasone dipropionate
- Amelometasone
- Beclometasone (beclomethasone)
- Betamethasone (betametasone)
- Betamethasone esters
- Cortobenzolone (betamethasone salicylate)
- Ciclometasone (ciclomethasone, cyclomethasone)
- Clobetasol
- Clobetasone
- Clocortolone
- Cloticasone
- Cormetasone (cormethasone)
- Descinolone
- Desoximetasone (desoxymethasone)
- Dexamethasone (dexametasone)
- Diflorasone
- Diflucortolone
- Diflucortolone pivalate
- Diflucortolone valerate
- Dimesone
- Doxibetasol (doxybetasol)
- Fluclorolone
- Flumetasone (flumethasone)
- Flumetasone acetate
- Flumetasone pivalate
- Fluocinolone
- Fluocortin
- Fluocortin butyl (fluocortin butylate)
- Fluocortolone
- Fluprednidene (fluprednylidene)
- Fluticasone
- Fluticasone furoate
- Fluticasone propionate
- Halocortolone
- Halometasone
- Icometasone
- Icometasone enbutate (icometasone butyrate acetate)
- Isoprednidene
- Locicortolone (locicortone)
- Locicortolone dicibate (locicortone dicibate)
- Meclorisone
- Meprednisone (methylprednisone)
- Meprednisone acetate
- Meprednisone hydrogen succinate (methylprednisone hemisuccinate)
- Mometasone
- Paramethasone
- Paramethasone acetate
- Paramethasone disodium phosphate
- Paramethasone phosphate
- Prednylidene
- Prednylidene diethylaminoacetate
- Rimexolone
- Ticabesone
- Timobesone
- Triamcinolone
- Ulobetasol (halobetasol)
- 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
- Fluazacort
- Fluclorolone acetonide (flucloronide)
- Fludroxycortide (flurandrenolone, flurandrenolide)
- Flumoxonide
- Flunisolide
- Fluocinolone acetonide
- Ciprocinonide (fluocinolone acetonide cyclopropylcarboxylate)
- Fluocinonide (fluocinolide, fluocinolone acetonide acetate)
- Procinonide (fluocinolone acetonide propionate)
- Formocortal
- Halcinonide
- Itrocinonide
- Rofleponide
- 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
- 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
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Mixed
(SEGRMs) |
- Dagrocorat
- Fosdagrocorat
- Mapracorat
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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
- Relacorilant (CORT-125134)
- RTI 3021–012
- RTI 3021–022
- Telapristone
- Tibolone
- Toripristone
- Ulipristal acetate
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- See also
- Receptor/signaling modulators
- Glucocorticoids and antiglucocorticoids
- Mineralocorticoid receptor modulators
- List of corticosteroids
|
English Journal
- [Binocular Fluocinolone Acetonide Intravitreal Implant for Therapy-Resistant Diabetic Maculopathy].
- Linz K1, Auffarth GU1, Kretz FT2.
- Klinische Monatsblatter fur Augenheilkunde.Klin Monbl Augenheilkd.2015 Apr 8. [Epub ahead of print]
- PMID 25853942
- Response of Inflamed Pulps of Rat Molars after Capping with Pulp-capping Material Containing Fluocinolone Acetonide.
- Louwakul P1, Lertchirakarn V2.
- Journal of endodontics.J Endod.2015 Apr;41(4):508-12. doi: 10.1016/j.joen.2014.12.004. Epub 2015 Jan 30.
- INTRODUCTION: Capping inflamed dental pulp tissue is currently a controversial issue. To reduce pulp inflammation and stimulate pulp healing, a pulp-capping material containing fluocinolone acetonide (PCFA) has been developed. This study was aimed to evaluate the inflammatory response and hard tissu
- PMID 25649295
- Spontaneous dislocation of a fluocinolone acetonide implant (retisert) into the anterior chamber and its successful extraction in sympathetic ophthalmia.
- Almeida DR1, Chin EK, Mears K, Russell SR, Mahajan VB.
- Retinal cases & brief reports.Retin Cases Brief Rep.2015 Spring;9(2):142-4. doi: 10.1097/ICB.0000000000000119.
- PURPOSE: To report a case of spontaneous fluocinolone acetonide (Retisert) implant dislocation and migration into the anterior chamber.METHODS: Retrospective case report.PATIENTS: One patient with sympathetic ophthalmia uveitis was well controlled by fluocinolone acetonide implants.RESULTS: The fluo
- PMID 25411930
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Related Pictures
★リンクテーブル★
[★]
- 英
- fluocinolone acetonide
- ラ
- fluocinoloni acetonidum
- 商
- フルコート、フルゾン、フルベアン、フルポロン、ポリシラール、デルモラン、Fluonid, Synalar
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