フルオシノロンアセトニド
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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: Androgens and antiandrogens • Estrogens and antiestrogens • Progestogens and antiprogestogens • Mineralocorticoids and antimineralocorticoids
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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
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- 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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- Dagrocorat
- Fosdagrocorat
- Mapracorat
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Antagonists
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- 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
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- See also
- Receptor/signaling modulators
- Androgenics
- Estrogenics
- Mineralocorticoidics
- Progestogenics
- Steroid metabolism modulators
- List of corticosteroids
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UpToDate Contents
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English Journal
- Emerging drugs for diabetic macular edema.
- Schwartz SG1, Flynn HW Jr, Scott IU.
- Expert opinion on emerging drugs.Expert Opin Emerg Drugs.2014 Sep;19(3):397-405. doi: 10.1517/14728214.2014.938048. Epub 2014 Aug 21.
- INTRODUCTION: Diabetic macular edema (DME) is the most common cause of visual impairment due to diabetic retinopathy. The treatment of DME has recently undergone a paradigm shift. Traditionally, photocoagulation was standard treatment, but pharmacologic therapies are becoming increasingly used for t
- PMID 25141904
- SAFETY AND EFFICACY OF FLUOCINOLONE ACETONIDE INTRAVITREAL IMPLANT (0.59 mg) IN BIRDSHOT RETINOCHOROIDOPATHY.
- Bajwa A1, Aziz K, Foster CS.
- Retina (Philadelphia, Pa.).Retina.2014 Jul 3. [Epub ahead of print]
- PURPOSE:: To report the treatment outcomes of the fluocinolone acetonide intravitreal implant (0.59 mg) in patients with birdshot retinochoroidopathy whose disease is refractory or intolerant to conventional immunomodulatory therapy.METHODS:: A retrospective case series involving 11 birdshot retinoc
- PMID 24999722
- Ciprofloxacin plus fluocinolone acetonide versus ciprofloxacin alone in the treatment of diffuse otitis externa.
- Lorente J1, Sabater F2, Rivas MP3, Fuste J4, Risco J5, Gómez M6.
- The Journal of laryngology and otology.J Laryngol Otol.2014 Jul;128(7):591-8. doi: 10.1017/S0022215114001157. Epub 2014 Jul 7.
- OBJECTIVE: We aimed to evaluate the clinical efficacy of ciprofloxacin plus fluocinolone acetonide (antibiotic plus corticosteroid) ear drops compared to ciprofloxacin (antibiotic) ear drops in diffuse otitis externa.METHODS: This was a multicentre, randomised, parallel-group, double-blind study inv
- PMID 25000552
Related Links
- Synalar (fluocinolone) treats inflammation caused by allergies, eczema, and psoriasis. Includes Synalar side effects, interactions and indications. ... Synalar side effects Get emergency medical help if you have any of these signs of ...
- Find patient medical information for Synalar topical on WebMD including its uses, side effects and safety, interactions, pictures, warnings and user ratings. ... This medication is used to treat a variety of skin conditions (e.g., eczema, dermatitis ...
Related Pictures
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- 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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