フルオシノロンアセトニド
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2017/04/27 02:33:30」(JST)
[Wiki en表示]
Fluocinolone acetonide
|
|
Clinical data |
AHFS/Drugs.com |
International Drug Names |
Pregnancy
category |
|
Routes of
administration |
Topical |
ATC code |
- C05AA10 (WHO) D07AC04 (WHO) S01BA15 (WHO) S02BA08 (WHO)
|
Legal status |
Legal status |
- In general: ℞ (Prescription only)
|
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
|
CAS Number |
|
PubChem CID |
|
IUPHAR/BPS |
|
DrugBank |
|
ChemSpider |
|
UNII |
|
KEGG |
|
ChEBI |
|
ChEMBL |
|
ECHA InfoCard |
100.000.607 |
Chemical and physical data |
Formula |
C24H30F2O6 |
Molar mass |
452.488 g/mol |
3D model (Jmol) |
|
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
|
InChI
-
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
|
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
- 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. doi:10.1002/14651858.CD010469.pub2. PMID 26866343.
Glucocorticoids and antiglucocorticoids (H02)
|
|
Glucocorticoids |
Natural |
- Cortisone
- Cortodoxone (cortexolone, 11-deoxycortisol)
- Desoxycortone (deoxycortone, cortexone, 11-deoxycorticosterone)
- Hydrocortisone (cortisol)#
- Hydrocortisone aceponate
- Hydrocortisone buteprate
- Hydrocortisone butyrate
- Prebediolone acetate
- Pregnenolone
- Pregnenolone acetate
- Pregnenolone succinate
|
|
Synthetic |
- Cortisol-like and related (16-unsubstituted): Chloroprednisone
- Cloprednol
- Difluprednate
- Fludrocortisone
- Flugestone acetate (flurogestone acetate)
- Fluocinolone
- Fluorometholone
- Fluperolone
- Fluprednisolone
- Loteprednol
- Medrysone
- Methylprednisolone
- Methylprednisolone aceponate
- Methylprednisolone acetate
- Methylprednisolone suleptanate
- Prednicarbate
- Prednisolone
- Prednisone
- Tixocortol
- Methasones and related (16-substituted): Alclometasone
- Beclometasone
- Beclometasone dipropionate
- Betamethasone
- Betamethasone dipropionate
- Clobetasol
- Clobetasone
- Clocortolone
- Cortivazol
- Desoximetasone
- Dexamethasone
- Dexamethasone acefurate
- Dexamethasone isonicotinate
- Diflorasone
- Difluocortolone
- Fluclorolone
- Flumetasone
- Fluocortin
- Fluocortolone
- Fluprednidene
- Fluticasone
- Fluticasone furoate
- Fluticasone propionate
- Halometasone
- Meprednisone
- Mometasone
- Paramethasone
- Prednylidene
- Rimexolone
- Triamcinolone
- Ulobetasol (halobetasol)
- Acetonides and related (16,17-cyclized): Amcinonide
- Budesonide
- Ciclesonide
- Deflazacort
- Desonide
- Fluclorolone acetonide (flucloronide)
- Fludroxycortide (flurandrenolone, flurandrenolide)
- Flunisolide
- Fluocinolone acetonide
- Fluocinonide
- Formocortal (fluoroformylone)
- Halcinonide
- Triamcinolone acetonide
- Triamcinolone benetonide
- Triamcinolone furetonide
- Triamcinolone hexacetonide
|
|
|
Antiglucocorticoids |
- SGRMs: Dagrocorat§
- Fosdagrocorat§
- Mapracorat†
- Antagonists: Ketoconazole
- Mifepristone
|
|
Synthesis modifiers |
- Acetoxolone
- Aminoglutethimide
- Carbenoxolone
- Enoxolone
- Ketoconazole
- Metyrapone
- Mitotane
- Trilostane
|
|
- #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
|
Vasoprotectives (C05)
|
|
Antihemorrhoidals for topical use |
corticosteroids |
- Hydrocortisone
- Prednisolone
- Betamethasone
- Fluorometholone
- Fluocortolone
- Dexamethasone
- Fluocinolone acetonide
- Fluocinonide
|
|
local anesthetics |
- Lidocaine
- Tetracaine
- Benzocaine
- Dibucaine
- Procaine
- Oxetacaine
- Pramocaine
|
|
other |
|
|
|
Antivaricose therapy |
heparins or heparinoids for topical use |
- Organo-heparinoid
- Sodium apolate
- Heparin
- Pentosan polysulfate
|
|
sclerosing agents for local injection |
- Monoethanolamine oleate
- Polidocanol
- Inverted sugar syrup
- Sodium tetradecyl sulfate
- Phenol
|
|
other |
|
|
|
Capillary stabilising agents |
bioflavonoids |
- Rutoside
- Monoxerutin
- Diosmin
- Troxerutin
- Hidrosmin
|
|
other |
|
|
Drugs used for diseases of the ear (S02)
|
|
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
|
|
Corticosteroids |
- Betamethasone
- Dexamethasone
- Fluocinolone acetonide
- Hydrocortisone
- Prednisolone
|
|
Analgesics and anesthetics |
- Lidocaine
- Cocaine
- Phenazone
|
Glucocorticoid receptor modulators
|
|
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)
- Desoxycortone acetate
- Desoxycortone cypionate (desoxycortone cyclopentanepropionate)
- Desoxycortone enanthate (desoxycortone heptanoate)
- Desoxycortone glucoside
- Desoxycortone pivalate
- 11-Deoxycortisol (cortodoxone, cortexolone)
- Cortifen (cortiphen, kortifen)
- Cortodoxone acetate
- 21-Deoxycortisol
- Δ7-Prednisolone
- Δ7-Prednisolone 21-acetate
- Amebucort
- Butixocort
- Chloroprednisone
- Cloprednol
- Corticosterone
- Corticosterone acetate
- Corticosterone benzoate
- Cortisol (hydrocortisone)
- Hydrocortamate (hydrocortisone diethylaminoacetate)
- Hydrocortisone aceponate (hydrocortisone acetate propionate)
- Hydrocortisone acetate
- Hydrocortisone bendazac
- Hydrocortisone buteprate (hydrocortisone butyrate propionate)
- Hydrocortisone cypionate (hydrocortisone cipionate)
- Hydrocortisone hemisuccinate (hydrocortisone hydrogen succinate)
- Hydrocortisone phosphate
- Hydrocortisone sodium phosphate
- Hydrocortisone sodium succinate
- Hydrocortisone tebutate
- Hydrocortisone valerate
- Hydrocortisone xanthogenate
- Hydrocortisone 17α-butyrate
- Hydrocortisone 21-butyrate
- Cortisone
- Deprodone
- Dichlorisone
- Dichlorisone acetate
- Dichlorisone diacetate
- Difluprednate
- Endrisone (endrysone)
- Etiprednol
- Etiprednol dicloacetate (etiprednol dichloroacetate)
- Fludrocortisone (fludrocortone)
- Fluorometholone
- Fluperolone
- Fluprednisolone
- Fluprednisolone acetate
- Fluprednisolone hemisuccinate
- Fluprednisolone sodium hemisuccinate
- Fluprednisolone valerate
- Halopredone
- Halopredone acetate (halopredone diacetate)
- Isoflupredone (9α-fluoroprednisolone)
- Loteprednol
- Mazipredone (depersolone)
- Medrysone
- Methylprednisolone
- Methylprednisolone aceponate (methylprednisolone acetate propionate)
- Methylprednisolone acetate
- Methylprednisolone hemisuccinate (methylprednisolone hydrogen succinate)
- Methylprednisolone sodium phosphate
- Methylprednisolone sodium succinate
- Methylprednisolone suleptanate
- Prebediolone
- Prednisolone
- Prednazate
- Prednazoline
- Prednicarbate (prednisolone ethylcarbonate propionate)
- Prednimustine
- Prednisolamate (prednisolone diethylaminoacetate)
- Prednisolone acetate
- Prednisolone disodium phosphate
- Prednisolone hydrogen tetrahydrophthalate
- Prednisolone meta-sulfobenzoate
- Prednisolone sodium meta-sulfobenzoate
- Prednisolone palmitate
- Prednisolone phosphate
- Prednisolone piperidinoacetate
- Prednisolone pivalate
- Prednisolone sodium phosphate
- Prednisolone sodium succinate
- Prednisolone sodium sulfate
- Prednisolone sodium tetrahydrophthalate
- Prednisolone steaglate (prednisolone stearoylglycolate)
- Prednisolone succinate (prednisolone hemisuccinate)
- Prednisolone sulfate
- Prednisolone tebutate
- Prednisolone valerate
- Prednisolone valeroacetate (prednisolone valerate acetate)
- Prednisone
- Prednisone acetate
- Prednisone palmitate
- Prednisone succinate
- Pregnenolone
- Pregnenolone acetate
- Pregnenolone succinate (pregnenolone hemisuccinate)
- Resocortol
- Tipredane
- Tixocortol
- Methasones and related (16-substituted): 16α-Methyl-11-oxoprednisolone
- Alclometasone
- Alclometasone dipropionate
- Amelometasone
- Beclometasone (beclomethasone)
- Beclometasone dipropionate
- Beclometasone salicylate
- Beclometasone valeroacetate (beclometasone valerate acetate)
- Betamethasone (betametasone)
- Betamethasone acetate
- Betamethasone acibutate (betamethasone acetate isobutyrate)
- Betamethasone adamantoate
- Betamethasone benzoate
- Betamethasone dipropionate
- Betamethasone divalerate
- Betamethasone phosphate
- Betamethasone salicylate
- Betamethasone sodium phosphate
- Betamethasone succinate
- Betamethasone valerate
- Betamethasone valeroacetate (betamethasone valerate acetate)
- Ciclometasone (ciclomethasone, cyclomethasone)
- Clobetasol
- Clobetasone
- Clocortolone
- Clocortolone acetate
- Clocortolone caproate
- Clocortolone pivalate
- Cloticasone
- Cormetasone (cormethasone)
- Cyclomethasone (ciclometasone)
- Descinolone
- Desoximetasone (desoxymethasone)
- Dexamethasone (dexametasone)
- Dexamethasone acefurate (dexamethasone acetate furoate)
- Dexamethasone acetate
- Dexamethasone cipecilate (dexamethasone cyclopropylcarbonate cyclohexanecarboxylate)
- Dexamethasone diethylaminoacetate
- Dexamethasone dipropionate
- Dexamethasone isonicotinate
- Dexamethasone linoleate
- Dexamethasone meta-sulphobenzoate
- Dexamethasone palmitate
- Dexamethasone phenylpropionate
- Dexamethasone phosphate
- Dexamethasone pivalate
- Dexamethasone sodium meta-sulphobenzoate
- Dexamethasone sodium phosphate
- Dexamethasone sodium sulfate
- Dexamethasone succinate
- Dexamethasone sulfate
- Dexamethasone tebutate
- Dexamethasone troxundate
- Dexamethasone 17α-valerate
- Dexamethasone 21-valerate
- Diflorasone
- Diflucortolone
- Diflucortolone pivalate
- Diflucortolone valerate
- Dimesone
- Doxibetasol (doxybetasol)
- Fluclorolone
- Flumetasone (flumethasone)
- Flumetasone acetate
- Flumetasone pivalate
- Fluocinolone
- Fluocortin
- Fluocortin butyl (fluocortin butylate)
- Fluocortolone
- Fluocortolone acetate
- Fluocortolone caproate
- Fluocortolone pivalate
- 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
- Acetonides and related (16,17-cyclized): Acrocinonide (triamcinolone acroleinide)
- Amcinafal (triamcinolone pentanonide)
- Amcinafide (triamcinolone acetophenide)
- Amcinonide (triamcinolone acetate cyclopentanonide)
- Budesonide
- Ciclesonide
- Cicortonide
- Ciprocinonide (fluocinolone acetonide)
- Deflazacort (azacort)
- Descinolone acetonide
- Desonide (hydroxyprednisolone acetonide)
- Desonide disodium phosphate
- Desonide phosphate
- Desonide pivalate
- Dexbudesonide
- Drocinonide
- Fluazacort
- Fluclorolone acetonide (flucloronide)
- Fludroxycortide (flurandrenolone, flurandrenolide)
- Flumoxonide
- Flunisolide
- Fluocinolone acetonide
- Fluocinonide (fluocinolide, fluocinolone acetonide acetate)
- Procinonide (fluocinolone acetonide propionate)
- Flupamesone (triamcinolone acetonide metembonate)
- Formocortal
- Halcinonide
- Itrocinonide
- Rofleponide
- Tralonide
- Triamcinolone acetonide
- Triamcinolone acetonide dipotassium phosphate
- Triamcinolone acetonide hemisuccinate
- Triamcinolone acetonide phosphate
- Triamcinolone acetonide sodium phosphate
- Triamcinolone benetonide
- Triamcinolone furetonide
- Triamcinolone hexacetonide
- 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
- Non-steroidal glucocorticoids: AZD5423
- GSK-9027
|
|
Mixed (SEGRAs)
|
- Dagrocorat
- Fosdagrocorat
- Mapracorat
|
|
Antagonists
|
- 7α-Hydroxy-DHEA
- 17α-Methylprogesterone
- Aglepristone
- Asoprisnil
- 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
- Telapristone
- Tibolone
- Toripristone
- Ulipristal acetate
|
|
|
See also: Receptor/signaling modulators • Androgenics • Estrogenics • Mineralocorticoidics • Progestogenics • Steroid metabolism modulators • List of corticosteroids
|
UpToDate Contents
全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.
English Journal
- Efficacy and safety of fluocinolone acetonide, hydroquinone, and tretinoin cream in chinese patients with melasma: a randomized, double-blind, placebo-controlled, multicenter, parallel-group study.
- Gong Z1, Lai W, Zhao G, Wang X, Zheng M, Li L, Yang Q, Dang Y, Liu L, Zou Y.
- Clinical drug investigation.Clin Drug Investig.2015 Jun;35(6):385-95. doi: 10.1007/s40261-015-0292-8.
- BACKGROUND AND OBJECTIVES: This study aimed to determine the efficacy and safety of fluocinolone acetonide, hydroquinone, and tretinoin (FAHT) cream for the treatment of moderate and severe facial melasma. The primary objective was assessment of clinical efficacy, instrumental measured efficacy, and
- PMID 25989732
- Sustained-release fluocinolone acetonide intravitreal insert for macular edema: clinical pharmacology and safety evaluation.
- Sadiq MA1, Agarwal A, Soliman MK, Hanout M, Sarwar S, Do DV, Nguyen QD.
- Expert opinion on drug safety.Expert Opin Drug Saf.2015 May 20:1-10. [Epub ahead of print]
- INTRODUCTION: Inflammation plays a key role in the pathological processes leading to macular edema. Sustained release, low-dose intraocular corticosteroid delivery devices provide long-term anti-inflammatory therapy. Recently, a novel fluocinolone acetonide intravitreal insert (FAi, Iluvien), has be
- PMID 25994877
- Spontaneous dislocation of fluocinolone acetonide implant pellets from their suture struts.
- Itty S1, Callanan D2, Jones R2, Pecen P1, Martel J1, Jaffe GJ3.
- American journal of ophthalmology.Am J Ophthalmol.2015 May;159(5):868-76.e1. doi: 10.1016/j.ajo.2015.01.031. Epub 2015 Jan 30.
- PURPOSE: To characterize spontaneous dislocation of the fluocinolone acetonide sustained release implant (Retisert; Bausch & Lomb) drug pellet from its strut.DESIGN: Retrospective, observational case series.METHODS: The medical records of 224 patients in whom 407 fluocinolone acetonide implants
- PMID 25640410
Japanese Journal
- Degradation of Corticosteroids during Activated Sludge Processing
- Pemphigus, discoid lupus erythematosus, and dermatomyositis during an 8-year follow-up period: a case report
- 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 ...
- 21 Apr 2013 ... Fluocinolone acetonide cream is a steroid drug that's used to treat a variety of skin conditions, including psoriasis, eczema, and...
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
- 関
- トリアムシノロン