Fluocinolone Acetonide - Wikipedia

Corticosteroid anti-inflammatory drug Pharmaceutical compound Fluocinolone acetonide

Clinical data
Trade names	Synalar, others
AHFS/Drugs.com	MonographMonograph
Pregnancycategory	AU: A
Routes ofadministration	Topical, ophthalmic intravitreal injection
ATC code	C05AA10 (WHO) D07AC04 (WHO) S01BA15 (WHO) S02BA08 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only[1] UK: POM (Prescription only) US: ℞-only In general: ℞ (Prescription only)
Pharmacokinetic data
Metabolism	Liver, CYP3A4-mediated
Elimination 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	67-73-2 Y
PubChem CID	6215
IUPHAR/BPS	7077
DrugBank	DB00591 Y
ChemSpider	5980 Y
UNII	0CD5FD6S2M
KEGG	D01825 Y
ChEBI	CHEBI:31623 N
ChEMBL	ChEMBL989 Y
CompTox Dashboard (EPA)	DTXSID0040674
ECHA InfoCard	100.000.607
Chemical and physical data
Formula	C24H30F2O6
Molar mass	452.495 g·mol−1
3D model (JSmol)	Interactive image
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 fluorinated corticosteroid primarily used in dermatology to reduce skin inflammation and relieve itching.[2] 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.[3] Preparations containing it were first marketed under the brand name Synalar.

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.[4]

Fluocinolone acetonide intravitreal implants have been used to treat non-infectious uveitis. A systematic review could not determine with any confidence whether fluocinolone acetonide implants are superior to standard of care treatment for uveitis.[5] A fluocinolone acetonide intravitreal implant with the brand name Iluvien is sold by biopharmaceutical company Alimera Sciences to treat diabetic macular edema.[6]

It was approved for medical use in 1961.[7]

Classification

[edit]

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Fluocinolone is a group V (0.025%) or group VI (0.01%) corticosteroid under US classification.

Brand names

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Fluocinolone acetonide is available under the brand names Flucort-N, Iluvien, Synalar, Yutiq,[8] and others.[2][9]

References

[edit]

1. ^ "Regulatory Decision Summary for Iluvien". Drug and Health Product Portal. Health Canada. 23 October 2014.
2. ^ a b "Fluocinolone (Topical) Monograph for Professionals". Drugs.com. 19 January 2024. Retrieved 7 July 2024.
3. ^ Mills JS, Bowers A, Djerassi C, Ringold HJ (1960). "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 (13): 3399–3404. Bibcode:1960JAChS..82.3399M. doi:10.1021/ja01498a041.
4. ^ Hara ES, Ono M, Pham HT, Sonoyama W, Kubota S, Takigawa M, et al. (September 2015). "Fluocinolone Acetonide Is a Potent Synergistic Factor of TGF-β3-Associated Chondrogenesis of Bone Marrow-Derived Mesenchymal Stem Cells for Articular Surface Regeneration". Journal of Bone and Mineral Research. 30 (9): 1585–1596. doi:10.1002/jbmr.2502. PMC 5569386. PMID 25753754.{{cite journal}}: CS1 maint: overridden setting (link)
5. ^ Reddy A, Liu SH, Brady CJ, Sieving PC, Palestine AG (August 2023). "Corticosteroid implants for chronic non-infectious uveitis". The Cochrane Database of Systematic Reviews. 2023 (8) CD010469. doi:10.1002/14651858.CD010469.pub4. PMC 10464657. PMID 37642198.
6. ^ "Real-world study shows long-term safety, efficacy of Iluvien in DME". Healio. 2 July 2020. Retrieved 28 October 2020.
7. ^ Fischer J, Ganellin CR, eds. (2006). "Tables of Structural and Functional Analogues: Systemic Hormonal Preparations". Analogue-based Drug Discovery. John Wiley & Sons. p. 485. ISBN 978-3-527-60749-5.
8. ^ "Yutiq- fluocinolone acetonide implant". DailyMed. 16 October 2023. Retrieved 25 December 2023.
9. ^ "Fluocinolone ophthalmic implant Uses, Side Effects & Warnings". Drugs.com. 6 October 2023. Retrieved 7 July 2024.

v t e Glucocorticoids and antiglucocorticoids (D07, H02)
Glucocorticoids	Natural Cortisone Cortisone acetate Cortodoxone (cortexolone, 11-deoxycortisol) Desoxycortone (deoxycortone, cortexone, 11-deoxycorticosterone) Desoxycortone esters Hydrocortisone (cortisol)# Hydrocortisone esters Hydrocortisone aceponate Prebediolone acetate Pregnenolone Pregnenolone acetate Pregnenolone succinate Synthetic Cortisol-like and related (16-unsubstituted): Chloroprednisone Cloprednol Difluprednate Fludrocortisone Flugestone acetate (flurogestone acetate) Fluocinolone Fluorometholone Fluorometholone acetate Fluperolone Fluperolone acetate Fluprednisolone Fluprednisolone esters Loteprednol (+tobramycin) Medrysone Methylprednisolone Methylprednisolone esters Methylprednisolone aceponate Prednicarbate Prednisolone# Prednisone Tixocortol Tixocortol pivalate Methasones and related (16-substituted): Alclometasone Beclometasone Beclometasone esters Betamethasone# Betamethasone esters Clobetasol Clobetasol propionate Clobetasone Clocortolone Clocortolone esters Cortivazol Desoximetasone Dexamethasone# Dexamethasone esters Diflorasone Diflucortolone Diflucortolone valerate Fluclorolone Flumetasone Fluocortin Fluocortolone Fluocortolone esters Fluprednidene acetate Fluticasone Fluticasone furoate Fluticasone propionate Halometasone Meprednisone Mometasone Mometasone furoate 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
Antiglucocorticoids	Antagonists: Aglepristone Ketoconazole Mifepristone Ulipristal acetate
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 Glucocorticoid receptor modulators Mineralocorticoids and antimineralocorticoids List of corticosteroids

v t e 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 Tribenoside
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 Calcium dobesilate
Capillary stabilising agents	bioflavonoids Rutoside Monoxerutin Diosmin Troxerutin Hidrosmin other Tribenoside Etamsylate

v t e 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 (+ciprofloxacin) Prednisolone
Analgesics and anesthetics	Lidocaine Cocaine Phenazone

v t e Glucocorticoid receptor modulators
GRTooltip Glucocorticoid receptor	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 esters 11-Deoxycortisol (cortodoxone, cortexolone) Cortifen (cortiphen, kortifen) Cortodoxone acetate 21-Deoxycortisol Δ7-Prednisolone Δ7-Prednisolone 21-acetate Amebucort Chloroprednisone Chloroprednisone acetate Cloprednol Cloprednol acetate Corticosterone Corticosterone acetate Corticosterone benzoate Cortisol (hydrocortisone) Benzodrocortisone (hydrocortisone benzoate) Hydrocortamate (hydrocortisone diethylaminoacetate) Hydrocortisone esters Cortisone Cortisone acetate Deprodone Deprodone propionate Dichlorisone Dichlorisone acetate Dichlorisone diacetate Difluprednate Endrisone (endrysone) Etiprednol Etiprednol dicloacetate (etiprednol dichloroacetate) Fludrocortisone (fludrocortone) Fludrocortisone acetate Fluorometholone Fluorometholone acetate Fluperolone Fluperolone acetate Fluprednisolone Fluprednisolone esters Halopredone Halopredone acetate (halopredone diacetate) Isoflupredone (9α-fluoroprednisolone) Isoflupredone acetate Loteprednol Mazipredone (depersolone) Medrysone Methylprednisolone Methylprednisolone esters Prebediolone Prebediolone acetate Prednisolone Prednazate Prednazoline Prednicarbate (prednisolone ethylcarbonate propionate) Prednimustine Prednisolamate (prednisolone diethylaminoacetate) Prednisolone esters Prednisone Prednisone esters Pregnenolone Pregnenolone acetate Pregnenolone succinate (pregnenolone hemisuccinate) Resocortol Tipredane Tixocortol Butixocort (tixocortol butyrate) Butixocort propionate Tixocortol pivalate Methasones and related (16-substituted): 16α-Methyl-11-oxoprednisolone Alclometasone Alclometasone dipropionate Amelometasone Beclometasone (beclomethasone) Beclometasone esters Betamethasone (betametasone) Betamethasone esters Cortobenzolone (betamethasone salicylate) Ciclometasone (ciclomethasone, cyclomethasone) Clobetasol Clobetasol propionate Clobetasone Clobetasone butyrate Clocortolone Clocortolone esters Cloticasone Cloticasone propionate Cormetasone (cormethasone) Cormetasone acetate Descinolone Desoximetasone (desoxymethasone) Dexamethasone (dexametasone) Dexamethasone esters Diflorasone Diflorasone diacetate Diflucortolone Diflucortolone pivalate Diflucortolone valerate Dimesone Dimesone acetate Doxibetasol (doxybetasol) Fluclorolone Flumetasone (flumethasone) Flumetasone acetate Flumetasone pivalate Fluocinolone Fluocortin Fluocortin butyl (fluocortin butylate) Fluocortolone Fluocortolone esters Fluprednidene (fluprednylidene) Fluprednidene acetate Fluticasone Fluticasone furoate Fluticasone propionate Halocortolone Halometasone Icometasone Icometasone enbutate (icometasone butyrate acetate) Isoprednidene Locicortolone (locicortone) Locicortolone dicibate (locicortone dicibate) Meclorisone Meclorisone dibutyrate Meprednisone (methylprednisone) Meprednisone acetate Meprednisone hydrogen succinate (methylprednisone hemisuccinate) Mometasone Mometasone furoate Paramethasone Paramethasone acetate Paramethasone disodium phosphate Paramethasone phosphate Prednylidene Prednylidene diethylaminoacetate Rimexolone Ticabesone Ticabesone propionate Timobesone Timobesone acetate Triamcinolone Triamcinolone diacetate Ulobetasol (halobetasol) Ulobetasol propionate 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 Drocinonide phosphate Fluazacort Fluclorolone acetonide (flucloronide) Fludroxycortide (flurandrenolone, flurandrenolide) Flumoxonide Flunisolide Flunisolide acetate Fluocinolone acetonide Ciprocinonide (fluocinolone acetonide cyclopropylcarboxylate) Fluocinonide (fluocinolide, fluocinolone acetonide acetate) Procinonide (fluocinolone acetonide propionate) Formocortal Halcinonide Itrocinonide Rofleponide Rofleponide palmitate 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 Nicocortonide acetate Nivacortol (nivazol) Oxisopred RU-26988 RU-28362 Non-corticosteroids with some glucocorticoid activity: 15β-Hydroxycyproterone acetate 17α-Hydroxyprogesterone Bromoketoprogesterone Chlormadinone acetate Cyproterone Cyproterone acetate Danazol Delmadinone acetate Desogestrel DU-41165 Etonogestrel Flugestone Flugestone acetate (flurogestone acetate) Fluoromedroxyprogesterone acetate Fluoxymesterone Gestodene Medrogestone Medroxyprogesterone acetate Megestrol acetate Metribolone Norgestomet Osaterone acetate Progesterone Promegestone RU-2309 Quingestrone Segesterone acetate (nestorone) Tetrahydrogestrinone Nonsteroidal glucocorticoids: AZD-5423 GSK-9027 Mixed(SEGRMsTooltip Selective glucocorticoid receptor agonists) Dagrocorat Fosdagrocorat Mapracorat Antagonists 7α-Hydroxy-DHEA 17α-Methylprogesterone Aglepristone Asoprisnil Asoprisnil ecamate C108297 C113176 CORT-108297 Cyproterone acetate Dazucorilant Exicorilant (CORT-125281) Guggulsterone Ketoconazole Lilopristone LLY-2707 Metapristone (RU-42633) Miconazole Mifepristone (RU-486) Miricorilant (CORT-118335) 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 Zavacorilant Others Antisense oligonucleotides: IONIS-GCCRRx (ISIS-426115)
See also Receptor/signaling modulators Glucocorticoids and antiglucocorticoids Mineralocorticoid receptor modulators List of corticosteroids

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