Fluocinolone acetonide

Fluocinolone acetonide
Clinical data
Trade names	Synalar, Iluvien, others
AHFS/Drugs.com	Monograph; Monograph
Pregnancy; category	AU: A; ;
Routes of; administration	Topical, ophthalmic intravitreal injection
ATC code	C05AA10 (WHO) D07AC04 (WHO) S01BA15 (WHO) S02BA08 (WHO);
Legal status
Legal status	AU: S4 (Prescription only) ; 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
	show IUPAC name
CAS Number	67-73-2 ;
PubChem CID	6215;
IUPHAR/BPS	7077;
DrugBank	DB00591 ;
ChemSpider	5980 ;
UNII	0CD5FD6S2M;
KEGG	D01825 ;
ChEBI	CHEBI:31623 ;
ChEMBL	ChEMBL989 ;
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;
	show SMILES
	show InChI
	(what is this?)

Fluocinolone acetonide is a corticosteroid primarily used in dermatology to reduce skin inflammation and relieve itching.^{[citation needed]} 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] A fluocinolone acetonide intravitreal implant with the brand name Iluvien is sold by biopharmaceutical company Alimera Sciences to treat diabetic macular edema (DME).^[4]

It was approved for medical use in 1961.^[5]

Classification[]

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

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. PMC 5038923. PMID 26866343.
^ "Real-world study shows long-term safety, efficacy of Iluvien in DME". Healio. 2020-07-02. Retrieved 2020-10-28.
^ Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 485. ISBN 9783527607495.

External links[]

"Fluocinolone acetonide". Drug Information Portal. U.S. National Library of Medicine.

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[1] 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)

[2] 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-3] 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. PMC 5038923. PMID 26866343.

[4] "Real-world study shows long-term safety, efficacy of Iluvien in DME". Healio. 2020-07-02. Retrieved 2020-10-28.

[Fis2006-5] Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 485. ISBN 9783527607495.

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show v t 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

Fluocinolone acetonide

Contents

Classification[]

See also[]

References[]

External links[]