Fluocinolone acetonide

Last updated
Fluocinolone acetonide
Fluocinolone acetonide.svg
Fluocinolone acetonide (Ball-n-Stick).png
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
Legal status
Legal status
Pharmacokinetic data
Metabolism Liver, CYP3A4-mediated
Elimination half-life 1.3 to 1.7 hours
Identifiers
  • (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
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.607 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C24H30F2O6
Molar mass 452.495 g·mol−1
3D model (JSmol)
  • 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=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 Yes check.svgY
  • Key:FEBLZLNTKCEFIT-VSXGLTOVSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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. [2] 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.

Contents

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. [3]

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. [4] A fluocinolone acetonide intravitreal implant with the brand name Iluvien is sold by biopharmaceutical company Alimera Sciences to treat diabetic macular edema (DME). [5]

It was approved for medical use in 1961. [6]

Classification

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

See also

Related Research Articles

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Intravitreal is a route of administration of a drug, or other substance, in which the substance is delivered into the vitreous humor of the eye. "Intravitreal" literally means "inside an eye". Intravitreal injections were first introduced in 1911 when Ohm gave an injection of air into the vitreous humor to repair a detached retina. In the mid-1940s, intravitreal injections became a standard way to administer drugs to treat endophthalmitis and cytomegalovirus retinitis.

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<span class="mw-page-title-main">Alimera Sciences</span>

Alimera Sciences, Inc. is a biopharmaceutical sales company based in Alpharetta, Georgia that specializes in the commercialization and sales of prescription ophthalmic pharmaceuticals. The company's main selling focus is on diseases affecting the back of the eye, or retina. The company is the licensee for Iluvien, a fluocinolone acetonide intravitreal implant.

<span class="mw-page-title-main">Intravitreal injection</span> Method of administration of drugs into the eye by injection with a fine needle

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References

  1. "Regulatory Decision Summary for Iluvien". Drug and Health Product Portal. Health Canada. 23 October 2014.
  2. 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. doi:10.1021/ja01498a041.
  3. 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.
  4. 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.
  5. "Real-world study shows long-term safety, efficacy of Iluvien in DME". Healio. 2020-07-02. Retrieved 2020-10-28.
  6. 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   9783527607495.