Chemistry:Fluocinolone acetonide

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Short description: Corticosteroid anti-inflammatory drug
Fluocinolone acetonide
Fluocinolone acetonide.svg
Fluocinolone acetonide (Ball-n-Stick).png
Clinical data
Trade namesSynalar, Iluvien, others
AHFS/Drugs.comMonograph
Monograph
Pregnancy
category
  • AU: A
Routes of
administration
Topical, ophthalmic intravitreal injection
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismLiver, CYP3A4-mediated
Elimination half-life1.3 to 1.7 hours
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC24H30F2O6
Molar mass452.495 g·mol−1
3D model (JSmol)
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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.

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.

Society and culture

Brand names

Yutiq.[7]

References

  1. "Regulatory Decision Summary for Iluvien". Drug and Health Product Portal. Health Canada. 23 October 2014. https://hpr-rps.hres.ca/reg-content/regulatory-decision-summary-detail.php?lang=en&linkID=RDS00500. 
  2. "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. 1960. doi:10.1021/ja01498a041. 
  3. "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. September 2015. doi:10.1002/jbmr.2502. PMID 25753754. 
  4. "Corticosteroid implants for chronic non-infectious uveitis". The Cochrane Database of Systematic Reviews 2023 (8): CD010469. August 2023. doi:10.1002/14651858.CD010469.pub4. PMID 37642198. 
  5. "Real-world study shows long-term safety, efficacy of Iluvien in DME". 2020-07-02. https://www.healio.com/news/ophthalmology/20200702/realworld-study-shows-longterm-safety-efficacy-of-iluvien-in-dme. 
  6. "Tables of Structural and Functional Analogues: Systemic Hormonal Preparations" (in en). Analogue-based Drug Discovery. John Wiley & Sons. 2006. p. 485. ISBN 9783527607495. https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA485. 
  7. "Yutiq- fluocinolone acetonide implant". 16 October 2023. https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f270cad8-ed82-4969-b785-831a1910bfa6.