Misplaced Pages

Fluocinolone acetonide

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Corticosteroid anti-inflammatory drug

Pharmaceutical compound
Fluocinolone acetonide
Clinical data
Trade namesSynalar, others
AHFS/Drugs.comMonograph
Monograph
Pregnancy
category
  • AU: A
Routes of
administration		Topical, ophthalmic intravitreal injection
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
MetabolismLiver, CYP3A4-mediated
Elimination half-life1.3 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-dioxapentacycloicosa-14,17-dien-16-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.607 Edit this at Wikidata
Chemical and physical data
FormulaC24H30F2O6
Molar mass452.495 g·mol
3D model (JSmol)
SMILES
  • O=C\1\C=C5/(/C=C/1)(C)2(F)(3(C2O)(4(OC(O4C3)(C)C)C(=O)CO)C)C5F
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
  • Key:FEBLZLNTKCEFIT-VSXGLTOVSA-N
  (what is this?)  (verify)

Fluocinolone acetonide is a fluorinated 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. 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.

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. A fluocinolone acetonide intravitreal implant with the brand name Iluvien is sold by biopharmaceutical company Alimera Sciences to treat diabetic macular edema.

It was approved for medical use in 1961.

Classification

This section does not cite any sources. Please help improve this section by adding citations to reliable sources. Unsourced material may be challenged and removed. (July 2024) (Learn how and when to remove this message)

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

Brand names

Fluocinolone acetonide is available under the brand names Flucort-N, Iluvien, Synalar, Yutiq, and others.

References

  1. "Regulatory Decision Summary for Iluvien". Drug and Health Product Portal. Health Canada. 23 October 2014.
  2. ^ "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. 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 9783527607495.
  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.
Glucocorticoids and antiglucocorticoids (D07, H02)
Glucocorticoids
Natural
Synthetic
Antiglucocorticoids
Synthesis modifiers
See also
Glucocorticoid receptor modulators
Mineralocorticoids and antimineralocorticoids
List of corticosteroids
Vasoprotectives (C05)
Antihemorrhoidals for topical use
corticosteroids
local anesthetics
other
Antivaricose therapy
heparins or heparinoids for topical use
sclerosing agents for local injection
other
Capillary stabilising agents
bioflavonoids
other
Drugs used for diseases of the ear (S02)
Infection
Corticosteroids
Analgesics and anesthetics
Glucocorticoid receptor modulators
GRTooltip Glucocorticoid receptor
Agonists
Mixed
(SEGRMsTooltip Selective glucocorticoid receptor agonists)
Antagonists
Others
See also
Receptor/signaling modulators
Glucocorticoids and antiglucocorticoids
Mineralocorticoid receptor modulators
List of corticosteroids
Portal:


Stub icon

This drug article relating to the cardiovascular system is a stub. You can help Misplaced Pages by expanding it.

Stub icon

This dermatologic drug article is a stub. You can help Misplaced Pages by expanding it.

Stub icon

This ophthalmology article is a stub. You can help Misplaced Pages by expanding it.

Categories: