Fluocinolone

Fluocinolone
Names
Trade namesSynalar, Iluvien, others
Other namesFluocinolone acetonide
IUPAC name
  • (6S,8S,9R,10S,11S,13S,14S,16R,17S)-6,9-Difluoro-11,16,17-trihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
Clinical data
Drug classCorticosteroid (glucocorticoid)
Main usesSkin: Eczema, psoriasis[1]
Eye: Uveitis, diabetic macular edema[2][1]
Side effectsSkin: Irritation, dry skin, folliculitis, acne, decreased pigmentation, skin atrophy, infection[3]
Eye: Increased eye pressure, eye pain, conjunctival bleeding, blurry vision, dry eyes[2]
Routes of
use		Topical
External links
AHFS/Drugs.comTopical: Monograph
Eyes: Monograph
Legal
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetics
MetabolismLiver, CYP3A4-mediated
Elimination half-life1.3 to 1.7 hours
Chemical and physical data
FormulaC24H30F2O6
Molar mass452.495 g·mol−1
3D model (JSmol)
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 checkY
  • Key:FEBLZLNTKCEFIT-VSXGLTOVSA-N checkY

Fluocinolone, sold under the brand name Synalar among others, is a corticosteroid.[2] It is applied to the skin to treat eczema and psoriasis.[1] It is used as an implant within the eye to treat uveitis and vision problems due to diabetic macular edema.[2][1]

When applied to the skin common side effects include irritation, dry skin, folliculitis, acne, decreased pigmentation, skin atrophy, and infection.[3] When used in the eye common side effects include increased eye pressure, eye pain, conjunctival bleeding, blurry vision, and dry eyes.[2] Other complications may include cataracts, retinal detachment, and infection in the eye.[2] It works by decreasing inflammation.[3]

Fluocinolone was first made in 1959.[4] It was approved for medical use in 1961.[5] In the United Kingdom it costs the NHS about £10 for a tube of 60 grams and about £5,500 for a dose to place in the eye as of 2021.[1] This amount in the United States costs about 30 USD and 9,200 USD respectively.[6][7]

Medical uses

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.[8]

The cream can be mild to strong depending on the concentration.[1]

Dosage

It may be given by injection into the eye of 190 micrograms.[1]

Chemistry

It is used as fluocinolone acetonide, a salt of fluocinolone.[2] Chemically it is known as 6α-Fluorotriamcinolone; 6α,9α-Difluoro-11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione.

Classification

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

Society and culture

A fluocinolone acetonide intravitreal implant with the brand name "Iluvien" is sold by biopharmaceutical company Alimera Sciences to treat diabetic macular edema (DME).[9]

References

  1. 1 2 3 4 5 6 7 BNF 81: March-September 2021. BMJ Group and the Pharmaceutical Press. 2021. pp. 1236, 1291. ISBN 978-0857114105.
  2. 1 2 3 4 5 6 7 "Fluocinolone (EENT) Monograph for Professionals". Drugs.com. Archived from the original on 27 November 2021. Retrieved 12 December 2021.
  3. 1 2 3 "Fluocinolone (Topical) Monograph for Professionals". Drugs.com. Archived from the original on 27 November 2021. Retrieved 14 December 2021.
  4. ↑ 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)
  5. ↑ Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 485. ISBN 9783527607495. Archived from the original on 2020-08-01. Retrieved 2021-12-12.
  6. ↑ "Fluocinolone Prices, Coupons & Savings Tips - GoodRx". GoodRx. Retrieved 14 December 2021.
  7. ↑ "Iluvien Prices, Coupons & Patient Assistance Programs". Drugs.com. Archived from the original on 21 April 2021. Retrieved 14 December 2021.
  8. ↑ 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.
  9. ↑ "Real-world study shows long-term safety, efficacy of Iluvien in DME". Healio. 2020-07-02. Archived from the original on 2020-08-15. Retrieved 2020-10-28.
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