Fluocinolone

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Fluocinolone
Fluocinolone acetonide.svg
Fluocinolone acetonide (Ball-n-Stick).png
Names
Trade namesSynalar, Iluvien, others
Other namesFluocinolone acetonide
  • (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
US NLMFluocinolone
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)
  • 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 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. 1.0 1.1 1.2 1.3 1.4 1.5 1.6 BNF 81: March-September 2021. BMJ Group and the Pharmaceutical Press. 2021. pp. 1236, 1291. ISBN 978-0857114105.
  2. 2.0 2.1 2.2 2.3 2.4 2.5 2.6 "Fluocinolone (EENT) Monograph for Professionals". Drugs.com. Archived from the original on 27 November 2021. Retrieved 12 December 2021.
  3. 3.0 3.1 3.2 "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.

External links

Identifiers: