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{{Short description|Corticosteroid anti-inflammatory drug}} {{Short description|Corticosteroid anti-inflammatory drug}}
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<!--Clinical data--> <!--Clinical data-->
| tradename = Synalar, Iluvien, others | tradename = Synalar, others
| Drugs.com = {{drugs.com|monograph|fluocinolone-topical}}<br />{{drugs.com|monograph|fluocinolone-acetonide-eent}} | Drugs.com = {{drugs.com|monograph|fluocinolone-topical}}<br />{{drugs.com|monograph|fluocinolone-acetonide-eent}}
| pregnancy_AU = A | pregnancy_AU = A
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'''Fluocinolone acetonide''' is a ] primarily used in ] to reduce skin inflammation and relieve itching.{{Citation needed|date=November 2019|reason=Please clarify which it is corticoid: gluco- or mineralo-}} It is a synthetic ] 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.<ref>{{cite journal | vauthors = Mills JS, Bowers A, Djerassi C, Ringold HJ | title = Steroids CXXXVII. Synthesis of a New Class of Potent Cortical Hormones. 6α,9α-Difluoro-16α-Hydroxyprednisolone and its Acetonide | journal = Journal of the American Chemical Society | volume = 80 | pages = 3399–3404 | date = 1960 | issue = 13 | doi = 10.1021/ja01498a041 }}</ref> 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 ]. '''Fluocinolone acetonide''' is a fluorinated ] primarily used in ] to reduce skin inflammation and relieve itching.<ref name="AHFS" /> It is a synthetic ] 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.<ref>{{cite journal | vauthors = Mills JS, Bowers A, Djerassi C, Ringold HJ | title = Steroids CXXXVII. Synthesis of a New Class of Potent Cortical Hormones. 6α,9α-Difluoro-16α-Hydroxyprednisolone and its Acetonide | journal = Journal of the American Chemical Society | volume = 80 | pages = 3399–3404 | date = 1960 | issue = 13 | doi = 10.1021/ja01498a041 }}</ref> Preparations containing it were first marketed under the brand name '''Synalar'''.


Fluocinolone acetonide was also found to strongly potentiate TGF-β-associated ] 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.<ref name="pmid25753754">{{cite journal | vauthors = Hara ES, Ono M, Pham HT, Sonoyama W, Kubota S, Takigawa M, Matsumoto T, Young MF, Olsen BR, Kuboki T | display-authors = 6 | title = Fluocinolone Acetonide Is a Potent Synergistic Factor of TGF-β3-Associated Chondrogenesis of Bone Marrow-Derived Mesenchymal Stem Cells for Articular Surface Regeneration | journal = Journal of Bone and Mineral Research | volume = 30 | issue = 9 | pages = 1585–1596 | date = September 2015 | pmid = 25753754 | pmc = 5569386 | doi = 10.1002/jbmr.2502 }}</ref> Fluocinolone acetonide was also found to strongly potentiate TGF-β-associated ] 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.<ref name="pmid25753754">{{cite journal | vauthors = Hara ES, Ono M, Pham HT, Sonoyama W, Kubota S, Takigawa M, Matsumoto T, Young MF, Olsen BR, Kuboki T | display-authors = 6 | title = Fluocinolone Acetonide Is a Potent Synergistic Factor of TGF-β3-Associated Chondrogenesis of Bone Marrow-Derived Mesenchymal Stem Cells for Articular Surface Regeneration | journal = Journal of Bone and Mineral Research | volume = 30 | issue = 9 | pages = 1585–1596 | date = September 2015 | pmid = 25753754 | pmc = 5569386 | doi = 10.1002/jbmr.2502 }}</ref>


Fluocinolone acetonide ] have been used to treat non-infectious ]. A systematic review could not determine with any confidence whether fluocinolone acetonide implants are superior to standard of care treatment for uveitis.<ref>{{cite journal | vauthors = Reddy A, Liu SH, Brady CJ, Sieving PC, Palestine AG | title = Corticosteroid implants for chronic non-infectious uveitis | journal = The Cochrane Database of Systematic Reviews | volume = 2023 | issue = 8 | pages = CD010469 | date = August 2023 | pmid = 37642198 | pmc = 10464657 | doi = 10.1002/14651858.CD010469.pub4 | pmc-embargo-date = August 29, 2024 }}</ref> A fluocinolone acetonide intravitreal implant with the brand name '''Iluvien''' is sold by biopharmaceutical company ] to treat ] (DME).<ref>{{cite web|url=https://www.healio.com/news/ophthalmology/20200702/realworld-study-shows-longterm-safety-efficacy-of-iluvien-in-dme |title=Real-world study shows long-term safety, efficacy of Iluvien in DME |website=Healio |date=2020-07-02 |access-date=2020-10-28}}</ref> Fluocinolone acetonide ] have been used to treat non-infectious ]. A systematic review could not determine with any confidence whether fluocinolone acetonide implants are superior to standard of care treatment for uveitis.<ref>{{cite journal | vauthors = Reddy A, Liu SH, Brady CJ, Sieving PC, Palestine AG | title = Corticosteroid implants for chronic non-infectious uveitis | journal = The Cochrane Database of Systematic Reviews | volume = 2023 | issue = 8 | pages = CD010469 | date = August 2023 | pmid = 37642198 | pmc = 10464657 | doi = 10.1002/14651858.CD010469.pub4 | pmc-embargo-date = August 29, 2024 }}</ref> A fluocinolone acetonide intravitreal implant with the brand name Iluvien is sold by biopharmaceutical company ] to treat ].<ref>{{cite web|url=https://www.healio.com/news/ophthalmology/20200702/realworld-study-shows-longterm-safety-efficacy-of-iluvien-in-dme |title=Real-world study shows long-term safety, efficacy of Iluvien in DME |website=Healio |date=2020-07-02 |access-date=2020-10-28}}</ref>


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==Classification== ==Classification==
{{unreferenced section}}
Fluocinolone is a group V (0.025%) or group VI (0.01%) ]. Fluocinolone is a group V (0.025%) or group VI (0.01%) ].



==Brand names == ==Brand names ==
* Yutiq<ref>{{cite web | title=Yutiq- fluocinolone acetonide implant | website=DailyMed | date=16 October 2023 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f270cad8-ed82-4969-b785-831a1910bfa6 | access-date=25 December 2023}}</ref> Fluocinolone acetonide is available under the brand names Flucort-N, Iluvien, Synalar, Yutiq,<ref>{{cite web | title=Yutiq- fluocinolone acetonide implant | website=DailyMed | date=16 October 2023 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f270cad8-ed82-4969-b785-831a1910bfa6 | access-date=25 December 2023}}</ref> and others.<ref name="AHFS">{{cite web | title=Fluocinolone (Topical) Monograph for Professionals | website=Drugs.com | date=19 January 2024 | url=https://www.drugs.com/monograph/fluocinolone-topical.html | access-date=7 July 2024}}</ref><ref>{{cite web | title=Fluocinolone ophthalmic implant Uses, Side Effects & Warnings | website=Drugs.com | date=6 October 2023 | url=https://www.drugs.com/mtm/fluocinolone-ophthalmic-implant.html | access-date=7 July 2024}}</ref>


== References == == References ==
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Revision as of 07:20, 7 July 2024

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

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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.{{cite journal}}: CS1 maint: PMC embargo expired (link)
  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.
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