Fluocinolone acetonide: Difference between revisions

Fluocinolone acetonide
Clinical data
Trade names	Synalar, others
AHFS/Drugs.com	Monograph; Monograph
Pregnancy; category	AU: A; ;
Routes of; administration	Topical, ophthalmic intravitreal injection
ATC code	C05AA10 (WHO) D07AC04 (WHO) S01BA15 (WHO) S02BA08 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Metabolism	Liver, CYP3A4-mediated
Elimination half-life	1.3 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-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one;
CAS Number	67-73-2 ;
PubChem CID	6215;
IUPHAR/BPS	7077;
DrugBank	DB00591 ;
ChemSpider	5980 ;
UNII	0CD5FD6S2M;
KEGG	D01825 ;
ChEBI	CHEBI:31623 ;
ChEMBL	ChEMBL989 ;
CompTox Dashboard (EPA)	DTXSID0040674 ;
ECHA InfoCard	100.000.607
Chemical and physical data
Formula	C24H30F2O6
Molar mass	452.495 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:FEBLZLNTKCEFIT-VSXGLTOVSA-N ;
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Latest revision as of 15:00, 5 September 2024

Fluocinolone acetonide is a fluorinated corticosteroid primarily used in dermatology to reduce skin inflammation and relieve itching.^[2] 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.^[3] 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.^[4]

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.^[5] A fluocinolone acetonide intravitreal implant with the brand name Iluvien is sold by biopharmaceutical company Alimera Sciences to treat diabetic macular edema.^[6]

It was approved for medical use in 1961.^[7]

Classification

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,^[8] and others.^[2]^[9]

References

^ "Regulatory Decision Summary for Iluvien". Drug and Health Product Portal. Health Canada. 23 October 2014.
^ ^a ^b "Fluocinolone (Topical) Monograph for Professionals". Drugs.com. 19 January 2024. Retrieved 7 July 2024.
^ 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.
^ 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)
^ 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.
^ "Real-world study shows long-term safety, efficacy of Iluvien in DME". Healio. 2 July 2020. Retrieved 28 October 2020.
^ 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.
^ "Yutiq- fluocinolone acetonide implant". DailyMed. 16 October 2023. Retrieved 25 December 2023.
^ "Fluocinolone ophthalmic implant Uses, Side Effects & Warnings". Drugs.com. 6 October 2023. Retrieved 7 July 2024.

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[1] "Regulatory Decision Summary for Iluvien". Drug and Health Product Portal. Health Canada. 23 October 2014.

[AHFS-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.

[pmid25753754-4] 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.

[Fis2006-7] 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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[2]

[3]

[4]

[5]

[6]

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[9]

@@ Line 1: / Line 1: @@
 {{Short description|Corticosteroid anti-inflammatory drug}}
+{{Use dmy dates|date=July 2024}}
+{{cs1 config |name-list-style=vanc |display-authors=6}}
 {{Drugbox
 | Verifiedfields = changed
@@ Line 6: / Line 8: @@
 | alt =
 | image2 = Fluocinolone acetonide (Ball-n-Stick).png
 | alt2 =
 <!--Clinical data-->
-| tradename = Synalar, Iluvien, others
+| tradename = Synalar, others
 | Drugs.com = {{drugs.com|monograph|fluocinolone-topical}}<br />{{drugs.com|monograph|fluocinolone-acetonide-eent}}
 | pregnancy_AU = A
@@ Line 20: / Line 22: @@
 | legal_AU = S4
 | legal_CA = Rx-only
-| legal_CA_comment = <ref>{{cite web | url=https://hpr-rps.hres.ca/reg-content/regulatory-decision-summary-detail.php?lang=en&linkID=RDS00500 | title=Search Page - Drug and Health Product Register | date=23 October 2014 }}</ref>
+| legal_CA_comment = <ref>{{cite web | url=https://hpr-rps.hres.ca/reg-content/regulatory-decision-summary-detail.php?lang=en&linkID=RDS00500 | title=Regulatory Decision Summary for Iluvien | work = Drug and Health Product Portal | publisher = Health Canada | date=23 October 2014 }}</ref>
 | legal_UK = POM
 | legal_US = Rx-only
@@ Line 60: / Line 62: @@
 }}
-'''Fluocinolone acetonide''' is a [[corticosteroid]] primarily used in [[dermatology]] 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 [[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.<ref>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)</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 [[neomycin]].
+'''Fluocinolone acetonide''' is a fluorinated [[corticosteroid]] primarily used in [[dermatology]] to reduce skin inflammation and relieve itching.<ref name="AHFS" /> 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.<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 [[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.<ref>Hara ES, Ono M, Pham HT, Sonoyama W, Kubota S, Takigawa M, Matsumoto T, Young MF, Olsen BR, Kuboki T. Fluocinolone Acetonide is a Potent Synergistic Factor of TGF-β3-Associated Chondrogenesis of Bone Marrow-Derived Mesenchymal Stem Cells for Articular Surface Regeneration. J Bone Miner Res. 2015. http://onlinelibrary.wiley.com/doi/10.1002/jbmr.2502/abstract</ref>
+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.<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 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.<ref name="Brady">{{cite journal |vauthors=Brady CJ, Villanti AC, Law HA, Rahimy E, Reddy R, Sieving PC, Garg SJ, Tang J |title= Corticosteroid implants for chronic non-infectious uveitis |journal=Cochrane Database Syst Rev|volume=2016 |pages= CD010469 |date=2016 |issue= 2 |pmid= 26866343 |doi= 10.1002/14651858.CD010469.pub2|pmc=5038923}}</ref> A fluocinolone acetonide intravitreal implant with the brand name '''Iluvien''' is sold by biopharmaceutical company [[Alimera Sciences]] to treat [[diabetic macular edema]] (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 [[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.<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 }}</ref> A fluocinolone acetonide intravitreal implant with the brand name Iluvien is sold by biopharmaceutical company [[Alimera Sciences]] to treat [[diabetic macular edema]].<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>
 <!-- Society and culture -->
-It was approved for medical use in 1961.<ref name=Fis2006>{{cite book |last1=Fischer |first1=Jnos |last2=Ganellin |first2=C. Robin |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=485 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA485 |language=en}}</ref>
+It was approved for medical use in 1961.<ref name=Fis2006>{{cite book | chapter = Tables of Structural and Functional Analogues: Systemic Hormonal Preparations | veditors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=485 | chapter-url = https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA485 |language=en}}</ref>
 ==Classification==
+{{unreferenced section|date=July 2024}}
 Fluocinolone is a group V (0.025%) or group VI (0.01%) [[Topical steroid#USA system|corticosteroid under US classification]].
-==See also==
+==Brand names ==
+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>
-* [[Topical steroid]]
-* [[Fluocinonide]]
-* [[Ciprocinonide]]
-* [[Glucocorticoid]]
-==References==
+== References ==
 {{reflist}}
-== External links ==
-* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/fluocinolone%20acetonide | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Fluocinolone acetonide }}
 {{Glucocorticoids}}
@@ Line 89: / Line 86: @@
 {{Glucocorticoidics}}
 {{Portal bar | Medicine}}
+{{Authority control}}
 [[Category:Acetonides]]
@@ Line 95: / Line 93: @@
 [[Category:Diketones]]
 [[Category:Diols]]
-[[Category:Fluoroarenes]]
+[[Category:Organofluorides]]
 [[Category:Glucocorticoids]]
 [[Category:Otologicals]]

v t e Drugs used for diseases of the ear (S02)
Infection	Acetic acid Aluminium acetotartrate Aluminium triacetate (Burow's solution) Boric acid Chloramphenicol Chlorhexidine Ciprofloxacin Clioquinol Gentamicin Hydrogen peroxide Miconazole Neomycin Nitrofurazone Ofloxacin Polymyxin B Rifamycin Tetracycline
Corticosteroids	Betamethasone Dexamethasone Fluocinolone acetonide Hydrocortisone Prednisolone
Analgesics and anesthetics	Lidocaine Cocaine Phenazone