Jump to content

Fluocinolone acetonide: Difference between revisions

From Wikipedia, the free encyclopedia
Content deleted Content added
No edit summary
No edit summary
Line 60: Line 60:
'''Fluocinolone [[acetonide]]''' is a [[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.<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 [[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.<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 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, Hai PT, 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>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>


Flucinolone is a group IV (0.01-0.2%) or group V (0.025%) [[Topical steroid#USA system|corticosteroid under US classification]].
Flucinolone is a group IV (0.01-0.2%) or group V (0.025%) [[Topical steroid#USA system|corticosteroid under US classification]].

Revision as of 14:13, 31 May 2015

Fluocinolone acetonide
Clinical data
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
  • C
Routes of
administration
Topical
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
MetabolismHepatic, CYP3A4-mediated
Elimination half-life1.3 to 1.7 hours
Identifiers
  • (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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.607 Edit this at Wikidata
Chemical and physical data
FormulaC24H30F2O6
Molar mass452.488 g/mol 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
 ☒NcheckY (what is this?)  (verify)

Fluocinolone acetonide is a 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.[1] 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 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.[2]

Flucinolone is a group IV (0.01-0.2%) or group V (0.025%) corticosteroid under US classification.

See also

References

  1. ^ 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)
  2. ^ 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