Fluocinolone acetonide
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| Systematic (IUPAC) name | |
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(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
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| AHFS/Drugs.com | International Drug Names |
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Topical |
| Pharmacokinetic data | |
| Metabolism | Hepatic, CYP3A4-mediated |
| Biological half-life | 1.3 to 1.7 hours |
| Identifiers | |
| CAS Number | 67-73-2  |
| ATC code | C05AA10 (WHO) D07AC04 S01BA15 S02BA08 |
| PubChem | CID: 6215 |
| IUPHAR/BPS | 7077 |
| DrugBank | DB00591 |
| ChemSpider | 5980 |
| UNII | 0CD5FD6S2M |
| KEGG | D01825 |
| ChEBI | CHEBI:31623  |
| ChEMBL | CHEMBL989 |
| Chemical data | |
| Formula | C24H30F2O6 |
| Molecular mass | 452.488 g/mol |
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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 V (0.025%) or group VI (0.01%) corticosteroid under US classification.
See also
References
- ↑ 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)
- ↑ 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
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