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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H30F2O6.2H2O
Molecular Weight 488.5188
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUOCINOLONE ACETONIDE DIHYDRATE

SMILES

O.O.[H][C@@]12C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]4(F)[C@@]2([H])C[C@H](F)C5=CC(=O)C=C[C@]45C

InChI

InChIKey=IZAKVVPJGZHECV-UPXIRYIGSA-N
InChI=1S/C24H30F2O6.2H2O/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;2*1H2/t13-,14-,16-,17-,19+,21-,22-,23-,24+;;/m0../s1

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
MOL RATIO 2 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C24H30F2O6
Molecular Weight 452.4882
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Fluocinolone Acetonide is a corticosteroid that binds to the cytosolic glucocorticoid receptor. After binding the receptor the newly formed receptor-ligand complex translocates itself into the cell nucleus, where it binds to many glucocorticoid response elements (GRE) in the promoter region of the target genes. The DNA bound receptor then interacts with basic transcription factors, causing the increase in expression of specific target genes. The anti-inflammatory actions of corticosteroids are thought to involve lipocortins, phospholipase A2 inhibitory proteins which, through inhibition arachidonic acid, control the biosynthesis of prostaglandins and leukotrienes. Specifically glucocorticoids induce lipocortin-1 (annexin-1) synthesis, which then binds to cell membranes preventing the phospholipase A2 from coming into contact with its substrate arachidonic acid. This leads to diminished eicosanoid production. Cyclooxygenase (both COX-1 and COX-2) expression is also suppressed, potentiating the effect. In another words, the two main products in inflammation Prostaglandins and Leukotrienes are inhibited by the action of Glucocorticoids. Glucocorticoids also stimulate the lipocortin-1 escaping to the extracellular space, where it binds to the leukocyte membrane receptors and inhibits various inflammatory events: epithelial adhesion, emigration, chemotaxis, phagocytosis, respiratory burst and the release of various inflammatory mediators (lysosomal enzymes, cytokines, tissue plasminogen activator, chemokines etc.) from neutrophils, macrophages and mastocytes. Additionally the immune system is suppressed by corticosteroids due to a decrease in the function of the lymphatic system, a reduction in immunoglobulin and complement concentrations, the precipitation of lymphocytopenia, and interference with antigen-antibody binding. Like other glucocorticoid agents Fluocinolone acetonide acts as a physiological antagonist to insulin by decreasing glycogenesis (formation of glycogen). It also promotes the breakdown of lipids (lipolysis), and proteins, leading to the mobilization of extrahepatic amino acids and ketone bodies. This leads to increased circulating glucose concentrations (in the blood). There is also decreased glycogen formation in the liver. Fluocinolone Acetonide is used for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses. Also for the treatment of chronic non-infectious uveitis affecting the posterior segment of the eye (Retisert). Preparations containing Fluocinolone Acetonide were first marketed under the name Synalar.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
2.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SYNALAR
Primary
Retisert

Cmax

ValueDoseCo-administeredAnalytePopulation
54 ng/mL
0.8 mg single, topical
FLUOCINOLONE ACETONIDE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
354.8 ng × h/mL
0.8 mg single, topical
FLUOCINOLONE ACETONIDE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
14.8 h
0.8 mg single, topical
FLUOCINOLONE ACETONIDE plasma
Homo sapiens

Doses

AEs

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
generally applied to the affected area as a thin film from two to four times daily depending on the severity of the condition. In hairy sites, the hair should be parted to allow direct contact with the lesion.
Route of Administration: Topical
In Vitro Use Guide
Fluocinolone Acetonide (10(−6) M) inhibited the expression of inflammatory cytokines and matrix metalloproteinases in murine immortalized keratinocytes
Substance Class Chemical
Record UNII
85JNE553V5
Record Status Validated (UNII)
Record Version