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
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
DescriptionSources: http://www.drugbank.ca/drugs/DB00591Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012787s071lblrev.pdf
Sources: http://www.drugbank.ca/drugs/DB00591
Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012787s071lblrev.pdf
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2034 Sources: http://www.drugbank.ca/drugs/DB00591 |
2.0 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | SYNALAR Approved UseSYNALAR® Cream is indicated for the relief of the inflammatory and pruritic manifestations of corticosteriod-responsive dermatoses. Launch Date1963 |
|||
| Primary | Retisert Approved UseRetisert is indicated for the treatment of chronic non-infectious uveitis affecting the posterior segment of the eye. Launch Date2005 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
54 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1874579 |
0.8 mg single, topical dose: 0.8 mg route of administration: Topical experiment type: SINGLE co-administered: |
FLUOCINOLONE ACETONIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
354.8 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1874579 |
0.8 mg single, topical dose: 0.8 mg route of administration: Topical experiment type: SINGLE co-administered: |
FLUOCINOLONE ACETONIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
14.8 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1874579 |
0.8 mg single, topical dose: 0.8 mg route of administration: Topical experiment type: SINGLE co-administered: |
FLUOCINOLONE ACETONIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
6 ug 1 times / day multiple, intravitreal Highest studied dose Dose: 6 ug, 1 times / day Route: intravitreal Route: multiple Dose: 6 ug, 1 times / day Sources: Page: p.425 |
unhealthy, 24 –51 n = 6 Health Status: unhealthy Condition: Subfoveal choroidal neovascularization Age Group: 24 –51 Sex: M+F Population Size: 6 Sources: Page: p.425 |
Disc. AE: Central retinal vein occlusion... AEs leading to discontinuation/dose reduction: Central retinal vein occlusion (16.7%) Sources: Page: p.425 |
2 ug 1 times / day multiple, intravitreal Studied dose Dose: 2 ug, 1 times / day Route: intravitreal Route: multiple Dose: 2 ug, 1 times / day Sources: Page: p.1196 |
unhealthy, 43.2 n = 5 Health Status: unhealthy Condition: Posterior uveitis Age Group: 43.2 Population Size: 5 Sources: Page: p.1196 |
|
0.6 ug 1 times / day multiple, intravitreal Recommended Dose: 0.6 ug, 1 times / day Route: intravitreal Route: multiple Dose: 0.6 ug, 1 times / day Sources: Page: p.1584 |
unhealthy n = 127 Health Status: unhealthy Condition: Diabetic macular edema Population Size: 127 Sources: Page: p.1584 |
Disc. AE: Increased intraocular pressure... AEs leading to discontinuation/dose reduction: Increased intraocular pressure (2.4%) Sources: Page: p.1584 |
2 ug 1 times / day multiple, intravitreal Studied dose Dose: 2 ug, 1 times / day Route: intravitreal Route: multiple Dose: 2 ug, 1 times / day Sources: Page: p.17, 18 |
unhealthy n = 168 Health Status: unhealthy Condition: Non-infectious uveitis Population Size: 168 Sources: Page: p.17, 18 |
Other AEs: Intraocular pressure abnormal... Other AEs: Intraocular pressure abnormal Sources: Page: p.17, 18 |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Central retinal vein occlusion | 16.7% Disc. AE |
6 ug 1 times / day multiple, intravitreal Highest studied dose Dose: 6 ug, 1 times / day Route: intravitreal Route: multiple Dose: 6 ug, 1 times / day Sources: Page: p.425 |
unhealthy, 24 –51 n = 6 Health Status: unhealthy Condition: Subfoveal choroidal neovascularization Age Group: 24 –51 Sex: M+F Population Size: 6 Sources: Page: p.425 |
| Increased intraocular pressure | 2.4% Disc. AE |
0.6 ug 1 times / day multiple, intravitreal Recommended Dose: 0.6 ug, 1 times / day Route: intravitreal Route: multiple Dose: 0.6 ug, 1 times / day Sources: Page: p.1584 |
unhealthy n = 127 Health Status: unhealthy Condition: Diabetic macular edema Population Size: 127 Sources: Page: p.1584 |
| Intraocular pressure abnormal | 2 ug 1 times / day multiple, intravitreal Studied dose Dose: 2 ug, 1 times / day Route: intravitreal Route: multiple Dose: 2 ug, 1 times / day Sources: Page: p.17, 18 |
unhealthy n = 168 Health Status: unhealthy Condition: Non-infectious uveitis Population Size: 168 Sources: Page: p.17, 18 |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| yes |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes | ||||
| yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Asthma steroid pharmacogenetics: a study strategy to identify replicated treatment responses. | 2004 |
|
| Fluocinolone acetonide topical oil for scalp psoriasis. | 2004 Dec |
|
| Utilizing combination therapy to optimize melasma outcomes. | 2004 Sep-Oct |
|
| Fluocinolone acetonide ophthalmic--Bausch & Lomb: fluocinolone acetonide Envision TD implant. | 2005 |
|
| Hydroquinone 4%, tretinoin 0.05%, fluocinolone acetonide 0.01%: a safe and efficacious 12-month treatment for melasma. | 2005 Jan |
|
| Comparison of the analysis of corticosteroids using different techniques. | 2005 Jan |
|
| Effects of drug treatment on inflammation and hyperreactivity of airways and on immune variables in cats with experimentally induced asthma. | 2005 Jul |
|
| The nitrosterols--a step forward from the steroid anti-inflammatory drugs? | 2005 Jul |
|
| Long-term follow-up results of a pilot trial of a fluocinolone acetonide implant to treat posterior uveitis. | 2005 Jul |
|
| Gateways to clinical trials. | 2005 Jun |
|
| Steroids for choroidal neovascularization. | 2005 Mar |
|
| The safety profile of long-term, high-dose intraocular corticosteroid delivery. | 2005 Mar |
|
| Photochemistry and phototoxicity of fluocinolone 16,17-acetonide. | 2005 Mar-Apr |
|
| Retisert (Bausch & Lomb/Control Delivery Systems). | 2005 Nov |
|
| Evidence of remodeling in peripheral airways of patients with mild to moderate asthma: effect of hydrofluoroalkane-flunisolide. | 2005 Nov |
|
| A large 12-month extension study of an 8-week trial to evaluate the safety and efficacy of triple combination (TC) cream in melasma patients previously treated with TC cream or one of its dyads. | 2005 Sep-Oct |
|
| Flunisolide decreases exhaled nitric oxide and nitrotyrosine levels in asthmatic children. | 2006 |
|
| A comprehensive review of the long-term and short-term treatment of melasma with a triple combination cream. | 2006 |
|
| Efficacy of nebulized flunisolide combined with salbutamol and ipratropium bromide in stable patients with moderate-to-severe chronic obstructive pulmonary disease. | 2006 |
|
| Once-daily intranasal corticosteroids for allergic rhinitis. Examining Treatment issues. | 2006 Apr |
|
| Long-term continuous efalizumab therapy in patients with moderate to severe chronic plaque psoriasis: updated results from an ongoing trial. | 2006 Apr |
|
| Postinflammatory hyperpigmentation: evolving combination treatment strategies. | 2006 Aug |
|
| Long-term release of fluocinolone acetonide using biodegradable fumarate-based polymers. | 2006 Aug 28 |
|
| [New drugs in the treatment of noninfectious uveitis]. | 2006 Dec |
|
| Validation of a melasma quality of life questionnaire for Brazilian Portuguese language: the MelasQoL-BP study and improvement of QoL of melasma patients after triple combination therapy. | 2006 Dec |
|
| Ethnic considerations in the treatment of Hispanic and Latin-American patients with hyperpigmentation. | 2006 Dec |
|
| Intravitreal steroids in the management of macular oedema. | 2006 Dec |
|
| Inhaled flunisolide suppresses the hypothalamic-pituitary-adrenocortical axis, but has minimal systemic immune effects in healthy cats. | 2006 Jan-Feb |
|
| Efficacy of low-release-rate fluocinolone acetonide intravitreal implants to treat experimental uveitis. | 2006 Jul |
|
| Dark brown scaly plaques on face and ears. | 2006 Jun |
|
| Fluocinolone acetonide implant (Retisert) for noninfectious posterior uveitis: thirty-four-week results of a multicenter randomized clinical study. | 2006 Jun |
|
| Community-based trial of a triple-combination agent for the treatment of facial melasma. | 2006 Mar |
|
| Expression of TNF-alpha in oral lichen planus treated with fluocinolone acetonide 0.1%. | 2006 Mar |
|
| Treating chronic noninfectious posterior segment uveitis: the impact of cumulative damage. Proceedings of an expert panel roundtable discussion. | 2006 Oct |
|
| Topical glucocorticosteroids in rhinitis: clinical aspects. | 2006 Oct |
|
| Nebulized drug admixtures: effect on aerosol characteristics and albuterol output. | 2006 Winter |
|
| Fluocinolone acetonide intravitreal sustained release device--a new addition to the armamentarium of uveitic management. | 2007 |
|
| Pharmacotherapies for diabetic retinopathy: present and future. | 2007 |
|
| Emerging therapies for the treatment of neovascular age-related macular degeneration and diabetic macular edema. | 2007 |
|
| Hypertrichosis as a side effect of inhaled steroids in children. | 2007 Apr |
|
| Epithelial cells in the hair follicle bulge do not contribute to epidermal regeneration after glucocorticoid-induced cutaneous atrophy. | 2007 Dec |
|
| Injectable, in situ forming poly(propylene fumarate)-based ocular drug delivery systems. | 2007 Dec 1 |
|
| Cost-effectiveness of a fixed combination of hydroquinone/tretinoin/fluocinolone cream compared with hydroquinone alone in the treatment of melasma. | 2007 Feb |
|
| Cytomegalovirus retinitis after fluocinolone acetonide (Retisert) implant. | 2007 Feb |
|
| Strength and endurance of the respiratory and handgrip muscles after the use of flunisolide in normal subjects. | 2007 Jul |
|
| Compressor/nebulizers differences in the nebulization of corticosteroids. The CODE study (Corticosteroids and Devices Efficiency). | 2007 Jul-Aug |
|
| Vitreous band formation and the sustained-release, intravitreal fluocinolone (Retisert) implant. | 2007 Jun |
|
| A comparison of triple combination cream and hydroquinone 4% cream for the treatment of moderate to severe facial melasma. | 2007 Mar |
|
| Retisert: is the new advance in treatment of uveitis a good one? | 2007 Mar |
|
| Drug delivery methods for posterior segment disease. | 2007 May |
Sample Use Guides
In Vivo Use Guide
Curator's Comment: can also be used as intravitreal implant http://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/021737s000_PRNTLBL.pdf
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
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85JNE553V5
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76959717
Created by
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
