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.CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(=O)C=C[C@]5(C)[C@@]4(F)[C@@H](O)C[C@]3(C)[C@@]2(O1)C(=O)CO
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
Molecular Formula | H2O |
Molecular Weight | 18.0153 |
Charge | 0 |
Count |
|
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 |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 9 / 9 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
---|---|---|---|---|
1.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20202684/ |
0.5 μg 1 times / day multiple, intraocular dose: 0.5 μg route of administration: Intraocular experiment type: MULTIPLE co-administered: |
FLUOCINOLONE ACETONIDE aqueous humor | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
0 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/35988360/ |
0.25 mL 2 times / day multiple, auricular (otic) dose: 0.25 mL route of administration: Auricular (otic) experiment type: MULTIPLE co-administered: CIPROFLOXACIN |
FLUOCINOLONE ACETONIDE plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN |
|
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 |
---|---|---|---|---|
250 day EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20202684/ |
0.5 μg 1 times / day multiple, intraocular dose: 0.5 μg route of administration: Intraocular experiment type: MULTIPLE co-administered: |
FLUOCINOLONE ACETONIDE aqueous humor | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
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: |
unhealthy, 24 –51 |
Disc. AE: Central retinal vein occlusion... AEs leading to discontinuation/dose reduction: Central retinal vein occlusion (16.7%) Sources: |
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: |
unhealthy, 43.2 |
|
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: |
unhealthy |
Disc. AE: Increased intraocular pressure... AEs leading to discontinuation/dose reduction: Increased intraocular pressure (2.4%) Sources: |
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: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Intraocular pressure abnormal... Other AEs: Intraocular pressure abnormal Sources: |
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: |
unhealthy, 24 –51 |
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: |
unhealthy |
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: |
unhealthy Health Status: unhealthy Sources: |
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 |
---|---|---|
Poor sleep and daytime somnolence in allergic rhinitis: significance of nasal congestion. | 2002 |
|
Flunisolide HFA. | 2002 |
|
The output of flunisolide from different nebulisers. | 2002 Apr |
|
Gateways to clinical trials. | 2002 Jul-Aug |
|
One-year trial on safety and normal linear growth with flunisolide HFA in children with asthma. | 2002 Jun |
|
A comparison of methods for assessing hypothalamic-pituitary-adrenal (HPA) axis activity in asthma patients treated with inhaled corticosteroids. | 2002 Mar |
|
A curious keloid of the penis. | 2003 |
|
Efficacy and safety of a new triple-combination agent for the treatment of facial melasma. | 2003 Jul |
|
Recurrent oral ulceration. | 2003 Jun |
|
Evaluation of efficacy and safety of flunisolide hydrofluoroalkane for the treatment of asthma. | 2003 Mar |
|
Common hyperpigmentation disorders in adults: Part II. Melanoma, seborrheic keratoses, acanthosis nigricans, melasma, diabetic dermopathy, tinea versicolor, and postinflammatory hyperpigmentation. | 2003 Nov 15 |
|
Effect of topical nasal corticosteroids on patients with chronic fatigue syndrome and rhinitis. | 2003 Sep |
|
A randomized controlled trial of inhaled flunisolide in the management of acute asthma in children. | 2003 Sep |
|
Asthma steroid pharmacogenetics: a study strategy to identify replicated treatment responses. | 2004 |
|
Fluocinolone acetonide topical oil for scalp psoriasis. | 2004 Dec |
|
A comparative study of punch grafting followed by topical corticosteroid versus punch grafting followed by PUVA therapy in stable vitiligo. | 2004 Jan |
|
Improved quality of life with effective treatment of facial melasma: the pigment trial. | 2004 Jul-Aug |
|
Ocular pharmacokinetics of fluocinolone acetonide after Retisert intravitreal implantation in rabbits over a 1-year period. | 2004 Jun |
|
Flunisolide HFA for the treatment of asthma: an old friend reformulated. | 2004 May |
|
In vitro effects of flunisolide on MMP-9, TIMP-1, fibronectin, TGF-beta1 release and apoptosis in sputum cells freshly isolated from mild to moderate asthmatics. | 2004 Sep |
|
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 |
|
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 |
|
Efficacy of nebulized flunisolide combined with salbutamol and ipratropium bromide in stable patients with moderate-to-severe chronic obstructive pulmonary disease. | 2006 |
|
[New drugs in the treatment of noninfectious uveitis]. | 2006 Dec |
|
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26734587
Fluocinolone Acetonide (10(−6) M) inhibited the expression of inflammatory cytokines and matrix metalloproteinases in murine immortalized keratinocytes
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 20:43:24 GMT 2025
by
admin
on
Mon Mar 31 20:43:24 GMT 2025
|
Record UNII |
85JNE553V5
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Preferred Name | English | ||
|
Common Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
85JNE553V5
Created by
admin on Mon Mar 31 20:43:24 GMT 2025 , Edited by admin on Mon Mar 31 20:43:24 GMT 2025
|
PRIMARY | |||
|
76959717
Created by
admin on Mon Mar 31 20:43:24 GMT 2025 , Edited by admin on Mon Mar 31 20:43:24 GMT 2025
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ANHYDROUS->SOLVATE | |||
|
PARENT -> SALT/SOLVATE |