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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.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

HIDE SMILES / InChI

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

Description
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

Targets

Primary TargetPharmacologyConditionPotency
2.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SYNALAR

Approved Use

SYNALAR® Cream is indicated for the relief of the inflammatory and pruritic manifestations of corticosteriod-responsive dermatoses.

Launch Date

1963
Primary
Retisert

Approved Use

Retisert is indicated for the treatment of chronic non-infectious uveitis affecting the posterior segment of the eye.

Launch Date

2005
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.5 ng/mL
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
354.8 ng × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
250 day
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
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

Doses

DosePopulationAdverse 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
Health Status: unhealthy
Age Group: 24 –51
Sex: M+F
Sources:
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
Health Status: unhealthy
Age Group: 43.2
Sources:
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
Health Status: unhealthy
Sources:
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
Other AEs: Intraocular pressure abnormal...
AEs

AEs

AESignificanceDosePopulation
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
Health Status: unhealthy
Age Group: 24 –51
Sex: M+F
Sources:
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
Health Status: unhealthy
Sources:
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
Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical 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
PubMed

PubMed

TitleDatePubMed
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
Patents

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
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 Mon Mar 31 20:43:24 GMT 2025
Edited
by admin
on Mon Mar 31 20:43:24 GMT 2025
Record UNII
85JNE553V5
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FLUOCINOLONE ACETONIDE DIHYDRATE
Common Name English
6.ALPHA.,9.ALPHA.-DIFLUORO-11.BETA.,21-DIHYDROXY-16.ALPHA.-,17.ALPHA.-ISOPROPYLIDENEDIOXYPREGNA-1,4-DIENE-3,20-DIONE DIHYDRATE
Preferred Name English
PREGNA-1,4-DIENE-3,20-DIONE, 6,9-DIFLUORO-11,21-DIHYDROXY-16,17-((1-METHYLETHYLIDENE)BIS(OXY))-, DIHYDRATE, (6.ALPHA.,11.BETA.,16.ALPHA.)-
Common Name English
Code System Code Type Description
FDA UNII
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
PUBCHEM
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